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Read time: 7 minutes

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I got this question from a student in the October cohort of my course:

I’d love to hear any advice on helping people more senior than me recognize patterns of behavior that are stopping them from getting the results they want. 

A few examples: 

• Not giving clear guidance during a process--then being disappointed with the results

• Not setting priorities--then being disappointed their team isn’t working on the right things

• Not training new hires--then being disappointed when they take longer to ramp up

Ah, this is a dilemma.

How can you help a senior leader see they’re making life harder for themselves and their team?

If you don’t speak up, you’re robbing your organization of your good insights.

If you do speak up, you might put your employment and well-being at risk.

This puts you in a tough spot.

Today I want to share some ways you can share feedback with senior leaders, or anyone more powerful than you—while being respectful, helpful, and protecting yourself from their wrath.

Giving feedback to someone more powerful than you is a pattern break

Traditionally, the more powerful person gives feedback to the less powerful person.

So if you want to give feedback to a more senior person, it’s an inversion of norms. This causes a moment of potential chaos, which is why you want to control the energy and channel it in a positive direction.

Feeling nervous about giving your senior leader feedback is a good thing. It means you have survival instincts that help with self-preservation.

Giving a senior leader feedback shouldn’t be your first option:

• Your first option is to ask yourself, “What can I do that’s within my control to improve this situation?”

• Your second option is, “Can I live with this? How much does this bother me? Is it worth giving them feedback and what are my chances of success doing it?”

• Your third, fourth, and fifth option: Thinking more about the above

• Your final option: “I think I want to give this senior leader some feedback.”

In other words, make sure YOU aren’t the problem. Make sure you are managing up, asking clarifying questions, acting like an owner, etc to get what you need. It’s easy to blame a leader, but before you do that, try reflecting on how you could behave differently to improve outcomes for both of you. It’s low-agency to assume other people should change.

If you do want to give your senior leader feedback, proceed with the appropriate level of caution. You may want to adjust the tactics below based on your specific leader, their idiosyncrasies, worldview, your relationship, the level of trust they have in you, etc.

For example, you might realize your relationship or credibility isn’t strong enough for you to give them feedback—that’s an equally appropriate conclusion.

The only path I’d advise against: Going in with guns blazing, assuming you have moral high ground simply because you are right.

If you are self-aware and could realistically see your senior leader taking the feedback well, read on.

Here’s what I do that might be useful for you too. 

1. “Even more” technique

I’ve taught this framework to my clients, and they love it. I’m going to share it with you.

The framing of “even more” works so well because you’re speaking from a place of generosity and giving the benefit of the doubt.

You’re assuming they’re doing X—and that they should do it even more. You are assuming they are great--and you want to make them even stronger. 

🚫

You: “We might need to give guidance to new hires.”

Senior leader: “You think I don’t know that I need to give new hires guidance? I obviously gave them guidance. GTFO.”

✅

You: “We may need to give even more guidance to new hires.”

Senior leader: “Hmm yeah. I gave them some guidance, but that probably wasn’t enough.”

Why this works:

The “before” scenario is binary—the senior leader either did or didn’t give guidance. And if they didn’t, well, they messed up. They feel threatened that you noticed.

The “after” is a spectrum: You are generous in assuming that they did give guidance. You’re suggesting they may want to amp this up even more. This is much easier for them to accept.

This isn’t simply an issue of semantics or phrasing. This is about positioning to increase the chances they change their behavior.

Getting anyone to listen and change their behavior, especially someone more senior? That’s a huge win.

[The “even more” technique works with giving feedback to direct reports too. It’s super versatile.]

2. Use yourself as an example

Talk about yourself so it doesn’t seem like you’re pointing fingers. I do this whenever I want to say something the person might find insulting.

🚫 “You should try X.”

✅ “I used to struggle with this, and when I tried X, it really helped.” 

By the way, saying “you should try X” is fine--there’s nothing inherently wrong about it. The reason I would avoid it is because of the power dynamic and CONTENT of what I’m saying. 

If there’s a power dynamic and/or the content of what I’m saying might be sensitive for the person, that’s when I share about my own experience. 

I’m not saying YOU are struggling with X, I’m saying I used to and what I did. And if that lesson applies to what you’re dealing with, that’s cool, but no pressure.

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3. Adopt diplomatic, curiosity-forward language

Most people are extreme in one of two ways:

1. They think “respecting the person’s power” means being 100% supplicant. They do everything the powerful person says, and never push back even when they have reason to. → These people are spineless.

2. They share their POV in the most blunt, low-finesse way without any regard for their recipient’s person’s ego. They think, “Well, I’m right, so I should just say the thing with zero framing.” → These people are insubordinate.

Both are bad. Both lack judgment.

What you want to do is: Share your POV in a way that doesn’t threaten the senior person, and gets them to listen.

One simple way you can achieve this is by using diplomatic, curiosity-forward language. 

These phrases help you ease into the suggestion in a way that feels non-threatening:

• "We might want to try…”

• “I wonder if...”

• "Perhaps we could...”

• “What are your thoughts on...”

• “One approach might be...”

You adopt the vibe of a helpful team member who has your leader’s best interest in mind and wants to serve your organization. 

You are forward-looking. Instead of focusing on what went wrong (which risks making your leader feel defensive), you’re focused on what to potentially do going forward.

4. Bring data and examples to support your point

If you've been reading this newsletter for a minute, you know I bang on the drum of sharing your logic. I believe most people do not share their rationale enough.

Don’t just make a high-level, hand-waving statement.

Instead, share examples of what worked well in the past because it helps your feedback land. Supporting your claims makes you more persuasive and objective--and increases the chances your senior leader will take your recommendation.

Example 1: Guidance during projects 

🚫 “We need to give more feedback during projects.”

✅ “I noticed when we reviewed the design mockups weekly with the client, they loved the final result. For this project, early check-ins could help us make sure we’re aligned before going too far down a certain direction and could prevent rework.”

Example 2: Setting priorities 

🚫 “The team needs clearer priorities.”

✅ “The team made amazing progress when we all focused on the website update last month. It might help to have one or two clear priorities for the team this month that everyone can rally behind.”

Example 3: Training new hires 

🚫 “We should spend more time training new people.”

✅ “When we were able to dedicate that first week to training Steve, he got up to speed pretty quickly. The bit of upfront time seemed to have paid off, and taking a similar training approach for our next hire could help them ramp up just as fast. What do you think?”

Why this works:

• Ends with a clear, actionable suggestion

• Shows the upside of updating their approach

• Keeps it simple, logical, and positive

Personally, I think phrasing a recommendation as a statement reduces cognitive load. You can follow up with an open-ended question, like “what do you think?”

Notice how the examples above are concrete AND concise. Avoid long diatribes and over-explaining—use your judgment to share just enough context.

And for goodness sake, do not have a “well actually…” vibe when you share logic and data. This is obnoxious and will probably backfire. Notice how in the examples above, I’m sharing rationale, and doing it in a collaborative way.

To recap, here are the points:

1. Deploy the “even more” technique

2. Use yourself as an example

3. Adopt a diplomatic, curiosity-forward language

4. Bring data and examples to support your point

Which principle above do you want to try? Which do you think will work best with the senior leader you have in mind and why? Hit reply because I’d love to hear from you.

Thanks for being here, and I’ll see you next Wednesday at 8am ET.

Wes

Executive Communication & Influence course

The February 2025 cohort of my course is now open. I’m thrilled to see the testimonials from alumni continue to roll in too. Here’s what students are saying:

“I decided to join Wes’ course because I've been a huge fan of her newsletter for a long time. It's always easy to get stuck in your own head or to be verbose in your writing when people are constantly asking for something from you and there's no time to think about your audience. I found the frameworks and perspective Wes shared really valuable, especially in a world where concise and clear written communication is critical. I would recommend this class for anyone who needs to align a large group of stakeholders or bring a valuable recommendation to executives.”

- Angela Santurbano, Principal Product Manager, Square

“Highly, highly recommended. This is the rare communication course I’ve taken that focuses on how I actually get things done at work: Slacks, emails, last minute cross-functional meetings, and constantly managing up. It’s also the rare virtual course where the activities are challenging, actually mirror real life scenarios, and provide a valuable opportunity to practice skills. On top of all that, Wes is giving real-time constructive feedback to her students. Sign up!”

- Fred Geyer, Manager, Employee Onboarding Experience, HelloFresh

“This course was filled with clear, actionable insights to improve communication habits and practices in my everyday work. I'm excited to implement the strategies Wes covered.”

- Jess Mordo, Senior Manager, Senior Manager (Acquisition Marketing), Grammarly

“This course provides a practical set of tools and tactics to apply immediately to your writing. It sparked valuable discussions within my team, who also attended, and I highly recommend it to anyone frequently operating in a ‘debate and commit’ environment. Wes’s approach to clear, kind, and persuasive writing is especially relevant if you rely on channels like Slack or Teams.”

- Morgan King, Director of Client Support, Stitch Fix

“This was an excellent course. I appreciated the real-world examples, appropriate level and complexity of coursework, and the ask-me-anything Q&A sessions. Very well done!”

- Eric Livingston, Senior Director of Product Management, Salesforce

In the past week, operators from Adobe, Meta, Shopify, Autodesk, Grammarly, Klayvio, Chick-fil-A, eBay, Square, Equifax, Roblox, etc have signed up. Check out the course page to learn more and see if it’s a fit for you.

Connect with Wes

• Are you new to the newsletter? Subscribe for free

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• Work with me for 1:1 executive coaching

• Check out my 2-day intensive course. Join us: → Executive Communication & Influence for Senior ICs and Managers

⛑️ If you want to dramatically improve your ability to communicate clearly and concisely, check out my intensive 2-day course: Executive Communication & Influence for Senior ICs and Managers. You’ll learn alongside mid-career operators from Netflix, Stripe, Uber, Shopify, Meta, Figma, Anthropic, etc. → Save your spot

In this week’s newsletter, you’ll learn why being concise doesn’t mean skipping details or jumping in with zero context. Here’s what it actually means—and how to do it.

• Part I: Common misunderstandings

• Part II: The real reason why it’s so hard to be concise

• Part III: Ways to be more concise

Read time: 11 minutes

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Almost every operator I know wants to be more concise.

At first glance, it seems simple enough. Speak a little shorter and write fewer words, right?

This begs the question:

If it’s so simple, why aren’t all of us already concise?

I’m not naturally a concise person. I’ve worked with colleagues who were much more naturally succinct. When I asked them for tips on how to be more concise though, they couldn’t explain it—they’ve never been any other way.

For me, it’s a skill I’ve had to hone through active practice and experimentation over the years. While I wouldn’t say it’s my #1 strength, I’ve improved a lot and reaped the benefits in my work.

Here’s what’s worked for me. Let’s dive in.

Part I: Common misunderstandings

First, the idea of being concise is often misunderstood, so I want to share my perspective on what it means.

1. Concise does not mean short.

I am painfully aware that this topic attracts attention. (It’s like writing a book about how to be funny. Inevitably, someone won’t laugh at your jokes and will say you’re in no position to write about how to be funny.)

I can already hear folks saying, “Wes, it’s ironic that you wrote an essay that takes X minutes to read, and it’s about being concise. Shouldn’t it be a 1-2 minute read?”

If long-form isn’t for you, that’s cool.

But don’t conflate concision with word count. Being concise is about using an economy of words. It’s maximizing your word “real estate.” It’s about density, not absolute length.

You can have a 1,500-word memo that’s concise. You can have a 150-word memo that’s fluffy and meandering.

2. “It’s not concise enough” is not an excuse to avoid engaging with difficult problems.

It’s a pet peeve of mine when people refuse to engage with anything longer than a few sentences (or god forbid, a few paragraphs) because “you should be more concise.” When you ask for feedback, they say “make it more concise” as if they dropped a rare gem of wisdom. 

If you start sharing (necessary) details, they stop you and ask you to explain in a shorter way. They act like you're long-winded, when in reality, the nature of the situation is complex and those details add valuable context.

3. Some ideas can’t be reduced any further.

You know how in math class, you learned to reduce fractions?

You can reduce 22/64 into 11/32. But you can’t reduce 11/32 further even though the number feels kind of big.

It’s the same with ideas. When you try to simplify a topic BEYOND how much it can be simplified, you get into the territory of misrepresenting an idea.

If you write a memo that’s short, but you left out crucial information… This could do harm and lead to poor decision-making.

4. Being concise is a means to an end, not an end in itself.

Your goal is to be effective, so you should use as many words as necessary—no more, no less. If you use too few words, you might sacrifice clarity and persuasiveness.

Paul Graham has essays that are 500 words and some that are 3,000+ words. One of his recent essays is 10,455 words.

Is he “not concise” all of a sudden? I'm not saying you should write essays in Slack. But there’s nothing inherently wrong with a “longer” message, as long as it’s clear, value-add, and necessary.

Focus on being effective. Focus on reducing cognitive load. That’s more important than being short for the sake of it.

Part II: The real reason why it’s so hard to be concise

Alright, now that we are aligned on the premise, I want to discuss advice you’ve probably heard before, like “bottom line up front,” “don’t bury the lede,” and “cut to the chase.”

For years, I tried to take this advice but found it very hard to implement.

Until one day, I realized…

Most of the advice about being concise required one underlying component that wasn’t talked about: clear thinking.

I’ve come to believe that clear thinking is the hard part—it’s the bottleneck to being concise. If you don’t first clarify your ideas, you can’t communicate those ideas concisely.

For example, the common advice below doesn’t highlight the prerequisite of developing a clear understanding of what you want to say.

• Bottom line up front (BLUF): To put the bottom line up front, you have to develop a perspective about what the bottom line is.

• Don’t bury the lede: You might have multiple potential ledes. Deciding the lede requires making a choice, and only then can you start with that.

• Cut to the chase: What is your most important point? It’s not always obvious. It requires you to think about a few variables: who are you presenting to, how much do they already know, what’s the purpose of this meeting, etc. When you assert those things, then you can cut to the chase.

I believe if we acknowledge the real bottleneck to being concise, it’ll help us be more concise. It’s not necessarily about more tactics. It’s about realizing we may need to take a moment to figure out what we think.

You may be able to share your ideas, yes, but it doesn’t come out clean. It’s not crisp. 

This is completely normal. Ideas are often messy because you’re still working through what you believe. When you’re in this phase, be patient with yourself. Find a coworker who you can bounce ideas off of. Write your ideas—the act of writing is a forcing function to help you both clarify what you think and generate new, better ideas.

Over time, if you practice the principles below, you can improve how to quickly think on your feet and be concise.

Part III: Ways to be more concise

If you want to think clearly, and therefore communicate concisely, you will likely need to prepare. The higher the stakes, the more you may want to do so.

1. Figure out your main point.

“Figuring out your main point” sounds like one step, but it’s actually multiple steps:

1. Process the information

2. Make sense of it

3. Decide what’s important

4. Organize it

5. Say it out loud

It’s hard to do all these cognitive steps simultaneously.

This is why it’s so easy to start rambling: When we speak in a stream of consciousness, there is no information hierarchy, no prioritization (yet)—you’re saying everything as you think of it, with equal weighting.

Now, it’s possible to do all the steps above in succession relatively quickly, depending on how familiar you are with your topic.

If it’s something you’ve explained many times, you’ve already done the work of processing the information—so it’s easier to share concisely. If it’s something new, you might want to take a few seconds to gather your thoughts.

It’s unglamorous. It’s not a shortcut. But it’s what I’ve found consistently works.

Realistically, you might have back-to-back meetings, so “preparation” is more about taking a moment to be center yourself, rather than spending a certain amount of time.

Even a few seconds of preparation can make a positive difference. Ask yourself:

• What do you want to get out of this meeting? 

• What is the most important thing to share?

• What action do you need folks to take?

2. Try to state your main point in 2-3 sentences.

If you aim for one sentence, you’ll have analysis paralysis figuring out THE perfect sentence.

If you aim for ten sentences, it could easily turn into a monologue and spiral out of control.

If you aim for 2-3 sentences, it forces you to state your high-level thesis and what you need from the other person. The point is not to capture everything. The point is to frame the conversation upfront, which “buys you time” with your audience.

• Your audience can relax knowing where you’re taking them

• They can confirm if this is the right time/place to have this conversation

• They can easily focus on the context you share thereafter

When in doubt, ask yourself: How can I explain this in 2-3 sentences? You might end up saying 5-6 sentences, but it’s still better than if you weren’t aiming for something shorter at all.

3. Avoid explaining events chronologically.

We experience events in chronological order, but explaining what happened this way can be confusing for your recipient.

🚫 “Well this happened, then this other thing, and here’s the process of what I did for that. Oh yeah, then this thing but that’s not important, this important thing that’s completely buried, and then this other thing, and…”

✅ “Here’s the important thing I want to discuss. Here's what I need from you. Here are a few sentences about the situation, with the option to elaborate if needed.”

When you say your punchline upfront, you will instantly seem more competent, strategic, and organized. Try to keep the backstory short, and skip the play-by-play of what you did at each step (you can always share this if you're asked about it).

4. Constantly remind yourself to shorten your delivery.

Most of us start with good intentions of being concise. But then you start talking. And before you know it, you’re a few tangents deep and you’ve lost your way.

This is common. It’s why I find it helpful to develop an always-on filter humming in the background as a meta voice that’s hearing yourself talk. That meta voice is asking:

• Is this the shortest way you can explain this?

• Is this backstory REALLY necessary?  

• What are you really trying to say? Can you just say that?

• Should I get back to my main point?

More on aiming for the minimum viable backstory.

5. Exercise situational awareness.

People who speak in giant run-on sentences seem more junior. Imagine a leader you admire—they probably don’t sound rushed. They breathe in between talking. 

It’s hard to stop when you’re on a roll, but try to give people an opportunity to jump in.

• Notice if people are starting to lose interest. Don’t ignore those clues and continue powering through. If they aren’t listening anymore, you’re wasting your breath anyway.

• Pause sooner than you think and give the other person a chance to respond, so you can evaluate if they’re following along.

• Look for a natural stopping point to wrap up. You need to think about how to end gracefully, so you can head in that direction while you’re still talking. It only takes a split second and helps you sound more authoritative.

6. Don’t be too concise.

There is such a thing as being too concise. You might think, “If I’m too concise, my audience can just ask me questions right?”

Yes and no. Here’s an excerpt from my post on how to explain your ideas better:

There is some information you should volunteer without being asked.

Do not force other people to do the heavy lifting to draw basic information out of you piece by piece. This is lazy and irresponsible. Especially because the alternative is doable, simple, and relatively fast.

Even if you explain well, folks will still have questions because (a) you probably didn’t explain as well as you think and (b) they’ll bring up aspects you didn’t cover. When you cover the basics, you’re setting them up to ask better, more advanced questions.

Don’t leave out crucial information because you were trying to be concise. That’s winning the battle but losing the war. 

7. For written communication, use “main point above, context below.”

A common question I get is, “How can I be concise if the details actually matter? Do I just not share those details? That feels irresponsible.” 

Sometimes the context and explanation is just as important as whatever your bottom line is. This is why I love the framework I call “main point above, context below.” It’s a riff on the military framework BLUF (bottom line up front).

When you separate the main point from your context, you allow your reader to immediately understand your point, then get more details.

You give your reader agency because they can read as much or as little of the context as they need.

🚫 [Actions, backstory, and context jumbled together]

✅ [Main point above, context below]

8. For longer verbal communication, use signposting.

In a written medium like Slack or email, you have time to edit. But in a live conversation, it’s all happening in real-time.

In writing, your audience can skim at their own pace, reread anything that requires a second look, and see the overall structure of the page to understand what’s to come.

In verbal communication, though, your audience is limited by your pacing and what you reveal line by line. This is why it’s helpful to frame the conversation upfront—tell them where you’re taking them.

Examples of signposting when you speak:

“For context, we left off last week with [the problem the team was facing]. So I took a stab at solving these issues, and today I will review the changes I made.”

“The part that’s most important to point out is…”

“First, I’ll give a quick high-level view of the three major changes, then I’ll highlight specific in-product copy changes that I believe make the experience more intuitive.”

More on signposting and emotional signposting.

9. Offer to elaborate.

Don’t just say, “I can elaborate on anything.”

That puts the mental load on the other person to come up with good questions. If you’re the project owner and closest to the issue, you should proactively assert what to share.

🚫 “Let me know what you want to know.”

✅ “I can elaborate more on a few areas: For example, the other options I looked at, including (a) if we optimized for speed and could get this done in a week, (b) cheaper/more expensive options that I thought weren’t worth it, and (c) looking ahead a few steps, the risks I foresee and how I’m planning to derisk.”

The goal of being concise is to create understanding as quickly and easily as possible. Therefore, simply being succinct isn’t enough. You must also be clear, compelling, and coherent too.

It’s usually much easier to identify ways other people can be more concise than to catch it for yourself. When I coach my clients, I interrupt them and point out where they could have been more concise, then have them rephrase what they said to make it more concise. We drill, and it can take several attempts.

If you’re trying this yourself, I recommend saying different versions of the same thing in increasingly more concise ways. See how far you can push yourself.

What’s making you think differently? What are you most excited to try? Hit reply because I’d love to hear from you.

Thanks for being here, and I’ll see you next Wednesday at 8am ET.

Wes

PS Here are more ways to connect:

1. Follow me on Twitter or LinkedIn for insights during the week (free).

2. Check my availability to do a keynote talk for your team.

3. Work with me for 1:1 executive coaching. I find it extremely rewarding to give personalized guidance to ambitious operators. My current clients include leaders at startups funded by Sequoia, Accel, Bessemer, SV Angel, Kleiner Perkins, etc.

👋 Hey, it’s Wes. Welcome to my weekly newsletter on managing up, driving growth, and standing out as a high-performer.

⛑️ Update: It’s been an incredible few months of working with startup CEOs and tech directors/VPs, and I’m constantly amazed at how brilliant my clients are. I’ve noticed many conversations are about these four juicy topics: Managing up, communicating with executive presence, giving hard feedback to improve team performance, and delegating while maintaining high quality. My clients love having me in their corner to get detailed, no BS feedback or role-play tough conversations to build muscle memory. If you’re interested in how I can support you, learn more about coaching.

In this week’s newsletter, we’ll cover why, given relatively similar backgrounds and resources, most operators create mediocre work—but others are able to create magic.

• Part I: What it means to turn a yellow spot into the sun

• Part II: The wow factor, or lack thereof

• Part III: Setting a higher bar for what’s possible

Read time: 10 minutes

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I want to share one of Maven's company values that I believe is helpful for high performers everywhere: turning a yellow spot into the sun.

Picasso said,

“There are some painters who transform the sun into a yellow spot, but there are other painters who with the help of their art and their intelligence, transform a yellow spot into the sun.”

This is one of my favorite quotes. It encompasses one of the attributes I look for in new hires and encourage in team members.

Here’s a question: Given relatively similar resources (years of experience, hours in a day, access to channels), most people create average work, but some people exceed expectations. Why?

Because some operators are able to turn yellow spots into the sun.

Part I: What it means to turn a yellow spot into the sun

When people are given similar assets, there is a spectrum of quality for the results.

You can give 100 painters the same access to canvas, brushes, and Winsor & Newton watercolors. Most will turn the sun into a yellow spot. Some will turn a yellow spot into the sun—they will infuse life into the work, so the final product is surprising, breathtaking, and magical.

This analogy applies to anything you write, make, design, code, or build. There is art in what you do. If you’re building something new, there is nothing that’s purely mechanical and robotic. It all requires some judgment. Your sense of judgment is your art.

Turning a yellow spot into the sun means:

1. Turning a little into a lot. Most people do the opposite: they have near-infinite resources at their fingertips, but come back with mediocre work.

2. Creating work that surprises and delights. The output is better than what folks described or originally imagined. Shows flashes of brilliance.

Other aspects of turning a yellow spot into the sun:

• No one told you what to do step-by-step. You brought your skill, vision, and judgment to fill in the blanks. You made good decisions about what to do.

• In someone else’s hands, the work could have turned out average. It’s living the answer to the question, “If you weren’t there, how would this have turned out differently?”

• Some people do a mildly difficult task, and are knocked off their feet. They are completely overwhelmed and need time to recover. They need applause for what they just did. They need a lot of reassurance and validation, ongoing. This is not turning a yellow spot into the sun.

• Clean, elegant, resourceful; solving problems folks didn’t even know was annoying until you got rid of it. Among a range of potential outcomes, none of which were guaranteed, you created the best expression of what the idea could be.

Turning a yellow spot into the sun is shorthand for all of the above.

This even applies to technical topics that are mostly seen as the opposite of art. I’ve heard engineers talk about beautiful code. People outside your field might not appreciate the art the way fellow operators in your field can. When I see amazing emails, I think, “Damn, that is really good. It just works.”

Once I went to a new dentist and he said, “That crown is beautiful. Which dentist did it?” Most people wouldn’t think dentistry is art. But there’s opportunity for je ne sais quoi in every field.

Turning a yellow spot into the sun is not simply about “being resourceful.” Resourcefulness is part of it, but it feels too utilitarian and flat. It’s like saying your favorite artist and most brilliant work of art is “creative.” Like, yes, Tolkien was “creative” but that hardly captures what he was.

Turning a yellow spot into the sun captures the spirit of exceeding expectations that “being resourceful” simply does not.

Part II: The wow factor, or lack thereof

The best way to understand what turning a yellow spot into the sun means is by seeing examples of the opposite. I love this story from Fortune 500 CMO Stephanie McCarty about why she’s frustrated by traditional ad agencies:

“Here's my beef with ad agencies.

They do SO MUCH rework.

I get it. They want to go deep. They want to talk to people. They want to do surveys. But at the end of the day, what they come up with is almost the same strategy, with a slightly different spin. And now I've just paid $500,000 (or more) for something I’ve already paid $500,000 (or more!) for several times before. I can’t stand it.”

Agencies spend half a year researching your customer, brand, industry… and what they come up with is very similar to what you had originally.

This is the epitome of not turning a yellow spot into the sun. They have ALL the time, budget, and resources at their disposal, yet the thing they come up with is basic at best.

Another example: My team member was drafting a case study for a marketing instructor. The first draft was lackluster even though the instructor had one of THE most interesting backgrounds. I imagine an unskilled biographer could turn even the most interesting person’s story into a boring read, and vice versa.

It’s useful to have shorthand because I gave the team member feedback: “We kind of turned the sun into a yellow spot here.”

I like to tell folks: “There’s no strict budget and nothing is off limits IF you can make a strong business case.” You might spend hours sharing context, being a thought partner, riffing with them—but what they come back with was mediocre. If the progress you worked on together was 1 mile, their addition (after going off on their own) might be 1 inch beyond what you did. If this happens enough times, it’s probably not a fit.

I’ve also seen the range of “yellow spots into the sun” with job candidates. Most candidates have access to the same publicly available information about companies. But there is a spectrum of quality in what candidates do with this information.

Some candidates have pitches that are significantly better. Why is that?

They used good judgment: They picked up on the right clues, identified where they fit in, discerned the company’s needs, picked the right medium for their pitch, while minimizing their level of effort to stay leveraged. All of this contributes to their ability to turn a yellow spot into the sun.

While you might think turning a yellow spot into the sun is mainly about strong execution, it’s equally about inventiveness and vision. There are situations where I wouldn’t have been able to describe what the person ended up creating. I had a version of what “great” looked like in my mind—and they surpassed it in ways I wouldn’t have been able to articulate in advance.

For example, I had been working with a direct report on managing up more. One day, she sent me this fantastic Slack DM:

I had mentioned a few guidelines on what to include that would help me reply quickly. But I had no idea a quick approval DM could be so neat and impactful—until I saw this. She took something mundane and elevated it. She turned a yellow spot into the sun.

Doing great work without making a fuss

Turning a yellow spot into the sun isn’t only about your intention and skill. It’s also about actually choosing to execute in the first place.

An example of this is Arielle Kimbarovsky, Head of Marketing at Balsamiq. I met Arielle because Balsamiq is a newsletter sponsor. She shared a story that’s an example of turning a yellow spot into the sun. Here’s what she said:

“Something I did that completely changed my career in its early years: I kept a work journal. I noted down decisions I made as an IC and manager, decisions my managers made, the outcomes, the impact, and what I learned. I wrote down those "inside thoughts" we all have during meetings. I wrote down the advice I HATED and why, as well as the helpful stuff. I wrote down pivotal interactions with clients, peers, leaders, and direct reports. I wrote down specific phrases different leaders liked to use. It was almost scientific—I applied basic tactics I learned in science/psychology classes about field observation. I still reference that journal to this day.”

No one told Arielle to do this. No one was stopping her from doing it, so she didn’t need permission. It was internal for herself, so she didn’t even show this to anyone.

This is one of those things that all of us could theoretically do—but only a tiny percentage actually do or even think of doing. 

Most people in her shoes would have said, “I need a mentor. I need someone to teach me strategy. I need support. I need to ask execs to explain their decisions and get their feedback.” Not Arielle. Arielle took a little (i.e. the lived experiences she was getting on the job, like all her peers)—and she turned it into a lot.

I’ll give a non-work example too:

My mom came to stay with us and she noticed a random spot in our kitchen. We previously had a mini fridge there, so it was a hole in the island that wasn’t being used.

One day, I noticed she turned cardboard boxes into two makeshift shelves as extra storage space for our appliances. She had actually changed the dimensions of the boxes to fit into this space.

No one asked her to do this. She proactively identified and solved a problem we didn’t realize was annoying—until the problem was no longer there. Now, all the appliances fit neatly in a spot that was previously dead space. She didn’t make a big deal about it. She didn’t ask, “How do you change the dimensions of a box?”

She figured it out and did it. She turned a yellow spot into the sun.

The lesson above is not “don’t ask people how to change the dimensions of a cardboard box” or “always do something reversible.” That’s not it.

There is no set of rules (beyond the first principles I cover here each week) to memorize. It’s the same foundational principles, like knowing your assets/levers/constraints, asking the question behind the question, thinking rigorously, etc.

The psychotherapist Eric Maisel said, “We have enough experiences in a day to make art for a decade.” You probably don’t need more material, you need more insight.

• Before you say you’ve exhausted the well, dig deeper.

• Before you say the tactic doesn’t work, perhaps you’ve only scratched the surface.

• Before you say you need more, consider if you’ve fully explored making the best out of less.

• Before you move on to the next shiny object, consider if you’ve really squeezed every last drop of juice from your current endeavor.

Ask yourself: How can I do more with what I have in front of me?

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Part III: Setting a higher bar for what’s possible

I know when I see a “yellow spot into the sun” moment when I whisper “holy shit” under my breath to something because I think it’s so good. Most people would assume there isn’t room to make X much better. And then someone comes along, and makes it better.

It’s like Tessa Virtue and Scott Moir.

Among figure skaters, ice dance is the least cool, with singles figure skating, then pairs coming in second, and ice dance a far third. Until Tessa Virtue and Scott Moir. They single-handedly turned a very uncool sport into one that was powerful, athletic, and thrilling. How? 

Were they technically skilled? Yes. Were they artistically skilled? Yes.

But so were dozens of other Olympic skaters with technical and artistic skill. I would argue that until Tessa and Scott, no one was able to elevate the sport on a global stage. They brought an element of je ne sais quoi.

If you haven’t seen their 2018 Olympic performance, it’s worth watching. It has 22M views. They turned a yellow spot into the sun.

Elevating the mundane

I believe the big things that succeed are usually the result of many compounding micro-decisions along the way. People celebrate the strategy at the beginning and the outcome at the end, but if you look more deeply, there was usually good decision-making and craft at each step, which layered up to greatness.

That’s why turning a yellow spot into the sun isn’t only for dramatic projects. It’s equally about elevating stuff most folks think of as boring and small. For example, one of my clients replied to my scheduling email in a way that was crisp:

I chose a tactical, seemingly minor example on purpose. We all write emails every day, but this one made me pause and take note. There’s something elegant about how clean it is.

***

How do you know when you’ve turned a yellow spot into the sun? A good sign is when people say “wow” and comment on your work. I encourage you to point this out to your colleagues and ask them to point it out for you. Other times, you’ll come to a satisfying solution to a complex problem, and only you know how messy it could have been.

Keep an eye out for anything that makes you stop in your tracks, even small things. Note what makes it feel magical and add it to your mental swipe file.

What counts as turning a yellow spot into the sun is not a strict set of rules. It looks different for everyone and every project, just like there are successful founders of every personality, orientation, and style. It is idiosyncratic by nature.

That’s why there are no step-by-step directions. You will need to bring your own point of view.

Aim to do it, and do it in your own way.

What’s resonating with you? What did you find most helpful? Feel free to hit reply.

Thanks for being here, and I’ll see you next Wednesday at 8am ET.

Wes

PS If you found this valuable, here are more ways I can help:

1. Follow me on Twitter or LinkedIn for insights during the week (free).

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3. Work with me for 1:1 executive coaching. Hit reply and I’d love to share more.

To go deeper on giving the right amount of context, check out my 2-day intensive course, Executive Communication & Influence for Senior ICs and Managers. You’ll learn alongside mid-career operators from organizations like Netflix, Stripe, Uber, Grammarly, Meta, Amazon, Figma, Anthropic, and more. → Save your spot

Today, we’re going to cover how to give the right amount of context:

1. Remind them where you left off.

2. Be specific about what you need.

3. Mention if it’s an FYI.

4. Avoid being too detailed in the wrong ways, not detailed enough in the right ways.

5. Consider these variables to give more or fewer details.

6. Mention your criteria and assumptions.

7. Aim for the minimum viable backstory.

8. Main point above, context below.

9. Give a concise answer, then offer to elaborate.

10. Ask yourself what your manager will likely ask you.

I originally published a version of this essay in October 2019. Since then, I’ve expanded the post. If you find it helpful, please share with friends. Enjoy.

Read time: 8 minutes

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Giving the right amount of context helps teams move faster.

Too much context? Your manager can’t tell what’s important. They’ll need to wade through details, trying to sort information into a pile of what’s important vs what to ignore.

Too little context? Your manager has to follow up and pull information out of you that you should have mentioned proactively. There is such a thing as being too concise.

When you share the wrong level of context, you waste time on:

• Needless back-and-forth

• Avoidable follow up questions

• Misunderstandings and confusion (“Where are you going with this?”)

High-performing operators are exceptional at communicating and managing up. This is even more important in remote environments.

This begs the question: How do you give the right amount of context?

Welcome or welcome back to my newsletter! Giving the right amount of context requires practice. If you want to quickly improve and learn from me directly, check out my intensive 2-day live course: Executive Communication & Influence for Senior ICs and Managers. You’ll join mid-career operators from orgs like Netflix, Uber, Zillow, Grammarly, Meta, Square, Amazon, Spotify, etc. → Save your spot

1. Remind them where you left off.

Task switching takes a tremendous amount of energy. Your manager is probably reading your note in between meetings (or during one!). Assume they’re reading with partial attention. Remind them where you left off so they can task switch faster.

🚫 “Here’s the updated link.”

✅ “Here’s the updated pitch for X customer. I incorporated your feedback and included a change summary below. Let me know if you have any questions. I’ll plan on shipping tomorrow morning.”

You can top it off by saying, “Let me know if you have any other feedback. I’ll proceed unless I hear otherwise.”

This makes it super easy for your manager to quickly say, “Looks great, thanks.”

2. Be specific about what you need.

Years ago, I had a paid ad agency vendor say this in Slack:

“The new ad is updated in our Google Doc. It’s published in Facebook as well, but not running.”

What’s wrong with this statement?

When I read this, I don’t know if:

• Is the FB ad not running because something is broken, we got flagged, or something else terrible? Should we be worried? And if yes, what are you going to do about it?

• You updated the Google Doc. Now what? Is this an FYI or are you waiting on something from me?

Don’t assume your manager knows what you need from them. Be specific about what you need and what the next step is. Otherwise, they’ll assume you’re making progress–and will be surprised to find out you’ve been stalled for weeks.

🚫 “The new ad is updated in the Google Doc. It’s published in FB, but not running.”

✅ “Please approve the new ad copy (screenshot below). Once you approve, I’ll publish and go live on FB.”

3. Mention if it’s an FYI.

Folks think they’re being helpful by forwarding a random email. But without context or next steps, these messages are useless. Don’t make people guess if they need to take action. If your recipient has to follow up to ask why you sent this, you’ve already slowed everyone down.

🚫 [No context]

✅ “FYI. Sharing because you mentioned wanting to see examples of X.”

4. Avoid being too detailed in the wrong ways, but not detailed enough in the right ways.

Details aren’t the problem. The problem is too many of the wrong details. This is mostly about the content of your argument, not the structure, so it’s hard to discuss without real examples that would be meaningless after redacting.

Let’s say a customer asked why they got fewer students from the second cohort of their course. You could say this:

🚫 “Consider extending the enrollment period. For cohort 1, your course was announced on May 13, providing 6 weeks to accept students, up until the August 1 start date. For cohort 2, you announced the course on October 7 and only accepted for the following 10 days.” ← This is confusing.

✅ “Consider extending your enrollment period. For your first cohort, you had 6 weeks to fill the cohort. But for your second cohort, you only had a bit more than 1 week. So next time, I recommend giving students more time to sign up.”

Notice how too many of the wrong details distract from the main point:

• Too many numbers: cohort 1, May 13, 6 weeks, August 1, cohort 2, October 7, 10 days. Numbers attract the eye, but too many of them add cognitive load—it’s hard to tell what numbers to pay attention to.

• This is not just about shortening for the sake of shortening. This is about clarity. The main point of this paragraph is to say: You had 5x as much time to fill your first cohort.

• Providing is one word, but clarity overrides conciseness. Saying “you had 6 weeks” reads more easily than providing 6 weeks.

How do you tell what details to include? In this example, your recipient doesn’t need to know the exact dates of when the course was announced and when applications ended—they need to know the rough amount of time they were accepting students.

Consider what the person needs to know vs what’s secondary. Every detail adds cognitive load for your audience because they need to discern what’s important.

Now that you have this vocabulary about “too detailed in the wrong ways, not detailed enough in the right ways,” watch out for it in your own writing and help point it out in your peers’ writing.

5. Consider these variables to give more or fewer details.

Giving the right amount of context is hard because what matters to you isn’t necessarily what matters to your audience. So when in doubt, put yourself in your recipient’s shoes.

If the decision involves spending money or is customer-facing, err on the side of giving a bit more context. Customer or public-facing material affects your brand, and could lead to much bigger snafus, so it’s a higher stakes decision.

What’s the magnitude and longevity of the impact if things go wrong? Do we lose a few hundred dollars—or are we signing a 5-year legally-binding contract?

You can share LESS context when…

• You’ve made this type of decision many times and you have task-relevant maturity

• The decision is relatively cheap and reversible

• This is top of mind for your manager—not one of 25 projects they’re managing

Aim for MORE context when the decision is…

• Irreversible and expensive

• Customer-facing or public

• You’re making this type of decision for the first time

6. Mention your criteria and assumptions.

Most managers want to know that you did your due diligence and that you’re thinking ahead.

Let’s say you need to recommend a new platform or tool. It’s not that helpful to simply send your manager a list of software tools. If you do that, they have to do the hard part of comparing the options, analyzing, and deciding what to do.

When you show your thought process, your manager can point out gaps in your logic–or share information you’d find relevant.

🚫 “I recommend this platform.”

✅ “I recommend this platform because of XYZ criteria. The potential trade-off is A, but seems manageable because B. I vetted options, including [insert options] but thy didn’t seem ideal because [briefly mention why they weren’t ideal]. I chose [my recommendation] because it better fits our needs.”

The above format is extensible, meaning you can use this structure to explain your idea in 3 minutes or 30 minutes.

7. Aim for the minimum viable backstory.

Tell me if you’ve told a story like this:

🚫 “So I was meeting up with my former coworker on Thursday—no wait, was it Thursday? It must have been Wednesday because I went to Costco that morning, and that was the only morning I could stop in before work. Oh as I was walking to check out, I saw they had those keto bars and I normally would have gotten them, but I’m trying to avoid processed food. Anyway, I met up with them and…”

We’ve all been guilty of speaking like this with friends, but at work, this can make you look scatterbrained.

Backstory scope creep is real. You start with the intent of sharing only the basics, but before you know it, you’ve gone down multiple tangents—and you’re embarrassed to admit you forgot the original question!

It’s hard to be concise when you’re trying to process information, decide what to share, and speak the words—all in real time. By the time you realize you’ve shared too much context, you’re already in rambling territory.

The solution: Don’t try to do multiple cognitive steps at the same time. Take a few beat to gather your thoughts, and when possible, prepare a few high level notes for yourself.

More here: Start right before you get eaten by the bear.

8. Main point above, context below.

This is one of my favorite ways to structure messages because it gives your reader agency. You let your recipient read as much or as little of the context as they need.

The key is to visually put the context separately. This creates an obvious demarcation between the main point vs the supporting context.

Personally, I love this structure because your final recommendation and supporting rationale are often equally important. Sharing your logic gives you more ammo to convince your reader.

🚫 [Actions, backstory, and context all jumbled together]

✅ [Main point at the top, context below]

9. Give a concise answer, then offer to elaborate.

Offering to elaborate lets your manager chime in and tell you what kind of context they want. The key is to provide a brief list of options:

• This makes you look strategic and shows you were thoughtful about the decision.

• This makes your manager’s life easier because you give them something to build on or push back on.

You are the expert here, so you should try to drive the conversation, including what questions you think they should be asking.

🚫 “I can elaborate on anything.” ← This is not helpful.

✅ “I can elaborate more on a few areas: For example, the other options I looked at, including (a) if we optimized for speed and could get this done in a week, (b) cheaper/more expensive options that I thought weren’t worth it, and (c) looking ahead a few steps, the risks I foresee and how I’m planning to derisk.”

10. Ask yourself what your manager will ask you.

What questions does your manager usually ask? Answer those questions yourself. If you take anything away from this article, make it this.

Every manager has their own idiosyncrasies, worldview, values, etc.

That’s why the best thing to do is to pattern match. Consider what they’ve asked you in the past, when talking to you or others. Try to give context through that lens. Ask yourself:

• What questions does my manager usually ask?

• How much detail—and what type of detail—does my manager usually want?

It's your job to do the heavy lifting. By providing the right amount of context, you’ll take the mental load off your manager and you’ll shine as a high performer. Win-win.

Which of the items in this list do you already do? Which do you want to do more of?

One of my favorite parts of writing this newsletter is hearing from you. If you’ve applied what I write about and would like to share a story/example, hit reply or share in the comments. I’d love to hear about it.

Thanks for being here, and I’ll see you next Wednesday at 8am ET.

Wes

PS If you found this valuable, here are other ways I can help:

1. Follow me on Twitter or LinkedIn for insights throughout the week (free).

2. Share this newsletter to earn rewards, like my book recommendations (free).

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4. Practice how to give the right amount of context, manage up, and more in my 2-day intensive course: Executive Communication & Influence for Senior ICs and Managers

👋 Hey, it’s Wes. Welcome to my weekly newsletter on managing up, driving growth, and standing out as a high performer.

⛑️ If you want to dramatically improve your ability to write clearly and concisely, check out my intensive 2-day course: Executive Communication & Influence for Senior ICs and Managers. You’ll learn alongside mid-career operators from Netflix, Stripe, Uber, Shopify, Meta, Amazon, Figma, Anthropic, etc. → Save your spot

In this week’s newsletter, you’ll learn a simple writing technique that will make your messages easier to skim and more fun to read.

• What is signposting?

• List of my favorite signposting words

• When signposting is most valuable

Read time: 5 minutes

NOTE: Check out the related post on emotional signposting

As knowledge workers, we spend an enormous amount of time communicating.

This is why I believe one of the most thoughtful, selfless things you can do on a daily basis is reduce cognitive load in your writing. Your recipient shouldn’t have to decipher, guess, ask, follow up, parse through, or clarify what you meant because you sent a poorly-written Slack message.

Writing clearly is even higher stakes for longer memos where you have multiple important ideas to convey, but your message might be at risk of being visually unappealing, hard to skim, and overwhelming when you most need your recipient to stay engaged.

So how do you write more clearly if you’re sharing complex ideas that require nuance that’s hard to explain, without spending twice as much time drafting your memo?

Enter: signposting.

What is signposting?

Signposting is using key words, phrases, or an overall structure in your writing to signal what the rest of your post is about. This helps your reader quickly get grounded, so their brain doesn’t waste cycles wondering where you’re taking them.

You can use signposting throughout your writing: 

• Memo level: Headers, subheaders, toggles, paragraphs, white space

• Paragraph level: Topic sentences, bullet points, numbered lists

• Sentence level: Transition words or intentionally sequencing words in a sentence

With signposting, you add information hierarchy without relying on rich text formatting, although rich text formatting is a type of signposting in itself. For example, Paul Graham primarily uses plain text in his essays, but each paragraph has a clear topic sentence. Topic sentences are a type of signposting.

Other examples: Adding a section at the bottom of an email stating action steps: X, Y, Z. Or, numbering a list. Sometimes, people will only address your last question (very annoying) which requires following up to say, “okay, how about the other questions I asked?” It’s much more obvious if they ignore your questions if you’ve numbered them in a list.

The main benefit of signposting is it makes your writing more skimmable—it makes longer writing feel shorter, clearer, faster-paced. This increases the chances your recipient will actually read your whole document and, more importantly, take action.

List of my favorite signposting words

Signposting words, or transition words/phrases, serve as connective tissue between ideas. Does one idea flow to another? Does X happen despite or because of Y? I’m sure there’s an official grammatical term for transition or connector words, but for our purposes, I’m more interested in the practical application of this concept in daily business writing.

Here’s a list of signposting words I use regularly:

• For example shows you’re about to show an example. If the person doesn’t need examples, they can skip it. Some people say you can remove for example to be more concise, but you might have seen my rant about how being concise doesn’t mean being brief. As a reader, the benefits of seeing for example as a signpost outweigh the two extra words it adds.

• Because shows your rationale. It’s a powerful word because it makes you more persuasive regardless of what comes after the word because, according to a study done by Harvard researchers in the 1970s called the copy machine experiment. If there’s a way to restructure a sentence to use because, I’ll usually do it.

• First, second, third, next, finally: These provide visual clues if you’re writing paragraphs. They show information hierarchy using prose.

• Up until now, to date, going forward: These words highlight that change is happening. Humans are wired to notice change. Your manager likely cares less about what's going well vs what’s changing, evolving, and new. I like that this juxtaposition helps frame your idea and get your reader oriented in “the before times” vs “the after times.” Example: Until now, we’ve X. Going forward, we will do Y.

• For context: If the person doesn’t need context, they can skip this. This gives your reader agency and puts them in control, which they will appreciate.

• At this point: This brings it back to the current moment in time. You might have been explaining a trend or pattern, and you can use this transition to bring people to your conclusion in the present. It also helps heighten drama in your message.

• And, but, therefore, so: This shows the logic of your argument. You can’t swap but and therefore because you’ll literally change the meaning. One of my pet peeves is when people are sloppy and interchange these connector words. It forces your reader to guess the logical flow when they shouldn’t have to.

• This means: After you share an important piece of information, you can use this means to elaborate on the implications, trade-offs, or help your reader fully internalize your point.

• To be clear: This is great for proactively addressing common pushback you know you’re going to get.

• As a next step: Another one of my favorites. This phrase jumps out, keeps the ball moving, and highlights any upcoming action items.

These words can kick off paragraphs, or be used within a paragraph. And they pop when your reader is skimming, which makes your writing easier to consume. These phrases aren't the only way to signpost, but they illustrate the concept and are a good way to get started.

When signposting is most valuable

Signposting isn’t only about sentence structure. It’s about your underlying logic. Using signposting can help you think more clearly. A structure like “Up until now, we X. Going forward, we will Y” can turn a vague, abstract notion into a concrete, articulate idea that more clearly draws a line in the sand.

Show the emotional subtext. Have you ever read a note and thought, “Wait, is this good news or bad news?” I often read memos where the leader intended to share positive news, but the way it was written sounded ominous. Make sure to control for the emotional subtext. For example, I might signpost by saying “Good news: X” or use a few positive key words that pop.

You should signpost verbally too. Signposting is even more valuable when you’re speaking out loud because your listener can’t pause and reread, or zoom out to see the high-level structure of a two-page document. They’re listening to you, word by word, reveal the two pages of material. This can make folks feel impatient and out of control—unless you use signposting. 

For example, if you’re drafting scripts for marketing or in-product videos, signposting can make your videos clearer. At Maven, this was one of the principles that made the biggest difference for helping my team create strong scripts quickly.

“In this video, I’m going to share...”

“First… second… third…”

“What you’re seeing here is…”

“The reason this matters is…”

If you're recording an internal Loom video for coworkers on how you improved the product flow, you can give a verbal outline of what’s to come:

“For context, we left off last week with [the problem the team was facing]. So I took a stab at solving these issues, and today I will review the changes I made. Alright, let’s get into it.”

“The part that’s most important to point out is…”

“First, I’ll give a quick high-level view of the three major changes, then I’ll highlight specific in-product copy changes that I believe make the experience more intuitive.”

A good rule of thumb: The simpler your underlying ideas, the less you need to signpost. The more complex your ideas, or the lengthier your writing, the more you should consider it.

If you want to go deeper on signposting, check out the next post on emotional signposting.

I’d love to get your help growing our community of thoughtful, rigorous operators. If you enjoyed this post, consider taking a moment to refer a friend to unlock my favorite book recommendations for free.

Thanks for being here, and I’ll see you next Wednesday at 8am ET.

Wes

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Today, we’re talking about how to prepare for and run a meeting when you present to your CEO (or busy executives). We’ll cover:

1. Be prepared to move fast.

2. Encourage them to interrupt you.

3. Get right to the meat.

4. Have supporting documents ready.

5. Bring an agenda.

6. Remind them where you left off.

7. Take advantage while you have their attention.

8. Show a draft or mock-up.

9. Be specific about where you’re blocked.

10. Know your numbers.

11. Fewer status updates. More next steps or discussions.

12. Aim for a good decision, not necessarily your exact recommendation.

Let’s dive in.

Read time: 11 minutes

Meetings with CEOs and executives can go in any direction. Like doctors with bad handwriting, executives are notorious for zooming in on one detail or unexpectedly changing the topic. This is rightfully stressful for their teams, especially if you went in with one idea, and within five minutes, they’re asking you about something else.

One day, you’ll be asked to present to an executive in your company. This is a useful skill to develop and a highly visible opportunity to shine. Here’s how.

1. Be prepared to move fast.

Your executive is probably straightforward and their brain moves fast. Frame the conversation upfront and be direct with what you need. Are you looking for feedback? Sharing an FYI update? Getting their sign-off? Be explicit upfront because it will help them get oriented on how to absorb everything else you’re about to tell them.

Moving fast does not mean talking quickly with an urgent tone—this will only create unnecessary anxiety. Moving fast means being organized, direct, and clear.

There may be times when you’ll be shocked at how direct your CEO is with you. They might say, “Why do you need this?” or “This doesn’t look good enough to ship.” Their directness is a sign that they trust you enough to speak in shorthand—and they likely speak even more directly with senior folks on the team.

Obviously, there are many different kinds of CEOs. But most move faster than average and tend to be impatient creatures. If you’ve worked with this type of CEO before, you know the kind of speed I’m talking about. It takes a bit of an adjustment period to calibrate to their speed and to keep up. Being mentally prepared to move fast is half the battle.

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2. Encourage them to interrupt you.

Early in my career, I would prepare 3-5 minute presentations and was surprised when the executive I was presenting to got the point in 30 seconds. Now, on the other side, I often wish I could interrupt folks presenting to me because I “got the joke” a while ago, but feel like a jerk interrupting them.

I originally wrote this as “give execs permission to interrupt you,” but decided to go a step further. You should actually encourage them to interrupt you because:

• They already want to—nay, they are itching to.

• If they hold back, they’ll be distracted for everything else you’re saying.

• It makes the best use of limited time to skip parts you both already know.

Your goal is to get a shared understanding—not to deliver your full monologue. Let’s say you prepared a 15-slide Keynote deck. By slide three, they say, “Agreed. What do you need from me to move forward?” Don’t insist on going through the rest of the deck. (Yes, even if the graph on the last slide is a banger.)

Be glad that you were more prepared than you needed to be. You achieved your purpose: you got their buy-in. Take the win and keep it moving. More on this topic here.

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3. Get right to the meat.

Getting to the point doesn’t mean talking fast with a sense of panic. It means doing a bit of preparation, so you’re not processing out loud in a real-time stream-of-conscious.

When you say your punchline upfront, you will instantly seem more competent and organized. So keep the backstory short, and skip the lengthy play-by-play of how you got to where you are (unless you’re asked about it).

Before: “Well this happened, then this other thing, and here’s the process of what I did for that, oh yeah this thing but that’s not important, this important thing that’s completely buried, and then this other thing.”

After: “Here’s a few sentences about the situation. Here’s the important thing I wanted to discuss.”

The idea of BLUF (Bottom Line Up Front) originated in the military to ensure communication was as direct as possible. Here’s an example of a Slack message. Notice how my recommendation is upfront, then the context is below.

Getting right to the meat doesn’t mean jumping in without framing what you’re about to talk about and why. It means giving an appropriate level of context (as a very general rule of thumb, aim for a few minutes, but probably not 20 minutes without a break). If you don’t give any context, your CEO will be confused, frustrated, and will need to ask a bunch of questions to even understand what you’re talking about. That’s equally time consuming and unproductive as giving too much context. See item #6 on reminding where you left off. I’m writing another newsletter purely on how to give the right amount of context, so stay tuned.

4. Have supporting documents ready.

Have any supporting docs, spreadsheets, Notion pages, etc ready in case your CEO has questions about where you got your numbers. You might not need it, but it’s better to have it at your fingertips than to fumble around saying, “Wait, I know where that doc is, hold on…hold on… [silence] Oh, it’s here. Wait, no, never mind. I’ll get back to you on that.”

Ask yourself:

• What supporting docs might I need?

• What do I reference that they might want to know more about?

Open those tabs on your browser in advance, so you can easily screen share or look up a data point if needed.

5. Bring an agenda.

Ideally, share an agenda or a few notes of what you want to discuss in advance. If you really want to stand out, share a pre-read document before the meeting. This takes obvious preparation, and it’s harder to hide poor ideas in writing, so it doubly shows that you have your act together.

Even if you don’t have a written agenda, you should bring notes for yourself on your discussion points. Do you ever look at a note you made to yourself and think, wtf does this mean? You’d forgotten the context. This has happened to me many times, and it’s super annoying. You don’t have time to decipher what your notes mean when you’re in a fast-paced or high-stakes meeting.

Confusing: “Budget meeting”

Better: “Budget meeting - Get approval for doubling FB spend from $1k/day to $2k/day because X reason.”

Adding an extra line of context in my notes has saved me so much mental load. With a slightly more detailed note, you give yourself the ability to easily context-switch and stay fluid.

6. Remind them where you left off.

Your CEO is in back-to-back meetings all day, which means they are context-switching constantly. They just got off a call that ran long. They’re here now. What do you do?

To kick-off, share 1-2 sentences on why you’re meeting and remind them where you last left off. This is helpful because, I kid you not, sometimes you’ll start a meeting and your CEO will say, “Wait, why are we even doing this?”

This can be slightly terrifying to hear if you just spent the past two weeks on a project because your CEO agreed it was a good idea the last time you spoke.

Bad: [Jumps straight into the topic]

Good: “The last time we spoke about this two weeks ago, you said we should do X because Y. I agreed that made sense, so we did that, and today I want to share what we came up with, get your feedback, and share our plans for what’s next.”

7. Take full advantage while you have their attention.

You might have access to your CEO once a month or less. Get items approved in a batch because you’ll be able to run for longer without them becoming a bottleneck.

Have the immediate next step ready. Better yet—have the next few steps ready to get their approval while you have their attention. In general, it’s useful to think a few steps ahead anyway for your own benefit.

Ask yourself:

• When I’m done with this, then what? Then what after that? After that?

In a similar thread, you might want to have a few backup topics in case you finish your main topics early. If it was hard to get on the executive’s calendar, use the time they’ve already blocked off for you.

For example, I’ve had team members say, “Since we have 10 minutes left and we’re already here, I’d like to share my screen and run X by you to get your initial thoughts. Is that cool?” And my answer is almost always “Sure, let’s do it.”

8. Show a draft or mock-up.

This one is important. I’ll proactively tell folks I work with to bring drafts or mock-ups because meetings are so much more productive with them. It’s much easier for most people to give feedback when they have something in front of them, even if it’s a “shitty first draft” (per Anne Lamott). The goal is to capture the general spirit of what you’re trying to do and spark a response from your recipient.

You can spend 5-7 minutes describing your idea using words alone. Or you could show a draft and get feedback within 30 seconds. There’s a lot of tacit information in images, visuals, sketches, and examples, so use this to your advantage.

Whether you get a hard “no” or an excited “yes” doesn’t matter. The goal is to offer something concrete to push back on because it leads to clarity faster.

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9. Be specific about where you’re blocked.

If your CEO is on your critical path, they want to unblock you as soon as possible. They might ask, “What do you need from me?” or “Are you waiting on anything from me?” Proactively mention if/where they are the bottleneck and what you need to move forward.

Good: “You’re on the critical path for X because we’re waiting for you to give feedback.”

This is decent, but it still puts the responsibility on your CEO to figure out what to do.

Better: “You’re on the critical path for X because we’re waiting on you for feedback. I recommend we move forward without your edits because you’ve approved most of this copy before. Does this sound good?

In the “better” option above, you’re asserting what to do and making your recommendation easy to approve. Your CEO can simply say, “Yes, sounds good.”

Be clear upfront about why you're sharing in the first place, so they can get mentally oriented for what you're about to say. As an exec, I'm going to react differently if the information is an FYI, or if you need my approval, or if you need my input on how you're thinking about a problem.

10. Know your numbers.

In my first job out of college, I did a corporate rotational training program at Gap Inc in San Francisco. One of the first lessons: Anything you put on a slide, you should be prepared to explain and defend. This lesson was seared into my brain. This applies to numbers in reports, sales forecasts, strategy proposals, or hindsight docs.

If you’re even slightly doubtful of what a number means, figure it out before you cite it. Even if you’re not presenting this information, it’s good for you to be accurate and precise about what’s actually captured in a number. For example:

Less accurate: 65% of leads were driven by TikTok

More accurate: 65% of leads in X program were driven by TikTok in Q4 2023

Those two are not the same thing. In fact, the first is misleading and implies TikTok is a bigger lead driver than it actually is. This might seem obvious, but I’ve seen similar errors in logic and communication more often than you’d expect. Don’t play fast and loose when citing numbers.

Now, let’s say you’re mentioning this number because you want to convince your team to invest more in TikTok. When you reference this data point, depending on how much your CEO is plugged into your work on this project, you should be prepared to get some obvious follow-up questions: Are these the kind of leads we want? If this was our biggest channel, what was the next biggest channel? What was your methodology for calculating the 65%?

You might be thinking, “Oh god, they could ask me anything. How can I possibly prepare to go in any direction.” Good news: You don’t need to have answers to every question.

But you should have a high-level understanding of how your channel is performing and why. If there are obvious questions, you’ll want to answer those for yourself regardless to sharpen your customer/market insights and recommendations.

11. Fewer status updates. More next steps or discussions.

When you’re proud of what you’ve been working on, it’s natural to want to share status updates. But status updates are backward-looking. What's happened has already happened, and you can’t change the past. Most CEOs care more about what’s next because you can still impact the future to your advantage. You might get questions like:

• “Why does this matter? What’s coming up?”

• “What do you need my input on?”

• “Where are you blocked?”

• “What are the areas of risk or opportunity? What are we doing about it?”

When your CEO asks questions like this, it’s not because they want to badger you or they’re skeptical. It’s because they want to validate your thinking and understand how to support you going forward.

Now, sometimes the point of a meeting is to update your CEO on a project. In that case, by all means, share updates—but do so with clarity and intention. I learned this lesson early on: At my first job, I would rattle off recaps and progress updates that were too detailed for no reason. I got asked “so what?” enough times by leaders that I realized, “A laundry list of what I did and how I got there is not useful. I can share updates, but I should be discerning about it.”

The past is only relevant because it helps us make better decisions about the future. You have an opportunity to show that you’re focused on what’s next and what’s still within your control, so spend 20% on the past and focus 80% on what’s ahead.

12. Aim for the right decision, not necessarily your exact recommendation.

Given how much I talk about the importance of framing your ideas in this newsletter, it may come as a surprise to hear me say: Getting buy-in isn’t always the goal.

This took me a long time to learn: The point isn’t to get buy-in for your ideas at any cost—the point is to get to the right decision. Sometimes, the right decision is a “no.”

That's why you shouldn't feel resentful if you spent time drafting a proposal, but your team didn't move forward with it. Strategies, big projects, and initiatives should be vetted before they're simply rolled out. This was a breakthrough for me, and it’s a reminder I share with direct reports if they’re disappointed that their proposal wasn't adopted.

• If your idea led to productive discussions, you still added value.

• If your idea helped your team realize gaps that need to be filled, you added value.

• If your idea gave your team something to push back on, you still added value.

Now, obviously, you want to get better at being right. In the meantime, not everything you suggest will be implemented. Actually, most things you suggest over the course of your career won’t be implemented. You should still advocate for what you think is best for the company. When you do this, it shows integrity and maturity, which is something all CEOs and senior leaders will appreciate.

Many people assume meetings with CEOs will be a formal presentation, delivered from beginning to end with no interruptions. This might be the case for some meetings, but most will be more interactive and flexible.

A better mental model is to imagine a conversational presentation where you'd expect and want dialogue. So yes, have your ducks in a row and your talking points ready. But don’t be shocked if your CEO wants to zoom into a certain part midway through.

When you prepare for this dynamic, it allows you to address questions in the moment and stay focused enough to make all your key points. Give these principles a try, and I’d love to hear how it goes.

I’d love to get your help growing our community of thoughtful, rigorous operators. If you found this valuable, consider subscribing or taking a moment to refer a friend.

Thanks for being here,
Wes Kao

PS See you next Wednesday at 8am ET.

PPS Loving this and want to binge-read? You might like these other essays about managing up:

⛑️ One of the most common areas I coach tech executives on is raising the bar for their teams. By working with me, you’ll get an objective gut check of whether you’re too hard or too soft on your team (many leaders are too soft IMO), where you can push them (and how to do it productively), and more. If you’re interested in how I can support you, learn more about my coaching approach.

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In this week’s newsletter, I want to talk about why you should consider raising your standards and why this has the potential to dramatically improve your team’s chances of getting what you want.

• Part I: Why every leader should set higher standards

• Part II: Challenges when raising the bar

• Part III: How to normalize a culture of excellence

Read time: 13 minutes

Over the years, I’ve been told by co-founders, direct reports, and peers that I raise the bar of quality in everything we do. Setting a high bar—and holding teams to this standard—is one of my strengths.

I’ve heard from leaders and managers who want to set a higher bar in their own organizations, but aren’t sure how to start. Many are afraid to upset team members who are used to operating a certain way. In this post, I’ll attempt to make the case for why you should set a higher bar for yourself and your team.

First, why raise your standards?

Part I: Why to raise your high standards

A tale of two teams: One with high standards, and one that scoffs at the idea that their standards may be too low

For every team that says “This is as good as it’s going to get,” there’s a doppelgänger team out there who refuses to settle:

This team isn’t just ticking off boxes. They are innovating, challenging assumptions, and pushing the limits of their creativity.

They are always scanning for inspiration and keeping an ear to the ground for what customers want.

They realize they don’t have many levers, and can’t afford to cavalierly pull levers in a half-assed way.

They know there’s a spectrum of quality for any attempt. They know there’s no upper bound for how strong you can be at any skill where there’s craft and judgment involved, including writing, coding, design, sales, etc.

They acknowledge that aiming for a high bar can feel challenging in the moment, but being great at your job is rewarding and fun.

This team knows what excellence is and aims for it, sometimes hits it, and often acknowledges the gap between their vision vs their skill.

The second team doesn’t even realize they have low standards:

This team makes a half-assed attempt, then claims, “This channel (THE ENTIRE CHANNEL) doesn’t work.”

This team uses lazy excuses like “there’s a speed vs quality trade-off!” when they are not remotely close to moving fast enough or shipping work that’s high quality enough to breach that boundary.

This team leaves money on the table, every week, and with every project, because they make dozens of mediocre micro-decisions when executing.

They default to knee-jerk reactions like “if we set bigger goals, we need to hire more people” instead of realizing that a lean team of the right people can be just as effective.

They cite popular aphorisms like “perfect is the enemy of good” to justify subpar work, instead of admitting there’s room to improve their execution.

They do okay work, at an okay speed, but feel like they’re sprinting and producing A+ work. When you challenge them, they are insulted.

There is a disconnect: They think they are producing high-quality work, but objectively, it’s simply passable. And therein lies the problem:

Their standards are too low.

The benefits of having higher standards

As a founder or leader, your team’s standards will be as high as your expectations are. You set the bar for what’s acceptable and celebrated. In other words, your standards are the maximum of what folks on your team will deliver. In my opinion, this alone is a compelling case for why you should at least consider raising your standards.

If you’re an individual contributor, you have the opportunity to raise the bar too. I believe we all have the chance to give detailed feedback, rooted in logic, to sharpen each other’s work and therefore collectively become stronger as a team.

You could keep doing what you’re already doing, and NOT raise your standards. But if you do, you’ll reap the rewards, of which there are many:

• Leverage. When you change your team’s culture, you are creating a rising tide that lifts all the boats (i.e. team members) in the water.

• Reduce decision fatigue: Stop being the only one who catches stuff that slips through the cracks and being the only one who makes decisions.

• Produce better work output and outcomes: Eventually, you’ll spend less time giving feedback. (In the short run, you’ll need to give more feedback, which we’ll discuss later.)

• Maximize your chances of winning. If you feel you have a chance at winning in a growing market, and are well-positioned to do so, then your ability to execute is the difference between failing and winning.

• Motivate team members. High performers like working with other high performers. Having higher performers on your team attracts better talent.

Another reason why high standards matters: As a leader, you can’t see everything every person does every day. Managers, by definition, have less visibility into what each direct report is working on than the direct report does. You need your team to hold themselves to a high standard in the moments when no one is looking (which is most of the moments).

Part II: Challenges when raising the bar

Most people think they have high standards

You might be wondering, What if my standards are high enough already? How do I know if my standards are too low?

This is tricky because raising standards might look different for everyone. Some variables include your function, starting point, task-relevant maturity, skill level, and accuracy in assessing your own work. But I believe one thing: simply deciding to raise your standards is a big step.

When you decide to notice work that’s high quality, you will start to see examples everywhere that you can learn from and apply to your work. This is because when you decide to do a thing, your subconscious becomes more attuned to noticing things related to it. You can start to save screenshots, snippets, examples, make mental notes, etc of folks who do work that surprises and delights you. I see examples of people who do high-quality work everywhere, and it’s an endless opportunity to raise the bar for myself and further hone my ability to recognize quality.

One other thing to mention: defensiveness. Defensiveness is a natural reaction when confronting that your bar might be too low in certain areas, but it doesn’t have to be your response. It takes humility to admit that your expectations might not be high enough. Only once you do that, can you notice and learn from people who may have a higher bar than you. Simply choosing not to be defensive automatically puts you in the top quartile of folks who are likely to raise their standards.

When people get feedback that hints that their standards are too low, they often think, Oh, that thing you gave me feedback on is nitpicking. It’s unimportant. It’s over-optimizing. I intentionally didn’t do [x better thing] because I prioritized speed and shipping.

In reality, the truth is: I didn’t do [x better thing] because I didn’t think of it. I didn’t realize that a better way was possible. I wouldn’t have realized it unless you had pointed it out. Actually, I could have done this more elegant solution relatively quickly if I had identified it, but I don’t want to admit I didn’t see it as an option at the time.

Intellectual honesty is paramount. If a more elegant solution didn’t cross your mind, that’s okay. That’s a normal part of learning and improving. The part that’s not great? Pretending that feedback isn’t valid simply because your psyche feels threatened.

Ask yourself:

• When might you be brushing off legitimate feedback to protect your ego?

If, instead, you accepted the feedback and looked for truth in it, you might realize you can move just as quickly AND achieve higher quality. Or you might be able to achieve the “both/and” of what you initially thought were at odds.

Common excuses to avoid raising the bar

“It’s good enough.” This is tough because people have different standards for what bad vs good vs great looks like. What’s good enough for one team might be too low quality for another. For example, some people think their copy or design is strong, but I’ll think it’s barely passable. I’ve had colleagues on hiring committees rank candidates a 9/10 but I gave the same candidate a 4/10. In general, I agree aiming for good enough is useful, except when it’s an excuse to be mediocre. It’s like saying a product is a minimum viable product (MVP) when it’s minimum, but it’s not viable.

“There’s a trade-off between speed and quality.” You likely have plenty of room to do both before needing to make this trade-off. Chances are, you’re not remotely close to that edge. For example, when I moved to New York to work with Seth Godin, I had come from a series D startup in San Francisco backed by Sequoia Capital. I thought I knew what shipping fast meant—I did not. I had no clue. Seth Godin set a bar easily 10x higher than what I was used to. The wild thing is I wouldn’t have been able to imagine that this speed or quality was possible until I was pushed to do it. So instead of insisting “it’s not possible,” think about how you can get creative with scope or reframe the problem. In the long-term, invest in sharpening your craft to become more effective and efficient.

“It’s optimizing past the point of diminishing returns.” Obviously, stop before you hit the point of diminishing returns. The problem is people stop way before reaching the point of diminishing returns but claim they’ve hit diminishing returns.

“It’s too much work”: Raising the bar isn’t necessarily more work. It’s often about improving your intuition, decision-making accuracy, exposure to what’s possible, and taste level, so you’re making better judgment calls. For example, an experienced marketer can instantly point out areas to improve that others don’t or can’t see. These folks had more exposure and data points on what quality looks like, and then over time, they worked to hone their craft. So yes, it requires effort to hone your craft, but eventually it might mean less work because you’re more effective at translating your intent into reality. To be clear, sometimes raising the bar does require brute force and spending more time on a task, but in my experience, it’s not the main driver.

“Done is better than perfect.” Like all things, it depends. If you make a sloppy attempt, is done really better? Doing excellent work will take longer. But I’d argue that a careless job is slower because (a) it won’t get you to your goal, (b) it won’t be well-received by your leads or customers, (c) it won’t instill trust in your brand, so (d) you’re going to have to redo or (e) keep burning through new tactics.

“It’s not worth the ROI to make it better.” Some things might not be, but some things are worth it. Use your judgment. Don’t use this as an excuse to be lazy because you’re tired of solving a hard problem that isn’t bending to your will, and you’d rather move on to a fresh project.

“Quality is hard to define and varies by function, project, etc.” You and your team get to define what quality means to you. Sure, quality could mean different things—that’s not an excuse to avoid doing quality work though.

Part III: Normalize a culture of excellence

Aim for a culture of high standards, high feedback

I believe one of the best ways to raise your standards as an organization is to aim for a culture of high standards and high feedback. You need both. You can’t simply proclaim, “we’re raising our standards now” and expect everyone to know what’s expected of them.

Just saying it doesn’t do anything—you must create a new norm. I like this quote from Andy Grove, co-founder and former CEO of Intel:

"Values and behavioral norms are simply not transmitted easily by talk or memo, but are conveyed very effectively by doing and doing visibly."

Creating a new norm involves reinforcing the new standard every week, across every team, across different situations and conversations, in private and public, in big and small moments. This is how team members come to understand what a higher standard means in your organization.

Here’s a 2×2 matrix of standards vs feedback:

Organizations with high expectations, paired with a high degree of coaching, are the most rewarding for both the organization and individuals.

• High standards, low feedback: sink or swim

• High standards, high feedback: holy grail

• Low standards, low feedback: most companies are like this

• Low standards, high feedback: unsustainable and poor ROI

Some companies can get away with a sink or swim culture because they’re clear upfront about their expectations and they attract ambitious masochists. For example, McKinsey is known for 100-hour weeks. At GE, Jack Welsh famously fired the bottom 10%. People self-select to work in extreme environments like that.

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The people who chose to work at your company, well, aren’t at McKinsey and GE because they’re working for you. And you probably haven’t had high enough standards until now. So if you want to shift your culture to be more hardcore, you need to provide support and give people a chance to see how they like this new environment.

Who will come along for your new high-standard environment? People will fall into three buckets:

• No: These team members say, “No way. This isn’t what I signed up for.” They will grumble or revolt, and eventually leave.

• Yes: There might be team members who were always hardcore inside. They’ll be happy everyone else is finally embracing higher standards.

• Maybe: These “swing states” are team members who could go either way.

The “swing states” are people who COULD be excellent but are deciding whether they want to rise to the occasion with you. These individuals are sharp and motivated enough to be excellent, but also savvy enough to cruise if they choose to. Depending on the breakdown of people in your organization, the swing states could be your fulcrum.

This is where setting your culture and explaining the logic behind your culture is crucial. I think logic is underrated in most conversations. Most people think repeating a high-level, inspiring vision is enough, but actually, people need shit to make sense. So you need to say, “Hey, here’s what we do when something like this happens” AND “Here’s why we do it like this, and why it benefits you and the company.”

Why to give detailed feedback on work output

A major lever for raising the bar is giving your team members actionable feedback on work output on a regular basis. Unfortunately, when team members run their work by their managers, many managers are on one end of this spectrum:

• (A) Takes a quick look and says “looks good” regardless of whether it looks good

• (B) Recognizes the work isn’t good, but makes all the changes themselves because it takes too long to give feedback

I’ve been in both of these positions myself, and sometimes, it makes sense to let mediocre work slide or to do the work yourself. But I find many managers will act reflexively, and therefore lose opportunities to coach their teams, because they tell themselves the narrative that “I’m prioritizing shipping and moving quickly.”

The problem with this logic is very few pieces of work output will ever seem that important in isolation. When no individual piece of work is important enough to give feedback on, you never give detailed feedback on work output. The result: your team members never learn.

They never learn what excellence looks like because whatever they sent you, you said it looked good. Obviously, there are tasks that are low ROI. But there are absolutely projects and sub-parts of projects that are more highly leveraged. Once you stack rank and decide that X is worth the effort, you should execute well on X.

For example, the pitch DM your junior team member is using. It might seem small—it’s “just” a DM, right? But if it’s getting sent to hundreds of leads per week, and is the first touchpoint between a lead and your brand, you can’t afford not to optimize the conversion. The way your team member answered a question from the high profile customer—it’s “just” an email, right? That email could cost you a six-figure deal because the team member’s answer didn’t address the customer’s concerns or sell them on why to continue using your platform.

You might be thinking, “I don’t know if taking the time to give feedback on this piece of work is worth it.” In the grand scheme, does this email matter? This particular email? No.

But your employee’s ability to write persuasive copy, think clearly, and position ideas? Yes. That absolutely matters.

This is how individuals improve: One step at a time. One piece of work and one conversation at a time. If you refuse to have those conversations with your team, you can’t expect them to improve. (More on how I give Super Specific Feedback on work output, such as writing, product flows, marketing assets, and design.)

Don’t let things slide, i.e. don’t let folks get away with bad behavior

Yes to accountability, but how? Let’s narrow in on the team level because most leaders have more direct influence over their team. And if every leader did this with their teams, it would roll up to a company-wide culture of accountability.

I think the way you create accountability is to ”not let things slide.”

Here’s what usually happens:

• Your direct report turns in work that’s mediocre.

• You try to convince yourself it doesn’t bother you because you’d rather avoid figuring out how to give uncomfortable feedback.

• You decide to let it slide.

• Your direct report continues to do the thing. You hope they change.

• Surprise: They don’t change. This is now your new dynamic.

Here’s how it could be:

• Your direct report turns in work that’s mediocre.

• You point out why their work was only decent, give actionable feedback on what to do differently, and explain why this new approach is better.

• They realize they can’t “get away with” subpar thinking because you will lovingly call them out.

People have agency. If they don’t like the culture and expectations, they don’t have to work with you. The world is a big place—there are hundreds of thousands of employers out there. I owe you being clear about what I expect, setting a high bar, and offering support and feedback along the way. You get to decide if that’s something you find motivating, rare, and a career-changing environment. Or you can opt out. Either works.

Working on a team with high standards will sharpen you more than any course, book, mentorship, or formal learning opportunity will. It will change you as a person. You will not be able to unsee nuance, and excellence can become your default.

If you are lucky enough to be on a team with a high bar, I recommend maximizing your time learning on this team. One thing to note: Raising your standards is fulfilling and potentially career-changing, but by definition, higher standards mean that lower-quality thinking or lower-quality work doesn’t fly.

This means you have to be open to doing things differently than how you did them before. In the short term, these changes might feel painful or jarring. But soon, you’ll find that iron sharpens iron—and there’s a certain thrill from working on a team that cares about excellence.

Is it worth it? That’s up to you to decide. You can help set higher standards in your organization, no matter who you are, regardless of your title. You can be the one who says, hey, I think we should raise the bar.

Takeaways:

• Teams who have high vs low standards behave differently.

• You can’t simply proclaim, “we’re raising our standards now” and expect everyone to know what that means. You must create a new norm.

• There are many benefits of having higher expectations, including motivating your team. High performers like working with other high performers.

• There are common reasons to avoid raising the bar, but most are excuses.

• In the 2×2 matrix, aim for high standards and high feedback.

• Give actionable, detailed feedback on work output so your team has an opportunity to learn and improve with every project they do.

I’d love to get your help growing our community of thoughtful, rigorous operators. If you enjoyed this post, consider taking a moment to refer a friend to unlock my book lists and not-yet-published spiky points of view.

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Thanks for being here,
Wes Kao

PS See you next Wednesday at 8am ET.

PPS More articles on how to give feedback to raise your team’s standards:

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• 15 principles for managing up

• Start right before you get eaten by the bear

• The problem with glorifying failure

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Rigorous thinking is where flimsy ideas go to die. As a leader, having a team of rigorous thinkers is an organizational force multiplier that allows you to produce higher quality work, faster, even when resources are limited. Today, we’ll cover:

• Part I: What is rigorous thinking and why it matters

• Part II: How to create a culture of rigorous thinking

• Part III: Questions to promote rigorous thinking

I originally published a version of this essay on November 2018, and have expanded it. If you find this article helpful, please share it with your friends and colleagues. Enjoy.

Read time: 13 minutes

If you're a leader, you got to where you are because you’re killer at both strategy and execution. You simply can't get very far without being good at both. Now that you're in charge of people, though, your ability to increase impact depends on how well you manage other people. You need your team to become strategic A-players.

Unfortunately, high-performing managers (like you) can accidentally traumatize their teams. You want your team members to think for themselves and stop only doing what you say. But every time they have a question, you jump to answer it. Or worse, you give them a wrist slap for bringing you a new idea.

I get it. You barely have time to do your own job, and you definitely don't have time to clean up your team’s messes. But each time you unintentionally punish your team for stepping outside the box, you discourage them from trying new things.

So you have a dilemma: You want your team to think like an owner and bring you fresh ideas—AND you want those ideas to be defensible. How do you do this?

Enter: rigorous thinking.

Welcome or welcome back to my newsletter. Thinking rigorously requires practice. If you want to learn how to apply rigorous thinking to better influence and inspire others, check out my intensive 2-day live course: Executive Communication & Influence for Senior ICs and Managers. You’ll learn alongside mid-career operators from organizations like Netflix, Uber, Zillow, Grammarly, Meta, Square, Amazon, Spotify, etc. → Save your spot

Part I: What is rigorous thinking?

Rigorous thinking is asking critical questions about tactics, and having a systematic way of making decisions.

Rigorous thinking isn’t a single mental model. It’s an approach to problem solving that allows you to deconstruct ideas, gain clarity, and make decisions that are far more likely to be right.

Counterintuitively, rigorous thinking saves you time. Instead of jumping to execute the first idea you think of, you run through basic considerations to stress test your own logic. This, in turn, means less time wasted on fixing easily avoidable mistakes, and more time spent on ideas worth pursuing.

In this way, rigorous thinking acts as a force multiplier and fosters a spirit of entrepreneurialism and ownership among your team. It’s lonely and stressful to be the only one thinking about what to do, looking around the corner to anticipate what’s next. With a team of rigorous thinkers, you won’t have to—you’ll have a bench of eager, up-and-coming leaders who share that load with you.

Let's say you manage 4-5 direct reports. In a culture where rigorous thinking is expected, the idea is this:

Any idea goes, but each team member should be prepared to advocate for their idea and defend it. You should be prepared to walk through the upside, downside, data points rooted in reality, and how it works given your assets and constraints. Anyone can ask questions and probe, and these questions are received with gratitude and openness.

The opposite of rigorous thinking is lazy thinking: Lazy thinking is making assumptions you don't even know are assumptions.

Lazy thinking is assuming your idea simply works, or that someone else will be in charge of “figuring out the details.” Lazy thinkers consider anything they don’t want to do (usually the hard part of actually solving a problem) to be “the details.”

Lazy thinking is having a black box of logic where “suddenly it works and we have thousands of customers.”

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Rigorous thinking vs lazy thinking

Let’s compare these two scenarios:

🚫 Lazy thinking: "Hey boss, can we do [insert random tactic]?"

Result: You have to think through everything, which leads to decision fatigue. You’re running around correcting your team’s missteps. The mistakes range from minor to major oversights in strategic thinking.

Shiny object syndrome rules. Half-baked ideas come across your desk, so you have to think of polite ways to say why this isn’t a good idea without discouraging your team.

Your team doesn't understand why you always say no to their ideas. You look like the bad guy.

✅ Rigorous thinking: "Hey boss, I recommend we do ___. It's likely to work and is worth the time and budget because ___. The downside and potential risks are ___. But we can minimize the risk with a small experiment by doing ___.”

In this world, you rarely say no to an idea, because it's not about saying yes or no. It's about vetting an idea. You ask strategic questions, so your employee ends up realizing themselves that the idea won't work in its current iteration.

You work collaboratively to pressure test assumptions. They excitedly go back to the drawing board and come back to you with a stronger iteration and next steps. They hone their judgment and become more strategic over time, requiring less support from you.

You have less decision fatigue and get better results. Direct reports feel empowered and take ownership.

Part II: How to create a culture of rigorous thinking

1. Rigorous thinking starts at the top.

If you set a high bar and celebrate thoughtful decision-making, you send a signal that rigor matters. You don’t let your team get away with lazy assumptions, subpar work, or latch onto surface-level conclusions that don’t capture an accurate picture of the underlying truth.

At Maven, one of our values was rigorous thinking. A company’s culture often reflects the founders’ personality and values, and this was the case.

Here’s an excerpt from our values:

• We are relentlessly focused on solving problems and making the best out of less. We take a little and turn it into a lot, without fuss and with great execution. Often, this means seeing bugs as features or being creative in coming up with elegant solutions for big, hairy problems.

• Decision-making and writing are core skills of everyone on the team. We examine multiple points of view and make decisions in a thorough manner. We’re not afraid to be wrong, and we don’t delusionally ignore the truth for the sake of speed.

• We value qualitative data as much as quantitative, because while numbers never lie, they also never tell the full story. We then write down our thoughts because it is both the most efficient and effective form of communication.

We regularly had outside partners or contractors who had a peek into our culture comment on how rigorous Maven team members were. And the word rigorous itself was used regularly among our team as a compliment for thoughtful, conscientious work rooted in strong insights and logic. It was a culture where evidence-based thinking was rewarded.

One of my favorite quotes is from Picasso, who said, “There are painters who transform the sun to a yellow spot, but there are others who with the help of their art and their intelligence, transform a yellow spot into sun.” Rigorous thinking allows you to turn yellow spots into the sun.

2. No ideas are precious or off-limits

You may need to model for your team what healthy debate looks like. Mainly, this means leading by example because culture is basically people looking around to see what things are like around here. Your team members pick up on unspoken rules.

To establish a norm of rigorous thinking, you’ll want to encourage your team to speak up if they disagree, and to do so respectfully and openly. And when questions are asked of them, to react positively and see the questions as a gift. This part is important: A team member’s initial reaction may be to feel a little defensive, and that’s natural, but that’s not the reaction to act on. The way to react is to appreciate when a colleague cares enough to speak up.

The Maven team has an internal culture of debate. Anyone—of all levels and functions—could ask questions, probe, and challenge each others’ thinking, including folks from other teams. At the end of each bi-weekly all-hands meeting, we had an open Q&A. An engineer might ask a question to a program manager. A salesperson might ask a question to the Head of Growth. A customer support rep might ask a question to the CEO.

For write-ups about the company strategy, it was the same: everyone in the company was encouraged to add comments, ask questions, and challenge assumptions directly in a doc where everyone else could see comments. This strengthened our strategies because folks closest to the work would add insights that leaders missed, and folks further from the work would offer an outside perspective that was equally valuable. It increased buy-in and morale across the organization that every team member was involved in understanding our company goals and strategy. This might look different at larger companies, but I believe the underlying concept is sound and can be modified for functional teams (i.e. marketing team, product team, etc).

The fact that questions flowed in both directions (not only upward to the leadership team), helped normalize that anyone can speak up, and more importantly, no one’s ideas were precious or off-limits.

3. Create psychological safety

If you want to encourage sparring and healthy debates, you need a foundation of psychological safety. Your team has to trust that you care, and trust that you're asking hard questions because it's better for them, the team, and the idea itself. No one is trying to make anyone look bad or feel stupid.

With this understanding, your team is free to rigorously debate with each other to come up with the best possible outcome.

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This is not an interrogation. The way you ask matters. Don’t sit back, kick your feet up, and ask to be impressed. This attitude wouldn’t bring out the best in you, and it won’t bring out the best in your team.

Ask hard questions in a way that's supportive and driven by curiosity, not contempt. When you take this approach, you empower your team members to figure out and articulate a solution. You show you're there with them, and you believe in them.

It’s two people walking through an idea and scenario planning what it could look like, with the goal of finding the best solution. It’s win-win.

4. A yes or no without context is a missed opportunity for learning

If you only say yes or no to ideas, your team will keep coming back to you with a similar level of ideas. They won’t know why a strategic proposal worked or didn’t. If you want something to change, it’s your responsibility to invest the time to share your thought process, give feedback, and coach them on how to think differently.

The end result of whether you move forward with an idea isn’t as important as the thought process behind it. The world champion poker player Annie Duke coined the decision-making principle of resulting, which describes this well:

Resulting is the tendency to judge a decision based on its outcome rather than its quality. It's a natural human tendency to think that if a decision leads to a good outcome, it must have been a good decision. Likewise, if it leads to a bad outcome, it must have been a bad decision.

5. Be a sparring partner

It’s hard, if not near impossible, to learn how to think strategically by reading a book. Understanding a concept in theory is not the same as understanding it in practice. This is why managers must make the time to engage in conversation with their direct reports. Not just conversation about status updates and project management—but deeper conversations about upcoming decisions, challenges your team is facing, and detailed feedback on work output. This is how you unlock the power of hands on, on-the-job learning.

I've been surprised at how even junior team members have stepped up when given a chance to think rigorously. They often give the answer I would have said. And if they miss the mark, having them actively engaged in thinking about what to do makes my feedback feel more salient. If I never asked, I would have assumed I was the bottleneck who had to have all the answers. Over time, I've gotten fewer simple questions because my team anticipates I'll bounce it back, so they go straight to making a suggestion and sharing their point of view.

As a manager, you likely have more experience or context than your team members do. Something might feel obvious to you, but isn't to them, so try to stay curious and get more information before assuming incompetence. Many folks have endured years of finger-wagging and scar tissue from previous managers. To counter this, you have to almost over-encourage your team to share their point of view.

Remember: You hired intelligent people, and your best high performers already want to think rigorously. Be their thought partner. If given the chance, they will be excited to sharpen their thinking with your guidance because it's a skill that will serve them now and forever in their careers.

6. Let others speak

Let's be honest: We managers love sharing our brilliant ideas with a captive audience. It takes self-restraint and hyper-vigilance on our part to stop and let our direct reports talk. Great managers are eager and want to coach team members, so wanting to talk comes from a place of good intentions. But often when I finish talking, I'm surprised when my direct report summarizes 10-20% of what I shared. This reminds me of two things:

1. People can only remember so much in one sitting.

2. They will remember more if they’re actively speaking, not only listening.

Intellectually, most managers know this but forget when they’re amped up in the moment. A solution that’s worked for me is taking the decision-making out of the equation in real time, and instead, relying on an easy-to-remember question that becomes muscle memory: “What do you think?”

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7. Prioritize and unpack ideas with more specificity

Rigorous thinking is realizing that 90% of ideas are probably not worth doing, and the ones that are worth doing, won’t just magically work. It’s realizing that many ideas are decent, but decent doesn’t meet the bar for moving forward when you have limited resources (and resources are always limited, even at large organizations).

Even when you don’t move forward with an idea, though, there might be a nub of an insight that can evolve and take on a different form. When you share your rationale and logic, you allow others (and yourself) to push back on specific parts. Instead of throwing out an entire idea, you can discuss with more granularity.

One thing to note: rigorous thinking isn’t the opposite of intuition, even though it might seem so at first glance. I’m a proponent of noticing what your gut is telling you, and listening to your instinct. I use both rigorous thinking and intuition in lockstep, one feeding the other, and helping me develop conviction about what to do.

The point isn't to have all the answers. The point is to better understand your own ideas so, you can expend energy on ones that have a higher likelihood of success.

8. Rigorous thinking can be lightweight

This was a thoughtful question from reader Serena Mariani, Head of Consumer Marketing EU (Books) at Amazon:

I wonder about the reverse topic too—how do you balance thinking rigorously with completely killing the motivation for people to come up with daring ideas. As someone who spent years in big corporates and 4+ at Amazon where every idea must take the form of a thorough PRFAQ to be even looked at, I think I have seen both sides of this moon. Interested in what you think.

Rigorous thinking might be conflated with intense processes, long write-ups, and filling out documentation, but I see the two as different. Personally, I hate overkill processes that snuff out creativity and make the lift so high to share an idea that you want to skip sharing it altogether. That's why I love how you can do rigorous thinking while staying nimble and doing the least amount of process possible.

You might want to write up a strategy doc, but that’s because it helps you articulate your idea. It’s not a requirement.

Rigorous thinking can be as simple as spending 5 minutes running through a few basic questions.

Part III: Questions to promote rigorous thinking

Vague ideas are hard to discuss and debate. That’s why fleshing out the mechanics and logic behind your idea can help you gain conviction. With that in mind, here’s a non-exhaustive list of questions to get started:

1. What's the hard part?

2. What does success look like?

3. Is the juice worth the squeeze?

4. Who is this for? What is this for?

5. What are potential reasons not to do this, i.e. counterpoints?

6. What is our unfair advantage for doing this?

7. What are areas of risk and how might we mitigate?

8. Why is this likely to work and be a good investment?

9. What evidence, data, and examples am I pulling from?

10. What assets, levers, and constraints are we working with?

11. Who do we need buy-in from in order to move forward?

12. What’s the upside, downside, and trade-offs?

13. Where might I be making an assumption or logical leap that doesn’t make sense?

14. How can we test this in the lowest-overhead way possible?

15. How does this stack rank against other ideas for driving the business?

16. If we decided to move forward today, what would you need to bring this to life?

17. Can we do this ourselves, or do we need to tap into other teams?

18. Why would your target audience be excited to do the thing you want them to do?

Not every question here will be applicable to you, but at least a few should jump out and spark your thinking. And you may want to add your own go-to questions unique to your situation and function.

Keep in mind: Asking these questions is only a start. Much of the real learning for your direct reports will happen in conversation with you—when you debate and discuss ideas, with you as their sparring partner.

If you report to a busy executive and don’t have anyone available to bounce ideas with, you can still use these questions to deepen your own thinking. In my experience, it can be surprisingly hard to tell how good our own ideas are. Rigorous thinking helps you get a truer sense of this. You can see whether your argument holds water, if you're too detailed in the wrong places but not detailed enough in the right places, and if what you’re asserting makes sense on the surface, but might not hold upon further scrutiny.

Managers, try this tomorrow

The next time a team member approaches you with a question or problem, throw it back at them. Give them a chance to practice thinking rigorously.

Instead of answering right away, ask this:

“Great question. What do you think?”

“This is a great start. How do you see this working?”

Using the Socratic method takes longer than simply giving the answer. You might wonder if it's worth it. But if you stick with it, in the long run, your employees will get sharper and more self-sufficient.

Here’s the trade-off: You either spend the time upfront to train your team, or you take a few hours every day to correct their work forever. In most cases, training your team to think rigorously eventually takes a load off your plate, so everyone can produce more and better quality work, and have more fun doing it.

Summary:

• Rigorous thinking upfront will help you save time, make well-informed decisions, take better risks, and learn faster.

• Make this your go-to response: “Great question. What do you think?”

• Create psychological safety. Be a sparring partner for your team.

• A yes or no without context is a missed opportunity for learning.

• No idea is precious or off-limits from thoughtful feedback and inquiry.

• Rigorous thinking and intuition go hand in hand. They may seem at odds, but are mutually reinforcing.

• Practice self-restraint and let your direct reports talk.

• Rigorous thinking can be lightweight.

• Rigorous thinking is win-win because it prevents decision fatigue for managers and empowers team members to embrace an entrepreneurial mindset.

If you found this valuable, consider subscribing if you haven’t already, or take a moment to refer a friend. When you refer friends, you’ll unlock referral rewards of my personal book lists and not-yet-published spiky points of view.

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Thanks for being here,
Wes Kao

PS If you’re ready to level up, here are more ways I can help:

1. Follow me on Twitter or LinkedIn for insights during the week (free).

2. Check my availability to do a keynote for your team.

3. Work with me for 1:1 executive coaching. I find it extremely rewarding to give personalized guidance to ambitious operators. My current clients include leaders at startups funded by Sequoia, Accel, Bessemer, SV Angel, Kleiner Perkins, etc.

4. Enroll in my new course: Executive Communication & Influence for Senior ICs and Managers

👋 Hey, it’s Wes. Welcome to my weekly newsletter where I share frameworks for becoming a sharper marketer, operator, and builder.

To go deeper on managing up, check out my 2-day intensive course, Executive Communication & Influence for Senior ICs and Managers. You’ll join mid-career operators from organizations like Netflix, Uber, Zillow, Grammarly, Meta, Amazon, and more who will learn alongside you. → Save your spot

Managing up is a skill that will serve you starting today and throughout your career. It’s a topic I’m obsessed with and I’m excited to share this deep dive that compiles years of lessons into one place. In this week’s newsletter, we’ll cover:

1. Embrace managing up.

2. Focus on the punchline.

3. Show your thought process.

4. Flag potential issues.

5. Bring solutions, not complaints.

6. Use information hierarchy.

7. Keep your manager in the loop.

8. Are you being micromanaged, or do you need to communicate better?

9. Over-communication might be the right amount.

10. Proactively assert what to do.

11. Don’t only ask questions. Share your point of view too.

12. Anticipate questions.

13. Know when to get out.

14. Be explicit about what you need.

15. Expect to manage up forever.

Read time: 12 minutes

Early in my career, I didn’t know what “managing up” was. I thought that managers managed, but I wasn’t a manager. Therefore, it was my manager’s job to tell me what to do and my job to do it well.

It didn’t take long for me to realize this isn’t how it works, at least not in fast-moving organizations. When I realized that anyone, at any stage in their career, could be a leader, this changed how I showed up at work.

Managing up means being a competent operator who follows through, communicates appropriately, and drives toward business goals. This, in turn, elevates your actual and perceived value in an organization. This is all a mouthful, so “managing up” is useful shorthand.

To get anything done as a modern knowledge worker, you need to manage up and laterally to get what you need. Here’s how to do it.

1. Embrace managing up.

You don’t have to manage up, but your career will go further if you do.

I had no idea how busy my managers were over the years until I became a manager myself. It was like seeing in black and white, then all of a sudden seeing color. I had to replay old memories of my managers with this new realization in mind. Oh, so THIS is what y’all were doing when I thought you weren’t doing much.

Your area of responsibility is 100% of your time, but it might be 10% of your manager’s time—they have other direct reports, they’re responsible for producing quality output themselves if they’re a player-coach, they’re starting to draft next quarter’s priorities, they’re preparing talking points for this week’s all-hands meeting, they’re shielding your team from lame requests, and more.

🚫 “It’s my manager’s job to manage me. I’ll manage up when I’m promoted.”

✅ “I shouldn’t have to manage up. But if I do, I'll take control and further my career.”

🚫 “I’ll wait until my manager tells me to manage up more.”

✅ “My manager is busy with their job, plus a bunch of worries I don’t know about. They might feel awkward asking me to manage up more, so I'll take the reins and manage up proactively."

2. Focus on the punchline.

Give enough context to avoid back-and-forth follow ups. Don’t be coy when you can be direct. Don’t speak in stream of consciousness. Assume your manager is task switching or checking your Slack message between meetings—make it super easy for them to catch up on context and dive into what you want to discuss.

🚫 “This happened, then this other thing, this important thing that’s completely buried, and then this other thing.”

✅ “Here’s the minimum viable backstory, so we can spend time on the juicy stuff.”

3. Show your thought process.

Showing your thought process helps others understand your rationale, logic, and assumptions. The best part is even if they disagree, it gives something to push back on, which propels the process forward.

You don't have to have all the answers before speaking up, but you should try to address basic questions you might get. And you can preface with your level of conviction too—some ideas might be further along, while others are half-baked and still taking shape.

This gives your manager an opportunity to point out if you’re missing context, if you’re operating under different assumptions, or if you’re making a logical leap you didn’t realize you were making. All of which leads to productive conversations that get you closer to the right decision.

🚫 “I recommend this.”

✅ "I recommend X. Here's the rationale, data, and examples of why this should work. The potential risks are Y, but we can address by doing Z. If you agree, I can start by doing [first step]."

4. Flag potential issues.

When you wait to be told what to do, you put 100% of the responsibility on your manager to be the eyes and ears on the ground, assess areas of risk, define what success looks like, then tell you what to do. If you stay alert to help surface potential issues, you alleviate that burden.

Senior leaders can flag issues and solve them, then tell their manager afterwards. For junior folks, managers may want you to speak up the minute you realize something is bubbling so they can gut check and solve it with you.

This is an excellent opportunity to calibrate and learn how your manager thinks. You may think a problem is important/urgent, but through this process, learn from your manager why that problem is actually low frequency and low magnitude, and therefore is a lower priority than you thought. Or, it could be the other way around: You convince your manager that this issue is a bigger deal than they thought.

This is win-win. You reduce your manager’s decision fatigue and mental load, and you sharpen your judgment and show you’re vigilant about what’s best for the team.

🚫 “This is a problem.”

✅ “This is a problem. Here’s why it matters. I suggest doing X.”

✅ “An important customer said X. I don’t think it’s a big deal, but I wanted to bring it up and run it by you.”

✅ “I’m not sure how to solve X but wanted to surface it. My hunch is to monitor for now, but let me know if we should brainstorm what to do.”

5. Bring solutions, not complaints.

You don’t need to know the exact solution to every problem. As we saw in the previous principle, flagging an issue can be just as helpful. But complaining itself is rarely valuable.

🚫 Before: "This sucks."

✅ After: "This sucks, so here's what I'm thinking we can do..."

🚫 “This process is messy and time-consuming. It’s so dumb. I hate doing this.”

✅ “This process isn’t working because X. I’d like to update to Y process instead, which should be cheaper/faster/easier. Let me know what I might be missing or if you agree to proceed.”

Here’s what Rose Jia, Head of Growth Marketing (Grocery) at Amazon, has to say about her direct reports managing up, and managing up to her own manager.

As a manager, #5 (bring solutions, not complaints) speaks to me because I want to help solve and unblock, but I will never have as much context as my team. When they come to me with issues, I want to know what their thoughts are and what they think are potential solutions, so I can help weigh in. #7 (keep your manager in the loop) is also super important, so I can make make informed decisions across and outside of the team based on what I know is going on.

As a person managing upwards, I’m all about #7 (keep your manager in the loop) and #9 (over-communicate), making sure my manager is well-informed. It’s a great way to build a strong relationship with my manager and stay top-of-mind for future big projects.

6. Use information hierarchy.

Put your recommendation, action item, or question at the top, then context below. This allows folks to read as much or little of the context as they need. This is especially useful for remote teams, where a hefty amounts information is communicated asynchronously and in writing.

🚫 Action items, backstory, bottlenecks, and context all jumbled together

✅ Action items or question at the top, context separately below

7. Keep your manager in the loop.

Trust isn't binary. It's more multi-faceted than that. But one of the best ways to continually expand trust is to demonstrate consistent, reliable follow through and communication:

1. Say what you’re going to do.

2. Do it.

3. Tell your manager you’re doing it.

4. Tell your manager you did it.

Repeat. The problem is when you skip one of these steps. You might be doing the work, but if you forget to tell your manager, they have no idea if it’s being handled.

If you have bad news, speak up at your first itch that something may be wrong. By the time it’s a red flag, you might have fewer options on how to solve it. A big part of keeping your manager in the loop is making sure they know the good, the bad, and the ugly. You don’t want them to be caught off guard when their manager (let’s say, the CEO) catches an issue they should have heard about from their own team (that’s you).

🚫 [Silence]

✅ “We have 2 weeks until the deadline. We’re at 33/50 students, and with X leads in the pipeline, it's not enough to hit our goal. So this week, I’ll reach out to 100 new leads. I'd love to get your input on Y. Could we review tomorrow?”

8. Are you being micromanaged, or do you need to communicate better?

Poor communication skills and lack of managing up can lead to feeling micromanaged. In my experience, at least some people who complain about being micromanaged are probably bad at communicating, and thus require more hands-on management. For example, if you aren’t proactively sharing updates with your manager despite them begging to be kept in the loop, they have to follow up with you until they get what they need.

In my 15 years of working full-time, I’ve had actual micromanagers who nitpicked without logic behind their feedback and threw me under the bus in front of their managers. But, I’ll admit: I’ve also complained about “micromanagers” who, in hindsight, were doing the right amount of managing. I was just too immature to realize it at the time. Interestingly, I didn’t realize my role in contributing to the dynamic until I became a manager myself.

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They weren't micro-managing me. They were simply holding me accountable. The two are not the same thing.

🚫 “Micromanagers are the worst. I wish they'd get off my back and just let me do my job.”

✅ “I wonder what’s making them feel the need to micromanage. I'll review how I’m keeping them informed and align on what success looks like, so I can show I’m handling it. When we build up trust, the micromanaging should go down.”

Micromanaging is probably one of the most misused labels. When you empathize with your manager, you’ll realize they are ultimately responsible for anything their team does, including your work. They want to make sure goals are on track and their team’s output meets the bar for excellence. Help them help you.

Also, side note: Your manager probably feels over-worked and wishes as much as you did (if not more) that they didn’t have to follow up so much. Most people don’t want to add more work to their plate. Your incentives are aligned in that they want to be able to trust you.

9. Over-communication might be the right amount.

Different folks have different thresholds of wanting to be kept in the loop. It’s hard to tell a manager’s preferences until you start working with them, but you can always ask upfront and iterate.

A more hands-on approach at first makes sense because both manager and direct report are establishing trust. Once trust is established, the manager usually eases off. The concept of task-relevant maturity is useful here. If you are skilled in an area, you likely need to give fewer updates about it. If you’re new, your manager may want to stay closer until you show you’ve got it under control. Here’s an excerpt of Andy Grove, co-founder and former CEO of Intel, from his book High Output Management where he talks about task relevant maturity:

"How often you monitor should not be based on what you believe your subordinate can do in general, but on his experience with a specific task and his prior performance with it—his task relevant maturity... As the subordinate's work improves over time, you should respond with a corresponding reduction in the intensity of the monitoring."

Andy Gupta, a Maven instructor and former analyst at Goldman Sachs, said this:

Early on in my career at Goldman Sachs, after I received my first feedback to communicate better laterally, upward and downward, I understood what it means to be an effective team player and leader. I started proactively communicating, with slightly different styles depending on the audience. The result was I became my own boss in a way, I started having more fun, I could better control my schedule, and I received more leadership opportunities.

Puppy T, a product manager at Elsevier and former Data Lead at CB Insights, said this:

I was "micromanaged" for a while in my career. I felt disrespected and not trusted and frustrated at first, then I decided to find a way to resolve that. Everyday, I'd "over-communicate" and share every detail about what I was working on, my reasoning, etc.

After a while, the person said to me, "You know, you don't have to tell me everything, I trust you."

Keep in mind you have exposure to primary data and proximity to certain problems that your manager lacks because their scope is broader. You see what’s happening on the ground and you’re more able to notice patterns within your area of responsibility, and that’s valuable knowledge for your manager to see. Don’t withhold it. By sharing it, they can better support you and make better decisions across the team and organization.

10. Proactively assert what to do.

Suggest next steps—don’t wait to be told what to do. Almost every leader instinctively asks, “Okay, so what? What should we do with this information?” By making a recommendation, you take on some of the cognitive load of decision-making. Even if you don’t make the final decision, it helps you make progress and arrive at a stronger decision.

You want your manager to poke holes, share a different perspective, and point out areas of risk because it will help you thrash early and prevent avoidable mistakes that will slow you down. When you do take action, you’ll be able to move faster and make the most of your efforts.

🚫 “What should I do?”

✅ “I recommend X. Here's rationale, data points, or examples of why this should work. The risk is Y but we can address by Z. If you agree, I’ll start by doing [first step].”

Offering a recommendation doesn't mean your recommendation will be taken verbatim. Your goal isn’t to get a “yes” at all costs—your goal is to do what’s best for the company. Sometimes the best action might be a no go on your idea.

11. Don’t only ask questions. Share your point of view too.

The problem with waiting to be told what to do is… you’ll be told what to do. If you’re at a fast-paced startup, you’re probably there because you dislike being told what to do more than average. You’re curious, you like solving non-obvious problems, and you are a little rebellious. If you wanted to be told what to do, you would have joined Microsoft or Deloitte. Don’t wait to be told what to do.

There’s a lot of dialogue about the importance of asking questions, but not enough conversation about the flip side: why you should form a point of view and make assertions despite working with imperfect information.

A great question can be game-changing, but don't expect that simply asking "why" five times will part the skies. That only works in theory. In practice, you work with smart people. If it were really so easy to ask one question to change everything, they would have thought of it themselves already.

🚫 “Why? Why again? Why again? [Mic drop]”

✅ “Why? My initial POV is [insight and rationale, patterns you’re noticing]. I'm not 100% sure yet, so I’m curious how you’re thinking about it, where you agree, where you see gaps.”

Instead of asking what you should do, here's what you can say instead:

• "I came up with 3 ideas to improve X. Can I get your feedback?"

• "I spent 15 minutes scenario planning and think X is best because Y."

• "My initial hunch is leaning toward X, but I don't have high conviction on this and would like to discuss with you.”

• “Given what I’m noticing with X and Y, I believe Z is happening with our customers. If you agree, here’s my hypothesis about what we can do.”

I’m not saying to go off the rails and go ham without buy-in. You want to make sure your manager is aligned before you spend resources on a project that takes you away from other priorities. And to be clear, this doesn’t mean to jump straight into doing. It means your job is to turn vague ideas into more concrete, specific ones that allow you to have a productive conversation.

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12. Anticipate questions.

Anticipating questions is a skill that keeps on giving. It makes you better at marketing, sales, negotiation, public speaking, teaching, and more. If you can guess what your manager or colleagues will ask about, address it before they ask. This saves at least one cycle of back and forth, which adds up. When you consider the issue from their point of view, it helps you get their buy-in too.

It may take an extra ten minutes to get numbers to support your claim, but it's usually worth it. Some of the most compelling instant yeses I've given were when direct reports shared evidence that indeed made the situation feel inevitably, obviously straightforward. My reaction was, "Yes of course we should do this. Let's do it now."

🚫 “My idea is X. So what do you think?”

✅ “My idea is X. I thought you’d want to make sure the posts weren’t just performing well on social, but actually drove customers down the funnel. So I pulled the top 20 posts that drove the most ideal customers this quarter and…”

13. Know when to get out.

None of this works for managers who don’t have your best interest in mind or are insecure about their own work. No amount of managing up can resolve deeply troublesome issues, so use your best judgment.

🚫 “My manager undermines my work, throws me under the bus, and blames me for no reason. Managing up doesn’t work.”

✅ “Managing up works, but not in a toxic environment. I'll find an organization that’s a better fit and manage up to a manager who’s eager to work with me.”

14. Be explicit about what you need.

Are you looking for a thought partner to help you shape a new, fuzzy idea? Are you looking for emotional support and someone to listen? What kind of feedback would be most helpful? Share what you need specifically because you’ll be more likely to get it.

🚫 “Hey, can you take a look?

✅ “Hey, can you take a look? I’m looking for directional feedback on whether it makes sense to go down this path, no need for line edits yet.”

✅ “Can you approve this by 3pm today?”

✅ “I have updates on X. Let’s discuss by tomorrow EOD because Y.”

15. Expect to manage up forever.

In my twenties: "When I'm a leader, I don't have to manage up anymore."

In my thirties: "I'm going to have to manage up forever. This never ends."

At one point, I had been managing up for years, but in the back of my mind, I assumed I wouldn't have to do it anymore after I put in the years and hit an invisible threshold of seniority.

Until one day, I co-founded my own company. And.... I still had to manage up.

I looked around at other founders and executives, and saw that they were all still managing up. To their managers, their co-founders, their peers, their board, etc.

You might assume senior leaders and executives are “too trusted" to need to manage up. There's no such thing as too much trust. Every single leader has to manage up. Counterintuitively, senior leaders and executives are often best at it. They got to where they are because they know how to anticipate needs, communicate persuasively, and keep people in the loop.

The phrase "direct reports" conjures an image of a mid-level individual contributor, but actually, almost every manager is both a manager AND a direct report themselves. So it might be nice to know you're not the only one managing up. Your manager is doing it too. And so is their manager.

🚫 “I’ll only have to manage up when I’m junior or mid-level.”

✅ “I’m ready to manage up even if I’m 15+ years into my career.”

If you’re enjoying this newsletter, consider subscribing if you haven’t already. See you next Wednesday at 8am ET.

Thanks for being here,
Wes

PS If you’re ready to level up, here are four more ways I can help:

1. Follow me on Twitter or LinkedIn for bite-sized tips throughout the week (free).

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3. Work with me for 1:1 executive coaching. I find it extremely rewarding to give personalized guidance to ambitious operators. My current clients include leaders at startups funded by Sequoia, Accel, Bessemer, SV Angel, Kleiner Perkins, etc.

4. Practice how to manage up, present to executives, and more in my new 2-day intensive course: Executive Communication & Influence for Senior ICs and Managers