⛑️ If you’re looking to dramatically improve your communication and leadership, learn more about 1:1 coaching.

Read time: 3 minutes

Fundamentals is a new series that highlights my core concepts in communication, leadership, and influence. Even as my newsletter has grown to 80,000+ subscribers, I often find myself referencing these principles with clients and in my own work. Whether you're new here or a longtime reader, this concept deserves a spot in your toolbox.

This week’s fundamental principle: Signposting: How to reduce cognitive load for your reader

Updated thoughts

• Since writing this, I’ve realized that starting a sentence with a signposting phrase is even more useful than I thought. I didn’t realize how I had trained myself to speak and write this way because it’s become my default. Basically, when you start with a signposting phrase, you’re giving your reader a preview of what’s to come.

• ^ This is why kicking off a sentence with “The most important part to keep in mind is [this piece of info]” is infinitely easier to skim, than “[This piece of info] is the most important part to keep in mind.” If you start with “this piece of info,” your reader doesn’t know what to focus on until the back half of your sentence.

• I wrote signposting with written communication in mind, but it’s just as effective for verbal communication. It might actually be even MORE useful with verbal communication because your listener can’t read ahead. They have to listen to you reveal one word at a time.

• ^ For example, I love when I’m in a meeting and hear the speaker say, “The surprising thing is…” or “The biggest takeaway was…” My attention might have drifted, but hearing them say that signposting phrase allows me to snap back into focus and listen to what they have to say next.

• One common misunderstanding or misapplication of signposting, is readers thinking that simply adding headers is good enough. Headers, subheaders, toggles, paragraphs, etc are a type of signposting, but these formatting elements alone are not enough. I’ve read MANY docs that looked well-organized in Notion or Google Docs, but the content itself was weak, poorly argued, or generic. See this related post on how good design (or formatting) can hide poor logic.

I posted about signposting on LinkedIn. Here are some highlights on which signposting phrases folks found most helpful:

Read the full article →

Do this today

After you read the article, reflect on these prompts:

1. Look at the last long-ish memo you wrote. What signposting words could you use to make the flow better?

2. Think about a recent presentation where your audience seemed confused or asked lots of clarifying questions. How could you have used verbal signposting (“First... Second... The reason this matters is...”) to guide your audience?

3. Pick a meeting where you’ll need to communicate complex information. What signposting phrases could you use to help add structure to what you’re saying?

Thanks for being here, and I'll see you in two weeks on Wednesday at 8am ET.

Wes

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Course update: The May cohort is 75% full, plus new student reviews

The upcoming May cohort is currently 75% full. In the past week alone, operators Etsy, Amazon, Rakuten, PayPal, GoFundMe, Clay, DoorDash, etc have signed up.

Here are reviews from students who took the course last month:

“Wes discusses several issues which come up in work situations where you can improve your chances of getting what you want. Very clear tips on how you might be sabotaging yourself, how to communicate at the right level and how to be focused on the recipient, have logic and reduce cognitive load.”

- Rajesh Shenoy, Senior Staff Software Engineer/Engineering Manager (L7) @ Meta

“A masterclass in high-leverage communication. Wes provides incredibly tactical frameworks that teach you how to stop asking for permission and start driving outcomes. Essential for anyone operating in a fast-paced, asynchronous tech environment. 10/10.”

- Galit Alon, Engineering Manager @ GitLab

“Great sessions. I really appreciate Wes walking us through each topic and sharing clear examples to drive each home. I love the approach of making most of the exercises written, especially with a time limit. Helped train me to quickly comprehend and execute within minutes.”

- MD, Senior Manager, Technical Program Management @ Squarespace

“A course that is well-paced, engaging, and filled with thoughtfully-designed concepts and frameworks that are easy to immediately action upon. I walked away with several new communication tools in my toolbelt. Thank you, Wes!”

- Ruth Corson, Director of Global Digital Marketing, Basketball @ Nike

“This course is packed with valuable and actionable information. The flow and the quality of the information and the way that Wes presented the material kept my mind engaged the entire time. I am very energized by this course and can’t wait to start implementing my learnings. Must-do for everyone.”

- Anoush Kabalyan, Director of Growth Analytics @ Salesforce

If you’ve been thinking about joining, I hope to see you in class. Learn more about the course.

Connect with Wes

• Is this your first time here? Subscribe (it’s free)

• Follow me on LinkedIn for more insights

• Learn more about 1:1 coaching to sharpen your executive presence

• ✨ Improve your ability to sell your ideas, manage up, gain buy-in, and increase your impact in a 2-day workshop. Over 1,500 tech operators have taken this course, and every cohort so far has sold out. NOTE: The May cohort is 75% full and will fill up in the next few weeks. → Save your spot

👋 Hey, it’s Wes. Welcome to my bi-weekly newsletter on managing up, leading teams, and standing out as a high performer. Check out my intensive course on Executive Communication & Influence. You’ll learn alongside mid-career operators from Netflix, Stripe, Meta, Figma, Anthropic, etc. → Join the May 2026 cohort

⛑️ If you’re looking to dramatically improve your communication and leadership, learn more about 1:1 coaching.

Read time: 6 minutes

I often get readers who ask, “Wes, if I’m not naturally loud, how do I speak up or talk about my accomplishments? How do I gain more visibility, either internally in my company or externally online?”

As a fellow introvert, I can relate.

No joke, in elementary school, I was so shy I used to not raise my hand to use the bathroom during class because I didn’t want 30 of my classmates to look up when I came back into the classroom.

That’s right, I chose physical discomfort to avoid drawing attention to myself.

So I’ve come a long way over the years, as a founder who’s been on ~50 podcasts (including Lenny’s Podcast), spoken at SXSW twice, taught as a guest lecturer at top 10 MBA programs, in addition to leading countless internal team meetings, speaking at all-hands, sharing business updates, etc.

Here are a few ways I get myself to speak up and share more.

1. Decide to speak before the meeting starts.

Tell me if this sounds familiar:

You: “Hmm I don’t know if I agree with what Joe just said. Should I say something? I’m not sure. What if I don’t explain myself well? What if people disagree with me? Okay, I should speak. No I shouldn’t. Okay yes, I should. Oh no, the group has already moved on.”

Is this you? This was me too.

If you try to decide during the meeting, you’re going to miss your window. Decide BEFOREHAND that you’ll share your point of view and speak at least once during the meeting.

This way, you’re not debating whether to speak, you’re looking for an opening of when to do it.

2. Try to speak early on in a meeting.

I’ve worked with many coworkers who were naturally extroverted. They didn’t overthink, and they felt comfortable speaking up when they were 60% confident they were right. It’s hard to compete with colleagues who don’t rehearse what to say in their mind before saying it.

This is why I try to speak first in big meetings. I try to get it out of the way and prevent someone else from saying what I wanted to say.

Is this at odds with the advice of “leaders should speak last”? I would say no.

The variable here is power dynamics. If you are nervous about not being able to speak up, presumably it’s because you’re not the most senior person in the room. Many managers are confident speaking to their direct reports or folks more junior, but get self-conscious when presenting to senior leadership, peers, or the entire company. This is very normal.

So when you are among peers and higher ups, it’s fine if you speak first, especially if waiting to speak means you might end up not speaking at all.

3. Share more in writing.

Not all “speaking up” has to happen verbally. Another way to speak up more is to share more in writing. A well-written doc can get circulated in your organization and get shared in rooms you’re not in, with leaders much more senior than you. Some docs even outlive the person who wrote them.

If you have an idea that’s hard to describe in 45 seconds to an impatient audience, I recommend drafting a doc that’s easy to read and pitches your idea. In your doc, you can describe the problem, cost of inaction, potential solutions, etc.

When you make a business case and share an evidence-backed point of view, you show good judgment. If you show that X problem is costing your company money, you may get senior leaders’ ears to perk up.

When you write, you create an artifact. You create a concrete record of yourself contributing useful solutions, which builds your credibility.

In terms of sharing ideas externally, writing a newsletter/blog or sharing on LinkedIn is great too. I started my blog in 2010, where I shared teardowns of ad campaigns (like my analysis of this Airbnb ad), marketing insights, etc. Writing regularly helped sharpen my thinking back then, and still does every week. It shows you’re passionate about your craft and actively thinking about the world around you.

More on how to speak up, even if you’re afraid of being wrong.

4. Prepare go-to phrases to insert yourself.

When you're armed with a few go-to phrases, you’ll be able to jump in before the moment passes. So get ready to unmute yourself on Zoom and say:

“Yes, to add some color on that...”

“That's a great point. My POV on this is...”

“I love that you brought that up. The thing we need to remember is…”

The other benefit of having go-to phrases: you buy yourself time. Even an extra second can help give yourself a beat to think of how you want to articulate your idea.

5. Look more authoritative on Zoom.

I find it a lot easier to chime in on Zoom than in IRL meetings. If you work remotely, use this to your advantage.

Sit higher in your chair so you don’t look short on camera. Get a $50 box light on Amazon so you’re well lit. Try to have a good “shoulder line” so your shoulders look defined against your background. When you fill the frame and look good, you'll feel powerful and remind yourself you have a lot to share.

I actually think Zoom meetings are amazing for introverts. In an IRL meeting, it’s easy to get nervous if you see 10 or 15 or 20 people sitting around a table. But in Zoom, everyone is in a one inch box on your screen--this can help reduce anxiety from a public speaking perspective.

More on how to prevent insecure vibes.

6. Ask a colleague to keep you accountable.

One of my direct reports wanted to practice speaking up more in meetings.

I asked how I could best support her, and here’s what we agreed on: If we were in meetings together, I would send her a Zoom chat DM saying, “Hey I think you could share something on this. No pressure.”

Then she would often unmute herself to chime in.

If you aren’t in a position to ask your manager for help, do this with a trusted colleague. Give each other a gentle nudge and help boost each other up.

To recap, here are the tactics you can try:

1. Decide to speak before the meeting starts.

2. Try to speak first, or early on.

3. Share more in writing.

4. Prepare go-to phrases to insert yourself in meetings.

5. Look more authoritative on Zoom.

6. Ask a colleague to keep you accountable.

Thanks for being here, and I’ll see you in two weeks on Wednesday at 8am ET.

Wes

Course update: May 2026 cohort is now 55% full

I just wrapped up an incredible March cohort two weeks ago. Every time I run the course, I’m humbled by the talented operators who join and learn together.

Of the 1,700+ tech operators who have taken the course so far, there’s a wide range of functions represented, with the largest groups from product, engineering, and marketing:

New student reviews from this month’s cohort are rolling in. Here’s what folks are saying:

“At the risk of being hyperbolic, spending these 6 hours in the course may have been some of the most insightful and impactful hours of my career. The course was concise and extremely tactical, and illuminated countless improvements I can make to communicate more effectively with leaders, and be seen as a leader myself.”

- Cadence Greenberg, Senior Research Manager @ The New York Times

“I was skeptical with the value the training can bring in such a short time, but Wes managed to change my perspective on multiple concepts in minutes. The bonus material also gives me things to read and implement in the coming weeks and months.”

- Barbara Bihari, Senior Integration Manager, Strategic Partnerships @ Kayak

“This course is packed with frameworks and insights, and delivered in a way that is digestible and immediately actionable. I feel equipped with the right tools to out into the world and put this new information into practice. Wes is an engaging presenter and makes a large Zoom feel very communal. It’s also really well-paced for the amount of content we move through. Highly recommend.”

- Kaela Chandrasekaran, Staff User Researcher @ Asana

“This course is a gold mine and worth every penny. I’ve struggled with communicating my ideas, being concise, and ensuring I’m giving the right amount of context depending on my audience. Everything in this course was super actionable and I’ve already put some of these learnings into practice.”

- Beth Saunders, Senior Community Manager @ Amplitude

“I wish I had taken this course earlier. Wes shared some incredibly practical tools that, if applied, can meaningfully uplevel the way you work and communicate.”

- Manohar Sripada, Engineering Manager @ Meta

The upcoming May cohort is already 55% full. So far, the cohort includes operators from Adobe, Experian, OpenTable, Webflow, Visa, Google, Robinhood, Discord, Hims & Hers, Zendesk, Yelp, 1Password, Shopify, etc.

If you’ve been thinking about joining, I hope to see you in class. Learn more about the course.

Connect with Wes

• Is this your first time here? Subscribe (it’s free)

• Follow me on LinkedIn for more insights

• Learn more about 1:1 coaching to sharpen your executive presence

• Improve your ability to sell your ideas, manage up, gain buy-in, and increase your impact in a 2-day workshop. Over 1,700 tech operators have taken this course, and every cohort so far has sold out. → Save your spot

👋 Hey, it’s Wes. Welcome to my bi-weekly newsletter on managing up, leading teams, and standing out as a high performer. For more, check out my 2-day course on Executive Communication & Influence → The May cohort is now open

⛑️ If you’re looking to dramatically improve your communication and leadership, learn more about my coaching approach.

I originally published a version of this essay in September 2018, and have since expanded on the topic. Enjoy.

Read time: 5 minutes

I give a talk called “Storytelling for Technical Leaders,” where I share how technical founders and operators can tell better stories and be more compelling to their audiences.

About 1/3 of my private coaching clients are technical (eng managers, staff engineers, startup CTOs, VPs of data science, etc).

From working with dozens of technical leaders, here are the most common storytelling mistakes I see:

1. Over-reliance on technical details

Real-life is non-linear, but stories are linear. Therefore, stories are always a simplification.

Read that again. Stories are always a simplification. In order to simplify, you as the presenter will need to decide which details to include and exclude.

Many technical folks are afraid their audience will call them out for not being comprehensive enough. The paranoia is real and I’ve felt it myself. But the solution is not to be extremely comprehensive all the time, and to treat all details as weighted equally.

Your audience doesn’t want a story weighed down by caveats and technicalities in every other sentence. Your audience wants to be wooed, entertained, and taken on a journey — in addition to learning about your project and vision. If you lose your audience because they’re asleep, they won’t appreciate all the context and details you’re sharing anyway.

What about fellow technical folks or subject matter experts who have questions about specific details? They’ll ask. And you’ll be ready to answer and impress them with your depth.

Anytime you feel the urge to say, “Well, technically…,” you’re about to kill a good story.

Remember: What gets someone in the door isn’t necessarily what gets them to stay.

For example, think about J.Crew. The front of the store has tables with a rainbow assortment of t-shirts in fun patterns and neon yellow.

Nine times out of ten, I walk in…and buy a neutral color (white, black, navy, grey). Most customers do this , which is why retailers plan the inventory accordingly and have stockrooms full of basic SKUs.

But if they put only the most basic stuff on display, you would keep walking and never enter the store.

Hook your audience so you get them in the door. If your audience is eager to hear more, you’ll earn the opportunity to share details.

Ask yourself:

• Can I simplify my story to make it even more powerful?

• Can I remove tangential comments, so I can focus on my main point?

• Am I spending precious time describing context of secondary importance that I could share later?

More on the importance of sales, then logistics.

2. Trying to remember too many tactics

When you are in the moment, don’t try to remember a list of storytelling tips and strategies. This is more likely to make you anxious and worsen your performance.

By all means, practice your pitch. But once you’re out in the wild (in front of a room of colleagues, prospective customers, or at a networking event), let go of the laundry list of things you learned in preparation for telling your story. Don’t feel pressure to stick with word-for-word scripts.

Instead, stay present and focus on eliciting emotion: “How can I make this person’s eyes light up?”

I call it “ELU” for short.

ELU is the moment when your audience gets emotionally invested. We all know when people are listening to us to be polite. And you can tell when someone suddenly wakes up during the conversation and wants to hear more.

It’s hard to anticipate what will resonate with your audiences, so experiment with what you say   and look for that spark.

Ask yourself:

• How can I stay present, enjoy telling this story, and look for moments when my audience leans in with excitement?

More on Eyes Light Up.

3. Too much backstory

If you’re telling a story about your camping trip, don’t start when you were brainstorming options for tents and carpooling. Start right before you almost get eaten by a bear on a 13 mile hike.

I constantly remind myself to cut backstory, and am usually glad for it. Backstory can easily take up the majority of the time you have during an introductory call or meeting, so be mindful to avoid backstory scope creep.

Ask yourself:

• Can I cut out more of the backstory?

• Does my audience really need to know this part?

• What’s the bare minimum I need to set the context, so I can spend time on the juicy stuff?

4. Trying to tell a story that’s too long

Your colleagues do not have time to listen to a full hero’s journey story in a quarterly business review meeting.

Seriously, do not attempt to do a 12 step (some say 17 step!) hero’s journey type of story. Your business or project does not warrant this, and everyone will be catatonic by the time you finish.

Am I against long stories? No. Am I against boring, pointless, wtf are we talking about stories? Yes.

Long stories can be good IF you are a good storyteller. Most of us (technical or not) aren’t in this bucket. In order for storytelling to work, the story needs to hit a certain threshold of quality, and that bad is higher than people realize.

Therefore, storytelling is not as practical of a tool for most people who don’t have time to invest in getting good at it. It’s like tango. I’ve heard it takes a minimum of ten years for one to look even remotely passable doing tango. Compare that to lindy hop: it’s a forgiving dance. There are obviously professionals who are next level, but amateurs don’t look terrible and they still have fun.

Most founders and leaders should tell short stories where the narrative arc is a few minutes long at most. I might not even call them stories. I’d call this using evocative vocabulary or sharing a quick anecdote, where you use visual language to paint a picture for your audience.

This, you can easily do in as little 5-15 seconds. I did this often on Maven sales calls and internally when coaching my direct reports, and it led to the same positive outcome of telling stories but was much faster and easier to do well.

—

As usual, it’s not complicated . It’s just hard. There are hundreds of permutations and combinations of ways to tell your story, so it’s part art and part science. If it feels unnatural for you at first, it’s totally normal. Developing your muscle memory with storytelling is part of the process.

Thanks for being here, and I’ll see you in two weeks on Wednesday at 8am ET.

Wes

Connect with Wes

• Is this your first time here? Subscribe (it’s free)

• Follow me on LinkedIn for more insights

• Learn more about 1:1 coaching to sharpen your storytelling and executive presence

• ✨ Improve your ability to manage up, gain buy-in, and increase your impact in a 2-day workshop. Over 1,700 students have taken the course and rated it 4.6/5 stars. → Save your spot in the May cohort

To level up faster, check out my intensive course on Executive Communication & Influence. You’ll learn alongside mid-career operators from Netflix, Stripe, Meta, Figma, Anthropic, etc. → Join the May 2026 cohort

⛑️ If you’re looking for 1:1 coaching to dramatically improve your communication and leadership, learn more about my coaching approach.

Read time: 6 minutes

In my early twenties, I wished I had a manager who would “coach” and “mentor” me. I wanted this so badly.

One day, I realized, my manager taking the time to rip my work into shreds AND patiently share actionable feedback…

This WAS coaching me.

This WAS mentoring me.

This WAS investing in me.

I was too busy whining to realize, in fact, I was getting what I wanted all along.

Don’t romanticize being coached and mentored

You may have an idealized version of the perfect manager in your mind, but your manager won’t able to live up to that ideal.

“Coaching” and “mentoring” and “investing in your growth” don’t only show up in formal career conversations, or look a certain way.

If your manager cares enough to say, “Hey, this kinda sucks, but here’s how to make it better,” they are investing in you.

Who would you rather have?

• A manager who talks about your career during performance reviews, but doesn’t give you detailed feedback on a weekly basis.

• A manager who talks about your career path when you initiate, but gives you consistent, actionable, detailed feedback regularly.

Of course, you’d want both.

But if I were to choose, I’d say the latter is more important.

You might be thinking, “Alright Wes, my manager is already giving me some feedback. But how do I get more coaching from them?”

Read on, my friend.

1. Show your manager that giving you feedback is worth their time

Yes, it’s part of your manager’s job to give you feedback. No, this doesn’t mean they feel obliged to do it, mainly because giving good feedback takes effort and your manager is probably swamped.

You’re more likely to get feedback if you sell them on the upside of doing so. For example:

1. If your manager were to engage with you on this topic, how will it save money or make money for the company?

2. How will it allow you to add more value?

3. How will feedback now improve everything that comes after?

If your response is, “Getting an answer to my question doesn’t really impact my ability to add value to the business,” your question might not be worth the time to discuss.

Most senior leaders are ruthlessly focused on driving value for the firm. If addressing your question doesn’t contribute to that, it makes sense why they’d deprioritize it.

2. Become someone your manager wants to invest in

At the end of the day, managers invest in people they believe are worth investing in. It’s a bit circular, but it’s worth saying because there are a few implications.

Generally, you want to behave like someone who learns quickly, is going places, and is a strong performer. You want to act like an owner and do what’s best for the business. When you have a history of good judgment and continuous improvement, this makes your manager want to give you more feedback.

Try to react positively when managers give you any type of coaching. This matters because many managers have learned the hard way that they need to carefully phrase their feedback using words that will be more acceptable for their direct reports.

Otherwise, they risk being seen as an insensitive asshole.

If you’re a direct report, you do not want your manager to feel the need to “translate” too much because it reduces the chances they’ll give you feedback at all.

You benefit when your manager can speak freely with you. For example, you can say,

“Feel free to be super direct. If this sucks, tell me and share why/how I can improve because I want to learn. Feel free to rip it apart.”

3. If you’re not getting what you need, switch things up

It’s usually much easier for your manager to react to something specific, soon after it happened, than it is to ask about vague ways you can improve.

🚫 “What can I do get to the next level?”

✅ “What do you think I did well in the presentation to our SVP just now? What could I have done differently to be more effective?”

In the “before,” questions like this are hard for your manager to answer. They require your manager to think about everything you do, don’t do, where you fit in the org…then create a curriculum to teach you.

In the “after,” this is a much more manageable question that feels less loaded. Your manager can give you feedback about the meeting you were both in just now, which you can apply to future presentations.

Another example:

🚫 “Can you teach me about strategy?”

This is hard. Your manager has to think of how to teach you this intimidating, complex, large topic of strategy.

✅ “I drafted a strategy doc. Could you tear this apart? What are you skeptical about? No need to hold back. I want to make a strong argument and address any potential risks.”

Here we go. This ask minimizes cognitive load and is less intimidating to tackle, so it invites your manager to teach you about strategy on the job.

Other questions you can ask:

• “What would you do differently? What’s missing?”

• “What grade would you give this? What would make this an A+ in your eyes?”

• “What is the most interesting 20% of this? Most boring 20%?”

• “Could you mark which parts of this memo are confusing?”

• “What would you do if you were in this situation?”

• “Do you see any risks or logical gaps that I missed?”

Notice how these questions are designed to draw out insights from your manager.

When your manager is actively giving you their insights on how you can improve, this is coaching. This is mentorship. Don’t let it go to waste.

Further reading

If you’re a manager (or want to be one), here’s how to coach your direct reports:

Thanks for being here, and I’ll see you in two weeks on Wednesday at 8am ET.

Wes

✨ Next week: Free workshop for product managers

I rarely do free workshops, so if you’ve been curious about my course or if you found my Lenny podcast episode valuable, this is for you…

I’m excited to be featured in Lenny Rachitsky’s “The AI-Native Product Manager” series. As part of this series, I’ll be teaching a free workshop on the topic “How to Get Executive Buy-in as a PM.”

Product managers are one of the biggest groups represented in each cohort, and about 1/3 of my private coaching clients are product leaders. I believe the bar for product is getting higher each quarter, so if you are a self-aware and thoughtful product person, I want to help you stand out.

In this session, I’ll cover how to:

1. Present to impatient executives: Be prepared to move fast, speak directly, etc.

2. Manage up to senior leaders: Most PMs suck at managing up. We'll cover principles that will serve you now and throughout your career.

3. Anticipate questions and prevent skepticism: How to anticipate questions to avoid endless back-and-forth.

You will be able to apply these principles to stakeholders upwards, downwards, and laterally.

The free workshop will be on Friday, March 13 at 12:00 - 12:30pm ET.

There are already 4,584 people signed up, which is pretty nuts.

If you’re interested, click here to RSVP.

Connect with Wes

• Is this your first time here? Subscribe (it’s free)

• Follow me on LinkedIn for more insights

• Learn more about 1:1 coaching to sharpen your executive presence

• ✨ Course: Improve your ability to sell your ideas, manage up, gain buy-in, and increase your impact in a 2-day workshop. Over 1,500 tech operators have taken this course, and every cohort so far has sold out. → Save your spot in the May 2026 cohort

👋 Hey, it’s Wes. Welcome to my bi-weekly newsletter on managing up, leading teams, and standing out as a high performer. For more, check out my intensive course on Executive Communication & Influence for Senior ICs and Managers. Over 1,500 operators from Netflix, Anthropic, OpenAI, Figma, etc have taken the course.

✨ UPDATE: The March cohort is sold out, but the new May 2026 cohort is now open. → Save your spot

Read time: 4 minutes

Subscribe now

Fundamentals is a new series that highlights my core concepts in communication, leadership, and influence. Even as my newsletter has grown to 75,000+ subscribers, I often find myself referencing these principles with clients and in my own work. Whether you’re new here or a longtime reader, this concept deserves a spot in your toolbox.

This week’s fundamental principle: Question behind the question

Updated thoughts

• Before you launch into an answer that is overly tactical or too in the weeds, consider the QBQ. This will help you answer at the right altitude. (Practicing how to answer at the right altitude is a concept I teach in my live course.)

• Thinking about the question-behind-the-question might feel like an extra step, but once it becomes part of your muscle memory, it only takes a few extra seconds. It becomes second nature. Many times, I don’t even actively think about the QBQ because my brain naturally goes there.

• Some readers ask, “Can we just straight up ask ‘what’s the question behind the question?’” Personally, I don’t like doing this because it can sound a bit aggressive. I don’t want to risk insinuating that my recipient is being coy. Instead, I like probing to get a bit more context, or even better: asserting my interpretation and asking them to correct me if I’m wrong. Most people are very happy to tell you if you’re wrong.

• Iff a journalist asks me a question, their underlying QBQ might be: “What is newsworthy and quotable here?” So I try to answer questions in punchy sound-bites that highlight what’s new/interesting. This gives the journalist what they want and is win-win.

• If a senior exec asks you a question, the underlying QBQ might be, “How does this impact the business?” Execs are further removed from your work, and they usually care about driving revenue or saving on costs. Avoid diving straight into logistics.

• If a prospect/customer asks you a question, they might not be able to articulate what’s really gnawing at them. I’ve noticed the best salespeople answer my tactical surface question AND go deeper to get at the root of the issue.

Here are a few reader comments I want to highlight:

“Earlier in my career, my instinct was to answer as fast as possible to show I was on top of it. Taking a moment to consider the question behind the question was something I had to learn and practice. Not an easy skill but important to learn.

I have found that taking a quick pause before answering gives me a chance to gather my thoughts and decide what approach to take.” - Josh

“I’m familiar with the QBQ and I’ve [been] practicing a lot… especially this part: ‘Your question-asker might not know why they feel skeptical, so you're trying to hit a moving target,’ made me realize that I too often take for granted that people know and have clear what they want to ask.

Which is rarely the case. This will definitely help me not get stuck in never-ending back-and-forth as I often do, moved by my goodwill.” - Concetta Cucchiarelli

Read the full article →

Do this today

After you read the article, reflect on these prompts:

1. Think about a recent situation where you felt like you kept repeating yourself or getting random follow-up questions. What signs did you notice that suggested there was a deeper question you weren’t addressing?

2. Consider the colleagues you interact with regularly. What are their typical underlying concerns or priorities? How can you proactively address these issues?

3. Watch out for the next time someone asks you a question you don’t feel like you have enough context to answer. Use this script to uncover their true concern:“Great question. If you could share a bit of context on what's top of mind for you, it’ll help me get a sense of what’s most relevant to share.”

Thanks for being here, and I’ll see you in two weeks on Wednesday at 8am ET.

Wes

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• Learn more about 1:1 coaching to sharpen your executive presence

• ✨ Course: The March cohort has sold out. The new May 2026 cohort is now open. Improve your ability to sell your ideas, manage up, gain buy-in, and increase your impact in a 2-day workshop. Over 1,500 tech operators have taken this course. → Save your spot

⛑️ If you’re looking for 1:1 coaching, I work with tech leaders on managing up, advocating for your ideas, and strengthening your executive presence. Clients include operators at Amazon, Meta, DoorDash, Atlassian, OpenAI, etc. Learn more about my coaching approach.

Read time: 4 minutes

I once knew a CEO who had a habit of telling people, “I know you better than you know yourself.”

Their reaction was, “You don’t know me. GTFO.”

The thing is, the CEO often had good insights about his team. But folks were too busy feeling unfairly labeled to listen.

If you try to tell people how they are, their natural reaction will be to push back.

The solution: Avoid overly broad claims. Stick to facts of what you are able to observe. And frame your ideas as what they are: observations.

For example:

🚫 “You are X.”

✅ “You come across as X.”

✅ “You might come across as X.”

✅ “You seem X.”

This language is intentional because I don’t want to trigger people to argue with me.

It is harder to argue with me if I say, “You come across as X” vs proposing that I somehow have special insight into who you are deep down.

As a manager, I only see a slice of who you are. I don’t presume to know who you are at your core—I only know how you show up at work, and how you come across based on how you behave and what you say. So my feedback will be rooted in that.

Why you do not want to trigger people to debate you

Sometimes a debate is healthy and exactly what you’re looking for.

Other times, a debate is a distraction. You have a point, but your recipient is too hung up on some other comment you made, that they can’t focus on your main point.

I’m hyper-rational, and many of my coaching clients are tech operators who are hyper-rational too. If they sense BS, they will call you out on it. They will want to debate you. They will want to show how you are making a logical leap, and how you don’t actually have the grounds to be making such a sweeping claim.

This is not productive. I do not want to trigger someone to debate me, especially if I’m pretty sure about my point and I want them to focus on my point.

Therefore, it’s to your benefit NOT to over-reach. Don’t give your counterpart anything to get distracted by.

Speak accurately

Many problems can be avoided if you simply speak accurately. For example, see these two statements:

1. “X will Y.”

2. “X tends to Y.”

These two statements are not the same. The first implies complete certainty. The second implies that X generally does Y, but not always.

[Note: Don’t be too literal here. I’m not saying to never say “X will Y.” The context matters. If you are writing a strategy doc, you might say: “Investing in this channel will lead to more users.” The context itself implies that this is an assertion. Your reader likely knows that you can’t guarantee that this channel will lead to more users. In this case, the sentence structure is a reflection of your high conviction that this is the right path.]

Here’s an example of an overly-broad claim vs a narrower, more right-sized claim:

🚫 “You lack emotional regulation.”

^ This is a broad sweeping statement that assumes the person always lacks emotional regulation. Even if this is true, they are likely to feel threatened by this and want to prove how I’m wrong.

✅ “When you do X specific thing, you seem like you lack emotional regulation.”

^ This is a narrower claim. It’s more accurate and more objective. I point to the specific thing that leads me to believe the person could lack emotional regulation.

There is a difference in positioning, and it impacts whether your recipient hears you. It’s not only semantics.

If I say you lack emotional regulation, you might say, “Well Wes, I regulate myself plenty well in 90% of situations” and start debating me on this point.

If I say you SEEM like you lack emotional regulation, well, there’s not much you can debate there. I’m sharing how I’m interpreting your actions, and I’m clear that this is my interpretation, which might be how others see you, too. Most people are glad to hear how they might be viewed by other people. More on the importance of speaking accurately.

By phrasing your feedback more thoughtfully (which takes two seconds, as shown in the examples above), you can increase the chances your team actually listens without getting defensive.

Thanks for being here, and I’ll see you in two weeks on Wednesday at 8am ET.

Wes

PS Related reading for managers:

Connect with Wes

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Let’s say I send you a Slack DM that says, “Hey, this is a priority.”

What do you think I mean?

1. You should prioritize this over all other projects for the rest of Q1.

2. Focus on this over other projects if you’re on the fence.

3. This must be done by end of week.

4. This must be done by end of day.

5. Drop everything and do this in the next hour.

Trick question, because there’s no way to know.

To be clear, I like the word “priority” and use it myself. There’s nothing inherently wrong with the word, and I am not saying you should never use it. What I am saying is:

Vague language can have a large (negative) blast radius when used haphazardly. It can create anything from avoidable anxiety to hours spent going in the wrong direction due to miscommunication. Yet, it’s surprisingly common in the workplace. Most of us have used vague language at work, and have been on the receiving end of it.

Over time, I’ve realized it’s not helpful to say “ASAP” (and similar phrases like “time-sensitive” or “priority”) without additional context.

So how do you convey time-sensitivity in a more productive way?

Move from the abstract to the concrete

Instead of talking about urgency in a vague sense, do these two things:

1. Talk about the sequence

2. Clearly define the timeline

By doing this, we move from an abstract sense of “yikes this is important and time-sensitive” to a concrete sense of what to do about it.

Here’s are scripts of what this looks like in action:

1. “Do this first. Then do this second, then this third.”

I’ve used this with more junior team members, and they’ve shared feedback that being so clear and explicit was helpful.

The benefit here is you show the stack rank of priorities. You reiterate the hierarchy of what to do, which is particularly useful if you have multiple tasks on the docket.

2. “By x date/time…”

For example:

“By tomorrow…”

“By Thursday EOD…”

I always say that “over-communicating” is usually the right amount of communication. This is especially applicable when working with new team members, junior staff, external vendors, contractors, etc.

It’s even helpful with mid-level and senior folks:

🚫 “This strategy doc is a priority so we should review it soon.”

✅ “Let’s plan to review an initial draft of your strategy doc at our 1:1 on Thursday.”

This approach is helpful when delegating too. (Here’s more on how to delegate while maintaining high standards).

3. “If you only have time to do one thing…”

“If you only have time to do one of these tasks--do this one.”

“If you were to prioritize one goal this week, make it this one.”

This helps elevate one project/task over all others. This is useful if you want to emphasize one thing and really get your point across.

4. Mention what doesn’t have to get done yet

“I’m going to leave this here for you. You don’t have to do it immediately, but can you handle it by today at 3pm?”

“I need X by EOW. Items 2, 3, 4 can wait until next month.”

There are many things that aren’t hugely urgent, but still have to get done. It’s good to be clear on what can wait. Above, I show two different styles of communicating what doesn’t have to get done right away. The first is a bit more collaborative and the latter is more concise. I’ve used both styles depending on the person and project.

For related reading, here’s more on how to be concise.

5. Default is moving forward*

“Here’s what I’m going to do if I don’t hear from you by 5pm …”

You should use this approach with judgment and finesse because it can be easy to overstep.

Use this approach for lower-risk items, like smaller/tactical decisions, tasks your manager has approved before, or ideas where you’re already generally aligned.

🚫 “Hey manager, if you don’t approve my proposal by EOW, I’m going to assume you’re on board with shutting down our current operations and launching this new business unit and having me lead it.”

✅ “Hey manager, if you don’t approve my email reply to our vendor by 5pm, I’m going to assume you’re good with it.”

You may think, “Am I at risk of being too specific? Is this being too detailed?”

Maybe.

But I think both managers and direct reports can generally benefit from being more specific.

As a direct report, you often to need to “assign” tasks to your manager as part of managing up. I loved when my direct reports were clear in sharing exactly what they needed from me, by when, and why. I could get back to them much sooner and remove myself from their critical path. I might say “I can’t do that,” but I at least knew what they needed from me without a doubt.

As a direct report, I appreciated when my managers understood that I can’t read their mind. Being more concrete allowed us to have more productive conversations and allowed me to allocate my bandwidth accordingly.

In closing: You can use words like ASAP, time-sensitive, and priority. But don’t ONLY say that and expect your recipient to read your mind. Make sure to add more context by using the scripts above.

Thanks for being here, and I’ll see you in two weeks on Wednesday at 8am ET.

Wes

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• ✨ Improve your ability to sell your ideas, manage up, gain buy-in, and increase your impact in a 2-day workshop. Over 1,500 tech operators have taken this course, and every cohort so far has sold out. NOTE: The upcoming March cohort is 90% full. → Save your spot

👋 Hey, it’s Wes. Welcome to my bi-weekly newsletter on managing up, executive communication, and standing out as a high performer. For more, check out my intensive course on Executive Communication & Influence for Senior ICs and Managers.

⛑️ If you’re looking for 1:1 coaching, I typically work with director-level and above at companies like Amazon, Meta, DoorDash, Amplitude, etc. Learn more about my coaching approach.

Read time: 3 minutes

First, a few announcements:

1. As part of my yearly tradition, I’ll be taking a 4-week break from my newsletter for the holidays.

As usual, I’ll be taking the holidays to spend time with family, reflect on what I want to do more/less of, and set my intentions for the new year. I hope you have a wonderful holiday, and I’ll be back in your inbox on Wednesday, January 21, 2026.

2. Announcing: New March 2026 course cohort

I’ve opened a new cohort for March 2026. The course dates are Thursday, March 19 and Friday, March 20.

This year, I ran six cohorts and I’m humbled that every cohort has sold out. Over 1,700 operators have taken the course with a 4.6/5 star rating from 500+ student reviews.

Students and alumni are from companies like Uber, Amazon, Grammarly, Netflix, Workday, Meta, Google, Pinterest, Sephora, Twilio, Roblox, Shopify, Airbnb, Vimeo, Waymo, Figma, Unilever, HelloFresh, Cisco, Buffer, Peloton, 1Password, OpenTable, Microsoft, Lyft, Autodesk, Credit Karma, Stitch Fix, DailyPay, Lockheed Martin, Klaviyo, Hubspot, U.S. Bank, Novo Nordisk, Walmart, Plaid, Intercom, Coinbase, Coda, SoundCloud, Instacart, Samsung, Salesforce, Apple, Spotify, Anthropic, GitHub, Zillow, PayPal, Atlassian, Square, Stripe, etc.

If you’ve been wanting to invest in yourself and level up your executive communication, I hope you’ll join us. See the course details.

Here are my most popular posts from 2025. I’ve divided these posts into four categories. Feel free to start with the ones that jump out at you.

Happy binge-reading!

✨ Become a sharper operator

1. Why high performers make assertions: The difference between insights, suggestions, and assertions - An insight is just a starting point. The rare, courageous thing to do is to develop an assertion, i.e. a hypothesis and point of view that answers “so what?”

2. Stop apologizing for reasonable business decisions - Why saying sorry might unintentionally shift the power dynamics.

3. No, I don’t want to hop on a call - I do not want to hop on a call because you are too lazy to write a cogent message.

✨ Communicate more clearly and concisely

4. Take 3 minutes to delete these words and improve your writing forever - Before you hit “send,” delete these words from your writing. Your message will be stronger for it.

5. Use “but” strategically - “But” is a negating word. Here’s how to use this intentionally, so you sound direct and positive.

6. To sound more sincere, do this - If you aren’t careful, you may come across as less sincere because your writing doesn’t translate your intent.

✨ Improve how you manage up

7. Stop trying to change your manager - Because you don’t have the leverage to turn your manager into a different person. Here’s what to do instead.

8. Everything takes longer than you think - The problem isn’t that you’re not working fast enough. It’s that your expectations were never realistic to begin with.

9. What you give airtime to will expand - Successful operators intentionally direct their recipients’ attention. Focus less on what you can’t do, and more on what you can do.

✨ Become a better manager and leader

10. How to delegate while maintaining high standards - This is for managers who want to delegate AND maintain a high bar for quality of work. Here are tactics I learned over time that made delegating easier.

11. 7 Phrases I use to make giving feedback easier for myself - Here are practical phrases I use when sharing feedback because it allows me to speak freely.

Which of these are you most excited to read? Hit reply because I’d love to hear from you.

Thanks for being here, as always. Happy holidays, and I’ll see you in 2026.

Wes

Connect with Wes

• Is this your first time here? Subscribe (it’s free)

• Follow me on LinkedIn for more insights

• Learn more about 1:1 coaching to sharpen your executive presence

• ✨ Course: Improve your ability to sell your ideas, manage up, gain buy-in, and increase your impact in a 2-day workshop. Over 1,700 tech operators have taken this course, and every cohort so far has sold out. → Save your spot

👋 Hey, it’s Wes. Welcome to my bi-weekly newsletter on managing up, executive communication, and standing out as a high performer. To level up faster, check out my intensive course on Executive Communication & Influence for Senior ICs and Managers. You’ll learn alongside mid-career operators from orgs like Netflix, Stripe, Meta, OpenAI, Figma, etc. → Save your spot

Read time: 5 minutes

As an annual tradition, this week’s newsletter is a special edition where I share my top holiday gift ideas.

If you want my normal posts on becoming a sharper operator and leader, check out these popular articles:

• How to give a senior leader feedback (without getting fired)

• Signposting: How to reduce cognitive load for your reader

• Picking your battles when you are hyper-rational

• The unspoken skill of finesse

For everyone else, onward…

As usual, there are no affiliate links and I’m not an investor in any of these companies. These are simply products I personally use and believe are worth sharing.

Here’s the criteria for most of my purchases:

• Quality. I’d rather have fewer yet higher-quality items.

• Value. It’s an excellent value for how much utility it gives me.

• Form and function. It has to work well and be aesthetically pleasing.

• Delightful to use. It needs to be something I will reach for and love reaching for.

1. See’s Candies

I grew up in California, where See’s Candies is from, and I assumed everyone knew this delightful institution. Imagine my shock when I realized that most people haven’t heard of this brand. It’s a tragedy. There’s probably some aspect of nostalgia, but IMO See’s Candies is highly under-rated. My favorites are the dark caramel pattie—it’s dark chocolate with chocolate caramel on the inside.

For Christmas, I’ll usually get an box of assorted 1-2 lb box of chocolate and cylinder of Almond Royale to share. But I also insist on getting a separate box of the dark caramel patties that’s only for me. I save this precious box to stretch out the joy for as long as I can.

2. La Sportiva Bushido II shoes

A few years ago, I was going to hike the Chief in Squamish, British Columbia, and almost wore my All Birds from 2017. I am really glad I didn’t do this. Have you seen the soles of All Birds? There is literally zero grip. I’m pretty sure I would have died lol.

I asked my former coworker, who is one of the most outdoorsy people I know, if she had recommendations for good trail runners. She mentioned these shoes. I am obsessed with the amount of traction they have. I reach for these all the time, and use them for normal walks around my neighborhood.

For context, I have narrow feet, so if you have wider feet, these might be too narrow for you. Also, these shoes are very not waterproof, so if you want shoes that are waterproof/water-resistant, you may want to skip these or treat them with a waterproof spray.

I rarely ever re-buy a sneaker, but I bought another pair of Bushido’s recently. That’s how good they are. I believe there are different versions, so I can’t speak for newer iterations, because the ones I have are the Bushido II’s.

My husband Zak got the men’s Bushidos and he loves them too.

3. Round Lab Birch Juice sunscreen

Early in my career, I worked in the beauty/skincare industry. The Round Lab Birch Juice sunscreen is what industry insiders would call an “elegant formulation.” The texture is incredibly lightweight, easy to spread without tugging, and easy to absorb, so it doesn’t feel like you have anything on your skin. Plus, it’s fragrance free, which I like because I have an incredibly strong sense of smell and am picky about scents.

Normally, I buy one bottle at a time, but I actually got FOUR BOTTLES at once because it was a better deal on at Korean beauty site, and I was very confident that Future Wes would want to use multiple bottles of this stuff.

Zak loves this sunscreen too. He used to use Cerave’s Daytime SPF lotion, which he recommended in last year’s holiday gift guide, but now thinks that sunscreen is primitive compared to this Round Lab one. As two people who are very into sun protection, we both ogle at finding this sunscreen and are glad it exists.

4. Epicurean cutting boards from Crate & Barrel

Like every other person in their thirties and forties, I am now trying to reduce the amount of microplastics I’ve apparently been consuming my entire life. You thought you were safe and healthy by drinking tea? Joke’s on you, because there’s glue (plastic) on tea bags, and apparently everything else you come in contact with.

I used to have plastic cutting boards, but since learning that I’ve likely consumed the equivalent of multiple credit cards worth of plastic, I started looking for plastic-free alternative cutting boards. Wood is a classic choice, but I didn’t want the upkeep of oiling the wood or worrying about it cracking.

Enter: These Epicurean cutting boards. They’re made from a composite wood material, but are dishwasher safe and require no upkeep. I got a set of three sizes, and will probably get more.

These come in multiple styles, including options with grippy “feet” to prevent slipping, little grooves to catch juice when you’re cutting fruits/vegetables, etc. I got a minimalist version without rubber on the bottom because I like how simple it looks, but it does slip a bit. I’m okay with this, but if it bothers you, you may want to get the version that is non-slip.

5. IKEA fabric clothing storage

This clothing storage box/bin looks and feels more expensive than it is. It reminds me of the Monos packing cubes I recommended in my 2023 gift guide.

It’s high quality, feels sturdy, and comes in a nice neutral grey. Of all the IKEA clothing storage box/bin options, this one is by far the most aesthetically pleasing. I got multiple to put off-season clothing in.

This comes in different sizes, and I like the medium size (instead of the larger sizes because it’s easier to handle and keep clothing in certain categories. It’s easier to have all sweaters in one, then pants in another, etc. You could do a big size and mix items, but for me, I would probably end up forgetting what’s in the bin and needing to pull everything out to see what’s in it.

6. Tovolo classic popsicle molds

These were a Wirecutter recommendation for best popsicle molds, and they’re pretty great. I like how simple they are. There’s a practical little ledge on the popsicle stick that catches drips, and creates a semi-seal when the popsicles are forming. It’s relatively easy to take the popsicles out.

To recap, here’s the holiday gift list:

1. See’s Candies

2. La Sportiva Bushido II shoes

3. Round Lab Birch Juice sunscreen

4. Epicurean cutting boards from Crate & Barrel

5. IKEA fabric clothing storage

6. Tovolo classic popsicle molds

What’s calling out to you from this list? Hit reply because I’d love to hear from you.

Wes

PS For more inspiration, here are my holiday gift guides for 2023 and 2024.

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• Sell your ideas, manage up, gain buy-in, and increase your impact in my 2-day intensive course. Class starts in March 2026. Save your spot here: Executive Communication & Influence for Senior ICs and Managers

Read time: 3 minutes

Fundamentals is a new series that highlights my core frameworks in communication, leadership, and influence. Whether you're new here or a longtime reader, this concept deserves a spot in your toolbox.

This week’s fundamental principle: Strategy, not self-expression

Updated thoughts

• I originally wrote this post in November 2019, six years ago. And it’s STILL one of the most common posts I refer clients to during 1:1 coaching, and a framework I personally use multiple times per week in meetings and in writing.

• Originally, I wrote the post through the lens of giving feedback. But I’ve come to realize that “strategy, not self-expression” is so much more broadly applicable. It basically applies to anytime you want to sell any idea, to anyone.

• If you’ve ever wondered, “What should I say? What should I not say?” Think about “strategy, not self-expression.” It will help you focus your message and drive toward your ideal outcome.

• The best part about “strategy, not self expression,” is you have to ask yourself, “Will saying X get me closer to my goal?” My next thought is usually, “Wait, wtf is my goal with this conversation?” This is key, because I believe many of us are not actually sure what our goal is before we jump into action. By pausing to consider “What is my goal here?”, you’re already acting in a more strategic way than you were before.

• I realized, if self-expression makes me feel good—because let’s be real, there is a certain gleeful satisfaction I derive from venting or getting the last word—but it makes the other person upset or defensive for no reason, then what’s the point? I’m basically making it harder for myself to get what I want. I’m winning the battle, but losing the war. On the other hand, if I use a bit of self-restraint and stay focused on productive points, I can lead us to a win-win situation.

• I posted about this on LinkedIn and found these comments insightful:

Read the full article →

Do this today

After you read the full article, reflect on these prompts:

1. In what types of situations do you tend to veer into self-expression territory?

2. Think of a time when you focused on framing an idea to your recipient. How did that work better than a time when you were simply in self-expression mode?

3. The next time you’re in a situation where you want to persuade, think about what will get you closer to your goal. Ask yourself: Will saying this motivate the person to do what I want them to do? Is this strategy or self-expression?

Thanks for being here, and I’ll see you in two weeks on Wednesday at 8am ET.

Wes

Subscribe now

Connect with Wes

• Is this your first time here? Subscribe (it’s free)

• Follow me on LinkedIn for more insights

• Learn more about 1:1 coaching to sharpen your executive presence (now accepting clients for mid-February 2026)

• ✨ Course: Improve your ability to sell your ideas, manage up, gain buy-in, and increase your impact in a 2-day workshop. Over 1,500 tech operators have taken this course, and every cohort so far has sold out. The March 2026 cohort is now open for enrollment. → Save your spot

⛑️ To level up faster, check out my intensive course on Executive Communication & Influence for Senior ICs and Managers. You’ll learn alongside mid-career operators from orgs like Netflix, Stripe, Meta, OpenAI, Figma, etc. → Save your spot

⛑️ If you’re looking for 1:1 support, learn more about my coaching approach.

Read time: 4 minutes

“Could you review and give the greenlight on this?”

“Could you approve next week’s social media post?”

“Could I get an approval on this product flow?”

Depending on your role, you might ask your boss for approval once to several times a day.

Even directors and vice presidents need to manage up. And if you’re creating anything new, it makes sense to get buy-in each step of the way.

We can’t force our manager to approve our work, but we can embrace that it’s our responsibility to get better at securing their greenlight.

Getting the greenlight faster could save you hours per week. On the flip side, if you can’t get permission to proceed, your work might get stalled. And if your work gets stalled, you might later get blamed for delays.

When you ask your manager for approval, the top thing to do is: come prepared.

Your manager is ultimately responsible

Let’s say your manager takes “forever” to get back to you. Theoretically, if what you’re asking is simple, they should approve it quickly, right?

Not necessarily.

Your manager is ultimately responsible if anything bad happens on their team.

Let that soak in for a minute.

Your manager’s head is on the chopping block for any negative outcomes.

I didn’t fully appreciate this until I became a manager. I found myself hesitating to approve stuff that Past (Non-Manager) Wes would have expected her manager should instantly approve.

All of a sudden, I had to consider second-order effects, potential negative externalities, whether the output met the quality bar, etc. I didn’t want to say “looks good to me” if it didn’t, in fact, look good.

Ideally, the individual operator should feel accountable for their work. For what it’s worth, I only choose to work with people who feel personally responsible for their decisions. So if you are one of these people, keep that sense of care and integrity. It’s one of the most scarce things you bring to the table.

At the same time, any manager worth their salt is going to take responsibility when one of their team members messes up. A good leader is going to say,

“It’s on me. I should have caught that, or known better, or trained my team better.”

A good leader takes the heat on behalf of their team. Chances are, your manager has already (and continues to) take heat from their manager because of what you or your team has done.

Meanwhile, subconsciously, you know that once your manager approves, you’re kind of off the hook. “My boss said it was okay, so I did it.”

This is the real reason why managers and leaders can’t just quickly approve everything that comes across their desk.

Their job and their reputation is on the line in a way that yours isn’t.

Proactively share key information upfront

To empathize with your manager, think about the gravity of what it means when they give you their seal of approval.

So what can you do to make your manager’s life easier and get your work approved faster? There are things I personally do, and encourage my team to do:

Anticipate questions. If they’re likely going to ask you a question about X, you might as well ask yourself first.

Proactively share what your manager needs in order to make a good decision. Don’t force them to pull crucial information out of you! You are closest to a project, so you have context they don’t have. Decide what’s important to share, then volunteer this information proactively.

Be honest about potential risks, downsides, or sensitivities. When you proactively share what might go wrong, you show your manager that you’ve thought carefully about a project. This gives them confidence that you’re going in clear-eyed, and that you’re reducing the chances of unpleasant surprises.

Share information in a way that’s easy to digest. Do not bury the important part between paragraphs of secondary importance. This applies whether you’re speaking or writing.

Be explicit about what you need. Your manager wants to know: “How can I help you? What do you need from me?” I’ve listened to direct reports speak for 10 minutes, and at the end, still didn’t know what they wanted me to do. This is a good format to kick off the conversation so your manager knows what you need:

“I’d like to give you an update about X, and the thing I need from you is Y, ideally by Z date.”

Basically, don’t make your manager think too hard just to approve your work.

When you share an appropriate amount of context up front, they’ll be able to approve and get off your critical path. Then you can continue doing great work that makes you and your manager proud.

Connect with Wes

• Is this your first time here? Subscribe (it’s free)

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• ✨ Improve your ability to sell your ideas, manage up, gain buy-in, and increase your impact in a 2-day workshop. Over 1,500 tech operators have taken this course, and every cohort so far has sold out. → Save your spot

✨ Course update: Executive Communication and Influence for Senior ICs and Managers

You might be wondering, “If I’m an avid reader of Wes’ newsletter, is the course worth taking?”

Hundreds of students who love my newsletter have taken the course and found it extremely worthwhile.

This is because reading ≠ doing. In the course, the focus is on hands-on practice. Over 65% of the course is interactive, via exclusive exercises you cannot get anywhere else.

Here’s what previous students (and fellow newsletter readers) are saying:

“As a loyal reader of Wes’ newsletter, I loved the opportunity to learn even more from her firsthand, practice her strategies alongside other like-minded folks, and get feedback in real-time. And it was all packed into a brief time commitment that felt well worth it. I've already started using tactics from the course & seeing great results.”

- Ben Hannani Content Writer, Apple

“Structured course content distilled from Wes' newsletters. A good opportunity to take the time and work through those quick exercises to put those communication principles in practice!”

- Jorene Chai Staff Product Manager, Walmart

“I joined Wes' course as a fan of her newsletter, and I left with a sharper, more intentional approach to communication. I'm now more focused on reducing cognitive load for my receipts, and leading with clear, succinct messaging. Highly recommend this course for anyone who needs to align stakeholders or influence execs with clarity.”

- Sam Propis Staff Product Manager, WHOOP

“If you enjoy reading Wes' newsletter, sign up for the course now. It's one thing to read her blogs week after week, but watching Wes share her thought process live is invaluable. I've never seen anyone as eloquent, clear, and strategic--what a gifted and fun instructor. I've never been one for virtual courses but this knocked it out of the park.”

- Kathryn White, Marketing Manager, Proton.ai

The March 2026 cohort is currently open for enrollment. I hope to see you in class. → Save your spot

⛑️ If you’re looking for 1:1 coaching, I typically work with tech leaders on executive communication/presence. Learn more about my coaching approach.

Read time: 4 minutes

Operator #1 says to their manager: “How can I make your life easier? How can I add more value?”

Operator #2 says to their manager: “I noticed in our Monday morning meetings, we’ve needed to pull the X data and it’s a manual process. I’d like to create an automated table that tracks our weekly performance, so we can see trends more easily. This should take half a day to build. How does that sound?”

Which operator do you think adds more value?

It’s operator #2 for me. They noticed an area that was lacking, then suggested how to improve it in a way they could own fairly independently.

That’s adding a lot more value than putting the mental load on your manager to think about how you can help.

Asking how you can help is not as thoughtful as it seems

If you only ask your manager where you can help, your manager has to take multiple steps before they can accept your help.

Your manager has to consider:

• “What are all the things I need help with? There are a lot of potential things.”

• “What’s the overlap of things I need help with, that this person might actually have the skills, judgment, and capacity to do?”

• “How long would it take to explain this to them? This might actually cost me more time to teach them how to do this.”

• “How much do I believe in their ability to help?”

• “How much does this person already know? How much context do I need to get them up to speed?”

• “What's the risk if they mess something up?"

These questions come down to the ROI of accepting your help. Your manager is responsible for deploying you as an asset in a way that will maximize your value to the organization.

A good manager won’t simply dump stuff they don’t want to do onto you.

Why observing, asserting, and validating matters

Instead of only asking your manager where you can help, I recommend observing, asserting, and validating where you can help.

Observing matters for a simple reason: Your manager might not be able to articulate what they need. When you observe, you notice what might be helpful for your manager, even if they haven’t verbalized it.

To be clear, observing isn’t at odds with asking. You can ask AND be ready to observe. Look for clues, revealed preferences, implicit feedback, and what's unspoken. Observing is something you can do without anyone’s permission. You can start doing it today.

Asserting requires you to develop a point of view. In this case, you’re asserting a potential problem and what you could do to solve it. When you assert, you can be wrong.

But if everyone is scared of making assertions, then there’s no forward progress.

Everyone is too busy saying “Well, what do you think?”

And their peers say, “What do YOU think?”

“But what do YOU think?”

There’s no forward progress.

For further reading, here’s more on why high performers make assertions.

Validating. You do not need to fly blind. Once you assert, you should validate whether you’re going in the right direction.

It’s like playing Marco Polo. At every step, you’re checking to see if your assertion is directionally correct. What’s resonating with your manager? Where were you spot on? What else would do they suggest you look into?

Use this structure to assert your ideas

Let’s go back to the operator at the beginning of the post. The below script sounds simple, but it concisely captures all three parts of observe, assert, and validate:

Observe: “I noticed X. This is important because…”

Assert: “Here’s what I think we should do… / Here’s what I can do…”

Validate: “What do you think? / How does that sound? / Am I missing anything?”

So this is what it would look like in action:

Observe: “I noticed in our Monday morning meetings, we’ve needed to pull the X data and it’s a manual process. It requires about 2 hours of work each week, which adds up.”

Assert: “I can create an automated table that tracks our weekly performance, so we can see trends more easily.”

Validate: “This should take half a day to build and I'd like to take a stab at it. How does that sound?”

You want to be the type of person who takes work off your manager’s plate, not adds to it. You can ask how to make your manager’s life easier, but don’t only do that. Remember to observe, assert, and validate.

Thanks for being here, and I’ll see you in two weeks on Wednesday at 8am ET.

Wes

Connect with Wes

• Is this your first time here? Subscribe (it’s free)

• Follow me on LinkedIn for more insights

• Learn more about 1:1 coaching to sharpen your executive presence

• ✨ Course: Improve your ability to sell your ideas, manage up, gain buy-in, and increase your impact in a 2-day workshop. Over 1,500 tech operators have taken this course, and every cohort so far has sold out. → Save your spot

⛑️ If you’re looking for 1:1 coaching, I typically work with tech leaders on strengthening your executive communication, including how you position yourself and your work. Learn more about my coaching approach.

Read time: 7 minutes

NOTE: I originally started this draft 7 years ago (!). I’m keeping it as is, mainly because I want to preserve the frustration I felt at the time with experiencing reverse imposter syndrome.

I’ve done a ton of work to improve my reverse imposter syndrome, and have since helped dozens of clients do the same. I hope this post brings you solace and a new perspective on your own situation.

Recently, I’ve had my ears perked about imposter syndrome because I realized that I have the opposite of imposter syndrome—and my hypothesis is that many people who think they have imposter syndrome actually have the opposite.

I’m calling it Reverse Imposter Syndrome.

I basically realized I didn’t have imposter syndrome, but rather the opposite: that I’m quite good at my craft, and people who see my work up close would agree. The problem is: very few people see my (and your) work up close.

Sometimes I’m shocked at the hard problems I’m solving on a weekly basis and the elegant solutions I create. If you work in-house, your work is likely locked behind closed doors. Even your manager or close colleagues might not know the creativity that goes into the hardest parts of what you do. Literally the only people who see it are 1-3 people who you work most closely with.

It’s also likely that you don’t tell customers how the sausage is made. The reward for elegant solutions is the customer taking the action you want them to take. Again, in this situation, the customer and your own internal team do not see the work behind-the-scenes.

Most people judge us based on external signals, such as your most recent job title, how famous your past employers are (all the ex-Meta, ex-Amazon, ex-unicorn employees), etc as proxies for how good you are.

My worry isn’t that I’m not good enough. It’s that I’m good, but there aren’t enough external signals and clues for outsiders to see it.

Reverse imposter syndrome is a perception problem

The idea of imposter syndrome is widely known. There are debates surrounding the idea, but it’s generally defined as “A cognitive bias where someone feels like they are undeserving of success and are not competent. People with imposter syndrome may struggle to attribute their successes to internal factors.”

People online seem to say the opposite of imposter syndrome is the Dunning-Kruger effect, where one has “excessive confidence in their abilities, even though their actual skills don’t match up.”

What I’m talking about is different:

I define “reverse imposter syndrome” as primarily a perception problem.

You are confident in your abilities, but the external signals and clues about your work understate your actual ability.

If imposter syndrome is worrying that you’re not good enough or don’t know what you’re doing, then reverse imposter syndrome is the opposite: You know what you’re doing, you’re confident in your ability to deliver (and have the track record to show for it), but your external “brand” doesn’t reflect the strength of your actual abilities.

Another way to put it:

• Imposter syndrome is other people thinking you’re good, but you still don’t believe it for yourself on the inside.

• Reverse imposter syndrome is knowing you are good, but others don’t believe it (as much as you know it to be true).

Who might experience reverse imposter syndrome?

Many of my 1:1 executive coaching clients face reverse imposter syndrome.

In my experience, the operators/leaders most prone to having reverse imposter syndrome are folks who:

• are hard working

• don’t usually seek the spotlight

• got to where they are because they are sharp and able to drive results

• are used to their results “speaking for themselves”

• are traditionally more comfortable doing the work vs talking about the work

To be clear, reverse imposter syndrome is not an excuse to delude yourself into thinking you are actually better than everyone thinks you are. The people closest to your work (who have visibility into your skills) should believe you do excellent work, and you should have a track record that speaks to the outcomes you’ve driven.

Reverse imposter syndrome often involves how leaders are perceived by those around them.

For example, there is a difference between being strategic and being perceived as strategic. Many of the clients I work with have been driving strategy for years, but due to the way they speak about their work (in a way that’s overly tactical) or because most of their contributions were behind-the-scenes, they aren’t seen as strategic leaders. The people around them don’t view them as strategic.

To take action on this feedback, they should not necessarily learn to be strategic (we are assuming they already are). The way to combat this perceived lack of strategy is to actually speak more often and in a more compelling way about their strategies, be more vocal about their vision, share learnings more broadly with folks outside their own team, etc. Think of it as doing a mini PR campaign where you systematically update how you and your work are positioned. This is something I help clients with.

Folks who deal with reverse imposter syndrome have spent years driving results. So now they need to devote attention to learning a new skill: how to be perceived as someone who drives results.

I think all of us want our outsides to match our insides. It’s quite painful to know you are very good at your job, but know that other people don’t recognize this. For me, I felt resentful and jaded, and upon reflection, jealous of my coworkers who were better at talking about their work than I was.

At first, I tried to explain the problem away by saying people who know how to talk about their work as simply “great talkers.” But I took pride in being a “great doer.” I subconsciously felt like learning to promote my work was beneath me. I’ve since changed my mind on this completely.

I believe it’s every operator’s responsibility to invest in learning how to try to have your outsides match your insides. If we as a society want “deserving” people to rise to the top, then “deserving” people (that’s you) have to learn how to promote their work in a way that feels authentic and grounded.

Internal vs external work

So what should you do?

The go-to solution for normal imposter syndrome is primarily internal. You want to improve your own confidence, to help your own brain “catch up” and “update” your thinking to reflect how good you actually are.

The solution for reverse imposter syndrome, though, is external. If you have reverse imposter syndrome, you should work on how you’re positioned in the minds of others. This includes your colleagues, manager, senior leadership, etc.

I believe most posts about “personal branding,” “increasing your visibility,” and “how to talk about your work” are too surface-level and kind of cringe. Those tips might work if you are trying to grow your audience on social, but they do not work if you are an in-house operator who works with sharp leaders with good taste, who are not easily fooled.

After years of helping tech leaders position themselves and their work (resulting in successful promotions, getting invited to present to senior leadership, getting tapped for high profile projects, etc), I do not believe “positioning yourself” is one topic.

It’s actually a bunch of different sub-skills and behaviors that allow you to be seen as the competent, strategic operator you are. And you do these activities over time, consistently, to change how you are perceived.

If you want to work on your positioning, here’s more I’ve written on the “how”:

• How to position your work as strategic

• How to build a business case

• How to present to your CEO

• How to build your personal credibility (not your personal brand)

• How to control the narrative if your work is being questioned

• How to remove “insecure vibes”

• How to improve your finesse

• How to frame work requests (they are not “favors”)

• How to get an enthusiastic yes

• How to talk about deadlines at work

If you feel uneasy about your competence, your mind might jump to the conclusion that “I have imposter syndrome.” We’re so familiar with the phrase it seems like the uneasiness must be attributed to that.

But now that you have the language to identify reverse imposter syndrome, consider if that might be what you’re actually dealing with.

Thanks for being here, and I’ll see you in two weeks on Wednesday at 8am ET.

Wes

Connect with Wes

• Is this your first time here? Subscribe (it’s free)

• Follow me on LinkedIn for more insights

• Learn more about 1:1 coaching to improve your executive presence and address your reverse imposter syndrome

• ✨ Improve your ability to sell your ideas, manage up, gain buy-in, and increase your impact in a 2-day workshop. Over 1,500 tech operators have taken this course, and every cohort so far has sold out. The October cohort is sold out. The new March 2026 cohort is now open for enrollment. → Save your spot

NOTE: The October cohort is the last cohort of the year and is currently 95% full. It will sell out in the next few days. If you’d like to join us, I recommend signing up today. → Save your spot

Read time: 4 minutes

I’m excited to share a new newsletter series called Fundamentals, which will highlight my core concepts in communication, leadership, and influence.

Even as my newsletter has grown to 75,000+ subscribers, I often find myself referencing these principles with clients and in my own work. Whether you’re new here or a longtime reader, this concept deserves a spot in your toolbox.

This week’s fundamental principle: Start right before you get eaten by the bear

Updated thoughts

• Since publishing the post, some readers have asked, “What if the backstory really is important? Or interesting?” If it’s important or interesting, I wouldn’t call it backstory. This might be semantics, but I define “backstory” as information that’s ancillary, historical, not super related, nice-to-know. If what you want to share is truly crucial (and/or fun for the person to hear about), go ahead and include it. In other words, use your judgment about what you want to include.

• Most of us remind ourselves to be more concise, but there’s something about “start right before you get eaten by the bear” that is much more memorable and visceral.

• Some readers have told me they have Post-its by their computer monitors with the phrase “Start right before you get eaten by the bear.” I’m a fan of visual reminders, so this was especially cool to hear.

• When you become aware of “start right before you get eaten by the bear,” you start noticing how much time we all waste on backstory. You start noticing how other people’s backstory is not helpful as they think it is. Which helps YOU realize that your backstory is probably not as necessary as you think, either.

• I came up with this framework after learning the hard way. I’ve absolutely wasted 25 minutes out of 30 minute calls on backstory. Of course, I regretted it every time. Now, I ask myself, “How can I explain my situation in the briefest way possible, so I can give the other person more time to speak?”

• I posted about this on LinkedIn, and the comments were hilarious and spot on:

And here are some reader comments I thought were particularly salient:

• “It's funny [that] as a listener I don’t want a lot of backstory, but when I'm speaking, I feel like I need to provide a lot of backstory. Trying to get that paradox in sync.” - Tim Whitley

• “I find that when I want to go heavy into my back story - typically it's because I doubt my main point is strong enough to stand on its own. If I trust my idea and am primarily focused on providing value to my reader (rather than soothing my ego or making myself appear better/smarter) - this is much easier to do.” - Vanessa Hernandez

• “In a post that went out this morning, I initially had a ton of backstory. I thought it would give context. It didn’t. I hacked 2 paragraphs into 3 sentences, and it was exactly what the story needed.” - Kevin Alexander

• “All the examples really helped to show how painful it is for listeners when too much backstory is shared. I’ve been in so many of those meetings and listened to so many YouTube videos like that - 27 mins long to change a light bulb, or similar 😂” - Caleb Mellas

• “Dang! As a recruiter, I see this everyday with myself, my clients and candidates. I will be more conscious of the backstory creep and politely steer conversations to the main points.” - Joseph Waruiru

Read the full article here →

Do this today

After you read the full article, consider these prompts:

1. When are you most susceptible to sharing too much backstory?

2. What’s an occasion this week where you’ll practice starting right before you get eaten by the bear?

Thanks for being here, and I’ll see you in two weeks on Wednesday at 8am ET.

Wes

Connect with Wes

• Is this your first time here? Subscribe (it’s free)

• Follow me on LinkedIn for more insights

• Learn more about 1:1 coaching to sharpen your executive presence

• ✨ Improve your ability to sell your ideas, manage up, gain buy-in, and increase your impact in a 2-day workshop. Over 1,500 tech operators have taken this course, and every cohort so far has sold out. The October cohort is the last cohort of 2025 and is currently 95% full. If you’d like to join, I recommend signing up soon. → Save your spot

⛑️ If you’re looking to dramatically improve your communication and leadership, I typically work with tech leaders on: managing up to a CEO/SVP, advocating for your ideas, and strengthening your executive communication/presence. If you’re interested in how I can support you, learn more about my coaching approach .

Read time: 8 minutes

There's a popular saying that “‘no’ is a complete sentence,” and I would categorize this under “advice that sounds good in theory but is dangerous in practice.”

I appreciate the sentiment, which is meant to help empower people to set boundaries. I’m all for setting boundaries. But I find a lot of advice around this topic is too black and white, and I’m afraid people will take the advice literally and get themselves into trouble.

Straight up saying “no” might work in some settings, but in my experience, it can sound too harsh in many workplace cultures.

If your colleague has LEGITIMATE BUSINESS REASONS to ask you to do X, and you simply turn around and say “no,” you will sound like a jerk.

Even if your colleague has no grounds to be asking, you may still want to say “no” more politely.

Doing otherwise has a cost, which is that you come across like the bad guy…even when you’re not.

Part I: Power dynamics and validity of the request

I posted about this on LinkedIn, and a reader said (paraphrased), “You have to use flowery language for corporate, but in startups, it’s sufficient to say ‘sorry man, I can’t.”

As someone who’s spent 15+ in startups, I disagree that “sorry I can’t” is enough for most situations.

I would argue the two variables to take into account are:

1. Your power dynamics with the individual

2. The legitimacy of the business request

How valid is the request?

If a stranger is emailing you asking to pick your brain for free, you don’t owe them an explanation for saying no. You don’t even owe them a response.

But if your coworker is asking you to do your part in a project because it’s your job, you actually do owe them an explanation.

Think of how weird and confusing this would be if we all declined work requests without sharing our rationale:

Marketer: Hey design counterpart, could you design this infographic for our launch campaign?

Designer: No.

Marketer: Oh…okay. Um, You’re our brand designer, and part of your role is literally to design assets for marketing though?

Designer: *Shrugs*

Marketer: Could you share why you aren’t able to help? Should I share more context or something?

Designer: I don’t owe you an explanation.

Marketer: …

What are the power dynamics?

If you’re an SVP and an intern asks you to do something that’s clearly low priority, you can easily say no without explanation.

Even then, a 1-2 sentence explanation could be valuable because this is a learning moment for that intern about ROI, how to tell if something is worth doing, etc.

If a fellow SVP or your CEO has a legitimate request for you, you want to tread more lightly. Otherwise, it's understandable if they feel frustrated, confused, or think you're shirking your responsibilities.

Adding 5 seconds of context helps your recipient understand, which is better for everyone.

Part II: How to say no without sounding harsh

Luckily, there are easy ways to say no AND still sound collaborative.

You protect your boundaries, while showing you are a team player who cares about the broader business beyond your individual scope.

The goal is not to be nice for the sake of it. If you seem like a jerk, your coworkers are less likely to help you when you need it… and they may retaliate.

The next time you have a reasonable ask for them, they might say “no” without further explanation, and expect you to deal with it.

Here’s what you can do instead:

1. Focus on what you can do. End on an affirmative.

Use “but” strategically to offer what you can do. The structure is: “I won't be able to do that, but I can do this.”

🚫 “No.”

✅ “I won’t be able to participate, but this sounds like a cool project.”

✅ “I won’t be able to participate, but this sounds like a cool project. Perhaps you could ask X to see if they can help?”

✅ “I won’t be able to take on this project, but if it’s helpful, I can take a quick look to give feedback when you have a first draft.”

More on how to use “but” strategically.

Subscribe now

2. Cite trade-offs.

There are trade-offs with every decision. But those trade-offs are often not always top of mind. Make it top of mind for your recipient.

This tactic works best if the person has asked you to do other things.

🚫 “No.”

✅ “I can do [this new task], but it will mean delaying [this other thing you want me to do]. Which do you want to prioritize?”

3. Get more info to make an informed decision.

I’m all for protecting boundaries, but don’t assume your default answer should be no to a request. Try to get more information so you can make an informed decision.

🚫 “No.”

✅ “Could you share more about what this is for?”

Sometimes my answer is then, “Ah okay, I won't be able to do X, but I can do Y, which is actually even more useful for you and will be a faster turnaround time.”

If you understand the context behind their request, you might be able to support them even more effectively.

Or you might realize their original request makes sense as is, and takes precedence over what you’re currently working on.

4. Add “because” to share your rationale.

According to a study done by Harvard researchers in the 1970s, the word “because” makes you more persuasive regardless of the actual reason that you cite.

Instead of only saying “no,” add a “because.”

🚫 “No.”

✅ “No, because our current system won’t allow us to do X so we created a workaround.”

✅ “I won't be able to do that because our team is focusing on [business priority] right now.”

✅ “I'll need to check with [manager] because I’ll need to see if I have bandwidth to add that to my plate given current priorities. Let me get back to you.”

5. Avoid the word “no” altogether.

Notice how in many of the examples above, I avoided saying the word “no” altogether.

This is intentional. “No” can feel inherently more negative, and I can easily say the same thing without that emotional sentiment.

There’s no need to ban a word, though. If someone says “Is there a delay?” I will say “No, there’s no delay.” There’s no need to do mental gymnastics, so use your judgment.

5. Give the benefit of the doubt.

If a coworker is being an asshole or overstepping, I will ramp up my “don’t mess with me” energy. You should use your judgment about who you give the benefit of the doubt to.

But generally, saying “no” without explanation feels too rough for me to realistically say to colleagues I like working with.

If you work with generally competent, well-meaning people, it makes sense to assume they have a reasonable reason for asking.

You might think, “Wes, people understand ‘no is a complete sentence’ is not meant to be taken literally.”

TBH I’ve been surprised by how often people take things literally, so it’s worth mentioning out loud. I don't want you to accidentally damage your relationships.

Also, if your initial thought is, “Well Wes, you can't expect me to spend 15 minutes explaining a ‘no’ that should be straightforward.”

We're not talking about 15 minutes. We're talking about 5 seconds. Don’t be dramatic. The extra few seconds gives your teammates context so they can better understand.

I choose to offer my rationale because it helps me AND my counterpart come to a better decision about what's best for the business.

To recap:

1. Focus on what you can do. End on an affirmative.

2. Cite trade-offs.

3. Get more info to make an informed decision.

4. Add “because” to share your rationale.

5. Give the benefit of the doubt.

Which are you most excited to try in your own work? Hit reply because I’d love to hear from you.

Thanks for being here, and I’ll see you in two weeks on Wednesday at 8am ET.

Wes

Connect with Wes

• Is this your first time here? Subscribe (it’s free)

• Follow me on LinkedIn for more insights

• Improve your ability to sell your ideas, manage up, gain buy-in, and increase your impact in an intensive 2-day workshop. → See course details

• Learn more about 1:1 coaching to sharpen your executive presence and influence

✨ Course update: Last cohort of 2025

The October cohort is 70% full, and will fill up in the next few weeks. The next time the cohort will run is mid-2026, so if you’re interested in the course, you may want to sign up sooner rather than later.

On a related note, a common question I get is, “Can I take the course with my team?”

The answer is yes. Teams at Meta, DailyPay, Shopify, etc have already done the course as a team. In every cohort, there are several teams who participate. The course is designed for groups to take together because it will help you develop shared language and shared expectations.

Here are reviews from the most recent cohort a few weeks ago (August 2025):

“I really loved this course. I have followed Wes for some time and it was great to be able to interact with her and receive actionable feedback on my communication. This course has direct application to my day to day work and I already have so many ideas on how I can improve in my communication.”

- Derek Colvin, Sr Director of Product Management @ Abercrombie & Fitch

“In my 10-year career working in a range of startups and with various types of managers, this has been the most valuable course for being able to create actionable changes to how I communicate straight off the bat. I cannot recommend this course enough - you will gain so much from it, no matter your role, where you sit in your company, and what your communication default is currently.”

- Grace Homer, Content Marketing Manager @ Virtual Internships

“Long-time reader and fan of Wes's newsletter and to be able to take her course live was INCREDIBLE. Such simple frameworks with huge impact. I have a much clearer understanding of my strengths and weaknesses in my communication now. Also, learning from peers in the course was eye-opening to see different styles I can adopt myself. No question—take the course today.”

- Katrina Honer, Corporate Operations Program Manager @ Stanford

“After coming into a role that has a lot more touchpoints with execs and board members, this course has given me the tools (and more confidence) to communicate with these individuals (hopefully with much less anxiety).”

- Zheng Wang, Director, Internal Audit @ Sonos

Great course! So much material, insight and tools packed into two days, most of which is immediately applicable to work. Wes covers a lot of ground from theoretical principles to workshopping Slack messages which was so useful.

- Patrick Bowen, Staff UX Researcher, Google

If you are taking the course with a group of 5+ team members, email me to get the team discount. I hope to see you in class. → Save your spot

⛑️ If you’re looking to dramatically improve your communication and leadership, I typically work with tech leaders on: managing up to a CEO/SVP, advocating for your ideas, and strengthening your executive communication/presence. If you’re interested in how I can support you, learn more about my coaching approach .

Read time: 7 minutes

In the past 17 years of reporting to different managers, coaching tech operators on managing up, and teaching 1,300+ students in my course, I’ve come to realize that a lot of issues can be solved if you realize one thing:

You can’t really change your manager.

Let me explain, and share why this matters more than you think.

In a flat team structure, you and your manager might act like equals 99% of the time.

But in the 1% of of the time when there’s a difference, you need to cater to them. You mold yourself around them. This is how the manager/direct report dynamic works.

At this point, most folks say one of two things:

1. “But Wes, talking about power dynamics in this way is self-defeating. It’s so negative. It doesn’t have to be this way. I have a great relationship with my manager / direct report!”

2. “I’m not trying to change my manager, so I’m good. I don’t need to read this.”

For point #1, I’ve been fortunate to have strong relationships with managers and direct reports over the years. I’ve kept in touch with many of them as friends long after we’ve gone our separate ways. This doesn’t change the fact that there is still an underlying structural dynamic between a manager and a direct report.

For point #2, I find people think they’re not trying to change their manager, but then behave in ways that show they actually, in fact, are hoping to change their manager.

The fact that there is a power differential isn’t good or bad. It isn’t positive or negative. It simply is.

And the fact that most people automatically think this is bad and must be fixed or can’t be spoken out loud, is why I want to talk about this topic.

The structural dynamic of a manager/direct report relationship dictates that in the 1% of the time when one person’s preferences outweigh the other’s, your manager’s preferences will take precedent.

In productive environments, 99% of an issue is decided based on objective reasoning, logic, rationale, etc. I’m a huge proponent that every person has to defend their point of view, regardless of if you’re co-founder or the most junior team member. I hate when people pull rank, or think they’re above needing to explain themselves.

I’m talking about the 1% where there’s a standstill or deadlock, or where there’s simply a philosophical or values-driven difference in how you and your manager see the world.

These situations are not necessarily solved by logic, because two people with great logic can have different worldviews, and be equally right.

Part I: “Shouldn’t we meet in the middle?” and other unproductive mental models

Your manager has to like you to bring you deeper into their inner circle. Your manager has to find you valuable to advocate for and promote you.

Your manager doesn’t quite need you in the same way. Obviously, if their team were unhappy or ineffective, this would reflect on their effectiveness as a manager/leader, which would affect their ability to advance.

But as long as their teams are relatively happy and performing well, they don’t need your advocacy in the same way that you need their advocacy. Instead, they need THEIR manager to advocate for them.

(Now, your manager can’t directly control you or any of their team members. They must get things done THROUGH you, which means they must influence. So managers are not all-powerful by any means.)

If your manager finds it difficult to communicate with you, there’s always friction, and you just don’t get along that well, it doesn’t matter if this conflict is due to their personality defects.

I repeat: It doesn't matter if the tension is technically “their fault.” You have to find a way to deal with it, or work for someone else.

This might seem obvious, but I don’t think it is. I used to subconsciously resent that I had to change myself to fit around my manager's personality.

Shouldn't we meet in the middle?

What if their personality is objectively what's causing an issue--doesn't that count for something?

Why do THEY get to be how they are, but I have to change myself to fit around them?

It all felt… unjust.

This was an unproductive line of thinking for one reason: I didn’t have the leverage to change my manager into a different person.

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Part II: How to apply this to your relationship with your manager

So if you can’t change your manager, what does this mean? Here’s what you can do:

1. Structural dynamics and incentives win over “fairness”

If you expect “fairness” to win out, you will always feel slighted if it doesn’t.

So realizing that my manager’s preferences will take precedence was freeing for me. If “fairness” were the dominating factor, perhaps they should change. But since the structural dynamic is the dominating factor, it explains why they don’t have to change.

When you understand that, you can relax and stop blaming yourself.

2. Ideally, you should be simpatico from the start

Years ago, I read that you can never break in shoes, and when I saw that, I thought omg this is truth. Most of my shoes that fit, actually fit from the beginning.

It’s a matter of degrees. When I thought “I can break in these shoes,” I would buy shoes that clearly weren’t the shape of my actual foot, rubbed my ankle, were too loose/too tight, and think, “Oh, I can break these in.”

No. No, my friend, you cannot.

What “you can break shoes in” really means is, sometimes, if the shoe is the right material, you can change the shoe by, like 10% maximum. That’s as much as they’ll change to accommodate your foot. Otherwise, the shoe is the shoe. It is the way it is.

Also, to continue this analogy probably further than it needs to go:

Even for shoes that were comfortable from the beginning, they STILL kind of hurt after 10 hours of wear. Even the best fit/most comfortable shoes, after the demands of reality and usage, were still a little uncomfortable.

This means you really need to find shoes that almost feel laughably comfortable when you try them on, because when it interacts with reality, you will need that level of fit to make it work.

I know we often don’t get to choose our managers, but this was still valuable for me because it made me more intentional about the kind of people I want to work with.

3 Assess your level of leverage more accurately

We waste a lot of energy trying to change things we can’t change. Once I stopped subconsciously trying to change my manager, I could redirect that energy into areas where I could affect change.

This is not about “being more positive.” It’s about accurately assessing your leverage. If you misunderstand or miscalculate where you have leverage, you expend your energy accordingly.

Where people go wrong is when they THINK they have more leverage than they actually do. For example, when a salesperson slides into your DMs and demands to hop on a 30-min call, they have misread their leverage.

4. Try to make the most of your time together

I've had the most productive relationships with my managers when I've accepted them as who they are, and tried to learn as much from them as I could.

Instead of trying to force them to embody the type of ideal manager I wanted, I saw them for who they are and tried to appreciate the worldviews they had.

To do this, I tried to adopt their worldviews as a “hat” or “lens” I could take on and off. What was it like to make decisions through their lens? If I prioritized the things they prioritized, how would that impact what I did and how I did it?

You won’t report to your manager forever. You can take the best parts of what you learn from them and use it to inform how you want to lead yourself.

Thanks for being here, and I’ll see you in two weeks on Wednesday at 8am ET.

Wes

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✨ Course update: Executive Communication and Influence for Senior ICs and Managers

Last week, I wrapped up an incredible two days with the August cohort. Here’s what students who just finished the course are saying:

“Wes’s course helped me grasp the subtle but powerful difference between being good and being great at communication—a nuance I’d struggled to define until now.”

- Harshul Madan, Staff Product Manager @ Apple

“Lots of no BS suggestions you can apply to see immediate results, let alone the long-term effect if keep practicing to build muscle memory like you do in any sport. Helps you strengthen your form and elevate your baseline. TL;DR: Highly recommend if you’re looking for tons of practical knowledge and exercises—enjoy drinking from the firehose!”

- Tairan Zhang, Manager of Advanced Analytics @ Walmart

“All of the best wisdom from Wes bundled into two days. Now, I work with Wes' voice in my head, pointing out where I can be more clear, concise, and impactful.”

- Jess Mireau, CPO @ Kettle

“Incredible course. It is jam-packed with actionable frameworks and tips that will immediately uplevel your communication game. Wes provides a core foundation with exercises to help shift your thinking, allow for reflection and learning, and immediately make improvements to becoming a more intentional, effective, and efficient communicator. She is also an exemplary speaker—wastes no words, with high-value content.”

- Frances Karandy, Product & User Research @ Glean

“Really loved the structure of the course and the fact that it was compressed into just 2 days. Highly contextual to daily situations that happen and the comms challenges you run into especially in executive communication situations. Recommend this to anyone trying to uplevel their communication skills to succeed in their organizations.”

- Kanishk Dutt, Lead Product Manager @ DoorDash

“I love how this course takes all the wisdom of communication and distills it into concrete, implementable steps that are highly applicable to day-to-day situations at work (and in life).”

- Vincent Hu, Data Scientist @ Figma

Reminder: The upcoming October cohort will be the last cohort of 2025. The course dates are October 9 & 10. If you’ve been wanting to grow your impact and influence, this is your chance.

I hope to see you in class. → Save your spot

Read time: 7 minutes

Empathetic leaders often do a lot of invisible emotional labor.

One newsletter reader said this:

“I consider myself an empathetic leader and after conversations sharing tough news, I tend to have 1:1s with my team members so I can do a sentiment check after. While I am happy that they share openly with me, sometimes these conversations become about everything at work they don't like. How would you recommend handling this?”

Yes, your team should be able to talk about problems at work and how it’s impacting them.

At the same time, this is a matter of degrees. After a certain point, the more you only focus on what’s wrong, the more your team may feel angrier and more disempowered.

Putting a limit on your team sharing their frustrations prevents you from feeling drained and emotionally dumped on.

Setting that boundary is useful for both you and your team.

Here’s how:

1. Don’t try to be their therapist.

I believe most managers act as therapists sometimes, in the sense that you listen and support.

But as a manager, you must assess your direct reports’ work and potential.

Therefore, there’s a conflict of interest that actual therapists don’t have.

If your team thinks they can share all their frustrations completely unencumbered and at full strength, you can’t help but take this into account when considering their ability to be promoted. You can’t help but judge their emotional regulation and ability to handle stress.

In other words, you don’t want to mislead your team into believing they can talk to you too openly.

You want to listen AND you want them to be remember that you are still their manager—mainly for their own sake.

2. Listen, then direct the conversation in a more actionable direction.

I like to let the person share and to listen thoughtfully. Then, I try to direct the conversation in an actionable direction:

• How can we make this better?

• What’s within our control that we can do?

• How can I (their manager) potentially provide air coverage in the meantime?

For example, you can say something like:

“I hear you that X is really frustrating. I agree it shouldn’t have to feel this hard and you’ve been handling it well so far. What can we do to potentially improve this? What might help you feel more confident and grounded in this situation?”

^ Notice how I’m directing the conversation away from venting, and toward what we can do about the problem. You want your direct report to start thinking of potential solutions, and to know you support them in figuring out a solution.

The more airtime you give a topic, the more concrete and real it becomes. Obviously, this does not mean we can only talk about happy things and pretend problems don’t exist.

It means to find balance in:

(A) allowing direct reports to speak openly, knowing they can air their grievances

and

(B) reminding them that as individuals who have agency and your full support, it’s also part of their responsibility to try to think of a solution.

More on what you give airtime to will expand.

3. Don’t jump too quickly to offering solutions.

One of the common mistakes I see when leaders try to execute this empathetic-yet-realistic approach is they move on TOO quickly to a solution.

When you go straight to a solution without acknowledging what you heard, it reads like you’re dismissing them. It sounds like you were waiting for them to finish, so you could solve this and move on.

This might be efficient, but it’s not effective, because your team member likely doesn’t only want solutions--they also want to feel heard.

Instead, spend a few minutes restating what they said, so you demonstrate that you were, in fact, listening.

🚫 “Hmm I agree, this isn’t ideal. What might we do to improve this situation?"

✅ “Hmm I agree, this isn’t ideal. I knew this was a challenge but I didn’t realize until now that it was taking this much of your bandwidth every week. I’m glad you’re speaking up because I can see why you’re feeling frustrated. What do you think we could do to make this better?”

Notice the “after” was still concise, but comes across as more sincere. I wrote more about the “add one more line” rule.

4. Push back gently to encourage a right-sized reaction.

If I believe my recipient is being a bit hyperbolic, I may push back gently to help them see the situation through a different frame.

This is not only kind, but necessary.

If your direct report has an aggrandized extreme view of the situation, this has a real cost. Due to their beliefs, they may act assuming they have a moral high ground for being right, when in fact they have an incorrect or incomplete mental model about the situation.

You could say something like,

“X is definitely frustrating--[add an extra line about this so they see that you understand]. At the same time, we don’t want to catastrophize. X is a change for sure, but in some ways, it’s not super different from what we were doing before. For example, [ways the new process is similar to the old process]. But I totally see your point and agree the change will take some time to get used to.”

or

“I hear you that during launches, it’s a more hectic time. I’m here and ready to support, and I’m going to need to rely on you to tell me how I can help. Also, on the bright side, we have to do X every few quarters, so while this does make things more hectic, it’s also cyclical. We know this too shall pass. We know things will feel upended for a week or so, then will settle into a new rhythm, so I want us to remember that too."

I feel like modern discourse is often about how you should let people feel how they feel, there's no wrong way to feel, everyone processes news differently, etc.

And while I generally agree, I believe it’s our responsibility to help our team develop right-sized reactions or correct mental models about what’s going on around them.

In my first job out of college, I remember a VP at Gap Inc telling our team,

“It’s the holiday season. This is our busiest quarter and things will feel a bit nuts. This happens every year, and every year we get through it. Let’s hang in there.”

I remember thinking, “Oh yeah, this does happen every year. Okay this isn’t THAT bad. And even if this is a more stressful period, it’s a time-bound problem. It’s not going to last forever.”

More on how to help your team develop right-sized reactions.

Remember: If your team has gone too far into venting mode, this may impact their performance and feed delusions that aren’t useful for anyone.

I think most leaders focus 100% on validating their direct reports (to the point of feeling emotionally burdened and accidentally creating an overly-negative conversation) because pushing back (of any sort) creates a micro-moment of friction, which is inherently riskier than only listening.

But as a manager, you can listen thoughtfully, honor what they’re sharing, and help guide the conversation in a productive direction.

Your goal is to be both empathetic and real with your people, which I believe is ultimately what they want from you.

To recap, here are the four points:

1. Don’t try to be their therapist.

2. Listen, then direct the conversation in a more actionable direction.

3. Don’t jump too quickly to offering solutions.

4. Push back gently to encourage a right-sized reaction.

Which jumped out at you? Which 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 in two weeks on Wednesday at 8am ET.

Wes

Connect with Wes

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✨ Course update: Last cohort of the year

The August cohort is now sold out, and I’ve opened a new cohort for October 2025.

Heads up: The October cohort will be the last cohort until mid-2026. If you are interested in taking the course, I highly recommend joining the upcoming cohort.

Here’s what students from the most recent cohort are saying:

“I loved this course. The structure was perfect for the audience, with practical exercises to work on independently or as part of a small group. I learned a huge amount during the two days.”

- Jessica Phillips, Senior Operations Manager @ Uber

“Wes is the real deal. Her Substack newsletter has already been immensely helpful to learn from; her course takes it to another level. I'm so glad to have joined this recent cohort. For upskilling in executive communication and managing upwards, I don’t think it gets any better than Wes and her course!”

- Petronio A, Senior UX Researcher @ Mayo Clinic

“One of the most valuable courses I’ve taken as a senior IC. Clear, fast-paced, and packed with practical tools for communicating with precision and influence. The cohort format created space to reflect and sharpen my approach in real time. I’m walking away with more confidence, clarity, and intention in how I communicate. Highly recommend to any senior IC looking to level up their communication and impact.”

- Irene Liao, Senior Product Designer @ Checkout

“Thank you, Wes, for amazing 2 days of insightful and practical sessions on Executive Communication. I have learnt a lot from your course, especially after following you for two years on the newsletter. I have already set reminders and post-it-notes on my desk to remind me to take a moment to practice the techniques. This is the best learning style for me, and I am so glad I took the time to invest back into my communication development.”

- Teresa Huang, Head of Product @ Bupa

“Absolutely worth attending. This was one of the few professional development experiences I've had that was truly grounded in practical, real-world application. I especially appreciated the opportunity to learn directly from both peers and Wes.”

- Sarah Feldberg, Director, People & Culture @ Thrive Digital

“Excellent course. An enormous opportunity to learn from someone who has a gift for communication. I wish I had been able to take the class much earlier in my career. Worth every penny. Sign up now.”

- Joelle Godfrey, Senior Manager, Project Management @ Duracell

→ The course dates are October 9 & 10. I hope to see you in class! → Save your spot

⛑️ If you’re looking to dramatically improve your communication and leadership, I typically work with tech leaders on: managing up to a CEO/SVP, strengthening your executive communication, and delegating to a team of ICs while raising the bar. If you’re interested in how I can support you, learn more about my coaching approach.

Read time: 5 minutes

Some people seem more sincere than others. Why? I’ve thought about this a lot.

I’ve worked with colleagues who I know are decent people, but when we interact (especially in writing), they seem quite cold.

I’ve come to realize: Your writing skill influences whether people think you are sincere (or not).

If you are unable to translate your intent into impact, your recipients may think you’re kind of a jerk or you don’t care. This can accidentally damage relationships without you even knowing it’s happening.

For example, there are times when I get a note from someone and I think, “I feel seen and heard.” I feel acknowledged EVEN IF they’re denying my request, or telling me something I don’t want to hear. I still like the person and feel understood.

Other times, I get a note and think, “This person doesn’t really seem like they care.”

As operators and leaders, we will inevitably get customers, stakeholders, etc who complain or express frustration to us.

The way we respond can either build or diminish goodwill.

With a few minor word tweaks, you can sound more sincere and increase goodwill.

Your audience will judge you based on how you make them feel

Your audience will judge you based on how you make them feel. Not on what you intended to make them feel.

In other words, intentions don’t mean shit.

If you sound unhelpful, your recipient doesn’t think, “Gee, I bet this person is actually helpful. They’re just bad at communicating.”

No. Your recipient thinks, “This person is an asshole.”

I saw a note this week that I thought would be perfect to dissect. This note is already decent, and I have a great relationship with the operator who wrote the note. They’re competent, friendly, and fair, and I love working with them.

When I got their note though, I thought, “If I didn’t know this person, I wouldn’t realize how warm they actually are in person.”

If I were only judging them by their writing, I would think they didn’t really care about the problem I was telling them about.

The “One Extra Line” rule

A simple way to sound more sincere is to use what I call the “One Extra Line” rule:

Don’t only state that you understand. Add one extra line to show that you understand their frustration.

For example, here’s the email I received this week:

Before:

Hi Wes - sorry to hear about that frustrating experience.

This [redacted] can't be customized, but will start a thread to revisit the [redacted]. [Redacted]

^ This note isn’t terrible. He says “sorry to hear about that frustrating experience.” But it’s a bit matter of fact.

When you only say “I get that you’re frustrated” then move on quickly, you can come across as dismissive.

Do you really get that I’m frustrated…or are you trying to change the topic and move on as fast as possible?

After:

I recreated the email to write my “after” version. Here’s what it looks like if we use the “One Extra Line” rule:

Hi Wes - sorry to hear about that frustrating experience. I can definitely see why you’d want customers to X.

This [redacted] can’t be customized, but will start a thread to revisit the [redacted]. [Redacted]

Thanks for sharing your feedback, as always. Let me know if there’s anything else that comes to mind.

In the first paragraph, the note sounds more sincere because we added one line to validate why the person’s frustration is legitimate.

That one extra sentence can do wonders to elevate the warmth of the note.

To be clear, you don’t need to go overboard. One or two sentences will do.

By the way, I like to end with “thanks for sharing your feedback” even if I’m not able to accommodate someone’s request. I want to show appreciation that they spoke up. Personally, I like ending on something positive like this because it’s a free way to build goodwill.

Here’s another example of a real note that uses the “One Extra Line” technique. I got this email yesterday and was excited to share it with you.

I’ve emailed many times with this person, and feel a lot of goodwill toward them. Almost 100% of the time, I think, “They get it. I feel heard. I like this person. They genuinely care about me.”

The amazing thing is, I feel this way even when this person tells me things I don’t want to hear. Their genuine posture comes across, in part because they are a skilled writer, and also in part because they regularly use techniques like the “One Extra Line” rule.

Check out their note:

Hey Wes,

I completely understand your concern about [redacted], especially [redacted]. [Redacted] get how technical issues during [redacted] can be frustrating, and we want to support you in [redacted.]

Here, the person says she understands my concern, then she adds ONE EXTRA LINE which makes all the difference.

We’ve all heard the advice of “show, not tell,” but it can be hard to know how to apply.

The “One Extra Line” rule is an application of “show, not tell.”

In this case, telling is simply saying “I get you’re frustrated.”

Showing is proving to someone that you get it, which you can do easily by adding one extra line about the issue and validating their experience.

Remember: The next time someone expresses their frustration to you, don’t be too quick to move on.

If you want to make them feel seen and heard, add one extra line to expand on what they told you and demonstrate that you really hear them.

Have you noticed certain colleagues, account managers, etc seem more sincere than others? What do you notice they do or don’t do?

If you have any examples, feel free to share and I can potentially dissect the note in a future newsletter.

Hit reply because I’d love to hear from you. Thanks for being here, and I’ll see you in two weeks on Wednesday at 8am ET.

Wes

Connect with Wes

• Is this your first time here? Subscribe (it’s free)

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• Improve your ability to sell your ideas, manage up, gain buy-in, and increase your impact in an intensive 2-day workshop. The August cohort is 80% full. This is the second-to-last cohort of the year. → See course details

• Learn more about 1:1 coaching to sharpen your executive presence, influence, and ability to delegate

✨ Course update: Executive Communication & Influence for Senior ICs and Managers

I just wrapped up the July cohort last week, and the new student reviews are in. Here’s what the most recent students from Shopify, Uber, Duracell, etc are saying:

NOTE: The upcoming August cohort is 80% full. If you’ve been considering the course, I hope to see you in class. → Get the course details and enroll here

⛑️ If you’re looking to dramatically improve your communication and leadership, I typically work with tech leaders on: managing up to a startup CEO, strengthening your executive communication, and delegating to a team of ICs while raising the bar. If you’re interested in how I can support you, learn more about my coaching approach.

Read time: 9 minutes

Delegating isn’t hard.

Delegating while maintaining the level of quality you want…

without needing to jump in to do everything yourself…

or taking 3x as long because you’re correcting your team’s work after you delegated to supposedly save yourself time…

That is hard.

I’ve come to realize that the problem isn’t that managers don’t know they should delegate.

Every manager knows they should delegate.

So why is it so hard to do it consistently, and do it well?

You (the manager) are still ultimately responsible

The challenge is you (the manager) are ultimately responsible for the quality of decision-making and quality of output that comes out of your team.

You are basically putting your stamp of approval on everything your team ships.

There is a psychological weight to this, that we as managers are compensated for carrying and which comes with the role. But it’s a weight nonetheless.

Personally, I do not want to put my stamp of approval on stuff that I don’t think is that good. I do not want to say “looks good to me” if the thing does not, in fact, look good.

Not everything has to be done at an A+ level, but I refuse to accept I just have to lower my standards overall if someone else is doing the work. (Some amount of this is necessary but IMO most managers use this as an excuse to let standards drop in the name of “well someone else is doing it and they’ll do it differently so I should let it go.”

When I was learning to delegate, I did not need management experts telling me Captain Obvious advice, like “You need to prioritize! Do what’s most highly leveraged!”

Obviously I was trying to prioritize and be involved in stuff that was highly-leveraged and high ROI.

If you are an operator/founder who is actually building and responsible for driving outcomes, you know it’s not always so simple to “let go” or “deprioritize ABC.” Multiple areas of work are important and you don’t have so many levers to drive growth that you can haphazardly treat some as throwaway.

Over time, I realized a few things about delegating that really helped me embrace delegating, and even come to really enjoy it. I share the concepts below, and hope they help you too.

This post is not for managers who simply want to be hands-off

Some managers are very comfortable being quite distant from the day-to-day of what their team’s work actually entails.

That’s never been me. I’m a proud player-coach. Most of the leaders I respect are not so removed from the craft.

Many of my clients are leaders/founders who see value in being plugged into what their team is doing.

Personally, I believe you need some knowledge of the craft and context to be able to be a useful thought partner to your team. If you’re too distant and hands-off, you’re often not able to understand the nuances involved, which makes it harder for you to contribute, problem solve, etc beyond a surface level.

So this post is for you if you are a manager who wants to be plugged in with your team BUT want to stop doing everything yourself.

1. Delegating is not binary

Most people see it as binary: you do it yourself or delegate to others. But delegating is actually a spectrum.

A common challenge I work with clients on is knowing when to solve a problem yourself vs solving with/alongside your direct report vs delegating entirely to a direct report. It is situation-dependent, so we talk about what project/task you're thinking of delegating, who's a good candidate, their task-relevant maturity, and how to build in check-in points so you derisk the chances they come back with something of mediocre quality.

I love delegating and have helped many operators develop their own intuition around when/how to delegate.

When my clients realize delegating isn’t binary, they start seeing in shades of grey. You’ll start to see progress with how you’re improving how you delegate, and how your team is gradually and consistently taking on more of what you used to do.

2. Identify your direct report’s task relevant maturity

Continuing from the point above, the concept of task relevant maturity is super helpful. It reminds me that, again, delegating is not all-or-nothing.

Andy Grove, CEO of Intel, created this term in his classic book High Output Management. Here’s an excerpt:

“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.”

Basically, you should be more hands-on if your direct report is newer at the specific type of task you’re asking them to do.

For example, let’s say you manage a program manager. You fully trust them to run existing programs, and they have a track record of improving what you’ve designed.

But if going forward, you want them to create programs from scratch, this is a new skill. They do not have much experience doing this.

Just because the person was great at maintaining existing programs, does not mean they have the skills to invent and design new programs. Realizing that these are different skills is helpful for deciding how to support your direct report.

You may to stay more involved until you see that your direct report knows what to do, you’re trusting and verifying their work, etc. Once they get the hang of it, you can be less involved, or shift from directing mode to coaching mode.

3. Resist the urge to “hide” behind doing stuff you’re already good at

You may be lying to yourself when you say, “I’m the only one who can do this”.

I've observed (and have personally experienced) the urge to “hide” by doing stuff I’m already good at and know how to do. I say other people wouldn’t be able to do X, but that’s partially because I take pride in being good at X.

I believe this is an unspoken thought that many managers have.

This is more of the mindset aspect of delegating. IMO It's extremely important to be ruthless about calling yourself out and being intellectually honest.

There are going to be new things that are ambiguous, uncertain, there’s no right answer, and it's going to feel tempting to delay thinking about those and focusing on what you do know. You will always have too much on your plate, so it's your responsibility to assert what you should be doing.

If you’re reactive, you’ll end up being pulled in every direction, being spread too thin, and feeling resentful. And your manager/leadership won't know why because they’ll have expected you to define what you should be doing.

4. Take the time upfront to explain a project thoughtfully

Many managers toss a request over the wall with zero context and say “do this.”

Even if your direct report is senior, they would likely benefit from a bit of context. Even 5-10 minutes to cover why this project matters, what the goal is, potential areas of risk, etc makes a huge difference.

Consider it an upfront investment. Doing this will help your team save time, minimize miscommunication, execute with confidence, and ship faster.

For more on how to explain yourself well when delegating, check out the CEDAF framework.

5. Avoid owning IC work

Notice I said avoid owning IC work, not avoid doing IC work.

This is perhaps the most important item on the list. I would credit this as the main way I’m able to stay quite involved in my team’s work to be able to coach, teach, and help them improve their judgment, WITHOUT getting overwhelmed being too in the weeds.

In today’s environment and teams becoming more lean due to AI, many managers have to be more hands on, which means embracing IC work. Personally I think this is great because it keeps you sharp at your craft.

The idea is to avoid owning IC work as much as possible—knowing that if you are a player-coach, you will still end up doing 20%+ IC work even if you aim to do 0%.

When I managed more junior and mid-level folks, this worked well because:

(a) it’s much easier to react to an asset in front of you than to create from a cold start, so you use less brainpower

(b) my direct reports loved seeing my “before and after” examples when I gave edits

(c) you can give high-level structural feedback, then ask them to take another stab. This allows you to stay highly-leveraged yet involved in your team's work.

Not owning IC work, but still being hands on when your direct reports prepare stuff to review with you, has been the key for me.

You can also ask your team members to bring you multiple items to review in a batch. That way, your team can come organized, you can hammer through giving feedback on a few things, and you can both make the best use of your time. More on how I give feedback quickly.

Which item on the list are you most excited to try?

1. Delegating is not binary

2. Identify your direct report’s task relevant maturity

3. Resist the urge to “hide” behind doing stuff you’re already good at

4. Take the time upfront to explain a project thoughtfully

5. Avoid owning IC work

Hit reply because I’d love to hear from you. Thanks for being here, and I’ll see you in two weeks on Wednesday at 8am ET.

Wes

Further reading

If you liked this, you’ll like these posts on delegating, giving feedback, and developing high standards:

Course update: Second-to-last cohort

The August cohort will be the second-to-last cohort of the year. The cohort is already over 55% full, and has students enrolled from Amazon, Shopify, Google, Snowflake, Qualcomm, Sonos, Meta, Atlassian, etc.

Teams from DailyPay, StitchFix, Meta, etc have taken the course together, and in every cohort, there are multiple teams participating as a group. The course is especially valuable when taken with your team because having shared expectations & clear communication benefits everyone you work with.

I’m offering $100 discount per person for groups of 5+ team members, with higher discounts for larger groups. Reach out at wes@weskao.com for more info on how to enroll your team.

If you’ve been thinking about joining, I hope to see you in class.

→ Save your spot

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✨ Announcement: I’m updating my publishing cadence from weekly to bi-weekly. Going forward, you’ll hear from me every other week.

For context, the weekly format was great for nearly two years, and in order to continue sharing high quality insights, I realized I need more time to percolate between writing. Publishing twice a month seems like a good solution. I plan on keeping the newsletter free for now, and appreciate you being here!

I originally published a version of this essay in August 2020. If you find it helpful, please share with friends. Enjoy.

Read time: 5 minutes

Mediocre copy is a missed opportunity.

As an operator and leader, you need every lever you have to win. You could have an incredible idea… But if you have poor messaging, all your hard work is wasted. Bad messaging obscures your value.

On the other hand, good messaging is an amplifier. It takes a seed of something good and aggrandizes it.

The benefit is a transference of emotion. Of course you feel excited about your idea. With good messaging, you can TRANSFER that feeling to your recipient.

To improve your messaging, you can do three things:

• Improve your writing

• Improve your idea

• Improve both

It’s hard to quantify the value of clear thinking and clear writing

When writing is obviously bad, you delete it.

When writing is obviously good, you ship it.

But what if it’s not terrible, but it’s not good either?

Now we’re in a grey zone where there’s no easy fix.

I call this limbo writing.

It’s just kind of there. Neither dead nor alive.

Editing limbo writing takes a disproportionate amount of mental effort. Because the problem often isn’t the copy. The problem is that the underlying idea is fuzzy.

The lack of a point of view expresses itself as mediocre copy.

As a marketer, founder, or product owner, there simply aren’t enough levers to treat copy as a throwaway. We have to use every lever to the max.

Here’s how to fix limbo copy, depending on the underlying issue.

When the problem is the writing execution

There are lots of good resources on how to write well, so I’ll keep this short.

Add rhythm by varying the sentence structure. Rhythm is hard to put your finger on. It’s what gives writing a good pace. It’s why people say, “The book was long but it felt fast.”

Use a mix of short and long sentences for a dynamic feel. This is an easy and fun one. Read through your writing and mark sentences you want to make longer or shorter.

Trim excess fat to make your writing tighter. Say it in fewer words. If you feel bored reading it, remove it. If it’s too much backstory, remove it. Start right before you get eaten by the bear.

Strengthen your claim stronger by adding data points, surprising statistics, numbers. You won’t have to shout because these help make your point. Your reader comes to your conclusion themselves.

Swap out weak nouns and verbs. Get rid of adverbs while you’re at it. You can usually remove descriptors if your readers won’t need that detail.

Sound like a human, not what you think a business professional sounds like. No one talks like the corporate machines from your college career center manuals.

Avoid double negatives. Double negatives are confusing. Don’t make your reader think too hard.

When the problem is the underlying idea

Clarify what you want to say in the first place. Writing is the vessel to express your idea. If you don’t know what you want to say, no amount of good writing can compensate for the lack of an idea.

Finish the knock-knock joke. Does the idea feel incomplete? Sometimes, we write the first half of a knock-knock joke, but we forget the payoff. If that’s the case, add the “Who’s there?” to complete your thought.

Even a tweet has a narrative arc. Even in 280 characters, there’s a beginning, middle, and end. That’s why you can’t pull a few random sentences from a blog post and turn it into a tweet. It will feel incomplete because there’s no tension. Make sure whatever you’re writing is a standalone unit, whether it’s a work email or a 280 character tweet.

“I am not a crook” makes people think you are a crook. Plant ideas you want people to think of. My favorite example of what NOT to do is Richard Nixon saying, “I am not a crook.” Then everyone thought, “Hmm I couldn’t put my finger on it before… But you are TOTALLY a crook.” More on why to avoid incepting negative ideas.

Explicitly state your assumptions and rationale. It’s like showing your work in math class. Share the thought process behind your recommendation. This helps your manager give feedback on specific logical gaps instead of tossing out your whole idea. It creates the basis for a productive conversation.

Scarce + relevant = valuable. Teach something people don’t already know. What’s both surprising and true? Instead of summarizing and recapping, how can you make your contribution additive? There’s too much of the same-same already.

Clarify your stance. Have a spiky point of view rooted in evidence that others can disagree with.

Articulate the action you want your reader to take. Once you have your call-to-action, give them reasons to give you an enthusiastic yes.

Remember: Messaging is one of the few levers available for getting your customers to take action.

Besides the product design, the messaging is how you set expectations and offer surprise and delight.

It’s how you build closeness with your customer. It’s how you frame your product’s value.

Don’t waste this lever.

Have you dealt with limbo writing? Which tactic above 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 in two Wednesdays at 8am ET.

Wes

Connect with Wes

• Is this your first time here? Subscribe (it’s free)

• Follow me on LinkedIn for more insights

• Learn more about 1:1 coaching to sharpen your executive presence

• ✨ The new August 2025 cohort is open for enrollment: Improve your ability to sell your ideas, manage up, gain buy-in, and increase your impact in an intensive 2-day workshop. This is the second-to-last cohort of the year. → Save your spot

• PS Here are student reviews from the most recent May 2025 cohort:

→ The upcoming August 2025 cohort already has operators from Figma, Shopify, Adobe, EY, Meta, Qualcomm, Amazon, Gartner, and more. Join us: Executive Communication & Influence for Senior ICs and Managers