My top posts [bookmark this]

👋 Hey, it’s Wes. Welcome to my newsletter on managing up, leading teams, and standing out as a high performer. To level up faster, join my 2-day course on Executive Communication & Influence. → The November cohort is the last workshop of the year. Reserve your spot

An update about my newsletter:

I’m moving my newsletter from bi-weekly to an ad hoc publishing schedule. I recently started an exciting new project (will share more soon), and I only want to publish when I have insights worth sharing with you.

My full archive will continue to be free at newsletter.weskao.com. No action needed—if you’re on my email list, you’ll get a notification when I publish. If you’re not subscribed and want to be notified about new posts, click the orange button above.

In the meantime, I want to share some of my most popular posts. Feel free to bookmark so you can refer back to this page.

Top 7 most popular posts

1. 15 principles for managing up

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

3. Why high performers make assertions: The difference between insights, suggestions, and assertions

4. How to be concise

5. Start right before you get eaten by the bear

6. How I give the right amount of context (in any situation)

7. Rigorous thinking: No lazy thinking

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Presenting to leadership

• 15 principles for managing up

• How to present to your CEO

• WTF does it mean to “act like an owner”?

• Stop trying to change your manager

• Why high performers make assertions

• How to share your point of view (even if you’re afraid of being wrong)

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Improving your writing

• How to be concise

• Take 3 minutes to delete these words and improve your writing forever

• Tone and words: Use accurate language

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Giving the right amount of context

• How I give the right amount of context in any situation

• Signposting: How to reduce cognitive load for your reader

• Start right before you get eaten by the bear

• CEDAF: How to delegate while maintaining high standards

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Rigorous thinking

• Rigorous thinking: No lazy thinking

• Turning a yellow spot into the sun

• Are your standards too low? In defense of raising the bar

• “Looks good to me” is a lazy default

• Intellectual honesty

• The trouble with “good enough”

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Persuasion and influence

• Avoid incepting negative ideas

• Question behind the question

• How to get an enthusiastic yes

• Frustrated by rejection? How to plan before you ask

• To sound more sincere, do this

• Why you should get buy-in throughout a project

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Giving and receiving feedback

• Strategy, not self-expression

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

• Stop learning to give feedback. Learn to receive it.

• 11 ways to get better feedback from your manager

• How to coach your team (without making them defensive)

• 7 Phrases I use to make giving feedback easier for myself

• Super Specific Feedback: How to give actionable feedback on work output

• How I give high-quality feedback quickly

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Troubleshooting common workplace scenarios

• Everything takes longer than you think

• The unspoken power dynamics of Calendly

• Use “but” strategically

• How to deliver bad news when it’s not your fault

• Work requests are not “favors”

• Why “‘no’ is a complete sentence” is dangerous advice

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Leading productive discussions

• No, I will not hop on a call

• How to regain control of a meeting

• When to disagree and commit

• How to interrupt (and be interrupted) respectfully in the workplace

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Being more confident

• “Insecure vibes” are a self-fulfilling prophecy

• The problem with glorifying failure

• Reverse impostor syndrome

• I’m an introvert. This is how I get myself to speak up.

• Stop apologizing for reasonable business decisions

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Becoming a stronger operator

• The unspoken skill of finesse

• What finesse looks like

• How to on-board yourself when you join a new team

• How to sharpen your analytical thinking—even if you’re “not a numbers person”

• The #1 question every business case should answer

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Thanks for being here,

Wes

PS If you enjoyed this post, here are ways to go deeper:

• To get my next blog post, join my email list (it’s free)

• Learn more about 1:1 executive coaching

• Course: Improve your ability to sell your ideas, gain buy-in, and increase your impact in my 2-day workshop. Learn alongside operators from Netflix, Stripe, Meta, Figma, Anthropic, etc. → Save your spot

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✨ Course update: November is the last cohort of the year

The November cohort is the last cohort of the year. After this, the next cohort will likely be in mid-2027. If you’re interested and the November 19 & 20 dates work for you, I hope to see you in class.

To date, over 2,300 tech operators have taken this course with 942 reviews and 4.6 stars. Here’s what fellow operators are saying:

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