2026-07-22 20:03:05
👋 Hey, it’s Wes. Welcome to my bi-weekly newsletter on managing up, leading teams, and standing out as a high performer. To level up faster, check out my intensive 2-day course on Executive Communication & Influence.
Read time: 3 minutes
There is a difference between work that seems useful vs work that’s actually useful.
Your work can be:
Defensible
Meet all stated requirements
Look fine at first glance
Be wrapped in professional polish
...and yet still fundamentally miss the mark on adding actual value.
It’s a natural human tendency to optimize for “not getting into trouble” rather than “figuring out the truth.” Even environments that pride themselves on rejecting mediocrity can fall into this trap of surface-level adequacy.
I care a lot about quality, which is a tough topic that often feels subjective. But one question I’ve started asking myself and my clients who care about quality is:
“This is defensible. But is it good?”
***
Do we need to see a spike in abandonment rates to make our product flow better?
Do we need to wait until customers riot before we improve our service?
Do we need to wait until users start deleting our app en masse to make things better?
Many of us wait for dramatic, obvious clues that things are going south, assuming anything before that is fine.
I believe it provides a false sense of security to wait for obvious signs that something is wrong before you wonder if something is wrong.
One of my coaching clients is a COO. Their team keeps using the excuse of wanting more data before making an improvement to the product.
They say, “The unsubscribe rate of X email is in line with the average. We don’t need to improve our emails.”
Folks, we can use our eyes here.
The emails are confusing, ugly, and adds no value. We don’t need to gather data to tell us this. We are allowed to use our judgment. We MUST use our judgment.”
They are a small startup, they are not in a position to A/B test everything in order to make decisions. They have to use their creativity and taste.
Another client has gotten feedback for not being vocal enough and not having enough of a perspective. He’s a talented engineering manager, and his response was, “I feel like if the idea is decent, I’m good to go with it.”
If you work with decently competent people, there are many ideas that are decent. Is “decent” good enough? It depends on the situation, and of course you shouldn’t try to maximize everything.
But many times, “decent” doesn’t meet the bar for allocating finite budget and finite headcount on an initiative. If you only get a limited number of bets per quarter, you should have conviction that this is the bet you want to make.
There are many ideas that are okay. It doesn’t mean you should drop what you’re doing and do those ideas.
You can run around doing busy work, following “processes,” and doing defensible stuff like setting up customer calls, but still not make real progress.
It requires intellectual honesty to make sure you’d stand behind the decision you’re making. Don’t hide behind doing things that are defensible, but don’t actually move the needle.
Last week, we wrapped up another amazing cohort. The latest student reviews are rolling in. Here’s what your fellow operators are saying:
“This course was very valuable to me. I wish I had taken this course sooner. As an experienced designer, I am very comfortable with explaining the rationale behind decisions, but I struggled with the dynamics of communicating ideas to different stakeholders at different altitudes. This course was exactly what I needed to sharpen my skills. Thank you so much.”
- Taís Lessa, UX Design Lead @ Wikipedia
“The course was extremely well thought out, felt applicable in my every day work, and provided clear actionable tips I can use immediately. Highly recommend and would love to do another course with Wes again.”
- Grace Dawson Beatty, Head of Product Marketing @ Plaid
“This was a GREAT course. I don’t know where else I would have gotten such quality content, packaged well, and taught by a world-class person that’s been-there-done-that. The hardest part isn’t attended this class (which you should ABSOLUTELY do) but incrementally applying the tips, tricks, and tactics learned. Thanks, Wes!”
- Chris Viglietta, Workshop Instructor @ Clay
“The value from this course was evident the moment I returned to work. I feel like I can see under the hood of all my incoming and outgoing Slack messages now.”
- Evan Hart, Motion Designer @ Figma
“Dense, actionable, well-structured, and paced to keep you engaged. Even if you think you’re quite good at written (and spoken) communication, you’ll leave with fresh insights and stronger skills. I joined as a long-time subscriber to Wes Kao’s newsletter, and I’m glad I did. I still learned a ton of new stuff!”
- Kalina Tyrkiel-Szymańska, Senior Content Designer @ Zendesk
If you’re interested in joining, the upcoming September cohort already has students from Amazon, Capital One, Figma, Perplexity, GitHub, Netflix, OpenAI, etc.
→ Reserve your spot in the September cohort
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✨ Intensive course: Improve your ability to sell your ideas, manage up, gain buy-in, and increase your impact in a 2-day workshop. Over 2,000+ tech operators have taken this course, and every cohort has sold out. → Save your spot
2026-07-08 20:03:27
👋 Hey, it’s Wes. Welcome to my bi-weekly newsletter on managing up, leading teams, and standing out as a high performer. To level up faster, check out my intensive course on Executive Communication & Influence. UPDATE: The July cohort is 95% sold out, but a new September cohort is now open. This will be the second to last cohort of the year.
Read time: 4 minutes
I remember one of the last interviews I did before starting my own company. The interviewer asked, “Could you tell me about a time when you solved a problem?”
What I wanted to say: “I solve problems all day. I wish there weren’t so many problems to solve. But I can’t think of one at this moment.”
I can’t remember what I ended up saying.
But what I can tell you, is that I have a deep distaste for behavioral interview questions.
I hated them as a candidate, and I hated them on the other side as a hiring manager. I believe this type of question doesn’t tell you much except whether the candidate prepared a set of stories beforehand.
But, alas, behavioral questions are still the default for many organizations. Recruiters and hiring managers will use how you answer these questions as a proxy for your effectiveness. So if you’re interviewing, it behooves you to learn how to answer them well.
For example, you’ve likely heard of the classic STAR (situation, task, action, results) framework. As a hiring manager, I often got lost in candidates’ answers because they told stories that were meandering and hard to follow.
I realized that candidates were using the STAR method, but accidentally spending too much time on the situation part of STAR. Backstory scope creep was happening.
Maybe it’s because you’re getting warmed up, or because you believe describing the situation is crucial for the rest of your story to make sense.
The problem is, when you spend too much time describing the situation (i.e. the context or background), you take time away from the other parts of STAR, all of which are more interesting and relevant. The situation should be a brief set up, so you can let the other parts of your STAR story really shine.
Most candidates speak for too long in their initial response. I’ve been guilty of this myself. I’ve seen my interviewer’s eyes glaze over. I’ve listened to myself talking in real time, and thought, “Why am I saying this? This is boring and kind of irrelevant.” If you are ever bored by what you’re saying, don’t ignore it. Wrap up your thought, and pivot.
When in doubt, aim to keep the situation part as short as possible. Aim for 2-3 sentences and 10-15 seconds, then move on to the task, action, and results. This allows you to allocate the bulk of time on what the problem was, why it mattered, what you did to solve it, and how much money you made for your company. Those are the juicy parts.
Zooming out, this doesn’t only apply to interviews. I realized I have a tendency to optimize for being comprehensive, when often, the actual better goal is to be interesting. If you are the same, then switching from “I need to tell it all” to “I need to tell what’s most useful and relevant” will take practice. A lot of continuing to improve is simply realizing your own tendencies, then catching yourself and consciously choosing a different approach.
In terms of getting to the root cause of where this tendency to be comprehensive comes from, I believe it’s partially because we’re afraid if we leave out a detail, we’ll be punished for it. And in the past, perhaps we were. So it feels safer to err on the side of sharing too much.
On the other hand, deciding what context to include requires you to have a point of view. It requires you to choose “this, not that.” Your choices might be wrong, and that feels a little stressful.
But NOT making a choice, and defaulting to sharing everything with equal weight, is not the solution. You will end up overwhelming your stakeholder, in this case, the hiring manager. They want to get an accurate sense of your abilities and experience, but won’t be able to, because they’re asleep.
It’s tempting to want to be thorough, even in times that don’t require it. You must fight this temptation. Keep the backstory short, so you save time for the good stuff.
We’re just one week away from the upcoming cohort of Executive Communication and Influence for Senior ICs and Managers. There are a few seats left. If you’re looking to get noticed by senior leadership, earn a promotion, or improve your ability to influence without authority, I would love to see you next Thursday and Friday. Grab one of the remaining seats here.
If you can’t make the July cohort, I’m opening the new September cohort today. This will be the second to last cohort of the year.
With AI reshaping the way every knowledge worker does their job, I believe skills like clear thinking, having a point of view, and strong communication are more important than ever.
In this latest cohort, I’ve added a new section on how I personally use AI to improve my communication. I won’t cover prompts. This is about using AI as a thought partner without turning off your own brain.
If you’re curious whether the course is for you, here’s what fellow operators are saying:
“Highly recommend this course for any seniority. Practical lessons and engaging exercises/homework. Ready to implement my learnings tomorrow.”
- Jenna Ochoa, Sr. Manager Partner Marketing, Strategic Alliances @ Zendesk
“I’ve learned a ton on this topic through intuition and experimentation, and now there’s Wes’s clear frameworks, rationale, and principles to pair it with. Along with practical exercises, I am exiting this course immediately better. This might be the first professional course I can internalize and actually apply on a daily basis.”
- Celeste Ridlen, Head of Research & Insights @ Robinhood
“I got a ton of value out of this course, you move fast, cover a lot. Written communication, presentation to execs, informal / verbal, etc... The exercises are where the real learning is, easy to be an armchair expert but these helped me feel where my deficiencies are.”
- David Illing, Senior Data Engineer @ Credit Karma
“The course shows what great communication looks like and the bar you can aim for. The exercises were very useful in determining your current level and reading through answers from different students gives a lot of different perspectives. I will be coming back again and again to review the content as I gradually build up my communication skills.”
- Srihari Venkatesan, Engineering Manager @ Apple
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Learn more about 1:1 coaching to sharpen your executive presence
✨ Intensive course: Improve your ability to sell your ideas, manage up, gain buy-in, and increase your impact in a 2-day workshop. Over 2,000+ tech operators have taken this course, and every cohort has sold out. → Save your spot
2026-06-24 21:49:12
👋 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, Google, Stripe, Meta, Anthropic, etc. → Save your spot in the July cohort
⛑️ If you want to improve your executive presence, learn more about 1:1 coaching.
Read time: 6 minutes
When you think of “being inspiring,” you might think of emotional appeals.
The problem is, you are not Viggo Mortensen rallying men to fight Sauron.
You are a product manager trying to inspire your eng team to build a feature.
You are a director getting feedback about how you need to inspire senior leadership instead of being so matter-of-fact.
You are a head of data science who needs to inspire your business counterparts, so you can ship by the end of Q4.
This type of inspiration is different from the dramatic speeches in movies.
I believe being “inspiring” in the context of the workplace is actually about sharing a point of view that gets your audience excited to take action.
This is good news because being inspiring is not an entirely different skill than the day-to-day influencing you’re already doing. Most of work can be reduced to getting various people to do the thing you want them to do.
And if you can build on your existing ability to influence without authority, learning to “be inspiring” is a lot less intimidating than it might seem at first.
One main difference between the type of inspiration you see in media vs real life, is real-life inspiration often doesn’t look like anything major is happening. It just looks like two people having a conversation…because that is often what it is.
Being inspiring is not about how passionate your delivery is. You don’t have to get up in front of everyone, or try to cosplay what a bold leader sounds like. You can sound like yourself. Perhaps the most articulate and clear-eyed version of yourself, but still yourself.
Contrary to what you’ve been told, I believe being inspiring is more about how compelling your underlying argument is. While emotional appeals still play a part (you can’t look dead in the eyes when you speak), your colleagues actually care about the substance of what you’re saying.
In other words, your argument has to actually make sense. If you passionately talk about an idea that doesn’t make sense, it won’t matter. No amount of great delivery can save you.
At this point, a common mistake I often hear is the idea that emotion vs logic are opposites. This is the wrong mental model.
When it comes to positioning your ideas, emotion and logic are not opposed. They are interconnected. There’s no need to be overly focused on whether an argument is “emotional” or “logical” though, because research shows we are pretty bad at discerning between the two:
“In one study, twenty-one students prepared speeches that were written from either a logical or an emotional standpoint. The speeches were presented, filmed, and then evaluated by other college students.
Interestingly, there was no real consistency in the findings except that speeches bearing a message that the evaluator agreed with were rated as more rational (even if they were intended to be emotional), while those the evaluator did not agree with were considered to be more emotional (even though some of those were intended to be logical).
It seemed that whether a speech was considered logical or emotional depended on the listener. Researchers also concluded that, as a general rule, people seem unable to consistently distinguish between logical and emotional.”
Basically, whatever you agree with, you would claim is “logical.” And whatever you disagree with or find less compelling, you’d categorize as “emotional.” This is fascinating. It’s also why, in my experience, it’s better approach to use a completely different mental model.
Instead of thinking about whether your argument is logical or emotional, think about whether your argument will trigger a visceral reaction in your recipient.
To help your audience feel inspired to change, try to frame your ideas in a way that sounds visceral. What feels visceral? Arguments that are concrete, visual, and appeal to what your recipient cares about.
You might say, “But Wes, isn’t this just the classic question of ‘what’s in it for me?’”
Partially. But there are many potential reasons for what’s in it for your recipient. Not all of those reasons are equally compelling. So yes, asking yourself the question matters, but it’s only the first half of the job. What matters more is how you answer that question.
For example, let’s say you are a manager giving feedback to your direct report about why they should manage up.
🚫 “Your lack of managing up is impacting our broader team’s communication, and it’s hurting our team’s alignment and cross-functional collaboration.”
Team alignment… Cross-functional collaboration… Cue polite golf applause.
Intellectually, I know this rationale makes sense, but I don’t feel moved. In fact, I don’t feel anything at all.
✅ “Your lack of managing up means because you’re currently spending 3x as much time repeating yourself, addressing pushback, and answering random questions from all directions.
You’re not getting recognized for your hard work because cross-functional partners can’t tell if you’ve got this project under control.
If you manage expectations by sharing proactive updates on a regular basis, they’d be able to relax and trust that you’re handling it. And you’d have more freedom to operate.”
Wow, okay. When I hear this, I get a visceral reaction.
“You’re right. I am spending a lot of time repeating myself and addressing pushback… That’s not great.”
“Hmm it’s true I don’t want to create more work for myself. I don’t want to make my own life harder.”
“Yes, I want more freedom to make decisions without people breathing down my neck.”
The above are arguments that are concrete, visual, and hit at a visceral level. It helps your recipient see the cost of their current behavior, and what life could be like if they acted differently.
Therefore, they’re more likely to be motivated to take action. When in doubt, avoid appealing to an abstract benefit like saying an initiative is “crucial for our team’s success.”
Appeal to what’s raw and visceral.
On a related note, I can’t tell you what to say to be inspiring. You need to assert why your audience should care in your unique situation. But it’s encouraging to know this isn’t a minor part of the work. This is the work. There is no upper boundary to the metaphorical (and literal) riches you’ll gain by getting good at tapping into what people care about.
And if you do it well, you get rewarded by moving hearts and minds.
Thanks for being here, and I’ll see you in two weeks on Wednesday at 8am ET.
Wes
PS If you want to inspire your audience, it helps to strategize what to say, role-play to build confidence, and get feedback from someone who knows what they’re doing. This is what I do for my coaching clients. If you’re interested, here’s how coaching works.
We’re about a month away from the upcoming July cohort of Executive Communication and Influence for Senior ICs and Managers. The course is two days because it’s geared toward busy operators who want to learn efficiently then start putting the principles into practice in their own work.
If you’re curious and asking yourself “Is this course worth it?” check out these student reviews.
“An extremely practical and valuable playbook - a must-have for anyone who wants to level up how they communicate with peers and senior leaders. Wes’ frameworks instantly changed how I write updates, pitch ideas, and give direction.”
- Vinay, Senior Manager, Tech Product Management @ Amazon
“I learned so much about myself and after even the first exercise, had immediately applicable actions. The investment is worth it and it’s highly recommended.”
- Isaac, Lead Product Designer @ Docusign
“This course was rammed with useful and practical content for all facets of work within an organisation with others. How to explain yourself more effectively, be more succinct and generally start to move with more ease through work. Wes’s take aways were so valuable that you get as a leave behind as well.”
- Charlotte, Sales Account Executive @ Harvey AI
“Extremely worthwhile course. The opportunity to see other students’ responses and spawn new ideas on framings / variations from one’s own typical communication style made the difference.”
- Alice, Senior Staff UX Researcher @ Mozilla
“I love the practical nature of this course. I can take all the learnings and apply them right away, highly recommend to anyone who is trying to up their communication game.”
- Monish, Product Lead @ Gemini
“This course arms you with systems that you can apply no matter what role or stage of your career you are at. Very hands-on, loved the thoughtful peer group, and tons of resources to peruse after the course ends.”
- Sagar, ML Product TPM @ Meta
If you’ve been thinking about joining, I hope to see you in class. See course details.
Is this your first time here? Subscribe (it’s free)
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Learn more about 1:1 coaching to sharpen your executive presence
✨ Intensive course: Improve your ability to sell your ideas, manage up, gain buy-in, and increase your impact in a 2-day workshop. Over 2,000+ tech operators have taken this course, and every cohort so far has sold out. → Save your spot in the July 2026 cohort
2026-06-10 20:01:41
👋 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.
Read time: 2 minutes
If you stay silent, you’ll never be noticed. You’ll never contribute the way you could if folks heard your voice. You’re actually robbing your organization of your insights.
It took time to unlearn my “stay silent and be safe” mentality.
Luckily, you can build the muscle of speaking up and sharing your point of view. Here are 6 principles that helped me:
The more controversial the idea, the higher the burden of proof.
Update your assumptions about how you add value.
Share where your hunch is coming from because it’s coming from somewhere.
Describe why the problem matters, so people understand why you’re speaking up.
Don’t rely on your credentials. Your idea should make sense on its own.
Use language that accurately reflects your level of certainty
Check out the full article that expands one each of these points.
Since writing the original post, I’ve noticed junior folks often don’t speak up because they’re worried they’re wrong, or that their perspective isn’t worth much. I believe this is a huge missed opportunity for you and your organization.
Regardless of your seniority, if you are working deeply on a problem, you likely have useful insights rooted in evidence. You might be the ONLY person with this level of proximity to that problem. You are exposed to context, details, and dots that perhaps only you can connect.
Therefore, if you are junior:
Don’t only document facts, but let interpret what those facts mean for the business
Don’t only share what happened, but hold back on sharing the “so what”
Don’t only summarize data, but hold back your insights
You might think you are doing “your part” in the relay race, then passing the baton to others. But “your part” actually INCLUDES sharing your perspective.
Your team wants (needs) to hear your point of view.
I posted about this on social, and got some thoughtful replies. Here are some highlights:
After you read the article, reflect on these questions:
Think about a recent meeting where you held back from sharing your perspective. What kept you silent? In hindsight, was the risk of speaking up as high as you thought it would be?
Consider a hunch you’ve had recently about work. What specific data points, experiences, or patterns is that hunch based on? Practice articulating where your instinct is coming from.
What’s something you’re working on where you could practice explaining why the problem matters before jumping to your recommendation?
Thanks for being here, and I'll see you in two weeks on Wednesday at 8am ET.
Wes
Below are new student reviews from the cohort last month. You might be asking yourself, “Is the course worth it?” Check out what other tech operators are saying:
“I absolutely loved this course! I learned a lot of tools and frameworks that I started implementing immediately, even in routine communications at work and at home. I loved the energy in the room, and I’m very grateful to Wes, her team, and the amazing group of people who took this course.”
- Masha Vasilenko, Senior Data Scientist @ Hims & Hers
“With 2 immersive days, I got to practice and internalize frameworks. Wes coached a lot, carrying life-long learnings to benefit my career growth and communication. Definitely worth the time and effort to unplug from day-to-day work and dive in.”
- Yuanzheng Liu, Engineering Manager @ DoorDash
“Highly recommend this course for any seniority. Practical lessons and engaging exercises/homework. Ready to implement my learnings tomorrow.”
- Jenna Ochoa, Sr. Manager Partner Marketing, Strategic Alliances @ Zendesk
“Wow. Loved this course. So many useful tips that I started to implement immediately, even before the course finished. It’s incredible how the little changes can make a big difference. I strongly recommend this course for anyone looking to be a more well-rounded and successful communicator.”
- Mike Rios, People Architect and Change Catalyst @ Google X
“Cannot believe this course was only two days. Both felt like it flew by but also delivered an absolutely goldmine of information in that little time.
I recently moved into a new work where I am constantly communicating with and interfacing with executives and leaders, and while my communication skills have served me extremely well getting to this point, I have been feeling like someone who has been playing soccer their whole life who got thrown in a pool and told to play water polo. I am an athlete, I am fit, so why am I drowning?
Wes’ tips, tricks, principles, and instructions have made me confident to start practicing the new behaviors and developing new skills that are critical to my success. I felt so stuck two days ago and now I feel empowered and hopeful.”
- Mackenzie Guinon, Experience Researcher/Research Program Manager @ Asana
If you’ve been thinking about joining, I’d love to see you in class. Check out course details here.
Is this your first time here? Subscribe (it’s free)
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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 2,000 tech operators have taken this course, and every cohort so far has sold out. → Save your spot in the July cohort
2026-05-27 20:02:18
👋 Hey, it’s Wes. Welcome to my bi-weekly newsletter on managing up, leading teams, and standing out as a high performer. To level up faster, check out my intensive course on Executive Communication & Influence. You’ll learn alongside mid-career operators from orgs like Netflix, Stripe, Meta, Anthropic, etc. → Save your spot
⛑️ If you want to improve your executive presence, learn more about 1:1 coaching.
I originally published a version of this essay in March 2020. Enjoy.
Read time: 4 minutes
Some people have a great poker face.
You and I probably aren’t one of them.
The other day, I was having a tough conversation with someone who probably thought they had a poker face. The conversation went something like this:
Their words: “Yes, I totally understand. Please continue.”
Their face: “ARE YOU KIDDING ME? THIS IS BS. I HATE YOU, WES.”
Every day, we have dozens of conversations. Each one is an opportunity to build trust with the people you work with.
Your message isn’t just the content of what you say. When your facial expressions and body language don’t match your message, you diminish your ability to convey your point. The impact is you might come across as insincere.
When you’re mindful of your body language, you help set the emotional tone, which leads to more productive conversations.
In poker, a tell is a change in someone’s behavior when people are nervous or confident. Often it’s unconscious, meaning the person doesn’t know they’re giving themselves away.
Here’s a starter list of potential tells:
Eyes widening and not blinking
Nostrils doing a slight flare
Pressing your lips together into a line
Stretching your mouth downward every so slightly
Raising eyebrows
For example, you might clench your jaw in stressful conversations. Watch for the physical changes in your body when you’re nervous or stressed. Noticing is half the battle. Once you notice, you can learn to shift your body language.
If you’re giving hard news and want to show you’re empathetic... It doesn’t help to scowl and sit back with your arms crossed.
Soften your tone. Speak slower. Match your face to your message. Think about your most loving friend. How does their face look when you’re baring your soul? Channel that person.
On the other hand, if you want to appear authoritative, you can give fewer facial expressions altogether. Facial expressions are a clue. If you’re the most powerful person in the room, you don’t have to give other people clues. The idea is you’re sitting back waiting for them to please you. Think about the most senior person in a room when others are pitching them. Channel how their face looks.
Important note: When I say to “channel someone,” I don’t mean to mimic entirely. You should take inspiration, but be mindful not to overstep. You might accidentally insult someone more senior than you, so don’t overplay your hand. More on power dynamics here.
If you want to show you’re listening, try raising your eyebrows a little to make your face more “open” and leaning forward. Or furrow your brows a bit and nod as you listen. Think about the last time you probably talked longer than you should have, because your audience looked interested. Channel how that person looks.
If you look horrified as your colleague is sharing feedback with you, of course they’ll clam up or backtrack. They’re probably thinking, “Oh god, I shouldn’t have mentioned this.”
Your facial expressions and body language might prevent the person from finishing what they were saying. Or it might reveal that you’re skeptical, judgmental, or annoyed, which shifts the direction of the conversation.
When you’re mindful of your facial expressions and body language, you can prevent your brain from jumping to extremes. Your body stays calm, so your brain thinks, “Hmm, things are okay. We can figure this out.”
You’ll set a positive emotional tone for the conversation. This means the other person is more likely to be honest because they feel safe to speak freely.
Keeping your head straight makes you look more serious and authoritative. This should be your default head position. Try this exercise this week: Notice your head and whether you’re holding it straight.
When I first did this, I was surprised at how my head would default tilt to the side. I see this more in women because we’re trained to make others feel comfortable. If you want to appear more powerful, keep your head straight.
If you want to show that you’re non-threatening, tilt your head a bit. Cocking your head ever so slightly to the side, and leaning a bit forward, shows interest in the other person. It shows you are interested in listening.
This automatically calms you down. Whether you believe in meditation or not, the simple act of slowing your breathing physically reminds you to calm down.
When you stay calm, you create space for a productive conversation. You create space for people to express themselves. You can be more persuasive when you align your content (words) with your body language and facial expressions.
In short, you can better translate your intent, so the other person feels it.
To recap:
Understand your “tells.”
Send the right signals.
Create psychological safety and encourage people to tell the truth.
Keep your head straight (literally).
Slow your breathing.
The next time you’re in a high-stakes situation, be mindful of your facial expressions and body language. Do they match your message and intentions?
Thanks for being here, and I’ll see you in two weeks on Wednesday at 8am ET.
Wes
We wrapped up an amazing cohort two weeks ago. Here are the latest student reviews:
“This course was exactly what I was looking for: deeply insightful with takeaways that can be put into practice right away. I look forward to applying this wealth of knowledge to all areas of my life.”
- Sorina Arapu, Senior Tracking Engineer @ Paramount +
“Stellar course. Yes, you should take it. Beyond Wes’s expertise: course design and delivery was stand out. Expect crafted principles and well-considered exercises.”
- Mark Simithraaratchy, Founding Engineering Manager, Search AI @ Squarespace
“This was a great course that gave me examples and ideas on ways I can shift and change my communication style that I’m excited to immediately implement. I would highly recommend this course to anyone that wants to level up in how they communicate to anyone in their organization.”
- Joseph Ver, Manager, Data Solutions @ DailyPay
“I am so happy with what I got out of this course. The activity based learning was really helpful. Hearing decisive guidance from a communicator who goes against the grain of AI slop and concision to a fault was really refreshing. I feel much better equipped to communicate in a way that is authentic, thoughtful, and powerful.”
- Mira El Hussein, Product Operations Manager @ 1Password
“This was a great course. Really digging into the relationship between managing up and communication connected a lot of dots for me, and the course as a whole had a few ‘a ha’ moments calling out things I was doing that aren’t effective. 10/10.”
- Jason Showman, Senior Internal Communications Manager @ Webflow
“All I can say is wow. Worth every penny. Instead of dropping a bunch of theory, Wes walks you through real, tangible ways to improve your communication that you can put into practice immediately.”
- Rachel Sadacca, Demand Generation Lead @ Lattice
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2026-05-13 20:01:58
👋 Hey, it’s Wes. Welcome to my bi-weekly newsletter on managing up, leading teams, and standing out as a high performer. To level up faster, check out my intensive course on Executive Communication & Influence. You’ll learn alongside mid-career operators from orgs like Netflix, Stripe, OpenAI, Meta, Anthropic, etc. → Save your spot
⛑️ If you’re looking to dramatically improve your communication and leadership, learn more about my coaching approach.
Read time: 4 minutes
I once had a direct report, we’ll call him Matt, who kept submitting work with errors, typos, weird formatting, and bad writing that increased cognitive load for customers.
I would repeatedly remind him to use the clear text feature in Google Docs/Gmail, which, if this is the first time you’re hearing about it, is a game-changer. That little Tx button has saved me from sending emails where the “Hi First Name” looks obviously copied/pasted because the font was size 14 in Verdana when the rest of the email was size 12 in Arial. This isn’t even the point of the story, but I think more people would benefit from cleaning up their email formatting, so here’s how you do it:
One day, I sat him down and said,
“Matt, I need you to pretend like your reputation is on the line when you send work to me. I am judging you for this work. I know this isn’t your best. Even though you are signing these emails under our organization’s name, I need you to pretend you’re signing it as Matt, and sending this email to 50,000 of your friends and the public."
Your work is the average of what you ship. If you’re not proud of it, consider investing in improving your craft, finding a function that’s a better fit, or whatever else you think will allow you to show how good you really are.
A tiny percentage of you might say, “Wes, I would publish work with typos and bad grammar under my own name. I don’t mind.”
First of all, this:
Second, you might not mind, but your organization does. Sloppiness reflects poorly on your brand, distracts from your message, and erodes trust. If you’re going to do 90% of the work, you might as well do the last 10% to give it another read and put your stamp of approval on it.
Ask yourself:
If I were signing off with my name, would I make this better?
Is there sloppiness that might reflect poorly on me or my company?
Am I passing the burden to others to fix my errors?
Does the work I’m shipping represent my ability?
If you’re saying, “I just can’t be detail oriented and don’t want to try,” I will say, “Cool, I will hire someone who is or can be, because the details matter in this job.”
For most knowledge worker roles, being able to produce work that’s error-free most of the time is a prerequisite. I’m not saying you need to be in the 95th percentile of detail orientation.
You may be surprised to find that I’m not even that bothered by typos, and think they’re the least egregious type of error. I’m saying if you want to be trusted with more responsibility, you need to be able to produce work that is generally error-free because your manager can’t always be your safety net.
Back to the story of my direct report Matt. Matt admitted that he felt like I’d always catch his errors, so he felt more lax about it. I get that.
You might say, “Wes, you enabled him to be less detailed.”
Perhaps I did. But this quip is not as clever as you think. Because what’s the alternative? Let him send an email to 50,000 customers and make them suffer?
Andy Grove, co-founder and former CEO of Intel, said it well:
“The responsibility for teaching the subordinate must be assumed by his supervisor, and not paid for by the customers of his organization, internal or external.”
The idea of “let the person fail and they’ll learn” makes sense in theory, but in reality, it’s not worth sacrificing brand credibility and taxing your customers for an employee to learn a lesson. Don’t make your manager or customers pay for your weaknesses. You don’t and probably can’t turn weaknesses into strengths, but you can and should reflect on which weaknesses you want to improve on enough so they aren’t a blocker for you.
I’ll end with a story that should gives you hope.
Most people assume I was always good with details. The truth, is I used to be super disorganized.
For example, in junior high school, I missed assignments because I forgot about them, or jotted it in one of many notebooks, then forgot which one.
In my sophomore year of college, I did an internship at a tech PR firm. One of the senior leaders chewed me out because he asked me to organize an Excel spreadsheet, and when I turned in my finished work, he rightfully pointed out all the ways the spreadsheet was messy with random font sizes, centered vs left justified text, etc. I didn’t see it until he pointed it out. But from that day on, I knew what to look for and trained my eye to notice formatting.
Even to this day, I have myriad systems in place (checklists, calendaring, alarms before meetings, and yes, still using the clear formatting Tx button in Gmail) to make sure I don’t let a lack of detail orientation screw me over.
Most skills are learnable and you can make many mistakes, but don’t get stuck in a loop repeating the same mistakes over and over. Ideally, you graduate to making better, smarter mistakes, and you improve enough so your weaknesses don’t become prohibitive.
Thanks for being here, and I’ll see you in two weeks on Wednesday at 8am ET.
Wes
The May cohort is now sold out, but I opened a new July cohort with the dates of July 16th and 17th. The cohort opened last week and there are already operators from Figma, Amazon, Mozilla, Grammarly, Stripe, OpenAI, etc signed up.
In my private coaching practice, about 1/3 of my clients are technical. My clients include eng managers, staff engineers, startup CTOs, technical founders, VPs of data science, etc. And engineers make up the second largest function in my course:
Technical people can be hard to please. They’re usually hyper rational, logical, and have a low tolerance for hand-waviness.
This is probably why engineers like my course so much.
I built this course because I was frustrated that most communication resources were too basic or too vague. My course treats communication as a skill, one where there are underlying principles and a bell curve for the quality of your execution. My goal is to help you see differently, so you notice what you can improve in your own speaking and writing. Then you can build intuition over time, so communicating well becomes faster and more instinctive.
The question you might be asking is, “Is the course worth it?”
Here’s what engineers are saying:
“[Wes’ course] provides a great foundation to level-up your comms, and practical tools which you can use in nearly any scenario.” - Samuel Kramer, Forward Deployed Software Engineer, OpenAI
“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 course shows what great communication looks like and bar that you can aim for. The exercises were very useful in determining your current level and reading through answers from different students gives a lot of different perspectives. I will be coming back again and again to review the content as I gradually build up by communication skills.” - Srihari Venkatesan, Engineering Manager, Apple
“Great course that summarizes foundational wisdom, principles, and actionable steps for effective communication.” - Alexei Koulikov, Engineering Manager, Shopify
“I got a ton of value out of this course, you move fast, cover a lot. Written communication, presentation to execs, informal / verbal, etc... The exercises are where the real learning is at, easy to be an armchair expert but these helped me feel where my deficiencies are” - David Illing, Senior Data Engineer, Credit Karma
“Great course overall. Lots of great actionable advice and insight into what it means to execute at the next level.” - Oscar Funes, Senior Staff Engineer, PayPal
“Lots of communication and influence is super abstract. This course was a really great way to structure things tangibly. I am excited to try out these ideas and convey them to peers/reports.” - Suvir Jain, Engineering Manager, Stripe
I hope to see you in class. If you’ve been thinking about joining, check out course details.
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 2,000 tech operators have taken this course, and every cohort so far has sold out. → Join the July cohort