2025-10-01 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 course on Executive Communication & Influence. You’ll learn alongside mid-career operators from organizations like Netflix, Stripe, Meta, Figma, Anthropic, etc. → 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.
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).
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.
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 build your personal credibility (not your personal brand)
How to control the narrative if your work is being questioned
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
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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. The October cohort is sold out. The new March 2026 cohort is now open for enrollment. → Save your spot
2025-09-17 20:05:14
👋 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.
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
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
After you read the full article, consider these prompts:
When are you most susceptible to sharing too much backstory?
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
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
✨ 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
2025-09-03 20:03:37
👋 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. Note: The October cohort is 70% full and will be the last cohort of the year.
⛑️ 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.
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:
Your power dynamics with the individual
The legitimacy of the business 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: …
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.
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:
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.
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?”
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.
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.”
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.
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:
Focus on what you can do. End on an affirmative.
Cite trade-offs.
Get more info to make an informed decision.
Add “because” to share your rationale.
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
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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. → See course details
Learn more about 1:1 coaching to sharpen your executive presence and influence
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
2025-08-20 20:02:53
👋 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 → Now enrolling for the last cohort of the year
⛑️ 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:
“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!”
“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.
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.
So if you can’t change your manager, what does this mean? Here’s what you can do:
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.
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.
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.
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
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
✨ New October cohort: Improve your ability to sell your ideas, manage up, gain buy-in, and increase your impact in a 2-day workshop. → Save your spot
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
2025-08-06 20:03:15
👋 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. The October cohort is the last cohort of the year. → 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:
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.
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.
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.
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:
Don’t try to be their therapist.
Listen, then direct the conversation in a more actionable direction.
Don’t jump too quickly to offering solutions.
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
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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
2025-07-23 20:02:39
👋 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. The upcoming cohort is 80% full. → 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. 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.
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
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
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