2025-06-18 20:01:32
👋 Hey, it’s Wes. Welcome to my 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. (Scroll to the bottom for new team discounts)
⛑️ Update: I’ve opened up a few spots for 1:1 executive coaching clients in Q3. 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 presence, and delegating to a team of ICs while raising the bar. If you’re interested in how I can support you, hit reply or learn more about my coaching approach.
I originally published a version of this essay in March 2020. Since then, I’ve expanded the post. If you find it helpful, please share with friends. Enjoy.
Read time: 5 minutes
Language is a free way to be strategic. The right words can make you seem warmer, more authoritative, and more effective.
But the wrong words can unintentionally make you sound negative, passive, or confrontational. You can sound like you’re not a team player even when you are one in real life.
Use words to your advantage. Don’t shoot yourself in the foot by using language that diminishes your own intent and authority.
Here are easy fixes to common mistakes below. Before you hit “send,” delete these words from your writing. Your message will be stronger for it.
Saying fine sounds like you’re not fine. When you’re writing, you only have cold hard text—you can’t use facial expressions to show warmth. Therefore, you need to amp up the positivity to compensate.
Before 🚫: “I’m fine with that.”
After 👍: “I’m good with that.” “That sounds good.” “Great, I’m on board.”
“However” is a melodramatic way to say “but.” It makes ideas sound more negative than they have to be. It skews toward formal, corporate, and bureaucratic. If you need a negating word, use “but.” More on how to use “but” strategically.
Before 🚫: “It should take an hour or two each day. However, you can do your work on your schedule. The only exceptions are the two livestream sessions, which are scheduled for X date. However, we’ll record these and send them out to you, so if you can’t make those times, no big deal.”
After 👍: “It should take an hour or two each day. You can do most of your work on your own schedule. The only real-time sessions are two livestreams, which are scheduled for X date. For your convenience, we’ll record these livestreams so you can watch them on-demand at your leisure.”
On a related note, try to end your sentences on a positive word. “Leisure” is a better phrase than “no big deal.” Your reader’s eyes will see the first and last words more than the words in the middle.
Don’t make things sound worse than they actually are. If you share bad news, you don’t want to fan the flames and make a situation sound catastrophic when it’s not. If you must, use “but.”
Before 🚫: “Unfortunately, we currently only offer the two livestream sessions on X dates, but all livestream sessions are recorded and distributed to students the following day. All other content can be accessed 24/7.”
After 👍: “Absolutely. The two livestream sessions are only scheduled on X dates, but all livestream sessions are recorded and distributed to students the following day. All other content can be accessed 24/7.”
In the example above, if you offer livestream events on x dates, why do you need to say “unfortunately”? The customer might have asked for other dates, but it doesn’t mean their request was justified.
By saying “unfortunately,” you subconsciously accept blame. And this can make the customer feel even more upset and wronged. The bottom line: Phrase neutral news in a more neutral or positive stance.
More on why you should avoid incepting negative ideas.
Some of these aren’t technically double-negatives, but the “not” is confusing. When you say “not,” your reader has to think of what is, then think of the opposite.
Make it easier for people to understand you: state things in the affirmative as your default. You can always break this rule when it’s purposeful and intentional.
Note: You might think “I only have positive things to say” seems good. But! It has an implication of scarcity because of the word “only.” Your intent is that you have an abundance of good things to say, so you want to pick a phrase that evokes abundance, like “so many.”
Before 🚫: “I could not be more proud to...”
After 👍: “I am incredibly proud to….”
Before 🚫: “He’s not wrong.”
After 👍: “He has a point.”
Before 🚫: “I have nothing but positive things to say about them.”
After 👍: “I have so many positive things to say about them.”
Short phrases are usually okay with double negatives. For example, “I couldn’t have said it better” is easy to understand because it’s a commonly used phrase and it’s fairly short. The longer or more complex your sentence structure, the more you’ll want to avoid double negatives.
The problem with “can’t until” is you’re giving up your power unnecessarily. You’re giving a concession—you’re saying, “I’m sorry I can’t do the time you needed. The best I can do is this other subpar thing.”
Don’t state what you can’t do. State what you can do.
Before 🚫: “I can’t meet until 2pm.”
After 👍: “I can meet at 2pm and after.”
Let’s assume your default is to tell the truth. If you point out your honesty, this makes me think you are usually dishonest.
Before 🚫: “To be honest, I don’t think that’s a good idea.”
After 👍: “I don’t think that’s a good idea.”
Your sentence will be stronger without “just.” Seriously, try it. The next time you want to say “just,” remove it and notice how much more confident you sound (without losing your original meaning).
Before 🚫: “I just wanted to ask…”
After 👍: “I wanted to ask…”
You’ll come across as sincere (or more so) without these words. This one is somewhat stylistic, and I believe a well-placed “really” can add emphasis. But “truly” can sound melodramatic—and when you start to stack multiple of these emphasizer words, it can be a lot. Use sparingly and intentionally.
Before 🚫: “I really appreciate you and I’m truly glad to be part of this team.”
After 👍: “I appreciate you and I’m honored to be part of this team.”
Before 🚫: “I was truly excited.”
After 👍: “I was jumping out of my seat.”
Pro tip: You could simply delete very/truly/really. That works. If you want to go to the next level, try swapping out for a more evocative word. For example, notice how I changed “truly glad” to “honored.”
This one can be used in moderation. The reason I included it is because I hear operators say “no problem” for requests that are actually a lot of work for them. When you do this, you accidentally diminish the effort and care you put into a task.
It’s kind of like deflecting a compliment because you feel awkward. If someone shows you appreciation, it’s okay to accept their appreciation graciously. This makes both parties feel good.
Before 🚫: “Oh, it was no problem.”
After 👍: “My pleasure. Glad it was helpful.”
To recap, delete these words to strengthen your writing:
Delete “fine”
Delete “however”
Delete “unfortunately”
Delete double negatives
Delete “can't until”
Delete “honestly”
Delete “just”
Delete “truly,” “very,” “really”
Delete “no problem”
Which are you most excited to delete and why?
Hit reply because I’d love to hear from you. Thanks for being here, and I’ll see you next Wednesday at 8am ET.
Wes
I often hear students halfway through the course say, “This is so helpful. How can I train my team on these skills? How can I get everyone I work with to communicate like this?”
The truth is, if you are a manager or leader, you probably don’t have the time to sit down and teach your team how to communicate better. You can do it in bits and pieces along the way, which is what I did for years as a founder and manager.
But convincing your team to communicate differently, showing them how, and changing their behavior is difficult. I’m incredibly proud that students report having aha moments, say they didn’t realize what they could be doing better until now, and say they’ve already started writing or preparing for meetings differently.
It’s hard to get people to change their behavior. It’s hard to show what excellence looks like. It’s hard getting folks to admit they thought they were doing great, but realize they actually have plenty of room to improve.
Yet I hear this kind of feedback from students in every cohort.
This is by design. The course took over a year and hundreds of hours to put together, and is based on 15 years of experience as a VC-backed founder, marketer, and operator who’s been obsessed with communication.
When I was a manager, I thought, “I wish there were a course I could send my people to so I wouldn’t have to explain this from scratch.”
This is why I created my course. It includes all of my best frameworks, insights, and principles designed to improve your judgment and your team’s judgment around clear communication. It’s the practical course for real operators and real-world situations I wish I had years ago.
With this, I wanted to share an announcement re: new team discounts:
$100 discount per person for groups of 5+ team members
$125 discount per person for groups of 15+ team members
$165 discount per person for groups of 30+ team members
(The teams discount is the only discount available for the course.)
I’m not taking on any more private workshops for the rest of the year, and my keynote fee for a 1-hour talk is a much higher investment. The course is the most economical, efficient, and effective way to train your team on communication fundamentals that can save you hours per week for months and years to come.
Check out what students from the most recent cohort last month are saying:
If you’re thinking about joining, I hope to see you and your team in class. → Get the course details
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Learn about 1:1 coaching re: executive presence and communication
✨ The new August 2025 cohort is open for enrollment: Improve your ability to sell your ideas, manage up, gain buy-in, and increase your impact in an intensive 2-day workshop. Save your spot → Executive Communication & Influence for Senior ICs and Managers
2025-06-11 20:02:59
👋 Hey, it’s Wes. Welcome to my 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 → New August cohort is open
⛑️ If you’re looking to dramatically improve your executive presence and communication, learn more about 1:1 coaching.
I originally published a version of this essay in October 2019, and have updated/expanded the post. If you find it helpful, please share with friends. Enjoy.
Read time: 5 minutes
The problem isn’t that you’re not working fast enough. It’s that your expectations were never realistic to begin with.
For example, I was on the phone with my bank recently. I thought it would take 10 or 15 minutes... It took 51 minutes.
Almost an hour.
Whether you are troubleshooting a technical issue, hiring to grow your team, or running an errand…
Everything takes longer than you think.
Why does this matter? Because every day, we have to estimate how long things will take.
If you get better at estimating timing, you’ll be less stressed in all areas of life.
If you’re doing something for the first time, give yourself more time to figure it out.
Things will inevitably pop up. And by “things,” I mean anything and everything you could imagine to go wrong.
A few years ago, I was setting up an email automation using Zapier to connect two apps. I thought, “This is going to be easy. I have the documentation so it should take 30 minutes to do.”
It ended up taking 7 hours over two days.
I realized the documentation didn’t cover the use case I needed when I was fifteen minutes in. From there, it took multiple rounds of Google search, using live chat, and waiting for email responses from customer support before it finally worked.
Most of the stress could have been avoided if I reminded myself that things take longer than you think, especially when you’re doing something new.
Another example from last week:
I was using ChatGPT to combine spreadsheets where I had partial data in different CSV files. I thought, “I can use a user’s email as a unique identifier to combine the information across these spreadsheets.”
I tested my hypothesis on two initial spreadsheets, and the resulting downloadable file was nearly instantaneous and exactly what I wanted.
I was thrilled. I thought, “This should like 20 minutes total across all my data.”
It ended up taking 2-3 hours spread over a week.
As I started applying this process to my larger data set, I realized certain spreadsheets were missing certain pieces of information, that ChatGPT would get confused if I didn’t format the column headers to match across spreadsheets, etc. I ended up wanting to update my requirements partway through, which meant I needed to take a step back and redo certain parts.
Now, without AI, it would have taken much, much longer. I would have had to hire a freelancer to do it manually, or would not have done it at all.
This was my first time using ChatGPT to manipulate data like this, and I learned a bunch along the way, including breaking my task into smaller steps, the importance of cleaning the data a bit on my end, etc.
These kinds of starts and stops are extremely normal when you are learning by doing. It will be faster next time.
So it was still a win. But my original estimate that it would take 20 minutes was wrong.
Time and time again, I am reminded: Everything takes longer than you think.
This is why, if you’re doing something new, you should:
Build in buffers.
Build in time to get into flow.
Build in time to think.
Build in time to discover unknown unknowns.
Build in time to learn.
Build in time to recuperate.
Build in time to troubleshoot.
Of course, this doesn’t only apply to tasks immediately in front of you.
Higher level, macro goals take longer than you think, too. What you think might take weeks could take months. What you think might take months sometimes takes years. What you think might take years, could take decades.
This isn’t meant to be discouraging. Quite the opposite.
When you adjust your expectations about how long things take, you can make more realistic plans and stop beating yourself up for being “too slow.” You’ll be less frustrated, and can enjoy yourself more along the way.
Is there an area where you might want to admit that things take longer than you think? How might that be useful for setting expectations internally and for the work itself?
Hit reply because I’d love to hear from you. Thanks for being here, and I’ll see you next Wednesday at 8am ET.
Wes
Is this your first time here? Subscribe (it’s free)
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Learn about 1:1 coaching re: executive presence and communication
✨ The new August 2025 cohort is open for enrollment: Improve your ability to sell your ideas, manage up, gain buy-in, and increase your impact in an intensive 2-day workshop. Save your spot → Executive Communication & Influence for Senior ICs and Managers
PS Here are student reviews from the most recent cohort of May 2025 students:
“Fantastic course. If you struggle with communication, Wes teaches the fundamentals and provides tools to help improve your skills. My favorite part of the class was the Q&A session and reading answers from fellow students. We are all in this together and this course is a great representation of that. Highly recommend!”
- Matt Harvill, Group Product Manager @ Strava
“Really helpful class, well-organized, and touched on many common challenge areas.”
- Laura Pezdek, Product Marketing Lead @ Shopify
“This course is GOLD and I would recommend this to everyone regardless of level. It gives structured frameworks to build effective communication for the situations we all encounter in our jobs across all levels of stakeholders. I particularly liked that the course has hands on practice dipping your toes into the different frameworks, which makes it so much easier to keep practicing.”
- Berit Dangaard Brouer, Principal Engineer Data and Decision Science @ Maersk
“Wes provided useful—and sticky—frameworks for making sure my communication is persuasive. Her advice is already ringing in my head.”
- Taryn Williford, Content Marketing Manager @ Headway
“This session was deeply impactful. My biggest takeaway is the importance of managing up as a daily, intentional practice not a one-time effort. The idea of preparing for meetings with clarity on both what I want to convey and why it matters to my audience resonated strongly. It reinforced the value of thinking from the other person's perspective and aligning my communication accordingly. The insights from this session will directly help me structure my professional goals with more clarity and focus, instead of trial and error.”
- Sasikumar Sugumar, Executive Director @ J.P. Morgan Chase
“Great course with actionable steps to take and interactive exercises to put the learning into practice.”
- Emma Hong, Senior Product Marketing Manager @ Superhuman
“The exercises and examples helped me better understand where my communication has been getting in the way of my success and that of my team. I feel confident that I will communicate more clearly and concisely going forward while revisiting the contents of this course in the months to come.”
- Charissa Hoffer, Senior Product Manager @ Klaviyo
✨ The next cohort is August 14 & 15. Course details here ✨
2025-06-04 20:02:42
👋 Hey, it’s Wes. Welcome to my 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 new August cohort is now open for enrollment.
Read time: 4 minutes
Fun story: I once saw a CEO start an all-hands meeting by saying, “No one is going to get let go or anything today…”
You could immediately see the employees tense up.
The CEO was trying to make everyone feel better. There was news of other companies doing layoffs, the economy was in a rough place, and the CEO wanted to address what was unsaid. People were wary of losing their jobs.
Theoretically, saying “no one is going to get laid off” should be reassuring, right?
Unfortunately, when you say a negative thing, then say that negative thing ISN’T going to happen, people still think of the negative thing.
I’ve written about why you should avoid incepting negative ideas:
Ideas are fuzzy until you're able to put them into words, then they become concrete and real.
If you want an idea to become more concrete, verbalize it and spend time talking about it.
If you want an idea to remain in the background, avoid giving it air time.
Always incept positive ideas.
Incepting negative ideas creeps surprisingly often in daily language, until you train yourself to stop doing it.
The more concrete the idea, the stickier it is. And this can backfire when you’re talking about negative things in super visual, visceral ways.
I don’t think we point that out often enough. We usually talk about specificity and concreteness being good because they make your ideas more memorable. But what if you don’t want your idea to be so memorable? Then you may want to intentionally be more abstract.
I believe founders/leaders face this more because they’re more predisposed to being good at painting a picture. You regularly have to sell your vision and get stakeholders (investors, your executives, your team, customers) excited.
You would normally LEAN INTO your strength of painting a picture with your words, and getting getting folks to imagine what the future could look like.
So it’s useful to point out when you might NOT want to use this strength. When you don’t want negative ideas, scary visuals, or ominous scenarios to get seared into your audiences’ minds.
There are times when it’s more advantageous to be a bit abstract instead of concrete.
For example:
🚫 “We’re not shutting down, and we don’t have to go begging in the streets for more VC money yet. Also nobody is fired as of today. I’m not saying our product is terrible and doesn’t bring any value, but we have some work to do.”
✅ “We’re in a solid position with good runway and the right team in place. We have a lot of work ahead to get our product to where we need it to be, and the next six months will be crucial.”
The “before” has some pretty strong (negative visuals): Shutting down, begging in the streets, fired…
The “after” is less dramatic and less visceral. Notice how I’m not trying to 100% reassure everyone. I still want the team to feel a sense of urgency.
But if your team is already feeling a bit scared, then saying “we have a lot of work ahead to get our product to where we need it to be” is a good level of concrete vs abstract.
As a leader, everything you say will carry more weight than you think. So you want the team to feel a sense of “we gotta buckle down and focus,” but you don’t want to make them too fearful.
Have you heard a leader use scary language that ended up being counterproductive? What was your reaction hearing it? How will you be mindful of avoiding incepting negative ideas in your own communication?
Hit reply because I’d love to hear from you. Thanks for being here, and I’ll see you next Wednesday at 8am ET.
Wes
I just opened a new cohort for August 2025. The July cohort filled up sooner than expected, so the August cohort will be the only other chance to take the cohort this summer.
This course is not for everyone. I share more details on the course page about who this is for because I only want you to take the course if you will get extremely high ROI from it.
For example:
This is not for you if you want step-by-step instructions for every situation you might encounter with every stakeholder or type of meeting. My goal is to help sharp operators develop even better judgment, not to cover directions for every potential situation.
This is not for you if you expect to become excellent in communication overnight. You will likely change your behavior within 2 days, which is an ambitious goal and huge achievement. But becoming excellent at anything requires time and ongoing practice.
This is not for you if you want a slower-paced course over several weeks. This is a 2-day intensive designed for busy operators who want to reduce context-switching between work and the course. If you want something that feels slower or more spread out, do not take this course.
Alright, a few weeks ago, I wrapped up my most recent May cohort. The student reviews are in…
If you’re wondering if this is for you, check out what tech operators are saying:
And more student reviews:
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Learn more about 1:1 coaching to sharpen your executive presence and communication
✨ The new August 2025 cohort is open for enrollment: Improve your ability to sell your ideas, manage up, gain buy-in, and increase your impact in an intensive 2-day workshop. Save your spot → Executive Communication & Influence for Senior ICs and Managers
2025-05-28 20:03:07
👋 Hey, it’s Wes. Welcome to my 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—there are 7 spots left in the July cohort.
⛑️ Welcome, and thanks for being here. 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, learn more about my coaching approach.
Read time: 6 minutes
Years ago, I had a direct report who I adored.
They were hard working, had finesse when handling customers, and were eager to do a great job, which was all more than half the battle.
But they had some downsides:
They took feedback personally. They wouldn’t get defensive though. Instead, they would be overly-apologetic and feel terrible about disappointing me, to the point where I had to talk them off a ledge and attempt to help them develop a right-sized reaction to what I was saying.
They also had this strange tendency to speak with a CYA (cover your ass) vibe.
At first, it was hard to put my finger on it.
Over time, I realized they were trying to prove they were extremely committed—and therefore, the logic goes, they should be beyond reproach.
This person had felt traumatized from negative experiences earlier in their career, so I get where that came from. I want to write about this because this is something your manager or colleagues would probably never tell you because they’ll seem like a jerk.
So I’ll say it, because I believe if you want to advance in your career…
You should avoid having an overly obvious, performative CYA vibe.
It makes you seem nervous and afraid.
It prevents your manager from being able to speak plainly to you.
It can make people hesitant to give you feedback, lest you interpret it as questioning your intelligence/ability/commitment.
To be clear, different work cultures require different degrees of CYA. So if your work environment necessitates it, do what you need to do to protect yourself. In this post, I’m focusing on situations where there might be a mismatch in how fearful you’re acting vs how fearful you should be acting.
Often, we hold onto past negative experiences and carry them into our current environments, without stopping to question whether this new environment warrants that behavior.
So I’m not saying “stop all CYA.” I’m simply saying, don’t over-do the CYA.
Okay, back to my former direct report. Before a project started, they’d say stuff like this:
“Here's what I need to perform at my absolute best. I'm totally committed to doing a great job here. In order for me to make sure I’m delivering for you, can I ask for some guidance on this process?”
This isn’t egregious, and I know they had good intentions. And I liked that they checked in about expectations before getting started.
Still, there was something in the execution that felt weirdly formal, like trying too hard to be of service. It’s like saying, “I’m trying really hard. You can’t be mad at me because I’m trying so hard.”
It feels a bit uncomfortably servile. They’re downplaying their own agency while emphasizing they are being of service to their recipient (me, in this case). Normally, it’s good to be recipient-focused in your messaging, but this is too on-the-nose.
It feels like putting on a show of dedication, rather than simply being dedicated.
See if you can spot the difference between these statements:
🚫 “I'm totally committed to making this launch successful. To ensure I don't miss anything critical, could you outline exactly what metrics you'll be using to evaluate the results? I just want to make absolutely certain I'm focusing on the right priorities.”
✅ “As we prepare for the launch, I’d like to confirm which metrics matter most when we evaluate this project. That way, we can build our strategy around the most meaningful outcomes.”
^ At first glance, the two messages seem pretty similar. But the nuance in the execution makes a big difference.
The former makes you sound overly-eager and more junior than you actually are.
For example, asking about metrics you’ll be using to evaluate results heightens the fact that you are being evaluated, and that your manager has the power to evaluate you. This might be true, but you don’t need to emphasize it this way.
Notice how in the “after,” you still ask about the metrics and show effort, but you’re professional, calm, and grounded about it.
🚫 “I want you to know that I take this responsibility very seriously. I’ve blocked off my weekend to dive deep into these numbers because I believe this analysis deserves nothing less than 110% of my attention.”
✅ “I’ve reviewed the data and see some interesting patterns. I'll have the complete analysis by Monday, which gives me time to validate the findings.”
^ The “before” is trying prove that you are extremely dedicated to your job. It sounds like you want your manager to say, “Oh my gosh, you don’t need to work this weekend!”
It sounds like you want them to feel a bit guilty and try to convince you not to work so hard.
🚫 “I'm absolutely dedicated to executing your vision. To make sure I don't disappoint you, could you please share your expectations? I promise I’ll follow your direction and check in often to make sure I’m on the right track."
✅ “To make sure we're aligned, I’d love to discuss your key priorities and what success looks like. That way, I can make informed decisions as we move forward and bring you relevant updates.”
^ Again, on the surface, the “before” vs “ after” seem similar. The difference is in the underlying posture. The “before” has a performative, I’m-going-to-try-my-best vibe that seems like trying to prevent potential criticism downstream.
For example, emphasizing “your vision” and “your expectations” and “your direction” all heighten the power differential between you and your manager.
The “after” says the same thing—that you want to align on what success looks like, without the drama.
When you heighten the status difference between you and your manager, this might seem harmless on the surface. It’s just you being super committed and wanting to do a great job, right?
But peel back a layer, and there’s often a subconscious expectation:
“You (my manager) are the one in charge. I’m doing as you say. If this doesn’t work, it’s not my fault.”
Stop trying to absolve yourself of responsibility. Even if your role is primarily execution, your manager wants you to have a point of view. They want you to be an active participant and speak up about what’s best for the business.
Also, this is important: Your manager will still hold you accountable if you disagreed with their guidance, but didn’t speak up.
The fact that you “tried really hard” won’t save you.
The next time you catch yourself veering toward an overly-performative CYA statement, take a moment and pause.
Think to yourself: “My manager will likely hold me accountable for the results regardless. How can I say what I want to say in a way that is less dramatic, and more grounded, calm, and objective?”
Have you noticed colleagues who speak this way, or do you notice yourself speaking this way? What could you do differently next time?
Hit reply because I’d love to hear from you. Thanks for being here, and I’ll see you next Wednesday at 8am ET.
Wes
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Learn more about 1:1 coaching to sharpen your executive presence and communication
✨ The July 2025 cohort is open for enrollment: Improve your ability to sell your ideas, manage up, gain buy-in, and increase your impact in an intensive 2-day workshop. Save your spot: Executive Communication & Influence for Senior ICs and Managers (There are 7 seats left. After this, the next cohort will be in August or September.)
2025-05-21 20:02:36
👋 Hey, it’s Wes. Welcome to my 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.
⛑️ 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. Learn more about my coaching approach.
Read time: 2 minutes
There’s a difference between good struggle vs bad struggle.
I used to think all struggling meant I was “pushing myself” and “growing,” but that's not true. It took me a long time to learn this.
As an ambitious person, I had gotten good at gaslighting myself when I encountered a challenge that made me nervous:
“It’s not anxiety, it’s excitement!” I’d tell myself.
Sometimes anxiety is excitement.
But sometimes anxiety… is just anxiety.
At a certain point, I realized, “Actually I don’t really like doing X. And there are plenty of other ways I could invest my time that utilize my strengths.”
Good struggle is:
Thrashing to shape an idea
Practicing and learning a new skill
Answering hard questions about what to do
Messiness on the path to developing conviction
You can’t outsource this type of struggle, and it ends up being good for you in the long run.
Bad struggle is
Pontificating in circles
Overanalyzing and handwringing
Trying to change people you won’t ever get along with
Optimizing past the point of diminishing returns
Bad struggle doesn’t eventually lead to a positive outcome. It just makes you tired. Learn to distinguish between good struggle vs bad struggle. Invest your emotional energy in good struggle.
There’s an emotional cost to dealing with stuff you’re worried about. Do I want to be in this prolonged state? Sometimes, the upside is worth it—that’s why it’s useful to learn how to do hard things, because it gives you the optionality to decide whether to do the hard thing.
But we forget the other side of this optionality: You don’t HAVE to choose to do the hard thing. The “hard thing” is not necessarily better for you simply because it’s hard.
We have to stop blindly equating pain with growth, because sometimes pain does lead to growth, but other times, it’s a sign the environment you’re in is a bad fit.
If you always associate pain with growth, I believe you are likely to stay way too long in environments or functions that were never meant for you in the first place.
Environments where you’re barely able to survive much less thrive, and where you get pulled into a vicious cycle thinking you’re wrong for being the way you are.
And the solution isn’t to get better at gaslighting yourself about how you’re supposed to feel excited when you step outside your comfort zone.
The solution is to develop better self-awareness and instincts around when to keep pushing, and when to find a different activity or environment.
Have you ever conflated good struggle with bad struggle? What’s something you think might be ‘bad struggle’ that you can let go of, so you can spend more energy on ‘good struggle’?
Hit reply because I’d love to hear from you. Thanks for being here, and I’ll see you next Wednesday at 8am ET.
Wes
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2025-05-14 20:02:48
👋 Hey, it’s Wes. Welcome to my 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.
⛑️ Welcome and thanks for being here! 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.
I originally published a version of this essay in May 2020. If you find it helpful, please share with friends. Enjoy.
Read time: 3 minutes
When we want to impress, we often feel the urge to name every single thing we’ve done.
Every skill we have.
Every client we’ve ever worked with.
Anything we’ve attempted.
We think the more we add to the list, the greater our accomplishments will seem.
But more isn’t always better. Sometimes it’s actually worse. Why?
People judge us based on the average of our accomplishments, not the cumulative.
With averages, adding items can actually reduce your overall perceived value.
People have terrible memories and short attention spans.
At a networking event, stick to one or two things that people can distinctly remember about you.
Instead of listing every client you’ve worked with, mention the most famous ones. People will assume the other clients you worked with were just as famous—you just didn’t have enough room to list them.
Talk about how you’ve been an avid skier for 23 years. Don’t mention that you are also a beginner in woodworking.
To be sure, the fact that you’ve been carving woodblocks for the past six months is an interesting conversation topic. You should absolutely mention it if you’re looking to find common ground with others.
But in situations when you want to impress with your accomplishments, leave it out. Focus on the fact that you’ve been doing Brazilian Jiu Jitsu since you were 4 years old, you’ve won championships, and toured the world.
✅ Average: 3-time world champion in Brazilian jiu Jitsu, computer science major, fluent in French
🚫 Cumulative: 3-time world champion in Brazilian jiu Jitsu, computer science major, minor in political science, beginner at watercolor painting, fluent in French, beginner at choir singing, beginner at the trombone
You have more to be proud of than you think. Anything that would be shocking, surprising, or piques curiosity is fair game to include.
Another example: Let’s say you want to talk about customers you work with.
✅ Average: Worked with Stripe, Meta, Notion
✅ Conclusion: Listed 3 things. All 3 were strong. So 100% strength.
🚫 Cumulative: Worked with Stripe, widgetsforcheap.com, Meta, cogsandwidgets.com, Notion, morewidgets.co, widgets4u.com
🚫 Conclusion: Listed 7 things. 3 were strong. 42% strong. Some are strong but others sound spammy. Not sure how legit you are.
Famous leaders will often mention what they’re bad at because they want to appear relatable. When a head of state or CEO says they are terrible at physics, but love watching YouTube videos about it, it doesn’t diminish their power. It just makes them seem more approachable, and therefore more likable.
So if you want to seem relatable, you can talk about what you’re not great at. But makes sure you do this intentionally and sparingly, because in general, people like being on the same team as winners. More on the problem with glorifying failure.
The next time you’re debating whether to include one of your accomplishments or hobbies, ask yourself: Would this increase my average?
Have you experienced the urge to list everything you’ve done, every project you’ve ever touched, and every skill you have? How is this making you think differently about how you talk about your accomplishments?
Hit reply because I’d love to hear from you. Thanks for being here, and I’ll see you next Wednesday at 8am ET.
Wes
Are you new to the newsletter? Subscribe for free
Follow me on LinkedIn for more insights
Learn more about 1:1 coaching to improve your executive presence and communication
✨ The new July 2025 cohort is now open: Improve your ability to sell your ideas, manage up, gain buy-in, and increase your impact in an intensive 2-day workshop. Save your spot here: Executive Communication & Influence for Senior ICs and Managers