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
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✨ 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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Learn more about 1:1 coaching to sharpen your executive presence, influence, and ability to delegate
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
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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
2025-07-09 20:03:04
👋 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
⛑️ If you’re looking to dramatically improve your communication and leadership, I typically work with tech leaders on: managing up to a startup CEO, strengthening your executive communication, and delegating to a team of ICs while raising the bar. If you’re interested in how I can support you, learn more about my coaching approach.
Read time: 9 minutes
Delegating isn’t hard.
Delegating while maintaining the level of quality you want…
without needing to jump in to do everything yourself…
or taking 3x as long because you’re correcting your team’s work after you delegated to supposedly save yourself time…
That is hard.
I’ve come to realize that the problem isn’t that managers don’t know they should delegate.
Every manager knows they should delegate.
So why is it so hard to do it consistently, and do it well?
The challenge is you (the manager) are ultimately responsible for the quality of decision-making and quality of output that comes out of your team.
You are basically putting your stamp of approval on everything your team ships.
There is a psychological weight to this, that we as managers are compensated for carrying and which comes with the role. But it’s a weight nonetheless.
Personally, I do not want to put my stamp of approval on stuff that I don’t think is that good. I do not want to say “looks good to me” if the thing does not, in fact, look good.
Not everything has to be done at an A+ level, but I refuse to accept I just have to lower my standards overall if someone else is doing the work. (Some amount of this is necessary but IMO most managers use this as an excuse to let standards drop in the name of “well someone else is doing it and they’ll do it differently so I should let it go.”
When I was learning to delegate, I did not need management experts telling me Captain Obvious advice, like “You need to prioritize! Do what’s most highly leveraged!”
Obviously I was trying to prioritize and be involved in stuff that was highly-leveraged and high ROI.
If you are an operator/founder who is actually building and responsible for driving outcomes, you know it’s not always so simple to “let go” or “deprioritize ABC.” Multiple areas of work are important and you don’t have so many levers to drive growth that you can haphazardly treat some as throwaway.
Over time, I realized a few things about delegating that really helped me embrace delegating, and even come to really enjoy it. I share the concepts below, and hope they help you too.
Some managers are very comfortable being quite distant from the day-to-day of what their team’s work actually entails.
That’s never been me. I’m a proud player-coach. Most of the leaders I respect are not so removed from the craft.
Many of my clients are leaders/founders who see value in being plugged into what their team is doing.
Personally, I believe you need some knowledge of the craft and context to be able to be a useful thought partner to your team. If you’re too distant and hands-off, you’re often not able to understand the nuances involved, which makes it harder for you to contribute, problem solve, etc beyond a surface level.
So this post is for you if you are a manager who wants to be plugged in with your team BUT want to stop doing everything yourself.
Most people see it as binary: you do it yourself or delegate to others. But delegating is actually a spectrum.
A common challenge I work with clients on is knowing when to solve a problem yourself vs solving with/alongside your direct report vs delegating entirely to a direct report. It is situation-dependent, so we talk about what project/task you're thinking of delegating, who's a good candidate, their task-relevant maturity, and how to build in check-in points so you derisk the chances they come back with something of mediocre quality.
I love delegating and have helped many operators develop their own intuition around when/how to delegate.
When my clients realize delegating isn’t binary, they start seeing in shades of grey. You’ll start to see progress with how you’re improving how you delegate, and how your team is gradually and consistently taking on more of what you used to do.
Continuing from the point above, the concept of task relevant maturity is super helpful. It reminds me that, again, delegating is not all-or-nothing.
Andy Grove, CEO of Intel, created this term in his classic book High Output Management. Here’s an excerpt:
“How often you monitor should not be based on what you believe your subordinate can do in general, but on his experience with a specific task and his prior performance with it—his task relevant maturity... As the subordinate's work improves over time, you should respond with a corresponding reduction in the intensity of the monitoring.”
Basically, you should be more hands-on if your direct report is newer at the specific type of task you’re asking them to do.
For example, let’s say you manage a program manager. You fully trust them to run existing programs, and they have a track record of improving what you’ve designed.
But if going forward, you want them to create programs from scratch, this is a new skill. They do not have much experience doing this.
Just because the person was great at maintaining existing programs, does not mean they have the skills to invent and design new programs. Realizing that these are different skills is helpful for deciding how to support your direct report.
You may to stay more involved until you see that your direct report knows what to do, you’re trusting and verifying their work, etc. Once they get the hang of it, you can be less involved, or shift from directing mode to coaching mode.
You may be lying to yourself when you say, “I’m the only one who can do this”.
I've observed (and have personally experienced) the urge to “hide” by doing stuff I’m already good at and know how to do. I say other people wouldn’t be able to do X, but that’s partially because I take pride in being good at X.
I believe this is an unspoken thought that many managers have.
This is more of the mindset aspect of delegating. IMO It's extremely important to be ruthless about calling yourself out and being intellectually honest.
There are going to be new things that are ambiguous, uncertain, there’s no right answer, and it's going to feel tempting to delay thinking about those and focusing on what you do know. You will always have too much on your plate, so it's your responsibility to assert what you should be doing.
If you’re reactive, you’ll end up being pulled in every direction, being spread too thin, and feeling resentful. And your manager/leadership won't know why because they’ll have expected you to define what you should be doing.
Many managers toss a request over the wall with zero context and say “do this.”
Even if your direct report is senior, they would likely benefit from a bit of context. Even 5-10 minutes to cover why this project matters, what the goal is, potential areas of risk, etc makes a huge difference.
Consider it an upfront investment. Doing this will help your team save time, minimize miscommunication, execute with confidence, and ship faster.
For more on how to explain yourself well when delegating, check out the CEDAF framework.
Notice I said avoid owning IC work, not avoid doing IC work.
This is perhaps the most important item on the list. I would credit this as the main way I’m able to stay quite involved in my team’s work to be able to coach, teach, and help them improve their judgment, WITHOUT getting overwhelmed being too in the weeds.
In today’s environment and teams becoming more lean due to AI, many managers have to be more hands on, which means embracing IC work. Personally I think this is great because it keeps you sharp at your craft.
The idea is to avoid owning IC work as much as possible—knowing that if you are a player-coach, you will still end up doing 20%+ IC work even if you aim to do 0%.
When I managed more junior and mid-level folks, this worked well because:
(a) it’s much easier to react to an asset in front of you than to create from a cold start, so you use less brainpower
(b) my direct reports loved seeing my “before and after” examples when I gave edits
(c) you can give high-level structural feedback, then ask them to take another stab. This allows you to stay highly-leveraged yet involved in your team's work.
Not owning IC work, but still being hands on when your direct reports prepare stuff to review with you, has been the key for me.
You can also ask your team members to bring you multiple items to review in a batch. That way, your team can come organized, you can hammer through giving feedback on a few things, and you can both make the best use of your time. More on how I give feedback quickly.
Which item on the list are you most excited to try?
Delegating is not binary
Identify your direct report’s task relevant maturity
Resist the urge to “hide” behind doing stuff you’re already good at
Take the time upfront to explain a project thoughtfully
Avoid owning IC work
Hit reply because I’d love to hear from you. Thanks for being here, and I’ll see you in two weeks on Wednesday at 8am ET.
Wes
If you liked this, you’ll like these posts on delegating, giving feedback, and developing high standards:
The August cohort will be the second-to-last cohort of the year. The cohort is already over 55% full, and has students enrolled from Amazon, Shopify, Google, Snowflake, Qualcomm, Sonos, Meta, Atlassian, etc.
Teams from DailyPay, StitchFix, Meta, etc have taken the course together, and in every cohort, there are multiple teams participating as a group. The course is especially valuable when taken with your team because having shared expectations & clear communication benefits everyone you work with.
I’m offering $100 discount per person for groups of 5+ team members, with higher discounts for larger groups. Reach out at [email protected] for more info on how to enroll your team.
If you’ve been thinking about joining, I hope to see you in class.
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The new August 2025 cohort of Executive Communication & Influence is open for enrollment: Improve your ability to sell your ideas, manage up, gain buy-in, and increase your impact in an intensive 2-day workshop. This is the second-to-last cohort of the year. → See course details
Learn more about 1:1 coaching to sharpen your executive presence, influence, and ability to delegate
2025-06-25 20:03:14
👋 Hey, it’s Wes. Welcome to my 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.
✨ Announcement: I’m updating my publishing cadence from weekly to bi-weekly. Going forward, you’ll hear from me every other week.
For context, the weekly format was great for nearly two years, and in order to continue sharing high quality insights, I realized I need more time to percolate between writing. Publishing twice a month seems like a good solution. I plan on keeping the newsletter free for now, and appreciate you being here!
I originally published a version of this essay in August 2020. If you find it helpful, please share with friends. Enjoy.
Read time: 5 minutes
Mediocre copy is a missed opportunity.
As an operator and leader, you need every lever you have to win. You could have an incredible idea… But if you have poor messaging, all your hard work is wasted. Bad messaging obscures your value.
On the other hand, good messaging is an amplifier. It takes a seed of something good and aggrandizes it.
The benefit is a transference of emotion. Of course you feel excited about your idea. With good messaging, you can TRANSFER that feeling to your recipient.
To improve your messaging, you can do three things:
Improve your writing
Improve your idea
Improve both
When writing is obviously bad, you delete it.
When writing is obviously good, you ship it.
But what if it’s not terrible, but it’s not good either?
Now we’re in a grey zone where there’s no easy fix.
I call this limbo writing.
It’s just kind of there. Neither dead nor alive.
Editing limbo writing takes a disproportionate amount of mental effort. Because the problem often isn’t the copy. The problem is that the underlying idea is fuzzy.
The lack of a point of view expresses itself as mediocre copy.
As a marketer, founder, or product owner, there simply aren’t enough levers to treat copy as a throwaway. We have to use every lever to the max.
Here’s how to fix limbo copy, depending on the underlying issue.
There are lots of good resources on how to write well, so I’ll keep this short.
Add rhythm by varying the sentence structure. Rhythm is hard to put your finger on. It’s what gives writing a good pace. It’s why people say, “The book was long but it felt fast.”
Use a mix of short and long sentences for a dynamic feel. This is an easy and fun one. Read through your writing and mark sentences you want to make longer or shorter.
Trim excess fat to make your writing tighter. Say it in fewer words. If you feel bored reading it, remove it. If it’s too much backstory, remove it. Start right before you get eaten by the bear.
Strengthen your claim stronger by adding data points, surprising statistics, numbers. You won’t have to shout because these help make your point. Your reader comes to your conclusion themselves.
Swap out weak nouns and verbs. Get rid of adverbs while you’re at it. You can usually remove descriptors if your readers won’t need that detail.
Sound like a human, not what you think a business professional sounds like. No one talks like the corporate machines from your college career center manuals.
Avoid double negatives. Double negatives are confusing. Don’t make your reader think too hard.
Clarify what you want to say in the first place. Writing is the vessel to express your idea. If you don’t know what you want to say, no amount of good writing can compensate for the lack of an idea.
Finish the knock-knock joke. Does the idea feel incomplete? Sometimes, we write the first half of a knock-knock joke, but we forget the payoff. If that’s the case, add the “Who’s there?” to complete your thought.
Even a tweet has a narrative arc. Even in 280 characters, there’s a beginning, middle, and end. That’s why you can’t pull a few random sentences from a blog post and turn it into a tweet. It will feel incomplete because there’s no tension. Make sure whatever you’re writing is a standalone unit, whether it’s a work email or a 280 character tweet.
“I am not a crook” makes people think you are a crook. Plant ideas you want people to think of. My favorite example of what NOT to do is Richard Nixon saying, “I am not a crook.” Then everyone thought, “Hmm I couldn’t put my finger on it before… But you are TOTALLY a crook.” More on why to avoid incepting negative ideas.
Explicitly state your assumptions and rationale. It’s like showing your work in math class. Share the thought process behind your recommendation. This helps your manager give feedback on specific logical gaps instead of tossing out your whole idea. It creates the basis for a productive conversation.
Scarce + relevant = valuable. Teach something people don’t already know. What’s both surprising and true? Instead of summarizing and recapping, how can you make your contribution additive? There’s too much of the same-same already.
Clarify your stance. Have a spiky point of view rooted in evidence that others can disagree with.
Articulate the action you want your reader to take. Once you have your call-to-action, give them reasons to give you an enthusiastic yes.
Remember: Messaging is one of the few levers available for getting your customers to take action.
Besides the product design, the messaging is how you set expectations and offer surprise and delight.
It’s how you build closeness with your customer. It’s how you frame your product’s value.
Don’t waste this lever.
Have you dealt with limbo writing? Which tactic above are you most excited to try?
Hit reply because I’d love to hear from you. Thanks for being here, and I’ll see you in two Wednesdays at 8am ET.
Wes
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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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✨ 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