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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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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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:
Is this your first time here? Subscribe (it’s free)
Follow me on LinkedIn for more insights
Learn more about 1:1 coaching to sharpen your executive presence 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