2025-05-28 20:03:07
👋 Hey, it’s Wes. Welcome to my weekly newsletter on managing up, leading teams, and standing out as a high performer. For more, check out my intensive course on Executive Communication & Influence—there are 7 spots left in the July cohort.
⛑️ Welcome, and thanks for being here. If you’re looking to dramatically improve your communication and leadership, I typically work with tech leaders on: managing up to a CEO/SVP, strengthening your executive communication, and delegating to a team of ICs while raising the bar. If you’re interested, learn more about my coaching approach.
Read time: 6 minutes
Years ago, I had a direct report who I adored.
They were hard working, had finesse when handling customers, and were eager to do a great job, which was all more than half the battle.
But they had some downsides:
They took feedback personally. They wouldn’t get defensive though. Instead, they would be overly-apologetic and feel terrible about disappointing me, to the point where I had to talk them off a ledge and attempt to help them develop a right-sized reaction to what I was saying.
They also had this strange tendency to speak with a CYA (cover your ass) vibe.
At first, it was hard to put my finger on it.
Over time, I realized they were trying to prove they were extremely committed—and therefore, the logic goes, they should be beyond reproach.
This person had felt traumatized from negative experiences earlier in their career, so I get where that came from. I want to write about this because this is something your manager or colleagues would probably never tell you because they’ll seem like a jerk.
So I’ll say it, because I believe if you want to advance in your career…
You should avoid having an overly obvious, performative CYA vibe.
It makes you seem nervous and afraid.
It prevents your manager from being able to speak plainly to you.
It can make people hesitant to give you feedback, lest you interpret it as questioning your intelligence/ability/commitment.
To be clear, different work cultures require different degrees of CYA. So if your work environment necessitates it, do what you need to do to protect yourself. In this post, I’m focusing on situations where there might be a mismatch in how fearful you’re acting vs how fearful you should be acting.
Often, we hold onto past negative experiences and carry them into our current environments, without stopping to question whether this new environment warrants that behavior.
So I’m not saying “stop all CYA.” I’m simply saying, don’t over-do the CYA.
Okay, back to my former direct report. Before a project started, they’d say stuff like this:
“Here's what I need to perform at my absolute best. I'm totally committed to doing a great job here. In order for me to make sure I’m delivering for you, can I ask for some guidance on this process?”
This isn’t egregious, and I know they had good intentions. And I liked that they checked in about expectations before getting started.
Still, there was something in the execution that felt weirdly formal, like trying too hard to be of service. It’s like saying, “I’m trying really hard. You can’t be mad at me because I’m trying so hard.”
It feels a bit uncomfortably servile. They’re downplaying their own agency while emphasizing they are being of service to their recipient (me, in this case). Normally, it’s good to be recipient-focused in your messaging, but this is too on-the-nose.
It feels like putting on a show of dedication, rather than simply being dedicated.
See if you can spot the difference between these statements:
🚫 “I'm totally committed to making this launch successful. To ensure I don't miss anything critical, could you outline exactly what metrics you'll be using to evaluate the results? I just want to make absolutely certain I'm focusing on the right priorities.”
✅ “As we prepare for the launch, I’d like to confirm which metrics matter most when we evaluate this project. That way, we can build our strategy around the most meaningful outcomes.”
^ At first glance, the two messages seem pretty similar. But the nuance in the execution makes a big difference.
The former makes you sound overly-eager and more junior than you actually are.
For example, asking about metrics you’ll be using to evaluate results heightens the fact that you are being evaluated, and that your manager has the power to evaluate you. This might be true, but you don’t need to emphasize it this way.
Notice how in the “after,” you still ask about the metrics and show effort, but you’re professional, calm, and grounded about it.
🚫 “I want you to know that I take this responsibility very seriously. I’ve blocked off my weekend to dive deep into these numbers because I believe this analysis deserves nothing less than 110% of my attention.”
✅ “I’ve reviewed the data and see some interesting patterns. I'll have the complete analysis by Monday, which gives me time to validate the findings.”
^ The “before” is trying prove that you are extremely dedicated to your job. It sounds like you want your manager to say, “Oh my gosh, you don’t need to work this weekend!”
It sounds like you want them to feel a bit guilty and try to convince you not to work so hard.
🚫 “I'm absolutely dedicated to executing your vision. To make sure I don't disappoint you, could you please share your expectations? I promise I’ll follow your direction and check in often to make sure I’m on the right track."
✅ “To make sure we're aligned, I’d love to discuss your key priorities and what success looks like. That way, I can make informed decisions as we move forward and bring you relevant updates.”
^ Again, on the surface, the “before” vs “ after” seem similar. The difference is in the underlying posture. The “before” has a performative, I’m-going-to-try-my-best vibe that seems like trying to prevent potential criticism downstream.
For example, emphasizing “your vision” and “your expectations” and “your direction” all heighten the power differential between you and your manager.
The “after” says the same thing—that you want to align on what success looks like, without the drama.
When you heighten the status difference between you and your manager, this might seem harmless on the surface. It’s just you being super committed and wanting to do a great job, right?
But peel back a layer, and there’s often a subconscious expectation:
“You (my manager) are the one in charge. I’m doing as you say. If this doesn’t work, it’s not my fault.”
Stop trying to absolve yourself of responsibility. Even if your role is primarily execution, your manager wants you to have a point of view. They want you to be an active participant and speak up about what’s best for the business.
Also, this is important: Your manager will still hold you accountable if you disagreed with their guidance, but didn’t speak up.
The fact that you “tried really hard” won’t save you.
The next time you catch yourself veering toward an overly-performative CYA statement, take a moment and pause.
Think to yourself: “My manager will likely hold me accountable for the results regardless. How can I say what I want to say in a way that is less dramatic, and more grounded, calm, and objective?”
Have you noticed colleagues who speak this way, or do you notice yourself speaking this way? What could you do differently next time?
Hit reply because I’d love to hear from you. Thanks for being here, and I’ll see you next Wednesday at 8am ET.
Wes
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2025-05-21 20:02:36
👋 Hey, it’s Wes. Welcome to my weekly newsletter on managing up, leading teams, and standing out as a high performer. For more, check out my intensive course on Executive Communication & Influence.
⛑️ If you’re looking to dramatically improve your communication and leadership, I typically work with tech leaders on: managing up to a CEO/SVP, strengthening your executive communication, and delegating to a team of ICs while raising the bar. Learn more about my coaching approach.
Read time: 2 minutes
There’s a difference between good struggle vs bad struggle.
I used to think all struggling meant I was “pushing myself” and “growing,” but that's not true. It took me a long time to learn this.
As an ambitious person, I had gotten good at gaslighting myself when I encountered a challenge that made me nervous:
“It’s not anxiety, it’s excitement!” I’d tell myself.
Sometimes anxiety is excitement.
But sometimes anxiety… is just anxiety.
At a certain point, I realized, “Actually I don’t really like doing X. And there are plenty of other ways I could invest my time that utilize my strengths.”
Good struggle is:
Thrashing to shape an idea
Practicing and learning a new skill
Answering hard questions about what to do
Messiness on the path to developing conviction
You can’t outsource this type of struggle, and it ends up being good for you in the long run.
Bad struggle is
Pontificating in circles
Overanalyzing and handwringing
Trying to change people you won’t ever get along with
Optimizing past the point of diminishing returns
Bad struggle doesn’t eventually lead to a positive outcome. It just makes you tired. Learn to distinguish between good struggle vs bad struggle. Invest your emotional energy in good struggle.
There’s an emotional cost to dealing with stuff you’re worried about. Do I want to be in this prolonged state? Sometimes, the upside is worth it—that’s why it’s useful to learn how to do hard things, because it gives you the optionality to decide whether to do the hard thing.
But we forget the other side of this optionality: You don’t HAVE to choose to do the hard thing. The “hard thing” is not necessarily better for you simply because it’s hard.
We have to stop blindly equating pain with growth, because sometimes pain does lead to growth, but other times, it’s a sign the environment you’re in is a bad fit.
If you always associate pain with growth, I believe you are likely to stay way too long in environments or functions that were never meant for you in the first place.
Environments where you’re barely able to survive much less thrive, and where you get pulled into a vicious cycle thinking you’re wrong for being the way you are.
And the solution isn’t to get better at gaslighting yourself about how you’re supposed to feel excited when you step outside your comfort zone.
The solution is to develop better self-awareness and instincts around when to keep pushing, and when to find a different activity or environment.
Have you ever conflated good struggle with bad struggle? What’s something you think might be ‘bad struggle’ that you can let go of, so you can spend more energy on ‘good struggle’?
Hit reply because I’d love to hear from you. Thanks for being here, and I’ll see you next Wednesday at 8am ET.
Wes
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Learn more about 1:1 coaching to improve your executive presence and communication
✨ The new July 2025 cohort is now open: Improve your ability to sell your ideas, manage up, gain buy-in, and increase your impact in an intensive 2-day workshop. Save your spot here: Executive Communication & Influence for Senior ICs and Managers
2025-05-14 20:02:48
👋 Hey, it’s Wes. Welcome to my weekly newsletter on managing up, leading teams, and standing out as a high performer. For more, check out my intensive course on Executive Communication & Influence.
⛑️ Welcome and thanks for being here! If you’re looking to dramatically improve your communication and leadership, I typically work with tech leaders on: managing up to a CEO/SVP, strengthening your executive communication, and delegating to a team of ICs while raising the bar. If you’re interested in how I can support you, learn more about my coaching approach.
I originally published a version of this essay in May 2020. If you find it helpful, please share with friends. Enjoy.
Read time: 3 minutes
When we want to impress, we often feel the urge to name every single thing we’ve done.
Every skill we have.
Every client we’ve ever worked with.
Anything we’ve attempted.
We think the more we add to the list, the greater our accomplishments will seem.
But more isn’t always better. Sometimes it’s actually worse. Why?
People judge us based on the average of our accomplishments, not the cumulative.
With averages, adding items can actually reduce your overall perceived value.
People have terrible memories and short attention spans.
At a networking event, stick to one or two things that people can distinctly remember about you.
Instead of listing every client you’ve worked with, mention the most famous ones. People will assume the other clients you worked with were just as famous—you just didn’t have enough room to list them.
Talk about how you’ve been an avid skier for 23 years. Don’t mention that you are also a beginner in woodworking.
To be sure, the fact that you’ve been carving woodblocks for the past six months is an interesting conversation topic. You should absolutely mention it if you’re looking to find common ground with others.
But in situations when you want to impress with your accomplishments, leave it out. Focus on the fact that you’ve been doing Brazilian Jiu Jitsu since you were 4 years old, you’ve won championships, and toured the world.
✅ Average: 3-time world champion in Brazilian jiu Jitsu, computer science major, fluent in French
🚫 Cumulative: 3-time world champion in Brazilian jiu Jitsu, computer science major, minor in political science, beginner at watercolor painting, fluent in French, beginner at choir singing, beginner at the trombone
You have more to be proud of than you think. Anything that would be shocking, surprising, or piques curiosity is fair game to include.
Another example: Let’s say you want to talk about customers you work with.
✅ Average: Worked with Stripe, Meta, Notion
✅ Conclusion: Listed 3 things. All 3 were strong. So 100% strength.
🚫 Cumulative: Worked with Stripe, widgetsforcheap.com, Meta, cogsandwidgets.com, Notion, morewidgets.co, widgets4u.com
🚫 Conclusion: Listed 7 things. 3 were strong. 42% strong. Some are strong but others sound spammy. Not sure how legit you are.
Famous leaders will often mention what they’re bad at because they want to appear relatable. When a head of state or CEO says they are terrible at physics, but love watching YouTube videos about it, it doesn’t diminish their power. It just makes them seem more approachable, and therefore more likable.
So if you want to seem relatable, you can talk about what you’re not great at. But makes sure you do this intentionally and sparingly, because in general, people like being on the same team as winners. More on the problem with glorifying failure.
The next time you’re debating whether to include one of your accomplishments or hobbies, ask yourself: Would this increase my average?
Have you experienced the urge to list everything you’ve done, every project you’ve ever touched, and every skill you have? How is this making you think differently about how you talk about your accomplishments?
Hit reply because I’d love to hear from you. Thanks for being here, and I’ll see you next Wednesday at 8am ET.
Wes
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Learn more about 1:1 coaching to improve your executive presence and communication
✨ The new July 2025 cohort is now open: Improve your ability to sell your ideas, manage up, gain buy-in, and increase your impact in an intensive 2-day workshop. Save your spot here: Executive Communication & Influence for Senior ICs and Managers
2025-05-07 20:02:24
👋 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.
⛑️ Welcome and thanks for being here! If you’re looking to dramatically improve your communication and leadership, I typically work with tech leaders on: managing up to a CEO/SVP, strengthening your executive communication, and delegating to a team of ICs while raising the bar. If you’re interested in how I can support you, learn more about my coaching approach.
Read time: 6 minutes
There’s a lesson from sales that applies to communicating any idea:
Focus less on what you can’t do, and more time on what you can do.
Most people do the opposite: They spend too much time explaining why something isn’t possible. That is helpful for context, of course, so it's a matter of degrees.
If you beat a dead horse here, you end up sounding like a naysayer who lacks creativity and can’t get things done.
[A caveat: There are times when explaining thoroughly why something is not possible makes sense. If you think it’s truly important, definitely spend the time to do it. I’m not talking about those situations here. I’m talking about times when you are accidentally focusing too much on what you can’t do, when you could simply propose what you’re willing to do.]
Generally, you want to direct people’s attention to what you want them to think about.
Use this structure:
“I can’t do that, but I can do this."
Here are examples:
“I have a call during that time, but I can meet between 12-4:30pm. Does anything in that window work for you?”
“I can't approve the entire budget request, but I can allocate 70% of what you're asking for now and revisit the remaining next quarter once we see how the campaign performs.”
“I won’t be able to join the committee ongoing, but I’m happy to do a 1:1 call and be a thought partner to discuss the high level strategy if you want to bounce ideas.”
So that’s the basic structure.
Notice how in each example above, I mention very briefly what I can’t do, then immediately redirect to what I can or am willing do.
Now, let’s vary the phrasing. You don’t have to use the words can’t or won’t for this to work.
Often, I avoid can’t/won’t altogether because those words highlight what’s lacking, and I don’t want to highlight that.
Here’s an example of using the general structure without saying “I can’t do x.”
“We’ll need to update the ship date because X is taking longer than expected. But I can present what we have with 70% of the project complete, which includes sharing our results so far, learnings, and next steps. Let me know if this sounds good.”
Check out the color-coded annotations below:
^ I could have only said, “I can’t meet the original deadline because X is taking longer than expected.”
There are times you may want to say this in a matter-of-fact way. Other times, you may not want to admit so explicitly that you can’t meet the original deadline. On many teams, straight up saying “I can’t meet the original deadline” might invite avoidable pushback or upset colleagues, whereas saying “we’ll need to update the ship date” basically accomplishes the same thing—without sounding as negative.
And in the same breath, we pivot straight into what we are willing/able to do.
In either case, you still need to speak up (that part is a must regardless), so this structure allows you to speak up while increasing the chances that your recipient receives the news well.
The last variation of this is you may want to “sell” your idea a bit.
For example:
"I won’t be able to join the committee ongoing, but I’m happy to do a 1:1 call and be a thought partner to discuss the high level strategy if you want to bounce ideas ad hoc. Getting to riff and talk out loud with someone who’s outside the committee and doesn’t have skin in the game might be even more helpful.”
“We won’t be able to implement all those feature suggestions, but I will review with the team and take into account what you shared. I think the underlying premise of improving our user experience makes a lot of sense. Thanks for bringing this up.”
"Pulling all the data across our systems would take 2 weeks, which our team doesn’t have bandwidth for and is probably too long for you to wait. But I can create a dashboard with the metrics from our primary system, which covers about 80% of what you need and can be done in 2 days.”
Here’s the text with color-coded annotations:
This script template might seem simple on the surface, but it leverages principles of influence and behavioral economics under the hood.
In this case, I’m stacking concepts such as:
Loss aversion: Most people are more sensitive to loss than equivalent gains, so by minimizing what can’t be done, we’re reducing the perception of loss.
Peak-end rule: We’re deliberately engineering the end of the message to focus on your recommended next steps (positive).
Recency effect: The “can do” part will be remembered most clearly because it's the last thing your recipient heard, so it’s fresher in their memory.
Inverted but technique: This one isn’t a behavioral economics principle, but it’s one of my frameworks. Notice how I put the positive part after the “but.” This is strategic and directs my recipient’s attention to what I want them to think about. More on how to use “but” strategically.
Remember:
First, the thing you give airtime to tends to grow in importance in people’s minds. This is why you should avoid incepting negative ideas. Ideas are fuzzy until you put them into words, either spoken or written. The longer you give it airtime, and the more you repeat it, the more real and concrete it becomes.
Second, if you want an idea to feel more real, you should talk about it more. Repeat it more than you think you have to. You want to socialize the message, talk about it in different ways, share examples, link it to other ideas people already know, etc. All of this airtime reinforces the idea and makes it more concrete.
Third, this gives you more agency to influence the conversation in the direction you want it to go. Instead of the other person defaulting to controlling the frame, and you being purely reactive, you take the reins and assert what to do instead.
What’s a recent interaction when you could have focused less on what you can’t do, and more on what you can do? How will you respond differently going forward?
Hit reply because I’d love to hear from you. Thanks for being here, and I’ll see you next Wednesday at 8am ET.
Wes
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Learn more about 1:1 coaching to improve your executive presence
✨ The new July 2025 cohort opened a few weeks ago, and is already 50% full. Improve your ability to sell your ideas, manage up, gain buy-in, and increase your impact in an intensive 2-day workshop. Save your spot here: Executive Communication & Influence for Senior ICs and Managers
2025-04-30 20:02:55
👋 Hey, it’s Wes. Welcome to my weekly newsletter on managing up, leading teams, and standing out as a high performer. For more, check out my intensive course on Executive Communication & Influence.
⛑️ Welcome and thanks for being here! If you’re looking to dramatically improve your communication and leadership, I typically work with tech leaders on: managing up to a startup CEO, strengthening your executive communication/presence, and delegating while raising the bar. If you’re interested, learn more about my coaching approach.
I originally published a version of this essay in July 2020. If you find it helpful, please share with friends and coworkers. Enjoy.
Read time: 7 minutes
Early in my career, I worked with some of the smartest people at the Gap headquarters in San Francisco. I was bright-eyed and excited to be there, so I’d spend time after work putting together “trend boards” about styles that were trending in the market.
“I’m seeing a lot of high-end designers using plaid.”
“Leggings sales have been steadily going up while pants sales stayed constant.”
“A lot of brands are beginning to offer active wear this year.”
I would pat myself on the back when I pointed out an insight. I thought everyone else would pat me on the back too.
This wasn’t the case.
One of the senior merchants–my manager's manager–was a brilliant woman named Susie Park. Every time I knocked on her door to show her a mood board, she would say,
“And? What should we do? What are you suggesting? What action should we take?”
I rarely had a good answer. It was frustrating because I thought I had done my part, but each time, I was asked what we should actually do with the information I found.
I didn’t understand this until years later: Susie was trying to help me see that an insight alone isn’t enough.
An insight is just a start. It shows that you’re curious, you’re observing, you’re noticing what’s going on around you, you’re picking up on shifts in the wind.
But the next step is what actually moves the needle. The rare, courageous thing to do is to develop an assertion.
When you point out an insight, you’re calling attention to an observation, something you noticed and wanted to remark on. In response, your colleague could say, “Hmm interesting. That’s nice to know.” They carry on with their day. You carry on with yours. Nothing changes.
When you make a suggestion, you’re putting forth a recommendation. You’re proposing a few different options to choose from. But you’re still not on the hook because your boss ultimately decides what to do. And the person who decides holds the emotional burden of that decision.
When you make an assertion, all of a sudden, things get real. You’re on the hook because there’s more of you in what you’re positing. You’re now advocating for your point of view and trying to convince others to support you.
An assertion is your thesis. Assertions typically include:
A bias toward action: You aren’t just pointing out a fact in a vacuum. You’re connecting dots, interpreting the situation, and positing what your team should do with this information to move forward. An assertion has to answer, “So what?”
A point of view with personal conviction: You believe in this enough to look someone in the eye and try to convince them to do this. There’s an element of advocacy built into assertions.
Ownership: You are willing to take responsibility for trying this idea. You’re going to be the go-to person responsible. You’re saying, “If I were in charge, here’s what I would do, here’s where I would go, here’s what I’m betting on.”
A fact, as a standalone, is just a fact.
A fact, interpreted by you, is given meaning about what the implications are.
It’s not about isolated facts here and there–it’s those facts, as interpreted through YOUR LENS. This includes your background, the accumulation of your experiences, your values, your interpretation of the data, your instincts, your sense of judgment. All of these help you form an assertion that takes an insight to the next level.
Think of it this way: if you just had to follow directions down to a tee, your manager could hire someone on Upwork. They’re a lot more affordable than you are. And what’s even more affordable? Claude or ChatGPT.
Any repeatable, clearly defined task can be done better by AI than by a human. We want you to do the job that only humans can do. Connect dots. See patterns. Come to a conclusion about what you think this means–and what we should do about it.
One event could be experienced by ten people, who come up with ten different assertions.
One person could experience an event, and come up with ten possible assertions…. The hard part is picking the one you want to stand behind. We want to hear what you pick and why.
If someone ignores an insight or suggestion, you can shrug your shoulders and walk away. But an assertion demands action. In or out, yes or no. It’s about forward motion.
You might wonder, “Do I have to be 100% certain before I make an assertion?”
No, you’re not claiming to have all the answers. When you’re building something new, the work is messy and no one has the right answer.
The fact that no one has the right answer is precisely why assertions are so valuable.
Why?
First, there’s often no historical precedent about what to do. You don’t have a baseline to say you exceeded the results from last quarter, or explicit sign posts to let you know if you’re doing a good job.
Second, when you’re doing something new, you can’t just copy what someone else is doing. You have different assets, levers, and constraints than the organization you want to copy. So even if you literally did exactly what they did, you’d get different results.
But somehow, the project has to move forward. Assertions help move your project forward even when you aren’t 100% certain of what to do.
You want to be mindful that your language reflects your intent, meaning, and level of certainty. It’s irresponsible to say you’re certain when you’re not.
Here’s a simple framework for creating assertions:
“Based on my insight of X, I believe that Y is true. To go a step further, given X and Y, I think we should do Z. I think it’ll work because A and B. If it doesn’t work, there’s a risk of C happening, and I’ll take care of that by doing D.”
You’re saying, “I’m willing to look you in the eye and fight for this idea to become real. I’ve done the rigorous thinking about how this would work. And I will take responsibility if it goes awry.”
Many people ask a smart question, and stop there.
Asking smart questions is a start, but it isn’t enough. That’s step one. Step two is asserting your answer to said question.
When you just ask a question, it puts 100% responsibility on the other person to respond with their assertion.
Let’s assume you are tackling a problem with a non-obvious solution. It's a problem with multiple variables and complex parts that influence each other. Any change to the system could have unintended consequences.
The stakes feel high.
For hard problems like this, your counterpart has likely asked themselves smart questions many times before. If all it took were a question, they would have figured it out already.
Don't just ask questions. Professionals and A-players ask great questions, then assert how to answer those questions too. They don't claim to know everything, but they do have a point of view about how to solve the problem they just presented.
When you assert an answer, it moves the conversation forward because it helps fill in the blanks.
Share what you think we should do. You can do this by bringing your assertions, your hunches, your recommendations, your interpretations. It will help your team find better solutions faster.
The bottom line? Questions are good, but a question followed by an assertion is the next level. When you bring a question, be open and ready to share your take on it.
When you share an assertion, you could end up being wrong. Or your peers or boss could disagree with you.
We don’t like when people disagree with us. We don’t like being wrong. So we come up with all kinds of "rational" excuses about why we had an insight or suggestion... But stopped short of an assertion.
“If I had spoken up, it wouldn’t have mattered anyway.”
“I have a hunch, but I need more data before I can say anything out loud.”
“Who am I to assert what we should do? The leaders here know better than I do.”
Asserting is a generous thing to do because it gives other people something to work with. Even if someone disagrees with your assertion, you’re adding value because it helps your team come to a better understanding of the challenge or proposed solution.
Insights are a dime a dozen. Suggestions are a bit better, but still let you off the hook. Assertions are the realm of professionals who navigate ambiguity and rigorous thinking.
Assertions make an idea real. The sooner the ball gets rolling, the sooner you can iterate to make the idea better.
You can be the person who gets the ball rolling.
Where could you share your point of view more in your work? What assertions do you have that could help drive your work forward?
Hit reply because I’d love to hear from you. Thanks for being here, and I’ll see you next Wednesday at 8am ET.
Wes
Are you new to the newsletter? Subscribe for free
Follow me on LinkedIn for more insights
Learn more about 1:1 coaching to improve your executive presence
✨ The new July 2025 cohort is now open. Improve your ability to sell your ideas, manage up, gain buy-in, and increase your impact in an intensive 2-day workshop. Save your spot here: Executive Communication & Influence for Senior ICs and Managers
2025-04-23 20:02:49
👋 Hey, it’s Wes. Welcome to my weekly newsletter on managing up, leading teams, and standing out as a high performer. For more, check out my intensive course on Executive Communication & Influence.
⛑️ Welcome and thanks for being here. If you’re looking to dramatically improve your communication and leadership, I typically work with tech leaders on: managing up to a CEO/VP, 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: 7 minutes
Cold emails are hard mode.
But warm emails? Now we’re in business.
This is why I think it’s especially tragic when people mess up warm emails.
You’ve somehow gotten a friend/colleague to agree to introduce you… And you end up sending a middling note that was never going to pique the interest of the final recipient. What a waste.
Your friend sending the note can only do so much. They are likely going to forward your note with something like,
“Interested? Let me know, happy to make an intro.”
And you should be grateful for this. Don’t expect them to write an essay advocating on your behalf. The fact that they are sending your note along at all is a win.
You have to pull your weight.
Your note has to actually be good.
Your note is what will get your final recipient to say no or yes.
The focus of this post is warm intros specifically for sales pitches.
There are many reasons you might ask for a warm intro, but IMO, when you’re asking a friend…to connect you to their friend…so you can sell to their friend, you need to put a strong foot forward.
Before we start: This is not meant to be “how to send warm intros 101.” One of the investors in Maven, Chris Fralic, wrote an excellent piece on this in 2013 that’s still as relevant today.
Chris talks about sending what he calls the Self Contained Forwardable Email (SCFE). This is an email your connection can easily forward to the final recipient. There are other gems in there. So if you need a primer on warm intros, read that first.
Today, I want to dissect a warm intro note from one of my former colleagues.
Here’s the note:
Now let’s dissect this note, so you can apply the underlying principles to improve your own warm intro pitches.
My main problem with this note is it doesn’t really seem sincere.
I’m all for being concise, but there is such a thing as being too concise. The lever in a written pitch is words, so if you strip away most of the words, you strip away your ability to persuade.
In this case, it feels like the writer could go either way.
If you’re going to go through the trouble of asking for a warm intro (and using social capital for it), you might as well seem like you’re putting more effort into it.
Seeming more sincere goes a long way. There are many issues with LinkedIn DM thread bois who say “hey wanna hop on a call? I can 10x your leads in 3 days.”
Yes they lack personalization, and they probably can’t deliver on their promise.
But the thing that makes these messages particularly infuriating is the sense of entitlement.
They write two lines, and think they deserve 30 minutes of your time. They are strangers showing up unannounced, asking to be let into your living room.
It’s dangerous and not strategic to come across as entitled for one simple reason:
People are petty AF.
Do not underestimate how petty people can be. ESPECIALLY if you have no connection with them, and you need the phone call more than they do.
Yes, there’s advice of “don’t give away your power”, but I think many people misapply this. They think it means, “If I’m too respectful or eager, I’ll seem supplicant.”
Or worse: They have an accurate sense of the power dynamics, but due to poor execution…. they come across as entitled. This is unfortunate.
You don’t want to have to say, “But I had good intentions! I’m not actually entitled!”
You don’t get the chance to explain your intentions. Your words must be standalone.
Improve your writing, so your intentions can be felt by your recipient without you needing to add explanation.
Let me start by saying you can write excellent copy that’s boilerplate. You do not need to spend an hour customizing every outbound note. Here’s an example of a sales note that was 90% boilerplate, but still sounded personal, because the salesperson deeply understood and appealed to what their recipient cared about.
With that said, if you have the luxury of getting a warm intro, I recommend taking the extra 2-3 minutes to add a bit of personalization.
In my former colleague’s note above, the only personalized part is the potential course topic on brand and performance marketing. It’s a good start, but it doesn’t seem as thoughtful as it could be.
I’m sure she had good reasons for suggesting this topic:
Did you like a post this person wrote on this topic?
Is this topic trending on the platform?
Why do you think students would be excited to learn this topic from this individual, specifically?
If you have answers to these questions, include it in the note. This shows you’re reaching out to this specific person for a reason.
Your recipient is likely wondering, “Why are you reaching out to me specifically?”
You often already have answers to these questions off the top of your head. So incorporating the answers takes an extra moment, but can make a huge difference.
An obvious question an instructor might have is: What’s in it for me?
That’s an underlying question everyone asks themselves all the time. But let’s get more specific:
“Is there demand from Maven students on this topic?”
^ If you can show there’s demand for this topic, an instructor is much more likely to be interested.
“You mentioned you're curating a collection of growth courses. Who else is in this collection?”
^ This helps an instructor get a tacit sense of whether this is for “people like us.”
This is the place to name-drop to establish credibility. If you don’t have anyone in this collection yet, you can always say, “Our recent collections included instructors like [name people similar to or more successful than your target].”
This is a subtle way to show you are “picking” the instructor.
A note about tactics that play with power dynamics:
The poorly-executed way to “pick” the customer is to be too on-the-nose and act like you’re doing them a favor. This cheap “negging” trick might work on some people, but in my experience, it doesn’t work for most intelligent people.
They know you are trying to shift the power dynamics and make yourself the prize, and it’s off-putting.
The more skilled and subtle approach is to mention people who are at the same level or more successful. This does two things:
It says to your recipient: “We think you are as successful as X person,” with X person being someone they respect, admire, and believe is more successful. This is a flattering comparison.
It signals “people more successful than you have chosen to work with us.” This is a more subtle, effective way to signal that you have options. This shows you are the “prize” without being as explicit or crass.
Your recipient might have preconceived notions or misunderstandings about your product/category. How can you share a relevant piece of information that helps them think differently? How can you teach them something new?
For example, your recipient might think it’s a lot of work to create a course, so they won’t have bandwidth to build it.
In this case, you can either position your point as:
(a) This is a lot of work, but the revenue upside is higher than you think and you create an asset you can reuse for years to come.
or
(b) This is less work than you think—if you create a certain type of course, which is what I recommend. Here are links to courses like this.
Notice how the two statements above have opposite positioning.
This is a lesson in thinking flexibly, while still being rooted in facts. The arguments are opposite, but they are both true.
Based on what you think your audience will resonate with, you can choose which angle to go with, then offer data points, numbers, examples, etc.
“Is a course on your radar for 2025?”
The answer is probably no. This is a bad question because now they’re thinking, “Oh this isn’t relevant to me right now.”
You’ve killed any sense of urgency you might have had.
On the other hand, you could ask a better question with subtly different positioning:
“Have you ever thought about teaching a course?”
Given your target audience, the answer is probably yes.
If your goal in asking a question is to get the prospect more interested, make sure it’s a question they’ll answer the way you want them to.
If your company is small, however you want to define that, you may want your note to come from your cofounder/CEO.
You don’t HAVE to do this, but it will make you seem more sincere and less like your CEO is too good or too busy to interact with this person.
Before you say this is too much work, yes, it is a bit more work, but not as much as you think. For example, in previous companies, my team would draft notes for me and I/my assistant would send them from my email. It was quite fast.
It shows goodwill because you’re putting in effort first. When you put in effort first, you invite the other person to potentially do the same.
There’s no guarantee, but it increases the chances of getting a positive reply—or at least not rubbing the person the wrong way before they’ve even considered your request.
I don’t want to hear, “But Wes, people shouldn’t care if my deputy reaches out on my behalf!” This is similar to people saying “People shouldn’t feel offended that I’m asking them to pick from my Calendly.”
This is because I don’t live in the World of Should. I live in the World of Is, where I acknowledge how humans actually act, not how I personally would like them to act in an ideal world.
To recap, here are 6 ways to make your warm intro note stronger:
Try to sound more sincere.
Personalize more.
Answer obvious questions.
Address their preconceived assumptions.
Ask questions where the answer is likely to be yes.
Optional: Have the note come from your cofounder/CEO startup.
Which one of these jumps out at you? Which do you think you already do well, and which do you want to add to your toolkit?
Hit reply because I’d love to hear from you. Thanks for being here, and I’ll see you next Wednesday at 8am ET.
Wes
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