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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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
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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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Learn more about 1:1 coaching to improve your executive presence
✨ Update: The May cohort is sold out, but 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
We wrapped up an amazing April cohort last week, and I’m gearing up for the May cohort (sold out) in a few weeks. I just opened a new July cohort, which will likely be the only cohort this summer.
I put an obsessive amount of energy into making this course the best communication course for senior ICs and managers in tech. It’s not for everyone, but it’s the course I wish I had years ago that’s no-BS and takes into account the daily realities of being a hands-on operator.
The most rewarding part is seeing students’ eyes light up in class, then getting emails/DMs afterwards about how they’re applying what they learned. Here are some recent favorites:
Senior engineering manager @ Pinterest:
Senior manager @ big tech co:
Senior manager @ healthcare app valued at $1B+:
Product manager @ social media platform:
UX Researcher @ Meta:
The July cohort already has operators joining from: Shopify, Chan Zuckerberg Initiative, Asana, The New York Times, Linktree, Google, Meta, Roblox, Airbnb, National Geographic, Anthropic, and more.
2025-04-16 20:02:00
👋 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.
Read time: 7 minutes
One of my students said, “Sometimes you just need the right words to say what you want to say.”
This is why I’m a proponent of sharing great scripts and language, both in my course and here in this newsletter.
Having the right words can be the difference between doubting whether to speak up at all, or voicing your point of view confidently.
With that, here are 7 phrases I often use when sharing feedback that makes it easier for me to speak openly and quickly, and encourages my recipient to take action.
Use this when: You want to acknowledge effort, but you have lots of constructive feedback.
This phrase is quite versatile and I use it often.
IMO Many managers go awry when they want to acknowledge effort, but they accidentally compliment the work product itself. This sends mixed signals. Don’t do that. Only say “looks good” if you think it actually looks good.
Saying “this is a great start” acknowledges effort and says this is a good first stab—not a good final product.
This allows you to sound positive as you transition into sharing actionable feedback.
🚫 “This looks great.” ← Sounds like it’s good to ship as is.
✅ “This is a great start.” ← Clear that this is a good initial attempt.
Use this when: You want to make your feedback feel more objective and concrete.
Try to root your feedback in concrete observations. When you say “I noticed x,” it shows you are referring to something that happened in the physical, observable world.
It’s not a random, theoretical opinion. It’s not subjective vibes.
Your recipient can always share a different interpretation of what you observed, but sharing an observation immediately makes the conversation more grounded and credible.
🚫 “You are long-winded.”
✅ “I noticed in your response just now, it took a while to get to your main point. We’ve talked about being more concise, so I wanted to point this out as an example to keep an eye on.”
Use this when: “But” feels too negative.
“But” is a negating word. It cancels out whatever comes before it.
Technically, this isn’t positive or negative—it simply is. It’s neutral. “But” can have a negative undertone though, so if you want to avoid it…
Use “at the same time.”
“At the same time” allows you to mention two potentially competing realities, without discrediting either one. This is helpful when you want to disagree without seeming disagreeable.
🚫 “This idea works well for our current situation, but not for what we need going forward.”
✅ “This idea works well for our current situation. At the same time, going forward we will deal with new variables A and B, which makes me think we may want to consider [alternative option] too.”
More on how to use but strategically and how to give feedback to senior leaders without getting fired.
Use this when: You are giving feedback to peers or folks more powerful than you.
I called this the Even More technique, and it’s one of my favorites. This is fantastic for giving feedback to your manager, senior leadership, or anyone where they might think it’s jarring that you’re giving them feedback.
The framing of “even more” works because you are not assuming they are lacking, or that something is broken.
Nothing is broken. They are in a good place, and you are simply helping them become even more effective.
🚫 “You haven’t delegated anything strategic to your team, and I fear this is causing them to be overly dependent on you. This worries me.”
✅ “You've done a great job delegating operational tasks this quarter. Your team would grow even more if you start delegating some of the strategic thinking as well. This would give them a chance to practice new skills, be less dependent on you, and open up your bandwidth over time.”
Use this when: You want to show you understand your recipient’s intent, and want to help them better reach their ideal outcome.
This works because you establish up front what you believe the person was trying to do. This shows you understand their end goal, and you’re trying to help them get there.
We’re also quite specific and concrete by mentioning “it doesn’t work because Y” and offering an alternative, which shows your credibility as a thought partner. When you offer a recommendation, it shows you know your craft. You’re not a desk jockey who can only point out what sucks in your team’s work, but has no idea how to fix it yourself.
This is one of the best ways to avoid giving hand-wavy, overly high-level feedback.
🚫 “This email isn’t compelling.”
✅ “I believe you were trying to get the reader excited to take action, but the way the email is currently structured, it feels very logistics heavy. I recommend first selling them on why this matters, which you can do in a few lines, then share the logistics of what to do.”
Use this when: You want to be encouraging and build on what the person is currently doing.
Chances are, your recipient is already doing some things right. When you build on this, it feels less like they need to start a whole new behavior from scratch (which is intimidating), and more like they can turn up the volume on something they’re already doing (which feels more doable).
🚫 “You need to speak up.”
✅ “You’re already speaking up regularly in our team meetings, which is fantastic. Now, I’d love for you to speak up more in all-hands meetings to share what your team is working on with the broader company.”
Use this when: You want to speak accurately and share what evidence is informing your point of view.
I knew a CEO who loved to tell people he knew them better than they knew themselves. This drove his executive team insane.
Telling people you know them better than they know themselves is not productive. Don’t do this. It reeks of overreach, and it makes people want to debate you.
You can avoid all that messiness by doing this: Speak accurately about what’s informing your insight.
For example, I am quite direct with my executive coaching clients. I’ll point out minor things in the way they react or speak, that is making them come across as junior, not strategic, defensive, etc.
It can be pretty awkward to point out that someone’s natural reaction is making them look bad. So when I speak up about it, I tread lightly and use this technique.
🚫 “You are a dismissive person. You dismiss others.”
✅ “Based on our limited interactions, I’ve noticed you can come across as a bit dismissive. I’m sure this isn’t your intent and I’m only speaking from our conversations so far, but I thought I’d point it out. [Insert concrete examples.]”
Notice, I’m not saying, “you are always this way.” I’m being accurate in sharing the sources of my data points, which are a limited slice of who they are as a person.
I’m not presuming I know what you are like all the time because I do not have visibility into that. I’m simply saying, “From our interactions, this is what I’m picking up on.”
The example above is with my clients, so if you have a direct report where you have personally seen them operate across different settings, you can mention that as well. The point is, you want to avoid labeling people and putting them in boxes.
Btw if you think the script above feels “too soft,” remember, I’m assuming you’re saying something your recipient might be quite upset to hear. You can always remove the softness, but that softness is often what gets people to lower their defenses and actually hear you in the first place.
If the content of what you’re saying might be interpreted as quite harsh, it’s strategic to soften the surrounding pieces because this adds balance, so the entire message won’t be rejected in a knee-jerk reaction.
In my experience, people tend to be much more welcoming when they hear feedback through this lens, even if the feedback itself can be hard to hear.
To recap, here’s the list:
“This is a great start”
“I noticed”
“At the same time”
“Even more”
“I believe you were trying to do x, but it doesn't quite work because y. I recommend trying z.”
“Already”
“Based on the data points I have around x…”
Which of these words/phrases 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 next Wednesday at 8am ET.
Wes
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2025-04-09 20:03:28
👋 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.
Read time: 6 minutes
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I’m excited that my episode on Lenny’s Podcast just dropped.
First, I'm a huge fan of Lenny. He was an early investor in my company, Maven, and he was one of the first four instructors (!) that my cofounder and I pitched. Securing Lenny felt like such a win. This feels like a lifetime ago, but since then, I’ve continued to be inspired by what he’s building and the rigor of his approach.
I was especially honored to come onto the show as a second-time guest. The first time I appeared on his podcast was in August 2022. Today I’m sharing our latest conversation for April 2025—back with even more principles to apply to your daily work.
Here are takeaways from Lenny’s post sharing our podcast. I’ve linked to specific articles that dive deeper into almost each of these topics for further reading:
Communication is the highest-leverage career skill: If you’re not getting the reaction you want, focus on improving how you communicate rather than blaming others for not understanding.
The “sales, then logistics” framework: Always sell people on why something matters before diving into how to do it. Even executives who seem rushed need 30 to 60 seconds of context for why this matters now.
Being concise is about density of insight, not brevity: “Being concise is not about absolute word count. It’s about economy of words and density of the insight.” The bottleneck to being concise is often unclear thinking.
Use “signposting” to guide your audience: Words like “for example,” “because,” “as a next step,” and “first, second, third” help readers navigate your ideas without excessive formatting.
The MOO (Most Obvious Objection): Before sharing an idea, spend just a few seconds anticipating the most obvious objections. This simple practice dramatically improves your communication effectiveness.
Speak with accurate confidence: Don’t overstate hypotheses as facts or understate strong recommendations. Match your conviction level to the evidence available.
Give feedback using “strategy, not self-expression”: Focus on motivating behavior change rather than venting your frustrations. “Trim 90% of what you initially want to say and keep only the 10% that will make the person want to change.”
Managing up is about sharing your point of view: Don’t just ask your manager what to do. Present your recommendation with supporting evidence, which reduces their cognitive load and demonstrates your strategic thinking.
The CEDAF delegation framework:
Comprehension: Ensure they understand what needs to be done
Excitement: Make the task meaningful and motivating
De-risk: Anticipate and address potential issues
Align: Confirm mutual understanding
Feedback: Create the shortest possible feedback loop
Create a “swipe file”: Collect examples of effective communication that you can reference later. Even the act of noting these examples trains you to recognize effective patterns.
Small communication improvements compound: “These might seem minor, but (a) it compounds, and (b) all the ‘big things,’ everyone else is already doing. So there’s not a lot of alpha in that.”
Invest time up front: Spending a few extra minutes crafting clear communications saves hours of back-and-forth clarification later. “A little bit more up-front investment reaps a lot of benefits down the line.”
I always love hearing what readers/listeners find most helpful, especially because people can listen to the same episode but pick up on different things that apply most to their situation at the moment.
On LinkedIn, a bunch of you have listened to the episode and shared your biggest takeaways:
Meg Porter, a fractional VP of Product, said:
“THIS. Hypotheses are hypotheses. I believe X because of Y is another way to show that this is an objective hypothesis, because of *reasons* — it builds trust and credibility in teams, in c-suite, in investor relations.”
Matt Schaeffer, Marketing Manager at EV Connect, said:
This podcast episode from Lenny Rachitsky featuring Wes Kao has some strong examples of how to make ourselves and our companies stronger through better communication. I took these away for myself. What were your takeaways?
1. Everything needs to start with empathy - put myself in my audience’s shoes.
2. Relate my project to more global business goals (i.e. if the area of my idea hasn’t been prioritized, maybe it’s the wrong time to pitch it)
3. Make the ask of the audience very clear
4. Frame topics for people (not everyone is as familiar with the topic as I am!)
5. Re-read comms to ensure they’re clear and concise (remove 10 words) and take a couple minutes prior to each meeting I’m leading to make sure I’m clear on what I’ll say.
From Grace Gao, Head of Business Development at Sephora:
Even though I 𝑘𝑛𝑒𝑤 good communication was important, I often found myself slipping back into speaking off the cuff — unprepared and unaware of how my words were actually landing.
Communication should be intentional, strategic and practiced…
Then I listened to Wes Kao on Lenny Rachitsky's Podcast, where she shared actionable advice for upgrading the way we speak and write. Three tips really stood out, and after applying them for just a few days, I saw a noticeable shift:
✅ I felt more confident
✅ I spoke with greater clarity
✅ I aligned stakeholders more easilyHere are the 3 tips I used:
𝐓𝐢𝐩 𝟏: 𝐒𝐚𝐥𝐞𝐬 𝐭𝐡𝐞𝐧 𝐥𝐨𝐠𝐢𝐬𝐭𝐢𝐜𝐬
Before diving into the how of a project, secure the audience’s buy-in by explaining the why.
Instead of saying “Let’s do X, then do Y … ”, start by explaining
“We are doing this because …”
“This matters because ….”
“Here’s the support I’m looking for from you …”Why? A mini sales pitch gets people aligned and engaged. Setting expectation on action needed inspires collaboration.
𝐓𝐢𝐩 𝟐: 𝐏𝐫𝐞𝐩𝐚𝐫𝐞 𝐭𝐨 𝐛𝐞 𝐜𝐨𝐧𝐜𝐢𝐬𝐞
I used to think conciseness was a personal style or a sign of intelligence.
Wes reframed this for me: 𝑐𝑜𝑛𝑐𝑖𝑠𝑒𝑛𝑒𝑠𝑠 𝑖𝑠 𝑎 𝑟𝑒𝑠𝑢𝑙𝑡 𝑜𝑓 𝑐𝑙𝑎𝑟𝑖𝑡𝑦.
Now, before any meeting, I take a few minutes to jot down the answers to:
✅ What do I want to achieve from this conversation?
✅ What supporting points will I bring?
✅ Why would the other person care or help?This simple exercise boosted my confidence and sense of ownership in every interaction.
𝐓𝐢𝐩 𝟑: 𝐎𝐛𝐬𝐞𝐫𝐯𝐞 𝐚𝐧𝐝 𝐨𝐩𝐭𝐢𝐦𝐢𝐬𝐞
Treat communication like a sport.
Use a feedback loop to assess whether your words are having the intended impact. Level up by doubling down on what works and adjusting what doesn’t.
With this mindset, I started noticing small habits that limit my effectiveness. For example, speaking too fast when I’m excited, which blurs my message. Simply slowing down has improved how others engage with me.
Sylvia Carr, founder at Parse, said:
Wes Kao's practices for successful delegation are super smart, and they are even more fascinating when you think about applying it to AI--and soon, AI agents.
She shared the framework on Lenny Rachitsky's podcast this week:
Comprehension, Excitement, De-risk, Align, and Feedback (CEDAF)
It’s a super practical mental model:
(C) Comprehension: Does the person (or AI) have everything they need to understand the task? This includes tools, context, and clarity on the desired outcome.
(E) Excitement: Are you framing the task in a way that makes it exciting or meaningful? With people, connect it to their goals... With AI, giving some feeling like, “This is critical for my job!”, can make a big difference in response quality.
(D) De-Risk: The idea is to anticipate and address potential blockers or risks upfront before they derail the task. For example, if there’s a chance someone (or the AI) might misunderstand the scope or spend too much time on the wrong thing, you'd proactively clarify or set guardrails.
(A) Align: Confirm mutual understanding before moving forward. If you, like me, love The Pitt 🚑, you can see how the ER teams running a code do this all the time. Those stakes are way higher, so it's very doable. "Got it?"
(F) Feedback: How can you create the shortest feedback loop possible? Check in early and often to course-correct before too much time is spent going in the wrong direction.
It’s a cool way to think about the future of work, when we'll be delegating not just to people, but to AI agents, and you can see how these soft skills are quite transferrable.
If you’d like to dive deeper, here are the frameworks and principles I referred to in the podcast.
Strategy, not self-expression: How to decide what to say when giving feedback
The CEDAF framework: Delegating gets easier when you get better at explaining your ideas
Check out the full episode on YouTube, Apple, and Spotify.
Which principle or tactic jumped out at you? Which are you most excited to try for yourself?
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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2025-04-02 20:01:09
👋 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.
Read time: 6 minutes
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This is Part II of a two-part series. Check out Part I: Use “but” strategically
After last week’s post on how to use “but” strategically, I started noticing when “but” was used well all around me. And I realized I personally use the “inverted but” technique 10x more than I thought I did. It’s incredibly versatile.
This is the Baader-Meinhof phenomenon (i.e. frequency illusion) in action, where after you become aware of something, you start seeing it everywhere.
After getting some follow-up questions from readers, I’ve jotted some nuances to consider when you use “but” strategically.
First, a quick reminder. What is the Inverted But Technique?
“But” is a negating word. It cancels out whatever comes before it. Most people use a structure of saying, “The positive thing, but the negative thing,” which accidentally cancels out all the positive stuff.
We can use “but” strategically by inverting:
🚫 “The positive thing, but the negative thing.”
✅ “The negative thing, but the positive thing.”
Here’s an example:
🚫 “That's an interesting idea, but it might be challenging to implement.”
✅ “This might be challenging to implement, but it's an interesting idea.”
Notice when we put the positive stuff AFTER the “but,” you sound more positive while still getting your point across.
Here are nuances to keep in mind when using this in your communication.
The time scale matters: You want to say “[negative], but [positive]” in the same breath.
Do not spend the majority of time talking about the positive, if what you REALLY want to focus on is sharing constructive feedback.
This is not meant to be a “shit sandwich” either, where you hide your main point between words of praise.
The “inverted but” technique works best when it’s used to set an initial positive frame. Then you go right into sharing details about edits, feedback, etc.
When you spend too much time on the positive, you give a misleading message. It also feels disingenuous to go on at length about something positive you don’t really feel. Don’t do that.
Here’s a question from a reader:
“In my experience, the negative bit is often what demands further discussion ("the presentation is great" can stand alone; "there are a few issues" warrants follow-up). How do you employ a strategy like this without white-washing the discussion and never addressing the negative thing?”
The positive is used as an opener. With the “inverted but” technique, the positive is half a sentence at the beginning. Then I’d go into more detail on the feedback. So the vibe is less “this sucks, and here are all the things that suck” and more “you’re almost there, just focus on these things.”
✅ “There are a few issues, but overall the presentation looks great. In terms of areas to tighten, I’d streamline the narrative arc because…”
Notice how by the second sentence, I’m shifting gears to discuss areas to improve. This prevents you from white-washing the discussion.
I’m a big proponent of speaking accurately.
This might seem like it doesn’t need to be said, but I find many managers don’t want to seem too negative or make our team feel demoralized, so we end up saying nice things to try to make them feel better.
Saying nice things to make people feel better is not helpful for anyone. If you say a positive thing, it should be something you actually believe in.
Sometimes that takes a bit of creativity to find the bright spot, but I can usually find one pretty easily.
For example, let’s say the presentation is quite bad. I want to be honest and direct, without being dramatic or overly negative. I would be objective and evidence-based.
I might say something like this:
✅ “This wasn’t what I had in mind and I think it’s quite far from where we want it to be, but on the bright side, I love that you’re showing me this early so we can align and calibrate on what direction we do want to go in. [INSERT FEEDBACK]”
^ Notice how I’m not judging my direct report or subtly implying that they are incompetent, or that I’m disappointed in them, etc. There’s a common saying in management that we should criticize the work, not the person.
The script above does exactly this—it focuses on the work product in an objective, neutral way.
The gist is:
I shared my high level assessment that this slide deck wasn’t good, BUT (here’s the use of the inverted but) I am optimistic we can fix this and get to a good place.
This will all work better if you adopt a positive demeanor when you deliver feedback. If you sound repulsed or frustrated, your recipient will pick up on that emotional tone.
I have said extremely critical stuff to my direct reports and left intense red lines on their work, yet they told me they went back to their desks feeling motivated and excited to take another stab.
I believe a large part of this is because (a) I’ve set the expectation that I will give lots of feedback, but also (b) I actually genuinely believe they’re able to do a better job if we discuss how to make it better.
So when I talk about it, it comes across as sincere and positive because that’s how I actually feel.
Try to find one bright side of the situation that you can comment on. There is almost always SOMETHING positive—it might not be the quality of the work itself, but it can be the fact that the person brought it to you to align.
You can put this positive thing after the “but.”
The purpose of the “inverted but” is not to entirely negate the negative, it's to increase the chances that your recipient hears you without freaking out. If you frame positively, it will feel lighter and more doable than if you framed it in a critical, heavy way. They still might react negatively, but if you don’t use the “inverted but,” they might react even worse.
Another consideration: If your recipient really wants to ignore your feedback, they will. If history shows that this person is not open to feedback, or shows poor judgment in reading social cues, then changing how you position the feedback probably won’t make a difference. At that point, that is not a communication problem—this is a fit problem, a value alignment problem, a motivation problem, or some other problem. Communication can help you appeal to your recipient, but it can’t change who they are completely.
If you try the “inverted but” and it seems confusing, it might not be a good fit for your situation.
Play around with the sentence and see how it changes the sentiment, and make sure you are both positive AND clear.
What’s one piece of feedback, area of disagreement, or negative news you need to deliver this week that could benefit from the “inverted but” approach?
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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