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.
On the surface, this pitch is decent and there’s a lot it does right. At the same time, I believe it could be more persuasive with a few minor adjustments.
The main problem is this note doesn’t really seem sincere.
I’m all for being concise, but there is such a thing as being too concise. The problem with being too concise, is you give away real estate where you could be persuasive.
The lever in a written pitch is, well, words. If you strip away most of the words, you strip away your ability to persuade.
It seems like getting this person on the platform is a nice-to-have, but the writer could go either way. Like they barely want their prospect to join.
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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✨ 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
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
Today’s newsletter is sponsored by Balsamiq. Docs don’t sell your vision. Jumping straight to high-fidelity slows teams down. Balsamiq helps founders and PMs sketch and validate ideas fast—before pixels, code, or rework get in the way. No fluff. No bottlenecks. No wasted time. Try Balsamiq free for 30 days.
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
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 May 2025 cohort is now 95% full, and is the last chance to take the course this spring. 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
2025-04-02 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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2025-03-26 20:03:38
👋 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.
⛑️ If you’re looking for 1:1 support to amplify your leadership, my specialty is less about confidence and mindset (though I believe those are important), and more about practical techniques for getting more of what you want. I’d describe my approach as a blend of advising and coaching because I will share my POV on what I believe will help you. This isn’t for everyone, but this resonates, here’s more about coaching.
Read time: 5 minutes
This is Part I of a two-part series. Check out Part II: Nuances when using the “inverted but” technique
I believe the word “but” is unfairly vilified.
There’s common advice that says to swap “but” for “and,” mainly in an attempt to sound more positive.
While this works half the time, “but” and “and” are not actually interchangeable, so there is a limit to how much you can do this. The words have different meanings. When you swap every “but” for “and,” you can end up with logic that doesn’t make sense.
Luckily, there’s no need to remove every instance of “but.”
Today, I want to show you how to use “but” strategically.
I love this technique because it allows me to express my intent more accurately when I’m talking about content that’s inherently “negative.” I’m able to sound positive and speak directly without mincing words.
Here’s the key:
“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.
If your manager says, “You are proactive, hard-working, and collaborative, but…” The “but” instantly negates all those positive traits. You’re left wondering “Wait, did they mean any of those nice things?”
We can use “but” strategically by inverting:
Before: “The positive thing, but the negative thing.”
After: “The negative thing, but the positive thing.”
When you do this, you are applying the negating feature of “but” to work in your favor.
Here are examples of this in action:
🚫 “I agree with X, but not sure l agree with Y."
✅ “I'm not sure l agree with Y, but l agree with X.”
^ This ends on what you agree with, which feels more collaborative, even though you’re saying the same thing.
🚫 “The presentation looks good, but there are a few issues.”
✅ “There are a few issues, but overall the presentation looks good.”
^ In the before, you might mean that the presentation is mostly good to go, but the emotional takeaway for your direct report is that there are issues. They might think, No matter what I do, I can’t please my manager. I might be 99%, but my manager still points out the 1%.
In the after, the focus is that the presentation generally looks good. Yes, there are issues to improve on, but those are doable and we’re close to the finish line. This helps your direct report feel recognized.
Note that in both of these examples, you’re speaking directly about areas of improvement. But in the latter, you sound much more positive—which will be more motivating for your team.
A few other examples:
🚫 “That's an interesting idea, but it might be challenging to implement.”
✅ “This might be challenging to implement, but it's an interesting idea.”
🚫 “This looks great, but I won’t be able to participate.”
✅ “I won’t be able to participate, but the event looks like it’ll be amazing.”
🚫 “I like that you did this analysis, but I don’t agree with all of it.”
✅ “I don’t agree with all of your analysis, but I love that you are speaking up and articulating your hunches.”
First, your recipient’s brain is more likely to focus on the negative parts of what you say, and it’s easy for us to come across as harsher than we intend. So when you “negate” the negative stuff at the beginning of the sentence, you don’t fully negate it. You effectively soften it, so it more accurately reflects your actual sentiment.
Second, ending on the positive, well, feels more positive. After kicking off with your inverted-but sentence, you can give detailed feedback through this more encouraging lens. This engenders goodwill, which creates positive momentum they are likely to take forth into complying with your request. If you frame positively, it will feel lighter and more doable than if you framed it in a critical, heavy way.
Third, many of us don’t speak up out of fear of sounding abrasive or accidentally threatening others. So when I say “negative” in the template for saying the “negative, then positive,” it isn’t only about giving constructive feedback.
It’s equally about disagreeing with colleagues, which can feel just as uncomfortable. I believe having a tactic that allows you to disagree AND sound collaborative, will encourage you to speak up more. This is good for you and your recipient.
Overall, you will be able to express yourself/share your POV, and sound more positive. It’s win-win. And the only change you made was swapping the order of what comes before vs after the “but.”
A few readers have asked, how does this compare to the “yes, and” technique from improv?
The point of “yes and” is to encourage brainstorming, and create a sense of building on each other’s ideas. But there are times when you want to be clear that you disagree, and simply saying “yes and” can be confusing.
I’ve talked to folks who were hardcore fans of “yes and,” and couldn’t tell if they actually agreed or disagreed with me. It felt a bit like they were using semantics to avoid admitting that they felt differently.
To be clear, I’m a fan of “yes and,” and use it often myself. And (see what I did there), depending on the situation, the “inverted but” (i.e. putting the positive part after the “but”) might be a better option because it allows you to disagree, be clear about what you mean, and sound more positive than if you didn't use it.
Consider the “inverted but” another tool in your toolkit to express what you want to say and increase the chances that your recipient takes it well.
Ask yourself:
The next time you disagree with a colleague, lead with what you disagree with, then use “but” to highlight what works or where you agree. Notice if this makes you feel more confident sharing the negative part.
Look out for “but” statements in your meetings and written communication, both from yourself and others. Is the positive or negative part coming after the “but”?
For your next piece of feedback, draft it both ways. Which version (traditional or inverted) feels more likely to motivate your recipient to take action?
This won’t work for every sentence structure, so you have to use your judgment. But it works for a surprising number of situations.
What’s a recent communication where you could have used the Inverted But Technique?
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
PS Check out Part II: Use “but” strategically
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So far, the May 2025 cohort has students joining from: Coinbase, Google, Workday, Walmart, GitHub, Shopify, Credit Karma, Adobe, Uber, Microsoft, National Geographic, Maersk, Oracle, Flatiron School, Amazon, Hubspot, Klayvio, JPMorgan Chase, 1Password, Apple, Meta, Superhuman, and more.
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2025-03-19 20:03:40
👋 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: 5 minutes
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One of the things that never fails to surprise me is how often you have to repeat information for people to really internalize it.
This applies pretty much at all levels, even when folks are earnest and trying their best to pay attention. It applies when you’re managing up, down, and laterally.
Today I want to share an example of why you have to repeat key information (especially potential trade-offs) and remind senior leaders of your strategy not once, not twice, but throughout the life of a project.
Tell me if this sounds familiar:
You: Hey senior leader, I want to give you a heads up about X risk. Do we feel comfortable with this?
Executive: Yes, that sounds like a reasonable risk. Thanks for surfacing. Let’s do it.
[One month later]
Executive: How did X risk happen? Did we know about this?? Why didn’t we prevent this???
This happens surprisingly often.
Every day, good operators get blamed for stuff that isn’t their fault because they haven’t set expectations properly.
Here’s how to ensure the enthusiastic yes you started with actually lasts throughout your project.
Why might your leader be surprised by something they already agreed to?
First, because they have a lot going on and might not remember the details of your project. Senior leaders typically oversee multiple direct reports, multiple teams, and multiple functions—each with projects, updates, decisions, risks, trade-offs, and evolving circumstances.
Second, because even if you mentioned a risk proactively, most humans secretly hope the downside situation won’t actually happen. Even if it’s an acceptable risk, we still hope for the best case scenario. Even if your leader admits you did mention that X issue might happen, they might still be surprised when it actually happens.
Both elements above—your leader being busy/having a lot going on in their world and understanding downside but hoping for upside—these are structural issues. These are big issues to fight against.
Which is why mentioning a risk once isn’t enough.
One of my coaching clients is a PM pitching their CEO on a new product launch. It took months of convincing, but eventually the CEO agreed. The PM was clear about the biggest risk: potential cannibalization.
PM: “If we launch this new product, our existing product will likely be cannibalized. We’re not sure for how long, but perhaps 6 months. I want to make sure we’re okay with this.”
CEO: “Okay, this makes sense. I agree with moving forward.”
Later that year, the product went live. The sales numbers started rolling in, and, lo and behold, the existing product took a hit:
CEO: “Wait, why is our existing product being cannibalized here?? This is really bad.”
PM: “Umm we discussed this when kicking off this initiative that our existing product would be cannibalized, at least for a bit until both business lines stabilized.”
CEO: “I don’t know why we didn’t prevent this more. I might have agreed, but didn’t realize our business would take this big of a hit. I’m not sure this new launch was worth it. Honestly I don’t even know why we decided to do it in the first place.”
Unfortunately, despite the work that went into the launch and its success in hitting targets, the project felt like a disappointment.
What could the PM have done to prevent this?
Most operators get buy-in at the beginning of a project—this is what allows you to move forward in the first place.
Some operators will close the loop with a recap at the end of a project.
But in my experience, very few operators reinforce expectations in the middle.
This is leaving a lot of proverbial money on the table because “the middle” is actually the MAJORITY of how the project exists.
If you don’t continue to “sell” during this phase, you risk losing the momentum you started with—or risk losing support for finishing the project at all.
Let’s continue with the PM and CEO example above.
The PM should have built alignment throughout the launch process.
You can do this by reminding your audience of your strategy at multiple touchpoints:
Beginning: Get initial buy-in for the strategy and trade-offs.
Middle: Remind the team of the strategy, including setting expectations about trade-offs, what you’re doing to minimize the impact of these trade-offs, and why the upside is worth pursuing.
End: Proactively share context as you share metrics. Instead of expecting the numbers to speak for themselves, add narrative to numbers. Contextualize what these numbers mean so your audience knows what’s “good” or “bad.”
“Selling” in the middle phase might look like sharing reminders for anything that might come as a surprise. For example, in a bi-weekly update, you could include a line like, “We’ve accounted for temporary cannibalization for the first 6 months of the new product. I’ve built this into our sales forecast and are aware this will likely happen.”
We must reduce cognitive load as much as possible for our recipients.
We cannot expect others to read our minds, connect dots, or keep our projects top of mind.
Remember: Buy-in is not binary. For projects with a longer time horizon, you need to get buy-in on a continual basis to remind your leaders and team about your strategy.
Have you ever had a leader act surprised by something they previously agreed to? What was your response? What’s one situation where you could reinforce buy-in throughout the project?
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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✨ The May 2025 cohort is now 55% full, and is the last chance to take the course this spring. Improve your ability to sell your ideas, manage up, gain buy-in, and increase your impact in my 2-day intensive course. Save your spot here: Executive Communication & Influence for Senior ICs and Managers
