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
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
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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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Learn more about 1:1 coaching to improve your executive presence
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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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✨ The May 2025 cohort is now 65% 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
Here’s what students from last month’s cohort are saying:
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.
If you’ve been thinking about joining, you’ll be in good company. I hope to see you in class.
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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2025-03-12 20:02:11
👋 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.
✨ Course update: I opened the new May 2025 cohort a few weeks ago, and it’s already 40% full. This cohort will be the only opportunity to take the course this spring (the next time the course will be offered will be in the summer). To learn more, here are the course details.
Read time: 6 minutes
We all know comparison is the thief of joy, but for most of my life, I was very skilled at comparing myself to others. I could describe in great detail and specificity exactly where I was lacking, and why someone else was better than me.
I was proud of my intellectual honesty. Weaker operators might make themselves feel better, but not me. I was committed to staring my weaknesses in the eye.
Having an unvarnished view of myself was useful, to a point. On the one hand, the paranoia fueled me to work extremely hard. I wasn’t delusional about where I stood, and I was constantly learning from others around me.
On the other hand, most of the time, I felt shitty about not making enough progress vis-a-vis my peers.
When a friend would compliment me or be impressed at something I accomplished, I was quick to point out a bigger fish.
One day, I realized: The urge to put myself down is an invented obligation.
The good news was this was all in my own head.
The bad news was this was all in my own head.
If I wanted to stop being in a rat race, it dawned on me that I could…choose not to enter another race race. But I had to consciously choose to stop participating in this imaginary competition.
I wrote the below on LinkedIn in October 2023, when I had just left my startup, Maven. This was the first time popping my head up after three intense years of company building, and I spent that summer taking stock of where I was and reflecting on what I wanted to do more/less of. Could I be a more hospitable, friendly voice to myself? Yes, I realized.
Here’s the post below.
There’s always another rat race if you want to be a rat in a race. When I graduated from UC Berkeley, I thought, “Now I’m no longer in the Haas student rat race.”
When I left the fashion industry and joined a startup, I thought, “Now I’m no longer in the corporate retail rat race.”
When I moved from SF to New York and bootstrapped a company, I thought, “Now I'm no longer in the Silicon Valley tech operator rat race.”
When I started growing my audience as a creator, I thought, “Now I’m no longer in the FTE rat race.”
When I was a solopreneur in between my two companies, I thought, “Now I'm no longer in the CMO path rat race.”
When I started a VC-backed company with Tier 1 investors, I thought, “Now I’m no longer in the solopreneur rat race.”
When I left my startup and started working on my own, I thought, “Now I'm no longer in the tech founder rat race.”
Each time, I just joined a new race, with new rats.
I thought I was out of the race, until I looked up and found myself suspiciously comparing myself to others without realizing it was happening.
Now, I want to break the cycle. It's enough racing. I've raced since I was 16 years old, and I'm 37 now. I'm actively breaking the cycle, and it will take effort. It's moving a battleship in the opposite direction than the one it's been sailing in for years.
“Already” is the word for this spring.
I want to remind myself of what I already have, how I’m already achieving my goals, and how I’m already the person I want to be.
Flash forward to March 2025, and I’m proud to say I’ve made a lot of progress. I definitely still catch myself feeling jealous of others (that probably won’t ever go away), but most days, I feel motivated by my work and think less about what other people are doing.
If you are prone to beating yourself up for not being as “far along” as you should be, let this be a sign that you can change how you think too.
Obviously, I’m not saying you should stop improving or get complacent. Like many things, the answer is not one or the other: You can recognize how you’re already the person you want to be in some ways AND continue working towards being more of that person. You can acknowledge how you’re already doing some things right AND continue sharpening your skills.
If you are someone who is too hard on themselves, you may need to actively train your brain to see through a different, more positive lens.
No, you won’t lose your edge or get soft. You are probably too high strung to ever be so relaxed that you lose your edge.
The risk is actually that when you’re overly focused on the negative, you develop a warped view of your abilities. You become under-confident compared to your actual skills. This negatively impacts the way you communicate with others, the way you advocate for your ideas, and how willing you are to make bold moves.
It warps your ability to see clearly. For example, you might think your situation is futile when it’s not. You might see a bigger gap than what’s actually there, and give up when you didn’t need to.
Meanwhile, focusing on ways that you are already doing well, already winning, already doing great, is a way to have a more ACCURATE view of your situation. When you are overly anchored on the negative, you need to reset by swinging the pendulum to be overly positive to have a chance at landing someplace neutral.
I call this type of thought experiment a “rubber band exercise”: You stretch the rubber band so you when you release the tension, the rubber band is a bit looser.
So here’s a rubber band exercise for you. Ask yourself:
In what ways am I already the person I want to be?
How am I already achieving my goals?
How am I already becoming who I want to be?
Remember: You can choose to run your own race. You can choose to celebrate what you’re doing right, and how you’re already the person you want to be.
Do you tend to compare yourself to others to a point where it becomes counterproductive? More importantly, how are you already on your way to doing the things you want to do or being the leader you want to be?
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
Since last fall, I’ve been focused on 1:1 executive coaching with a select group of clients, and on making my course the best communication and influence course for hands-on builders.
Every cohort, I meet the most interesting, sharp, thoughtful operators and I’m constantly in awe that I get to support leaders this like this.
We wrapped up the February cohort a few weeks ago, and I’m thrilled to share the latest student reviews:
“Wes’ course is a short, 2-day commitment that is packed with actionable advice and frameworks that you can put into practice immediately. This course changed the way I approach communication with my stakeholders.”
- Caro Galvin, Senior Product Manager @ GitHub
“I can't say enough good things about this course. Wes is so approachable and professional, and she offers an absolute treasure trove of resources, tips and frameworks that will change the way you approach your work and your life. If you're wondering if this course is worth the investment of time and money - the answer is a resounding yes.”
- Helen Jerman, Global Digital Content Manager @ ADI Global Distribution
“Great course! I appreciated Wes's actionable recommendations and the ability to practice tactical skills like rewriting communications of our own.”
- Cameron Langford, Founder & Principal Consultant @ First Principles Communications
“This was excellent. The course modules were cohesive and useful. The take-home materials we got have already been helpful to me in my day-to-day. Wes is a brilliant instructor and I particularly appreciated her feedback on the live exercises (rewrite this email, draft a script, etc.) for how targeted and direct it was.
It was also clear during the lessons that Wes was applying her own principles (signposting, right amount of context, etc.) to the course material itself. This made the lessons more effective, of course, but it was also a cool demonstration that ‘hey, this works’ that we could see for ourselves on the spot.”
- Tushar Chandra, Software Engineer @ Loop
“This course is a MUST, and one of the best learning experiences of my career. I can confidently say I would recommend this to anyone who is starting to interact more with leadership, or who wants to be prepared for when they do. (So…. Everyone.) I will probably never shut up about how much I loved this course and how immediately I am using the skills from it.”
- Desirae Odjick, Product Marketing Lead @ Shopify
The April cohort is full, but the May 2025 cohort is now open. The course dates are May 15 & 16 at 12:00 - 3:30pm ET with an optional Q&A afterward. If you’ve been thinking about joining, you’ll be in good company. I hope to see you in class.
→ Reserve your spot in the May 2025 cohort
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