Become a better communicator: Specific frameworks to improve your clarity, influence, and impact

Wes Kao is an entrepreneur, coach, and advisor. She co-founded the live learning platform Maven, backed by First Round and a16z. Before Maven, Wes co-created the altMBA with best-selling author Seth Godin. Today, Wes teaches a popular course on executive communication and influence. Through her course and one-on-one coaching, she’s helped thousands of operators, founders, and product leaders master the art of influence through clear, compelling communication. Known for her surgical writing style and no-BS frameworks, Wes returns to the pod to deliver a tactical master class on becoming a sharper, more persuasive communicator—at work, in meetings, and across your career. What you’ll learn: 1. The #1 communication mistake leaders make—and Wes’s proven fix to instantly gain buy-in 2. Wes’s MOO (Most Obvious Objection) framework to consistently anticipate and overcome pushback in meetings 3. How to master concise communication—including Wes’s tactical approach for brevity without losing meaning 4. The art of executive presence: actionable strategies for conveying confidence and clarity, even under pressure 5. The “sales, then logistics” framework—and why your ideas keep getting ignored without it 6. The power of “signposting”—and why executives skim your docs without it 7. Exactly how to give feedback that works—Wes’s “strategy, not self-expression” principle to drive behavior change without friction 8. Practical ways to instantly improve your writing, emails, and Slack messages—simple techniques Wes teaches executives 9. Managing up like a pro: Wes’s clear, practical advice on earning trust, building credibility, and aligning with senior leaders 10. Career accelerators: specific habits and tactics from Wes for growing your influence, advancing your career, and standing out 11. Real-world communication examples—Wes breaks down real scenarios she’s solved, providing step-by-step solutions you can copy today Transcript: https://www.lennysnewsletter.com/p/become-a-better-communicator-specific Brought to you by: • WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs: https://workos.com/lenny • Vanta—Automate compliance. Simplify security: https://vanta.com/lenny • Coda—The all-in-one collaborative workspace: https://coda.io/lenny Where to find Wes Kao: • LinkedIn: https://www.linkedin.com/in/weskao/ • Website: https://www.weskao.com/ • Maven course: https://maven.com/wes-kao/executive-communication-influence Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ In this episode, we cover: (00:00) Introduction to Wes Kao (05:34) Working with Wes (06:58) The importance of communication (10:44) Sales before logistics (18:20) Being concise (24:31) Books to help you become a better writer (27:30) Signposting and formatting (32:05) How to develop and practice your communication skills (40:41) Slack communication (42:23) Confidence in communication (50:17) The MOO framework (54:00) Staying calm in high-stakes conversations (57:36) Which tactic to start with (58:53) Effective tactics for managing up (01:04:53) Giving constructive feedback: strategy, not self-expression (01:09:39) Delegating effectively while maintaining high standards (01:16:36) The swipe file: collecting inspiration for better communication (01:19:59) Leveraging AI for better communication (01:22:01) Lightning round Referenced: • Persuasive communication and managing up | Wes Kao (Maven, Seth Godin, Section4): https://www.lennysnewsletter.com/p/persuasive-communication-wes-kao • Making Meta | Andrew ‘Boz’ Bosworth (CTO): https://www.lennysnewsletter.com/p/making-meta-andrew-boz-bosworth-cto • Communication is the job: https://boz.com/articles/communication-is-the-job • Maven: https://maven.com/ • Sales, not logistics: https://newsletter.weskao.com/p/sales-not-logistics • How to be more concise: https://newsletter.weskao.com/p/how-to-be-concise • Signposting: How to reduce cognitive load for your reader: https://newsletter.weskao.com/p/sign-posting-how-to-reduce-cognitive • Airbnb’s Vlad Loktev on embracing chaos, inquiry over advocacy, poking the bear, and “impact, impact, impact” (Partner at Index Ventures, Airbnb GM/VP Product): https://www.lennysnewsletter.com/p/impact-impact-impact-vlad-loktev • Tone and words: Use accurate language: https://newsletter.weskao.com/p/tone-and-words-use-accurate-language • Quote by Joan Didion: https://www.goodreads.com/quotes/264509-i-don-t-know-what-i-think-until-i-write-it ... References continued at: https://www.lennysnewsletter.com/p/become-a-better-communicator-specific Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. Lenny may be an investor in the companies discussed.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Speaker 00

  I often see operators who explain things poorly and then are shocked and horrified when people are confused or there's skepticism, there's apathy. I'm a big proponent of asking myself, if I'm not getting the reaction that I'm looking for, how might I be contributing? How could I explain this more clearly? How can I be more compelling? How can I anticipate any questions that they might have?

• 0:22Lenny Rachitsky?

  You are one of the best teachers of communication I've ever come across. I made a list of people's favorite tactics and frameworks and approaches that you teach in writing, any tactics you can share for someone to be a little more concise.

• 0:34Speaker 00

  I think the blast radius of a poorly written memo is way bigger than most people think. If you're just shooting off a message in a Slack channel with 15 other people and it's confusing, you didn't include information you should have included, there's going to be a bunch of back and forth. Whereas if you had just taken another look at it, those 15 people would be off to the races.

• 0:53Lenny Rachitsky?

  You have an awesome framework called MOO.

• 0:54Speaker 00

  MOO stands for most obvious objection. A lot of times, we're surprised by the questions that we get, especially in meetings, we feel blindsided. When really, if you thought for even two minutes about what are obvious objections that I am likely to get, you often immediately come up with what some of those things are. Are you going to be able to anticipate every single objection? No. But can you anticipate the obvious ones? Absolutely.

• 1:22Lenny Rachitsky?

  Today, my guest is Wes Cao. Wes co-created the Alt MBA program with Seth Godin. She co-founded a company called Maven, which I often collaborate with, which makes it easy for people to host live cohort-based courses. She recently left Maven to launch her own course on executive communication and influence. There's a quote that came to mind after I stopped recording this conversation with Wes by George Bernard Shaw. "The single biggest problem in communication is the illusion that it has taken place." By the end of this podcast, if you listen to what Wes suggests, you will be a lot closer to becoming a world-class communicator. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. Also, if you become a yearly subscriber of my newsletter, you get a year free of Perplexity

• 2:07Lenny Rachitsky?

  Pro, Superhuman, Notion, Linear, and Granola. Check it out at lennysnewsletter.com. With that, I bring you Wes Cao.

• 2:18Lenny Rachitsky?

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• 3:03Lenny Rachitsky?

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• 3:36Lenny Rachitsky?

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• 4:19Lenny Rachitsky?

  Get $1,000 off Vanta when you go to vanta.com/leni. That's V-A-N-T-A.com/leni.

• 4:31Lenny Rachitsky?

  Wes, thank you so much for being here and welcome back to the podcast.

• 4:36Speaker 00

  Thanks, Lenny. I'm very honored to be a second time guest.

• 4:40Lenny Rachitsky?

  Very rare honor. No pressure, but I think this is gonna be one of the highest leverage episodes I've done. And let me tell you why I think that's the case. In the newsletter and on the podcast, I often talk about just how important and high leverage the skill of communication is to product leaders, to leaders, just to like people in general. There's this quote that Boz, the CTO of Meta, he's been on the podcast, he wrote this famous blog post, "Communication is the job." And I think that's true for product people, but it's true for basically any sort of leadership role and anyone trying to get ahead. And you are one of the best communicators I've ever met. You are one of the best teachers of communication I've ever come across. You have one of the most popular courses on Maven on executive

• 5:24Lenny Rachitsky?

  communication. So I'm really excited to have you here and to help people become better communicators, better influencers and all these things. So thank you again for being here.

• 5:32Speaker 00

  Absolutely.

• 5:34Lenny Rachitsky?

  Okay, so something that I often do with guests on the podcast, not even often, always, I ping people that the guests have worked with and ask them, "What should I ask Wes? What should I know about Wes?" So let me read a few quotes about you in regards to your communication skills from folks that have worked with you. These are three different people.

• 5:54Lenny Rachitsky?

  Okay, so first, "Wes, single-handedly raised the quality of the entire company's writing by like 2X across the board. I always say the best writing course I ever took was working with Wes for a year."

• 6:07Speaker 00

  Wow.

• 6:09Lenny Rachitsky?

  Okay, that's one.

• 6:09Speaker 00

  Great.

• 6:10Lenny Rachitsky?

  "Wes never just throws things out there. She's precise with her use of language, meticulous about examining her own ideas before bringing them in front of others, and knows how to make her points in a way that people will understand them and buy into them." Okay. And third, Wes includes her reasoning with every proposal and the context behind all of her recommendations. So that everyone around her learns in order of magnitude faster. This also makes her an exceptional teacher because she can clearly define what excellence is. And why something is the goal and then break down the steps and principles involved. Okay, reactions.

• 6:46Speaker 00

  Those are really nice things. That's amazing. Yeah, thank you so much.

• 6:52Lenny Rachitsky?

  And these are people across different companies. So, okay, so that was just to highlight how good you are at this stuff. And what we're going to be doing with our chat is going through a bunch of your tactics that you teach. And that have helped people become better communicators, executive communicators, better at influence. Before we get into the specific tactics. Is there anything that you think is important for people to understand just broadly around the skill of becoming a better communicator?

• 7:17Speaker 00

  I often see operators who explain things poorly. And then are shocked and horrified when people are confused. Or there's skepticism, there's apathy, there's a lot of avoidable questions. And I'm a big proponent of asking myself. If I'm not getting the reaction that I'm looking for, how might I be contributing to that? So, you know, instead of blaming other people for not understanding me, I think about. How could I explain this more clearly? How can I be more compelling? How can I anticipate any questions that they might have? So I'm a big proponent of agency and realizing that we can only control our own behavior.

• 8:01Speaker 00

  And so the best place to start, if you're not getting the reaction you're looking for, is reflecting on how can I get better at the skill of communicating? And it absolutely is a skill.

• 8:11Lenny Rachitsky?

  So I'm hearing is like, if you're having a hard time, people buying into what you're trying to convince them to do. Or you're finding people are doing not what you asked them to do. It's likely an issue with your ability to communicate. It's probably not their fault.

• 8:26Speaker 00

  Yeah, I would say so. You know, you can't, you can't solve everything with improving your communication. But there's, you can increase the likelihood of getting what you want.

• 8:38Lenny Rachitsky?

  Cool. Okay. Anything else along these lines of just things that are important to understand just broadly around communication, executive communication?

• 8:46Speaker 00

  I think another big one that I teach in my course and really kick off with is practicing like it's game day, playing like it's game day. So I see a lot of operators who save their best behavior for executives only. So, you know, they want to shine when they're presenting to senior leadership, but with everyone else, they're kind of calling it it. And I just don't think that you're going to be able to get enough reps to actually get good at executive communication if you are only doing it with executives. Because many of us only present to execs once a month, right, or a couple of times a quarter. And that's just not a lot of chance to practice. So really treating every single stakeholder as if they are important, because they are, and you shouldn't be, you know, if you don't want to waste your CEO's time, you also shouldn't waste your cross-functional team members'

• 9:31Speaker 00

  time, or your manager's time, or your director's time. So that's something else that I ask to keep in mind.

• 9:39Lenny Rachitsky?

  And maybe a last question before we get into the tactics. When people think communication, they think email, they think meeting presentations, things like that. What's like a, how do you think about, when you talk about executive communication and communication in general, what's kind of the umbrella of things that includes?

• 9:53Speaker 00

  Yeah, I would say broadly, the two mediums are verbal communication and written. So verbal being meetings, conversations, presentations, and written being emails, strategy docs, Notion docs, Slack messages, text messages, those two categories broadly. And I also think about communication as more of a means to an end, which might be interesting for some people, because I teach a course on communication. So you would think that's like, you know, the end in and of itself, but I really see it as a means to an end, where the end is getting the ideal outcome you're looking for. So whether that is buy-in, or making a good decision as a team, or, you know, moving to the next step, whatever that might

• 10:38Speaker 00

  be, communication is really in service of that end goal.

• 10:43Lenny Rachitsky?

  Awesome. Okay, so I made a list of people's favorite tactics and frameworks and approaches that you've, that you teach in talking to folks that you've taught and folks that you've worked with. So I'm just gonna go through a bunch, and let's just help people get better at these things.

• 10:58Speaker 00

  All right, let's do it.

• 11:00Lenny Rachitsky?

  Okay, so the first is something you call sales, then logistics. What is that about?

• 11:07Speaker 00

  Yes, so a common mistake that I see is overestimating the amount of buy-in that you have from your audience. So that looks like jumping straight into talking about the logistics, the details of the how to do something, of the process, when in reality, your audience has not yet decided if they even want to do the thing. So, you know, what I see operators do in response then is go even deeper into the logistics and the how, thinking that, oh, if I just explain this more, then that person will want to do it, when really, a sales note is different than a logistics note. A sales note is meant to get people excited to do the thing you want them to do and to agree to do it.

• 11:51Speaker 00

  And only then, after they have bought in, does it make sense to share the logistics. So there's an order of operations here. If you switch the order of operations, you will likely get a slow response or just no response, right? We've all put a Slack message in a channel and got crickets and tumbleweed. So really, starting off with selling the person and making sure that they know why we're doing this, why this matters to the company, why now, and then sharing logistics tends to be a lot more effective.

• 12:22Lenny Rachitsky?

  Is there an example of that that might help illustrate that point or that approach?

• 12:26Speaker 00

  Yeah, so one of my clients is a head of operations, and she was trying to get the rest of her executive team, which she was a part of, to fill in some wins for the week so that they could share this out with the whole company. And this was going to be motivating, it was going to shine a light on folks. And she led with the logistics of which document to send, you know, to put the details in, what time to put it in by, the format that you should put these wins, and didn't really get much of a response from the leadership team, which makes sense, right? Because this totally sounds like one of those things that's another item to check off on your list. When you already have so many other things to do and here's this other process that like

• 13:11Speaker 00

  we're all supposed to do now, like yay, right? And so she wasn't really getting response. And that's because she dove straight into logistics. Whereas what she could have done is start by selling folks, selling the other executives on why are we doing this? Well, we're doing this because this is a chance to shine a light on your team members who are doing amazing work, for them to feel motivated and to feel like the rest of the company really sees them and understands what they're doing. And this is all something that is going to motivate your team, right? So sharing why this is helpful and useful and how this is in service of you and your team versus like, oh, this is a favor that you're doing for me to fill out this form

• 13:55Speaker 00

  and fill it out this way and by this date, et cetera, et cetera.

• 13:58Lenny Rachitsky?

  I know that execs often are, often want the opposite where they're just like, okay, I know, like, just tell me what you want to do. Just like, okay, just get to the point. I don't want time for all this context and background. Any advice on when to spend any time on the sales? Like, what are signs that, okay, maybe you don't have them sold yet? Or what are maybe contexts where you should probably still try to sell them first?

• 14:20Speaker 00

  Yeah, so I actually think that you should always do a little bit of selling, even for situations where people have generally bought in. Because most of us have a lot going on and we're not actively thinking about whatever you're talking about. So even though I agreed to something two weeks ago, by the time you're telling me about it again, like, I thought about a billion other things since then, right? So reminding me of why are we talking about this? Why does this matter? And then getting into it and framing that conversation upfront is way more likely for us to not get stuck on a cold start and not kind of go two steps back, one step forward. The other thing is you can frame a conversation and sell a bit at the beginning very concisely. So I'm not talking about spending 15 minutes out of a 30-minute meeting selling.

• 15:05Speaker 00

  I'm talking about one to two minutes, even a couple of sentences, and then transitioning into the main thing you want to talk about. So I'm a huge proponent of doing that and basically reminding people, why are we doing this? Why are we here today? Why does this, why does this matter? And then getting into the meat.

• 15:24Lenny Rachitsky?

  I love that. So basically, it's you can do this really briefly. It doesn't have to be a whole pitch for half an hour. It's just a reminder, here's, here's why we think this is important. And I think that's a tricky point because a lot of times it's like, oh, like a leader is looking at this thing you're asking them to do. And you're like, they're like, why are we even, why am I spending time on this? And just a reminder of like, okay, I see, I forgot this was going to be, this is part of our strategy. This is a big, this has this much impact potential. And or here's how it could help our team be more efficient. So.

• 15:52Speaker 00

  Yeah. And you can really do that in like 30 seconds.

• 15:55Lenny Rachitsky?

  Is there, is there like a, I don't know, structure to this? Is it just like, why, like, is there a kind of a template you like, or some way you recommend of selling first? Is it like, here's why we're doing this, like, starting like that? Anything along those lines?

• 16:08Speaker 00

  Yeah, I think explaining why we're doing this, why this benefits the business, what problem this is solving. Again, you can do a lot of this in a couple of sentences. And then I also like asking or stating what I need from the other person upfront. So saying, you know, hey, we're here today because two weeks ago, we were reviewing the product flow and realized that there were a couple of parts that were kind of confusing. So I took a stab at fixing those areas, rewriting the micro copy. And I want to present them to you today, see if you agree with these changes, and then we're going to roll them out. What I'm looking for from you is feedback on the changes and if you agree. So like, that was like 15 seconds, right?

• 16:50Speaker 00

  Like super fast. And then now we're all on the same page about why we're here. And you can listen more intently, knowing that I'm looking for a sort of kind of feedback.

• 16:59Lenny Rachitsky?

  I would love to hear it that way. I think, I think there's like an implication here that maybe is worth sharing of just. And this is a lot of this is about we're communicating effectively to execs, which will make you communicate better to most people. But especially with folks up the ladder, they don't have a lot of time. They have a million things in their head. Uh, maybe just share like why this is so important, like what the state of mind of a leader is that you need to kind of break through.

• 17:24Speaker 00

  Yeah, so I call it the yes, yes, yes, next, next, next mindset. Where, where I'm, you know, if I'm listening to direct reports present something to me. Very often I find myself thinking, got it. All right, yes, let's keep going, right? And, you know, on the other side of that, I've often presented to executives where I had a 15 slide deck. And execs would do that and I'd be like, whoa, whoa, whoa, like I have, I have a whole sequence. I have a whole order, you know, and sometimes they would, they would give me buy it or make the decision. Buy slide four, you know, and I'd be like, okay, well, you know, slide 13. Want to show you this, this great graph I put together, right? And, you know, what was really helpful for me was realizing that I should take the win.

• 18:07Speaker 00

  Okay, if my stack is already agreed, um, take the win and, and keep it moving, move on.

• 18:13Lenny Rachitsky?

  Yeah, what's that quote like if you've, if you've sold them, stop talking.

• 18:16Speaker 00

  Right, yes, yeah, you might, you might talk them out of agreeing.

• 18:20Lenny Rachitsky?

  Yeah. Okay, you mentioned being concise. Let's talk about that. You have some really good advice on just how, how to effectively be concise and not too concise. What's your advice there?

• 18:30Speaker 00

  Yes, one of my pet peeves is when people are too concise. And they equate being concise with brief, being brief. And being concise is not about absolute word count. It's about economy of words. It's about the density of the insight that you're sharing. And so you can have a 300 word memo that's meandering and long-winded. And a thousand word memo that is tight and concise. And so, uh, not equating concision with, with briefness, I think is, is a really, uh, big one to understand. The second thing is a lot of advice about being concise. I think misses an important point. So, uh, you know, we've all heard, don't bury the lead.

• 19:15Speaker 00

  Cut to the chase, main point, you know, put the main point at the top, bottom line, not front, right? And all of these pithy aphorisms assume that you actually know what your core point is. So you can't cut to the chase unless you know what the chase is. You know, you can't unbury the lead unless you know what the lead is. And so that I found is the bottom leg to being concise. It's, it's actually not really being clear of what you are thinking. That's what's leading to being long-winded. And you can kind of test this theory because most of us have a go-to story that we've told a bunch of times, right? We're like, you know exactly when people are gonna laugh, you know, when they're gonna gasp or hold their breath, right?

• 20:00Speaker 00

  And why are you so good at telling that story? And you're, why are you so concise about it? Because you've told it a bunch of times. You know, you know all of the beats. So in meetings, though, at work, we are very rarely talking about the same thing that many times. It's always something new. It's something that we are also probably likely processing ourselves and are in the midst of processing as we are in a quick turnaround time, telling someone else about it, telling our team about it. And so you're basically asking your brain to do a lot of different processes, especially in a real-time conversation. You're listening to the other person, absorbing, making sense of it, processing it, figuring out what you think and how you would react, and then trying to say something cohesive that makes sense, right?

• 20:44Speaker 00

  And then trying to be concise about it. So it's just a lot of different processes. And so the only solution I found consistently to being concise is preparation. It's not a very glamorous solution by any means, but the clearer I am going into a meeting, going into a conversation, going into a pitch, the better I am at being concise and being able to bring the conversation back to the most important points, at being able to stay flexible but also firm. Yeah, and preparation, I don't mean spending hours and hours preparing for a weekly meeting, even a couple of minutes, really, makes a huge difference. Most of us are so

• 21:26Speaker 00

  back to back in meetings that we're doing zero preparation. It's like, the meeting has started 30 seconds in and you're still unwinding from the last Zoom call that you were on, right? So, most of us are in that mental state. So, if you even take 30 seconds to one minute to ground yourself on, why am I in this meeting? What do I want to share? And make sure I get across in the time that we have, you're going to go in there so much more focused and so much more able to be concise.

• 21:51Lenny Rachitsky?

  So, the advice there, so this is for meetings, and I want to talk about writing also, but for meetings, the advice here is, before you get into a meeting, like, actually think about, why am I in this meeting? What do I want to get out of it? Instead of, in the meeting, like, figuring it out as you go, which, to your point, you're just going to ramble and be like, okay, here's what I actually want to say.

• 22:10Speaker 00

  Yeah, and what might I want to share in the meeting, too? You know, especially for more introverted folks, sometimes you need to decide beforehand that you want to speak, and you want to make sure you get a certain point across. So, even deciding that beforehand makes a huge difference.

• 22:25Lenny Rachitsky?

  Yeah, I found this extremely powerful, just like, five minutes before you get into a meeting, and it could happen earlier in the day, right? It doesn't have to happen right before the meeting, or, worst case, it's right before the meeting, just, okay, what do I want to get out of this? What am I here? What do I want to say? And just, like, giving your brain a little bit of time to prepare, super powerful. In writing, is there, like, any tactics you can share for someone to be a little more concise?

• 22:50Speaker 00

  I think the main tactic is to remind yourself to be concise. And usually, when I do that, I end up trimming 20%, at least, of what I wrote, tightening up some sentences. I also ask myself, how might I be adding cognitive load to whatever it is that I'm saying? So, you know, is there a tighter, clearer, cleaner way that I can ask what I'm asking, or present the information I'm presenting, or the, you know, make the recommendation that I'm making? And usually, if you even ask yourself that, your brain automatically comes up with stuff. You just see whatever you wrote differently, and you're like, oh shit, I should trim this entire paragraph, because, like, that's secondary, you know?

• 23:33Speaker 00

  And maybe you have your primary message in Slack, and then, within the thread, add, you know, some of the secondary stuff, right? I find that most of us, it's reminding yourself to be concise. And once you think of it, your brain naturally will see places where you can trip.

• 23:49Lenny Rachitsky?

  There's a layer of advice under this that you're not saying that I'm going to say, which is actually look at the thing you wrote at least once before you share it. Because I used to be really bad at this. I just like, okay, I don't have time. I wrote this doc, send it, get feedback. All right, send this email. I don't have time to like read this email. And I find just forcing yourself to look at it solves so much of this.

• 24:10Speaker 00

  Oh, yes, yes, definitely. I was, I was assuming before doing that, but you're right. The, you know, some people might not be. And yes, definitely reading your own message first is huge. And yeah, I find that even, even doing that, you can often spot a lot of, a lot of low hanging fruit.

• 24:31Lenny Rachitsky?

  Right, like you'll find the typos and grammar issues and you'll be, oh, I don't need this word. Along those lines, let me share two books. People always ask me, how did you, how did you learn to write? I'm like, I'm not a writer. I don't know what I'm doing, but two books really helped me write more effectively. And one is specifically to help you write more concisely called On Writing Well. And I don't know if you've read that.

• 24:51Speaker 00

  Yeah.

• 24:52Lenny Rachitsky?

  Okay. And it's basically like chapter after chapter of here's what you can cut. And you can cut more and look what more you can cut and cut this stuff. And he has like images of like screenshots of essays that students have written in his class. And he's like, look at all those words you cut and nothing is, is changed. It's exactly the same message and even is better with like 40% of the words cut.

• 25:12Speaker 00

  Is this by Sol Stein or, or another author?

• 25:15Lenny Rachitsky?

  I am, I don't have it here. It's somewhere in my bookshelf, so we'll look it up.

• 25:19Speaker 00

  Yeah, there's, there's, there's a writing book by Sol Stein that I absolutely love. And I feel like it might be called On Writing Well, but there are also, I could see there being multiple books called On Writing Well.

• 25:29Lenny Rachitsky?

  There's also Writing Well, I think by Stephen King. That's like another one that people love, but they're, On Writing Well is the one I really loved. Cause it's very like tactical.

• 25:36Speaker 00

  Going back to something that you were saying earlier with rereading what you wrote.

• 25:43Speaker 00

  I think the blast radius of a poorly written memo is way bigger than most people think. So if you're, if you're just shooting off a message in a Slack channel with 15 other people and it's confusing and you didn't include information you should have included, there's going to be a bunch of back and forth, like all 15 of these people are reading this, being like, okay, what do I do with this? Whereas if you had just taken another look at it, um, those 15 people would be off to the races. Like they would have read your message and then known exactly what to do next, or what their part was, or what you were looking for from them. Um, so I think about that a lot, too. It's not just, you know, me writing this and sending it off. It's who are all the, who are all the people who are going to come in contact with this message? Who are going to refer to it and use it?

• 26:27Speaker 00

  And if I just take 30 more seconds to make sure that it's clean, how much can I unblock from their work?

• 26:34Lenny Rachitsky?

  That's such a good point. I like that, that term blast radius. It's such a good point, just like there's so much negative leverage in writing inefficiently and in concisely, if you spend like, inconcisely, I don't know if the word is there, but uh, if you just spend like three minutes, spending a little more time making it more clear, just like the impact and leverage that has, that's such a good point. I looked up the books, it's so funny. Okay, so there's On Writing Well by William Zister. There's Stein on Writing by Sol Stein, which is what you said you were talking about. And then Stephen King has a book called On Writing. Yeah, like, yeah.

• 27:09Speaker 00

  Yeah. Comment title.

• 27:12Lenny Rachitsky?

  Not a, not ideal for SEO, but On Writing Well is the one that I love by William Zister. There's also one called A Series of Single, of Short Sentences. If you haven't seen that one, it's a really good read, read too. It's just like how to write short sentences and just the, the power of just keeping sentences short, which I struggle with.

• 27:26Speaker 00

  Yeah, I like that.

• 27:28Lenny Rachitsky?

  Okay, back to our agenda. There's another framework slash tactic that I've heard you recommend. It's called signposting. What is signposting?

• 27:38Speaker 00

  Signposting is.

• 27:40Speaker 00

  Using certain words, phrases, formatting and an overall structure in your writing that helps guide your reader and signals what is coming in the rest of the post. So this is especially helpful if you have a long memo. It adds structure to where are we going and what certain sections of paragraphs are about. So some of my favorite signposting words are, for example, shows that you're about to show an example, because, shows that you're about to share your logic and rationale behind something, as a next step is a great one. People's eyes kind of automatically

• 28:20Speaker 00

  zoom to as a next step, even first, second, third, kicking off a paragraph with that. You're not needing to rely on rich text formatting with bolding, italics, underlines, and all that craziness. If you kick off sentences with signposting words, you can often signal, here's what I'm about to talk about in this paragraph.

• 28:40Lenny Rachitsky?

  These are like power words for clarity. Like, there's this whole concept of power words, like free and

• 28:46Speaker 00

  Yeah, gift.

• 28:48Lenny Rachitsky?

  Yeah, for like copyrighting and I, these are basically power words for helping your brain see the structure and get to the thing you want to pay attention to. So I'll read back the words you just used. For example, because, as a next step, and then first, second, third.

• 29:05Speaker 00

  Yeah. Yeah, you can use signposting in writing and verbally too. So if you're doing a product demo, you might say something like, the most important part to pay attention to is blank, or the part that we were most surprised by is blank, or the, you know, the part that customers are, et cetera, right? So it's, you're signaling that whatever comes after this thing is something that you may want to pay attention to. So it's a great way, not only to add structure, but to also grab people's attention back if it has strayed sometime as they were either listening to you or, or reading.

• 29:41Lenny Rachitsky?

  Along those lines, I find, I find formatting really helpful here, just like bold and bullets. I know you have a pet peeve with too much formatting. How much is too much formatting?

• 29:51Speaker 00

  I really hate excessive formatting. So, you know, I've seen memos where 30% of the note was bolded. And that just negates the entire point of folding because if everything is folded, then none of, nothing is, is being highlighted, right? So I think using formatting in general more sparingly than you think you have to is probably a good rule of thumb. I also dislike when people overuse bullets and sentence fragments, phrases in bullets, when they should use complete sentences that actually show the connected tissue between ideas, that show the logical flow of what it is that you're saying.

• 30:32Speaker 00

  And, you know, it's, it's, it feels faster and more concise to put bullets and, and fragments, but a lot of times your reader on the other end of that is needing to decipher and interpret and guess what you actually meant. Um, so it net-net takes longer. And I also think that it can be a little bit of a crutch. It can be a little bit lazy because you are telling yourself that you're being concise when really if you had to turn your sentence fragment into a full sentence, a lot of times, like, it actually is harder than you think because you realize that you actually didn't really know exactly what you meant. So as you're trying to turn it into a full sentence, you're actually needing to use brain power.

• 31:15Speaker 00

  So that's like, I think, a great litmus test of like, was that, was that idea fully thought out? Because if it was, you should be able to really quickly turn it into a complete sentence, a complete sentence. Um, and, and many times you actually aren't. So I see people like basically think, oh, I want to make this easier to read, more skippable. I'm just going to throw a bunch of formatting and bullets and, you know, turn everything into bullets and, and it's not quite that easy of a solution.

• 31:40Lenny Rachitsky?

  This is very much along the lines of the whole Amazon six-page memo where Jeff Bezos just kind of realized if you can't write it out as a long memo and explain yourself in prose, you, you don't actually know what you're saying. And it's a really good filter for helping people actually crystallize and, and know themselves, okay, I see, I don't actually know what I'm doing here.

• 32:00Speaker 00

  Hmm.

• 32:01Lenny Rachitsky?

  And I love this, like, a microcosm of that. Can you just, like, make a bullet point a real sentence versus a fragment of a sentence?

• 32:05Speaker 00

  Hmm.

• 32:07Lenny Rachitsky?

  I'm thinking about as a listener being like, okay, how to actually get better at this? So maybe let's take a tangent. I know that you teach a whole course. You do all this stuff hands on with people to help them actually build these skills. For someone that hasn't taken the course or isn't taking it, what's like a good way to start practicing these skills and know if what you're writing is getting better, is good, is it like find a mentor, find someone that you think is a great writer and have them review stuff. Any tips there?

• 32:33Speaker 00

  Yeah, so I have a pretty first principles driven approach for this, which is to think about how long does it take me right now to get to the reaction I'm looking for from my recipient? If it takes a bunch of back and forth and a bunch of friction, then that's kind of my baseline. And once you start practicing some of these communication skills, how does that speed up? If you would have had seven different touchpoints of back and forth, does that shrink to two to three? Not every point of friction is going to be avoidable, but a lot of it is if you get better at communicating. So I like watching for the reaction and how quickly

• 33:18Speaker 00

  and how enthusiastically I'm able to get that reaction. And for the things that are working, do more of that. For things that are not working, adjust your execution because it might not be that the tactic doesn't work. It might be your execution of it, you know, wasn't great. And, uh, and, you know, keep, keep trying, basically.

• 33:36Lenny Rachitsky?

  So the advice here is just see how well your writing slash meeting slash suggestion goes, how well it does. And if it's not like, there's like the ideal immediately, yes, let's do it. And then there's the, I don't really understand. There's like the spectrum of response. And what I'm hearing is just pay attention to if the speed to getting what you want is increasing in general.

• 33:59Speaker 00

  Yeah. Yeah. I don't think that there's any single shortcut on how to get better besides that. Um, I do think that. Being fascinated by a topic and being excited about it makes it more likely that you're going to find it fun to try all these different things and try different ways to to get through to people. So I would approach it with a hypothesis driven experimental mindset and almost like a game, like when I do this, how does that other person react? You know, if I frame it this way, do I get a different reaction? When I try this, am I able to, you know, cut through the noise more? So yeah, so I really think it's about

• 34:40Speaker 00

  practicing. And I will say that the way not to do it is to try to incorporate 30 different tactics at the same time and then beat yourself up when you don't remember to do them. You know, it's really easy when you are learning a new field or function to get overwhelmed when you're when you're learning a new skill. And the way to build a habit is usually not changing so many different things at once. It's picking one thing that you want to try and keeping that top of mind, trying it in a bunch of different settings in different ways and then and then getting it better at that thing before moving on to the next thing. So that's like a really common thing I see in my course is people feeling overwhelmed.

• 35:23Speaker 00

  And I always remind folks that you're building a new habit here and, you know, take be patient with yourself, take it step by step.

• 35:31Lenny Rachitsky?

  There's a lot of stuff we're talking about here that a lot of people might be like, this is so minor, like what I just bullet point sentences, like be a little like tell them the why at the beginning. And I just want to share in my experience, the biggest jump I made in my career was actually getting better at these very specific skills. I have this manager Vlad, who's been on the podcast and I talk about him regularly, who was such a stickler about communicating well and being very clear and concise and thinking and just spending more time on documents and emails on strategy docs, just like, no, this isn't ready. Spend more time. Here's something that's not clear. And just doing that was such an accelerant for me. And it's all these little things. That's what's interesting

• 36:14Lenny Rachitsky?

  about it. It's like, everything seems really minor, but it all adds up to a lot of impact because to your point, people see it. Okay, cool. I get it. Let's go. Versus like, I don't like this idea. And then it's like, it all falls apart. So I guess any reactions to that?

• 36:28Speaker 00

  Yeah, all these little things compound and make a big difference. I

• 36:34Speaker 00

  Often hear people think, well, you know, this individual instance, this individual email, the Slack message is not worth spending a couple more minutes on. It's just an email or it's just a Slack message. The problem with that line of thinking is that no one instance of something is ever going to feel important enough to spend a little bit more time on then. And then, but when you zoom out, that's like, well, that's all your work then. This is like literally everything you've touched. This is all your work output then because every, you know, any piece of that process you thought wasn't, you know, wasn't worth spending time on. And now this is just the, the quality of your work and it's not as good as it could be.

• 37:14Speaker 00

  So, yes, like these might seem minor, but A, it compounds. And also B, all the quote unquote big things, everyone else is already doing. So there's not a lot of alpha in that. Whereas if you are paying attention to skills that people think are boring or too basic and realizing that there is, that's a lever that you can pull. That, you know, someone else thought, oh, we're hitting diminishing returns on that. I'm not gonna, I'm not gonna spend more time on that. But you realize that there's actually more juice left to squeeze there. And you decide to squeeze that juice. Well, now you have extra juice, right? That the other person doesn't have.

• 37:56Speaker 00

  So, yeah, in, in my experience, I find that people claim the point of diminishing returns way too early. And this isn't just for communication. This is for strategies, tactics, et cetera. Like they'll try something once, you know, a mediocre attempt and be like, this channel doesn't work. This tactic doesn't work, you know? It's like, really? Cause it's working for a lot of other people who are getting really creative with it. You know, I'm not saying that everything has to work for you, but like for you to claim this thing just doesn't work. Feels a little bit intellectually dishonest. Like, it's more likely that your skill level, your creativity, your execution ability was not good enough. And that's fine. Like, let's admit that to ourselves because if we admit that,

• 38:38Speaker 00

  then we can do the hard work of getting better at those things.

• 38:42Lenny Rachitsky?

  It feels like if you really boil this down, the advice kind of comes down to just spend a little more time on all these things you're putting out.

• 38:50Speaker 00

  I like thinking about it as a little bit more upfront investment. And it is an investment. It's not just time. It's an investment because, yes, it takes a little bit longer to make a Slack message a little bit better. But net-net, if you save a bunch of questions and back and forth, and people asking you things that you don't think they should be asking, then by investing a little bit of upfront effort, you've prevented all that from happening. So, yeah, it is a little bit more time in the moment, but reaps a lot of benefits down the line.

• 39:25Lenny Rachitsky?

  Today's episode is brought to you by Coda. I personally use Coda every single day to manage my podcast and also to manage my community. It's where I put the questions that I plan to ask every guest that's coming on the podcast. It's where I put my community resources. It's how I manage my workflows. Here's how Coda can help you. Imagine starting a project at work and your vision is clear. You know exactly who's doing what and where to find the data that you need to do your part. In fact, you don't have to waste time searching for anything because everything your team needs from project trackers and OKRs, the documents and spreadsheets lives in one tab, all in Coda. With Coda's collaborative all-in-one workspace, you get the flexibility of docs, the structure of spreadsheets, the power of applications, and the intelligence of AI,

• 40:10Lenny Rachitsky?

  all in one easy-to-organize tab. Like I mentioned earlier, I use Coda every single day, and more than 50,000 teams trust Coda to keep them more aligned and focused. If you're a startup team looking to increase alignment and agility, Coda can help you move from planning to execution in record time. To try it for yourself, go to coda.io/lenny today and get six months free of the Team Plan for startups. That's c-o-d-a dot i-o slash lenny to get started for free and get six months of the Team Plan. Coda.io slash lenny.

• 40:42Lenny Rachitsky?

  You mentioned Slack. I have a great quote also about you that I didn't read that I'm just gonna read right now from someone that worked with you. She said she searched the Slack channel at the company you worked at for old posts from Wes for inspiration for what to ask you. And she said, you had zero half-baked thoughts, 100% complete sentences, perfect punctuation, clear takeaways at the top of every message. It's the kind of thing you don't notice in isolation, but once you see everyone else's messages in a remote first company, it's a stark contrast.

• 41:11Speaker 00

  Yeah, thank you. I will also say that, you know, as someone who tries to walk the talk, I feel like I get a pretty good response rate, pretty quickly for the things that I ask for, for the recommendations I'm making. It's not, you know, it's not instant, it's not 100%, but over time, I've realized that improving my communication has led to people receiving my ideas better. You know, ideas that used to be locked in my head that I would get frustrated that no one else understood, people were now understanding. And that feels really good. That's very, very exciting. And it made me want to do it more, you know, and pay more attention to that. So that's kind of going back to what I said earlier

• 41:54Speaker 00

  about watching for what's working, you know, there's, momentum is really encouraging.

• 42:01Lenny Rachitsky?

  And I totally feel that if it starts, like if you start getting the things you want, that feels great. Okay, cool. Few more of that. Yeah. And again, it's like very minor things. Like it's, you know, it's like a couple more minutes on the Slack message, a couple more minutes of email.

• 42:15Speaker 00

  Very doable.

• 42:16Lenny Rachitsky?

  Like, yeah, which everyone can do. There's no like magic here. It's just spend a little more time and use some of these tactics that we're talking about. Speaking of that, let me talk about another tactic. You have, apparently you have some really good advice on finding the right level, level of confidence in what you're saying. There's always this like question of I come to a leader. How like confident should I be about this is the answer versus like here's a bunch of ideas. What do you think? What's your advice there?

• 42:41Speaker 00

  I find that people tend to naturally be on the spectrum a little bit too confident as a baseline or not confident enough. So people who are too confident might state hypotheses as if they are fact. So that really bothers me. That's another one of my pet peeves where, you know, if you say this is X or this will X, that is different than saying this could X or this might X or this will increase the likelihood of X. So I'm a big proponent of speaking accurately. You can avoid a lot of problems if you speak accurately about your level of conviction and about the actual amount of evidence that you have for something.

• 43:23Speaker 00

  It's okay for something to be an initial hunch. Say it's an initial hunch. Don't act like this is something that you are super sure about. You've proven out, you know, that this is absolutely, you know, this way because the rest of your team is listening to you at face value. And y'all might spend real headcount and dollars pursuing something that you have advocated for in a way where you kind of overreached with your level of confidence. So that's for people who are overconfident. It's equally a problem if you're underconfident. So I have some clients who, you know, their CEO asked them to share some recommendations with another team because, you know, they've run something before. And so they share all this amazing information.

• 44:07Speaker 00

  And at the end, they're like, oh, but you can ignore everything I just said. You know, obviously make your own decision, do what you think is best. And like, if you want to just ignore everything, that's totally cool too, you know? And it's like, you just didn't have to say that, you know? You could say, make your own decision, like take all this into account, you know? But like, you don't have to diminish to that degree. And so again, speaking accurately, like if you have really strong reasons to recommend something to, you know, to a cross functional team. It's almost irresponsible to act like you are not really sure. And it's just this like random idea. Hey, try it if you want to try it, you know? Like, we might lose a lot of money and time if you if we don't take this idea. Right?

• 44:51Speaker 00

  So, again, speaking accurately is so, so important.

• 44:56Lenny Rachitsky?

  Is a simple way to think about then kind of the the right balance is have a point of view, have a recommendation, present accurate facts and be clear when you are not. It's not actually 100% true, but here's a hunch I have or here's a theory we have.

• 45:10Speaker 00

  Yeah, I think sharing a point of view, sharing a recommendation and then backing it up with evidence, with logic, with first principles, with examples, with data if you have it, you know, you're not every situation you're going to have data for, especially if you're building something new. So this is where first principles comes in, like even explaining how you got to where you got to and why you think this is going to work. That all gives your team, your manager, something to push back on, to poke holes on or to align on and say, yeah, I agree here, but I disagree on this part. So you can talk about ideas with a lot more specificity when you share your thought process. And you can you can frame it all kicking off saying, my initial thinking is, or, you

• 45:54Speaker 00

  know, based on what we know, my hunch is blank. Right? So speaking accurately and then still bringing up those facts so that we can all make as informed of a decision as we can make, given what we know.

• 46:06Lenny Rachitsky?

  Advice I got that really helped here for me was to try to not be super, try not to be biased with how you frame everything. You have your suggestion for how to do something. It's easy to just bias all of the data to point in that direction. And I think it's, and if people notice that, they're like, oh, OK, well, I can't really trust this because I see you're just like, you clearly have an agenda. So it's a little bit like having an agenda and a POV, but be clear about what is actually true, be accurate.

• 46:36Speaker 00

  Yeah, I think anytime people have to discount what you're saying because you are biased in this way is not great.

• 46:45Lenny Rachitsky?

  Is there an example by any chance that highlights what you're describing here?

• 46:49Speaker 00

  Yeah, so in my course, I talk about not being a single minded martyr. So a single minded martyr is someone who very much has an agenda, who wants their recommendation to go through and is presenting a bunch of evidence supporting that direction.

• 47:07Speaker 00

  And then gets really frustrated when other people are not seeing it or are skeptical. And so one of my clients was a single minded martyr in a recommendation she was making. So she was on the growth acquisition side of her company and was having trouble with cross functional team members lending headcount to her project. And so everyone would say like, oh, yes, we believe in this. This is important, but wouldn't want to actually give her, you know, half of their engineer for two weeks. And we were talking about it. And as we were talking, she revealed that the CEO had at the beginning of the year said that the company wide goal is retention that year, that their biggest challenges and areas of opportunity were in retention,

• 47:53Speaker 00

  not necessarily in growth. And once she zoomed out and realized this, she was able to put her recommendation in context and realize that, you know, it's not just, you know, I'm the only one who cares about this company. Everyone is a hypocrite. They say they believe this, but like, don't actually want to work on it. You know, before that was, that was kind of her narrative. But once she zoomed out and realized she was being a single minded martyr, she could better fit her proposal in the context of what else was happening in the organization. I think actually this is a really big difference between more junior people versus more senior people. More junior people are like, I need to win. Like, I need to get a yes for this proposal and I'm going to keep advocating for it until I get a yes. Whereas really, sometimes the best decision for the company is not right now.

• 48:39Speaker 00

  Like, this doesn't actually fit our priorities right now, right? Or maybe yes, but let's right size the level of investment. So it might look like half whatever the proposal, you know, the, the, the size of what that recommendation actually was. And having the maturity to realize that, to put your idea into context is huge. Like, that took me a really long time to learn. And I think that goes under the umbrella of always do what's best for the company, not necessarily what's best for me, my career, my team, my wins. You know, if you, if you prioritize what's best for the company, that, that helps you have a

• 49:16Speaker 00

  A more right-sized way of still advocating for your ideas, but doing it with a bit more equanimity.

• 49:26Lenny Rachitsky?

  And also just connecting to what the company is. Just this idea of if the thing you're pitching is not aligned with what is important to the company right now, it's unlikely to be prioritized. Like, it makes sense. This is why leaders choose. Here's what matters most. We gotta do the things that are gonna help us drive this thing right now, like retention or revenue. And so that's just, I think, a sub-tactic there is just whenever you're pitching something, connect that to the goal of the person you're pitching to. So that they're like, oh, see, how's this gonna help me? That's great, let's do it. Great advice. And I think this is something a lot of people run into is just, why are they listening to me? Why don't they want, that's such a good idea. They hate me, it's something, oh, I bet they hate me. They don't trust me.

• 50:11Lenny Rachitsky?

  And when it's just like, okay, this isn't a priority right now. Let's come back to it another time. Okay, I'm gonna get to a couple more tactics and then I'm gonna shift directions to talk about managers and being a manager. You have an awesome framework called MOO. What does MOO, what does it stand for and what is it all about?

• 50:26Speaker 00

  MOO stands for most obvious objection, M O O. And the thought there is that a lot of times we're surprised by the questions that we get, especially in meetings where, you know, we feel blindsided, that was unexpected, and then we're on our back foot. When really, if you thought for even two minutes about what are obvious objections that I am likely to get when I share this, you often immediately come up with what some of those things are. So are you gonna be able to anticipate every single objection? No. But can you anticipate the obvious ones? Absolutely. And this is where knowing your own argument. In and out, including counter arguments, becomes so important.

• 51:10Speaker 00

  So knowing your counter arguments as well as you know the arguments for doing the thing. When you do that, when you, when you, you know, have prepared in that way, you're less likely to, to feel caught off guard.

• 51:22Lenny Rachitsky?

  When you hear you talk about this, it's like, obviously I shouldn't do this. But nobody, like, very few people actually do this, like, actually spend a couple of minutes. Okay, here's what I'm gonna pitch.

• 51:31Speaker 00

  Even a couple of seconds, really, like, really, like, even a couple of seconds, your brain will, will think of something.

• 51:37Lenny Rachitsky?

  Is there, is there a story or an example of this that you share that highlights this idea of the power of moo?

• 51:43Speaker 00

  I use moo multiple times a day, every day, every single day. Like, literally, whatever I'm about to say, I think, how might someone disagree with this? Or what might an objection be? So whatever it is I'm writing, saying, it's a really good mental filter because it encourages you to think a couple of steps ahead in kind of a structured way. Right? Like, if I'm about to say this, the person may then say this to me, well, if I take that into account, I can, I can volunteer that, you know, that information upfront, or I can frame it in a way where they're less likely to think that that's an issue. And so it's, it's, it's muscle memory for me at this point, but, you know,

• 52:24Speaker 00

  this might be something we, we include at the end, is something to start with, but putting moo on a post-it, most obvious objection. You know, what, what is someone likely to object about? And then just keeping that top of mind, it's a great way to train yourself to be, uh, to empathize with your audience and with your recipient. We all say that, and we all know we should do it, but for me, this is a really tactical, concrete way to do it.

• 52:49Lenny Rachitsky?

  I think what's great about a lot of the tactics you're sharing is not only is it gonna help you communicate it better, but it helps you actually. Think and crystallize it better for yourself because you may realize, oh, that's a really good objection. Like, oh, oh, the objection is probably going to be this won't drive enough impact for the business. Oh, that's a great point. Maybe I should not pitch this right now.

• 53:09Speaker 00

  Yeah, it definitely helps shape your own thinking. I think communication and thinking are so much more interrelated than we think, you know, I think people think there's a thinking as phase one and then communicating the thinking and the reality is a lot more intertwined. And I loved your example there that thinking ahead to what might be the most obvious objection actually then prompts you to realize that maybe there was a gap in, in what you were planning to present. And then you now have an opportunity to strengthen that pitch before you say it out loud.

• 53:45Lenny Rachitsky?

  There's a quote I have highlighted on this podcast a number of times that I love that is exactly along these lines by Joan Didion. I don't know what I think until I, until I write it down. I think I know exactly that feeling.

• 54:00Lenny Rachitsky?

  Okay, so there's a couple more things that people have shared that you are amazing at helping them get better at. One is just keeping your cool and staying calm during very high stakes, real time conversations when things maybe aren't going your way, or you just agree with someone. Any advice on that? It feels like you're really good at this.

• 54:18Speaker 00

  I think one thing that tends to, to throw people off is putting a lot of pressure on themselves to get the exact right answer. So if they are asked a question and they don't know the answer, you know, a lot of people will then kind of freak out. And I was taught early in my career that if you don't know the answer, you should say, let me look into it. I'll get back to you. So that's a fine approach. It's definitely better than making something up, right? So, so definitely don't make something up. But If you are more experienced and have some confidence in your subject matter area, just saying, "I'll get back to you," is sometimes a missed opportunity.

• 55:03Speaker 00

  You can ask for a bit more information to be able to continue the conversation in that moment. So, you know, let's say that your exec says, you know, what percentage of users came from mobile last month? And you don't have that number off the top of your head. So, person A says, "I'll get back to you, you know, let me look and talk back to you." Person B might say, "I don't have that number off the top of my head, but in the last quarter, the number has been 60 to 70% and it's grown in the past year." So, mobile is now, you know, a bigger part of our business, et cetera. Are you wondering if we are investing in mobile appropriately? Or like, where's that, you know, where's that question coming from, basically? Right?

• 55:47Speaker 00

  And so, being able to answer a similar question in the direction you think the person is asking about, and then validating why they're asking that question, allows you to still continue that conversation in the moment. And so, I call it the question behind the question. Sometimes you get a question, but underneath, there's a deeper, underlying concern. And many times, people don't even know that it's there, right? Subconscious. So, it's not nefarious, they're not withholding anything from you. But when you are explaining something and you're kind of getting multiple questions on the same thing, it's a good sign that there might be a deeper question behind the question. And it's our responsibility to figure out what might that be.

• 56:32Speaker 00

  And so, probing, asking for a bit more information, answering in that general direction, and then validating, these are all techniques you can use when you are in the moment, without feeling like, "Oh, I must have, you know, every single thing prepared." And the moment that I'm caught off guard, you know, everything goes to shit.

• 56:48Lenny Rachitsky?

  Another tactic along these lines that's very similar to what you're describing, but I'll, I'll share that I learned that was really helpful, is just, if you're not sure what to say, basically just reflecting back their question and just, just being like, "Let me just make sure I understand what you're thinking, what you're looking for. You want to understand monthly retention for..." and then maybe clarify. And that one gives you time to think about it as you're talking. Two, it helps the person recognize, "Oh, he hears me. Great, okay, this is good, he's thinking about this." And then at the end of that, you could be like, "Okay, I don't actually have that specific number." Uh, let me think about, oh, or I have the quarterly number. Okay. There, that's what I know. So there's like, there's like an interim step almost that I, uh, I'll add into your piece of advice of just

• 57:28Speaker 00

  Yeah, I love that.

• 57:29Lenny Rachitsky?

  Reflect back their question, just like better understand what they're looking for.

• 57:34Lenny Rachitsky?

  Awesome. Okay. Let's go back to what I said we do is let's pick one tactic that you think people should try first, maybe one or two. So let me read the ones we've gone through and then see what you think would be a good first step. So one is starting with sales before getting into logistics and giving people the why. Signposting, using specific words to help people guide the, the doc and not get overwhelmed. Finding the right level of confidence, having a POV, that sort of thing. Getting better at being concise. Moo. Not overusing formatting, something else you shared. And then this idea of when you don't know the answer, not saying, I'll get back to you as the default.

• 58:17Lenny Rachitsky?

  Maybe giving them a different answer, maybe asking them more questions. Okay. Across those, which do you think someone should try to like, okay, let me start here.

• 58:25Speaker 00

  I would start with most obvious objection. And also framing your conversation upfront. And that kind of relates to using signposting words if needed to help you frame that conversation.

• 58:37Lenny Rachitsky?

  Sweet. That's such an easy one to remember. Just move. Okay. So stick a post at somewhere. When you're about to share something in Slack and ask someone for something, present in a meeting, send a strategy and just think about for a few seconds, what might be the most obvious objection to what I'm trying to ask them to do. Great. Okay. So let's talk about management. And there's kind of two sides to it. Being a manager and being a person reporting to a manager, you have a bunch of really good advice here. One is there are managing up. One of my most popular posts in the early days was advice for managing up and just how important it is. What advice do you have for someone to get better at managing up? Why is that even so important? Why do you think people maybe underappreciate how important it is to manage up, manage your manager, let's say?

• 59:17Speaker 00

  One of the most, yeah, common myths about managing up, uh, that I definitely felt early on in my career was that. I would have to manage up if I were more junior, but eventually I would outgrow it. That I would get senior enough that I would no longer have to do it. And it was a rude awakening that no matter how senior I got, managing up, I not only had to manage up, it actually became more important. So I think managing up is, is one of those skills that if you invest in learning it, it serves you now and for the rest of your career. And I realized that many senior people are actually the best at managing up. That's partially how they got to be so senior in the first place. But also, you know, the more senior you get,

• 1:00:00Speaker 00

  the less likely that your manager is going to give you really well-defined tasks and problems on a silver platter and ask you to solve them. You're going to be dealing with more ambiguity and you're going to be dealing with sometimes a mandate, like make this number go up or like create this division, right? Where you need to manage up and make sure that your leader, your manager is in the loop about what you are about to try and what you were about to do and make sure that they're aligned. And so for me, realizing that managing up is something that is, is ongoing and that it, it shifts and evolves and looks different as you go in your career. That was a big unlock for me.

• 1:00:44Lenny Rachitsky?

  Just that even as you, like if you become even a VP, if you become a director and still something you want to invest in, any specific tactic or advice for how to manage up well?

• 1:00:54Speaker 00

  The biggest one is to share your point of view. So this, you know, some people are surprised by because they think I'm going to say, do a weekly recap of the tasks that you worked on or like, you know, what you contributed. And that is a good idea, you know, if you want to do it, you can do it. But I think the, the more highly leveraged way to contribute and manage up is by being more vocal about sharing your point of view. When you just ask your manager, hey, manager, what should we do? You're putting a lot of cognitive load on your manager to need to think about the problem, think about potential solutions, craft the solution and then tell you what to do. Whereas if you instead said, hey, manager, here's what I think we should do.

• 1:01:40Speaker 00

  How does that sound? Where do you see gaps? Am I thinking in the right direction? You give them something to build off of and that. Reduces the amount of mental lift that they have to put forth. And so sharing your point of view more readily, backing it up with evidence, that's a wonderful way of making your manager's life easier. And also showing that you are an active, rigorous thinker, who is thinking strategically about the business. You're not just waiting to be told what to do. You're not expecting them to figure things out and then tell you. You are actively looking around the corner, trying to solve problems, forming hypotheses in your mind, observing and noticing things.

• 1:02:22Speaker 00

  And again, sharing your point of view doesn't mean that you have the perfect answer. You can share that, hey, I've noticed this problem popping up in a couple of different places. Here's what I think might be happening. You know, or when you share a report, don't only share the report and expect your manager to come up with insights and takeaways. You should look at the report too and point out insights and takeaways. So it's really changing that posture from more reactive and more waiting to be told what to do or kind of staying in this narrow box, to being willing to share your recommendation, your point of view, share what you're noticing. And this is something that even junior people can do.

• 1:03:04Lenny Rachitsky?

  I was gonna say exactly that. I think not only is it something junior people can do, this is a really good way to get promoted and to take on more leadership opportunities. You coming to your manager with, here's something I think we should do. Here's a perspective I have, here's an opportunity. Because that's what, like, if you were in charge, you're like, how awesome would it be for people to come to me with amazing ideas and have clear recommendations that sound great? Like, that's exactly, everyone wants that. So if you can do that, amazing, who wouldn't want that? But then it's interesting is, similar to how writing helps you crystallize your thinking, you coming in with a recommendation forces you to really think deeply about it because that's putting your reputation online. So there's like a second order effect of, it makes you actually spend more time on the thing and be clear

• 1:03:49Lenny Rachitsky?

  about why you think this is a good idea and do more research. So a lot of wins here.

• 1:03:53Speaker 00

  There are a lot of situations where you might have the most visibility into a problem. You might have the most proximity into an issue. And so if you're not speaking up about it and sharing what you're observing, sharing what you're noticing.

• 1:04:08Speaker 00

  Your manager doesn't necessarily have visibility into that. And so I've heard so many managers say that they want their junior people to speak up more because their junior people have often close contact with customers, with support tickets, with cleaning data, a bunch of things where the manager would love to hear insights from that.

• 1:04:30Lenny Rachitsky?

  And if you're finding not success, if you're not having success with this, if you're hearing this and be like, but it never worked because my manager doesn't listen to me. Listen to the rest of this podcast we just did, which is basically advice on how to effectively convince someone of a thing. It's like tell them why this is a problem. Be really concise about it. Signpost words, all these things. That's exactly what this whole conversation's been about. Okay, let's see. We have a couple more really cool tactics that people have suggested we talk about. One is how to give feedback well, how to do better, how to be more effective at giving feedback. What's your advice there?

• 1:05:05Speaker 00

  I have a framework called strategy not self-expression. And so the idea here is that most of the time, by the time we are giving feedback to someone, we have been frustrated for a while. You know, I used to be very conflict averse, so I would wait and try to convince myself that I wasn't bothered by something until I really couldn't hold it in anymore. Then I would schedule a one-on-one with a coworker to tell them the feedback. And it would inevitably turn into a venting session where I was, in the name of sharing the impact of what they did, would share all of my frustrations and all of the ways that they have basically harmed me and made my life difficult. And this would be very counterproductive because the person would either feel like shit

• 1:05:49Speaker 00

  and feel really demoralized, or they'd get really defensive and they'd want to argue with me about how what they did actually was like not that bad, or it was partially my fault too, or whatever. And so I realized that. A better way of giving feedback is thinking about motivating the person's behavior change. The goal is behavior change. So if that's the goal, trim everything else that you were about to say that does not actually contribute to that goal. And only keep the part that will make the person want to change, help them understand the benefit to, you know, them as well as to the people around them.

• 1:06:27Speaker 00

  And so usually for me, that's trimming 90% of the initial stuff that I want to say and really keeping only that 10%. And that's made a really big difference. Whenever I am giving constructive feedback of any kind, I always keep that in mind. And when I don't do it, I almost always regret it.

• 1:06:46Lenny Rachitsky?

  Someone closer to me in my life has very needs is is working on the skill, which is like, there's just like a, I want people to know how messed they messed up. Justice, I need this to be fair. And there's like, uh, like what I always recommend is just think about what you want to get out of this conversation. Like, what do you want from them? And then, okay, what's the best way to get that versus just making sure they hear you and making sure they understand how screwed up this was. And that's basically what you're saying, right? It's like focus on the outcome you want to achieve, not like, something that's useful, like some, something that will make you just feel better.

• 1:07:23Speaker 00

  Yeah, I definitely think that having a space to vent and to share those frustrations is important. So you want to get that out before you go into the conversation with your counterpart. So whether it's talking to your therapist or your partner or friend, you want to basically get all that energy out because otherwise you bring it into the conversation and it doesn't take much to set you off. Like you might have a whole script, you're, you know, you're controlled, you're calm. And then you start talking and the other person raises an eyebrow and it's like, you know, acting a little incredulous at what you're saying. And that's all it takes for you to snap and be like, you're surprised? You're incredulous? Why are you incredulous? Like, right? Like, and then, and then you're off, right?

• 1:08:04Speaker 00

  So yeah, getting that, getting that energy out, I would say, step one, so that you can go into the conversation. Clear, grounded, setting that emotional tone that is more positive and that allows you to stay focused on only the part that will get them to behave in the way you want them to behave.

• 1:08:22Lenny Rachitsky?

  Such good advice. And I think we come back to, are you getting the outcomes you want? If you're not, this is another reason it might be the case, is you're just like, you just need them to hear your mind. I just need you to know. And I think a lesson here is that may not be what the best path to getting what you want. But it may feel good. Maybe people are like, ah, but I really want them to know this.

• 1:08:42Speaker 00

  There's that great Einstein quote about insanity being repeating things that you're doing, expecting a different outcome. And I feel like that applies so much to the workplace and to communication. You know, like, most of us have certain patterns that we're used to and certain ways of responding. And if that's, if you, if you believe that there is untapped upside, that like, whatever you are at is kind of a local maximum, and that there's, there's better out there, then that's where switching things up could be useful. And just not, not just doing everything that you've been doing and getting the same result that you might be getting.

• 1:09:19Lenny Rachitsky?

  This resonates with Toby Lutke when he's on the podcast, talked about how he had this quote that I love, that just no human in history has come anywhere near their potential. And everyone is way, way, way, way better than they think they are. And these are really cool tactics and really effective ways to actually get closer to your potential. Okay, two more things I want to talk about real quick. One is your advice on delegating, but also continuing to have high standards. This is something I spend a lot of time on, because a lot of people don't delegate because they're afraid it's not going to be as great. They want to just, I just want this to be really good. I don't trust that it's going to go as well. If I, if I did it my, my way, it'd be great. So just advice on how to delegate effectively while maintaining high standards.

• 1:10:04Speaker 00

  Yeah, I have a framework called CDAF.

• 1:10:06Lenny Rachitsky?

  I love all these acronyms.

• 1:10:09Speaker 00

  It's kind of like cedar, but with an F at the end. I need acronyms for myself. Like, all of these are really reminders for myself, because I need a short way to remind myself. So CDAF stands for, the C is comprehensive. So.

• 1:10:23Speaker 00

  Have I given this person that I'm delegating to everything that they need to understand what it is that I want them to do? That includes more simple things like logins to all the right software tools that they need to look up, whatever you need to look up, and understanding, you know, what the end result should look like, right? So that's all under C for comprehension. E is excitement. Am I explaining this in a way that is making this as exciting as it could be? There are a lot of tasks that aren't inherently that exciting, but by explaining the why behind why we're doing this, or why it's important to the project we're working on, that makes people more likely to understand and be excited about how this fits into everything. So E is for excitement.

• 1:11:08Speaker 00

  D is for de-risk. Am I de-risking any obvious risks from delegating this? So usually, when I ask clients this, they immediately think of something. They're like, oh, yeah, I wouldn't want my direct report to spend, you know, a ton of time going in the wrong direction, filling out 100 rows of the spreadsheet if like, actually it took longer than we expected. Okay, great. If that's a risk, then maybe you have them do 10 rows. See how long it takes, see if we need all the information that they're actually gathering, and then regroup, right? So what's an obvious risk? Another might be, you know, I can see this person misunderstanding and thinking I'm looking for this, where I'm really looking for that. Okay, perfect. Just tell them, you know,

• 1:11:53Speaker 00

  when I explain this, you might think I mean this, but really, I don't want that. I actually want this, right? So just vocalize it. The A is for align. So am I giving the other person a chance to speak up? And make sure we are actually aligned? That they are picking up what I'm putting down, right? Because you might, you might be explaining a bunch of stuff, but how much are they actually absorbing? You won't ever know if you wrap up your little spiel and then say like, okay, go off, like, come back to me when you're done, right? So give people a chance to ask questions, to see what parts are resonating, what parts they, you know, might be a little bit confused on. Usually when I do this, it's amazing because my team member will say, you know, what did you mean by this, this part? Or like, how does this part fit in? And I'm like, oh, my God, I totally forgot to like, mention this thing.

• 1:12:37Speaker 00

  Or, oh, yeah, I didn't even really explain that. Okay, so let me, let's go into that, right? And then F is feedback. So how can you have the shortest feedback loop possible? I am a huge fan of Shorting the feedback loop as much as possible and then shortening it again. So even within that initial conversation where I'm delegating something, instead of waiting a week,

• 1:13:00Speaker 00

  what if we waited a day and checked in on the initial direction that person was going? And let's do it even more. What if after I finish explaining, at the end of that conversation, we brainstormed a couple of things that that person wants to do? So within this same conversation I'm delegating, I'm already getting a sense of, you know, where do you want to go with this? Once you start, like, do you see any bottlenecks, you know? And so just really keeping that feedback loop super tight. I found that when I run through the CDF acronym, there's usually one letter that I could amp up a little bit more. Like, oh, like, I didn't really put much thought into making this exciting for the person. How can I connect this to their career goals or to the company's priorities this quarter? Or to something else, right?

• 1:13:45Speaker 00

  So it's a nice mental checklist.

• 1:13:49Lenny Rachitsky?

  So much of your advice comes back to this idea that we've touched on a couple of times, which is spend a little bit more time upfront. Is that how you described it? A little more time upfront?

• 1:13:56Speaker 00

  Yeah, a little bit more time, a little bit more of an investment.

• 1:13:59Lenny Rachitsky?

  Upfront to save you tons of time later. Okay, okay. So as you describe this, I don't know if you're realizing this, but you're basically just helping people work better with AI and agents. Like, this framework is exactly, I think, what people need to effectively delegate to this future world of this agent world of society of agents doing work for us. So it's like exactly what you, like, it's basically you're going to be delegating to these agents in the future. And this framework is a really cool way to frame it. So think about it, am I communicating this well comprehension? So CDF comprehension, this comprehension, again, just like, can I make this clear? Is that the way to think about that?

• 1:14:40Speaker 00

  Yeah, can I make this clear? Does this person have everything they need to be able to accomplish what I am asking them to do?

• 1:14:47Lenny Rachitsky?

  And then it's communicate why you're excited about this, basically the why. And it's interesting, there's this funny prompt technique I've learned, prompting engineering technique of just telling the AI, this is very important to my job. Just using that sentence, it does better.

• 1:15:01Speaker 00

  Interesting, yeah.

• 1:15:03Lenny Rachitsky?

  It takes it more seriously. That's just so weird, right? It's like, I have a post about this and that's one of the pieces of advice, just to tell her why this is important. Okay, I think people take it to the extreme as like, someone will die if you don't get this right. Like the people that actually works.

• 1:15:16Speaker 00

  That is okay.

• 1:15:17Lenny Rachitsky?

  It's wild. Okay, so CDAF comprehension, excited.

• 1:15:22Lenny Rachitsky?

  The de-risk, think about ways that you're good, you can de-risk, which is moo, basically. What's the most, it's like a similar concept, just like think ahead to what might be go wrong. Uh, make sure you're aligned, which is quite important in the AI space. Make sure you're aligned. And feedback, get a quick feedback cycle. And it's interesting with like deep research and some of these AI tools now, it's like, I'm off for half an hour. See you. And I imagine more and more of them will check in with you as it's going and ask you questions. I, I used deep research recently and it's really good at just like, okay, I'm at five questions for you before I go off and do this work, just to clarify what you want.

• 1:15:57Speaker 00

  Yeah, I found that um, AI will often um, shorten the feedback loop and align with you as well. Like when you prompt it, when it comes back, it will not do the entire task for me sometimes. It'll say like, you know, I've done the first part of this. Does this sound right? You know, is this, is this what you're looking for? If so, I will complete the next section. And then, and then sometimes I'm like, do the whole thing. Just stop trying to conserve energy and just do, I want you to do the whole thing, you know? Uh, but that's what it's doing. It's, it's breaking it into smaller chunks to de-risk that, you know, it's going to use all this bandwidth to process this thing. And I'm going to say, oh, that's not what I was looking for.

• 1:16:36Lenny Rachitsky?

  I want to come back to AI real quick, but before I do that, I have one more question for you. But let me just say, I feel like we've discovered an AI version of your course now. Basically how to delegate well to AI agents that I think people are going to find really valuable. Planting a seed. Okay, uh, before we get back to AI, you have this other concept that I love that actually learned from you years ago when I was working on my course called the swipe file. Swipe file. What is a swipe file? What is that about? What can help you with? Why should people be doing this?

• 1:17:03Speaker 00

  Yeah, so swipe files are really common for marketers. And I think other functions haven't caught on as much, but I think is uh, really, really useful. And basically swipe file is collecting inspiration that you can refer back to.

• 1:17:18Speaker 00

  Later on, so you know, some marketers will collect examples of copy, landing pages, ads, et cetera. For me, I have a file, an Apple Notes file called Smart Things People Have Said, where I will basically paste in phrases, words, you know, things people have said that I thought were well articulated, or sounded really intelligent, or sounded strategic. And I don't actually go back and look through my swipe file very often. I think other people do, but for me, even the act of adding it to my swipe file, I've already gotten value from it because it's training me to be more alert to noticing when something is working well.

• 1:18:00Speaker 00

  I think there's so much happening around us all the time that, you know, your coworker says something smart and you're like, oh, that was nice. And then you keep, you keep moving on, right? But when you stop and pause and think, oh, that was really effective, like, let me add it to my file and also think about why was that effective? And is that something I can borrow? So in my course, I encourage folks to create a work journal where they can jot down some of these observations, some of these phrases, and basically encourage yourself to be more alert to things you can borrow from other people all around you.

• 1:18:37Lenny Rachitsky?

  Something else about the swipe file, like you use quotes, it could be screenshots of cool designs, it could be strategy docs you found to be really effective, it could be conversion flows that are really cool, right? Could be just like whatever you're interested in.

• 1:18:51Speaker 00

  Yeah. And the great thing about that is you can then go back and analyze it and break down the structure, break down the argument, break down why was this so effective? Whereas if you're, if you're not capturing it, it's, it's easy to just move on to the next thing.

• 1:19:09Lenny Rachitsky?

  Yeah, cool. And I, I did this for a while, I stopped to be honest, but I really want to be doing this. So this is maybe some homework for someone because I know a lot of people stick with it, is just start like a folder or a notes, notes, note, whatever you use for your note taking and just start throwing stuff in there. And it's like, it could be messy, right? It's just like throw it in there.

• 1:19:27Speaker 00

  It can be super messy. I was gonna say, my backend system is super messy and it's fine. I am not, you know, It's not a problem I need to be solving. It works. I find things I need to find. So I like having as simple of a process as possible. So Apple Notes, like I open it, it's just, you know, on my home screen, I just add something. I'm not tagging anything and not putting it in certain rows and filling information out. I'm just including in the file. And if I want to go back and look at it, it serves its purpose.

• 1:19:58Lenny Rachitsky?

  Awesome. Okay. So last question, AI, I want to just come back to this briefly. We have a segment on the podcast called AI Courtenor. And we touched on this already, but I'm just curious how you have found AI to be useful in your work or your life? Whether you, it's helped you become better communicator? If there are anything you can share that could be helpful to folks?

• 1:20:17Speaker 00

  Yeah, I love Claude.

• 1:20:21Speaker 00

  There are days when I talk to Claude for like three or four hours prompting as a thought partner. So, yeah, I think that AI is really helpful for an initial draft of something to bounce off of. Sometimes I'll paste in an email that I am not quite sure how to respond to and ask Claude, tell me draft reply. And I'll usually give it some direction. So I found that sharing my point of view makes the output way better. If I just give it something and say like, what would you say? It's just not as good. Whereas if I say, you know, I am not sure about how to tell this person no.

• 1:21:03Speaker 00

  Because, you know, I previously kind of said yes, and so I kind of feel on the hook. But, you know, the street has changed. And so like, is there a nice way where I can be really respectful of our relationship? And also make them feel seen and heard, but, but like decline. So if I explain like, that's the problem I'm dealing with. And like, here's what I would ideally like to be able to do. Claude comes back with something that's like, pretty good. And then from there, I'll edit it to my voice. Because usually it's, it's a little bit too formal sounding. And so I'll make some edits and then I'll share it back to Claude and say, what do you think of this version? Would you make any improvements? And then we kind of go back and forth from there.

• 1:21:41Lenny Rachitsky?

  Wes, this is the most useful thing I've ever heard.

• 1:21:43Speaker 00

  Okay.

• 1:21:45Lenny Rachitsky?

  I need this immediately, just like nice ways to say no to stuff. This needs to be like an extension that I can have in my browser, just like, help me say no to this, please. Wow, such a great idea. Okay, good one. Okay, great. Wes, is there anything else that we we've gone through a lot? I imagine the answer is no. But before we get to our very exciting lightning round, is there anything else that you wanted to share or leave listeners with?

• 1:22:11Speaker 00

  Um, no, I feel like we covered a bunch of great frameworks, principles, so lots for folks to get started.

• 1:22:18Lenny Rachitsky?

  All the things. And I I think I love that so much of this will apply to being more effective with AI tools. And I feel like people can go through this again and just through that lens of how will this help me get more out of Claude and ChatGPT. I bet so much of this will actually apply, and I feel like there's an interesting course there. With that, Wes, we've reached our very exciting lightning round.

• 1:22:39Speaker 00

  All right.

• 1:22:40Lenny Rachitsky?

  Are you ready?

• 1:22:41Speaker 00

  Let's do it.

• 1:22:42Lenny Rachitsky?

  Okay, first question, what are a couple of books that you recommend most to other people?

• 1:22:46Speaker 00

  One is High Output Management by Andy Grove, which is a classic. Another one is Your Brain at Work by Dr. David Rock. And that one is all about better understanding your own brain and attention span so that you can allocate your mental resources appropriately. So that one's great. Ever since reading that, I hide my phone from view because there have been studies that show that even seeing your phone in the corner of your eye kind of changes, it's distracting. And I do the hardest things earlier in the day when you still you have, you know, more cognitive resources available. So that one's really good. Um, yeah, those two.

• 1:23:30Lenny Rachitsky?

  These are great. I completely get that phone thing. I'm just looking at my phone. I'm like, Dan, get out of here. Just like, go away.

• 1:23:35Speaker 00

  I will like stick it under my pillow, like on the couch, or like hide it under a notebook. It's it's huge. I'm always hiding my phone, so it's not in my line of sight.

• 1:23:47Lenny Rachitsky?

  I think Arianna Huffington has a product you can buy that's like a little bed for your phone that you put to bed before you go to bed in a different room, and it has a charger attached.

• 1:23:54Speaker 00

  Oh, that's cute.

• 1:23:55Lenny Rachitsky?

  So cute, so cute.

• 1:23:57Speaker 00

  I don't know if I need a separate bed for my phone, but you know, yeah.

• 1:24:00Lenny Rachitsky?

  But it's like a ritual, I guess, you know, and there's some theory behind it. Okay, next question, favorite recent movie or TV show you've really enjoyed?

• 1:24:08Speaker 00

  I love anything by Harlan Coben on Netflix. Basically, I don't even remember any specific movies or TV series. But anything he puts out, he's an author and then they, you know, they've turned a lot of his books into mystery thriller TV series and anything he puts out becomes number one on Netflix. And I appreciate that he gives the people what they want, that he knows his craft, he knows his genre. And yeah, he just has so many bangers. And like, I don't remember any specific one, but if it's a Harlan Coben show, I know it's gonna be good.

• 1:24:45Lenny Rachitsky?

  I'm looking at a list now. I just Googled real quick. So it's all like scary stuff, right?

• 1:24:49Speaker 00

  Yeah, they're like mystery thrillers and I think he does a good job playing with time and revealing information over time. And like, it's usually something about someone's past that is like now coming to haunt them. And so he'll go, he'll skip between present day to the past and then like slowly reveal stuff. And there's always a twist at the end.

• 1:25:10Lenny Rachitsky?

  There's a page, the Harlan Coben collection on Netflix that we'll link to that has all this stuff. I've never heard of this, so this is great. Next question, do you have a favorite product you recently discovered that you really love?

• 1:25:22Speaker 00

  I recently started using an electric toothbrush and it's been kind of life changing. So my husband got one and then a couple of weeks later, he gifted me one and I was like, wow, this is actually really nice.

• 1:25:34Lenny Rachitsky?

  Are you a sonic care person or oral B person or something else?

• 1:25:37Speaker 00

  It's oral B, but I've not tried any other brand. That was one that my, our dentist gifted my husband this electric toothbrush because he did Invisalign. And I'm sure Invisalign is like every dentist's dream, right?

• 1:25:50Lenny Rachitsky?

  Margins.

• 1:25:51Speaker 00

  I feel like every time I go, I get a cleaning, the dentist is like, so have you thought about, are you interested in Invisalign? And we're like, no, you know, and so like when they get a yes, I'm sure they're really excited. And then they lock you in with, with, or the brand locks you in with these replacement toothbrush heads that are way more expensive than they should be. So it's a whole razor and blades. Ink cartridge and printer model here. So I was kind of horrified by how expensive these replacement heads were, but.

• 1:26:18Lenny Rachitsky?

  But you got a free toothbrush.

• 1:26:21Lenny Rachitsky?

  I think the Oral-B is what I use, but it's, I think that's what the wire cutter recommended, but it's so loud and enough. Like, one of them is just really loud. I think it's the Oral-B, but it's better, apparently. So I went with wire cutter, but it's like, ah, it's so loud. I feel like there needs to be a wire cutter for like, good design and experience versus just the optimal, efficient version. Anyway, let's keep going. Do you have a life motto that you often find useful and work in life that you repeat yourself, share with folks?

• 1:26:50Speaker 00

  Yes, I actually have many, but I'll share two. One is, everything takes longer than you think. So this applies whether you are calling customer support for something, or running an errand, or building your career, building skills. I find it's useful to add buffers for yourself. This applies for launches too, right? Everything, just assume it will take longer than you think, and you'll be less stressed.

• 1:27:17Lenny Rachitsky?

  That connects everything we've been talking about. Just spend a little more time upfront to make it. And maybe, maybe if you spend more time upfront, it'll take less time than you think.

• 1:27:25Speaker 00

  The other one is a riff on "Always Be Closing" by Glengarry Ross. It's "Always Be Selling." So, this does not mean pawning your wares, but rather putting forth effort into convincing the other person of whatever your recommendation is.

• 1:27:42Lenny Rachitsky?

  Love them. Okay. Final question. So you've been a long time, I hate this word, operator, but I guess that's the way people describe this, where you've just been working at companies, building companies, and you recently left that to become creative person, started a course on Maven, you do executive coaching, things like that. Any just lessons or a lesson from that jump that might be helpful to folks that are maybe thinking about that?

• 1:28:07Speaker 00

  I think when you are an in-house operator, there's a lot about your role that you have a little bit less control over, basically. Like, there's, there's just certain things you have to do because it comes with the territory. Whereas when you are a solo operator, you know, running your own business, doing your own thing. You have a lot of freedom to craft your work around only your strengths, only the part that you are really good at, that adds a lot of value for other people, where there's market demand. And so for me, there was a bit of a shift where uh uh when I realized that I could craft my business, my work, around only the part that I'm best at. And that can be a narrow ass slice.

• 1:28:52Speaker 00

  Like, that's actually really, really freeing. And so I would encourage folks to think about what is the thing that you are, you know, extremely good at, that people find super valuable? The part that you love doing most? If you could, you know, not do all the other stuff you don't want to do? Um, and how can you think about doubling down on that?

• 1:29:12Lenny Rachitsky?

  That's such an important point, and that can the the claw tip you shared of how to say no well is such an important ingredient into that because so many things come at you and are interesting and enticing that it's hard to decline, that you realize, what the hell am I doing this? I can actually control where I spend time and why did I say yes to this?

• 1:29:32Speaker 00

  I actually um credit you with helping me come to this realization. Um, I mentioned you on a podcast the other day um about this because do you remember when Maven was uh launching an important feature? I think it was like our marketplace or something? And I'd asked you if you wanted to go on Clubhouse uh to be part of our launch.

• 1:29:56Lenny Rachitsky?

  But I'm sure I said no.

• 1:29:57Speaker 00

  Okay, yeah, you said no, you said no. And and I was like, wow, you know, out of curiosity, what's the thought behind it? And you said, I'm gonna bastardize this, but but you know, you could correct me, but you essentially said, I don't really like doing live um public speaking type things. And I've been fortunate enough to to build a career where um I can write, you know, I do my podcast and kind of work only on the part that I love doing. Um, and so I'm I'm okay saying no to these other, you know, really interesting opportunities. And I remember at that time thinking it was so groundbreaking that like you could say no to something that was legitimately a cool opportunity um and and be really confident about it because it wasn't your core competency.

• 1:30:42Speaker 00

  It wasn't like the thing you are best at. And I've really kept that in mind when opportunities come my way of like, am I excited about this? Is this what I'm really good at? Can I shine in this setting?

• 1:30:54Speaker 00

  Because when you are solo, like you get to choose the settings that you want to be in.

• 1:30:59Lenny Rachitsky?

  That's such a cool story. I don't exactly remember that, but I'm zero first surprise that what I said. And I what I what the way I put it now, when I folks invited me to stuff like this is just, I just find that our why on my time is so not worth doing a talk, doing a fireside thing, doing another podcast. It's just like, if I can spend more time on this newsletter and the podcast, the leverage is so much higher than just doing a talk because that takes so much time. And so, so I just have this like template now that basically says what I sent you. That is, that helps. And that's, but it's tough. It's so hard to say no. It's like, sometimes these opportunities are so interesting. And the person is like, wait, what? Because I don't think the people asking you for stuff know that I'm getting like 10 of them a day. And they're like, oh, he said none of my talk. He doesn't want

• 1:31:44Lenny Rachitsky?

  to be on my podcast. What a jerk. That's what I think. I don't know if that's a big thing. But anyway, okay, that's great. Yes. And I think I just, I just had a post about reaching a million subscribers, a newsletter, and actually have this image of the Ikigai concept, which is exactly what you just described, which is you want to try to find the thing that you love doing, that people value, and that you could make money doing. That's like the dream. And that's exactly what you have done as well. So, thank you for being here, Wes. This, I actually think we delivered on what I thought we wouldn't. I think this is going to be one of the most highest leverage conversations we've had. So, two final questions. Where can folks find your course? I know you also do executive coaching. So where can

• 1:32:27Lenny Rachitsky?

  folks learn more? And final question is just, how can folks be useful to you, Wes?

• 1:32:33Speaker 00

  You can find out more at weskao.com. I link to my course, to my coaching from my main page. I also post on LinkedIn as well. So you can follow me there. And I'm always looking to meet fellow operators who nerd out about communication. So if you put any of these principles into practice, I'd love to hear about it.

• 1:32:53Lenny Rachitsky?

  Awesome. And then we'll do that in the comments. They can DM you. I don't know. What's the best way to reach you on the website or Twitter?

• 1:32:59Speaker 00

  Yeah, a bunch of platforms, website, my email, LinkedIn, DM me. Yeah.

• 1:33:04Lenny Rachitsky?

  There we go. There we go. Wes, thank you so much for being here.

• 1:33:08Speaker 00

  Yeah, thank you so much, Lenny. This is fun.

• 1:33:13Lenny Rachitsky?

  Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.