Wes Kao: How sales-then-logistics framing wins exec buy-in

1. 0:00 – 5:34

   Introduction to Wes Kao

   1. WKWes Kao0:00

      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?"

   2. LRLenny Rachitsky0:22

      You are one of the best teachers of communication I've ever come across.

   3. WKWes Kao0:26

      (clicking)

   4. LRLenny Rachitsky0:26

      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.

   5. WKWes Kao0:34

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

   6. LRLenny Rachitsky0:52

      You have an awesome framework called MOO.

   7. WKWes Kao0:54

      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 gonna be able to anticipate every single objection? No. But can you anticipate the obvious ones? Absolutely.

   8. LRLenny Rachitsky1:18

      (Intro music) Today, my guest is Wes Kao. 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 conversational 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 Pro, Superhuman, Notion, Linear, and Granola. Check it out at lennysnewsletter.com. With that, I bring you Wes Kao. This episode is brought to you by WorkOS. If you're building a SaaS app, at some point, your customers will start asking for enterprise features like SAML authentication and SCIM provisioning. That's where WorkOS comes in, making it fast and painless to add enterprise features to your app. Their APIs are easy to understand so that you can ship quickly and get back to building other features. Today, hundreds of companies are already powered by WorkOS, including ones you probably know, like Vercel, Webflow, and Loom. WorkOS also recently acquired Warrant, the fine-grained authorization service. Warrant's product is based on a groundbreaking authorization system called Zanzibar, which was originally designed for Google to power Google Docs and YouTube. This enables fast authorization checks at enormous scale while maintaining a flexible model that can be adapted to even the most complex use cases. If you're currently looking to build role-based access control or other enterprise features like single sign-on, SCIM, or user management, you should consider WorkOS. It's a drop-in replacement for Auth0 and supports up to one million monthly active users for free. Check it out at workos.com to learn more. That's workos.com. This episode is brought to you by Vanta. When it comes to ensuring your company has top-notch security practices, things get complicated fast. Now you can assess risk, secure the trust of your customers, and automate compliance for SOC 2, ISO 27001, HIPAA, and more with a single platform, Vanta. Vanta's market-leading trust management platform helps you continuously monitor compliance alongside reporting and tracking risks. Plus, you can save hours by completing security questionnaires with Vanta AI. Join thousands of global companies that use Vanta to automate evidence collection, unify risk management, and streamline security reviews. Get $1,000 off Vanta when you go to vanta.com/lenny. That's V-A-N-T-A.com/lenny. Wes, thank you so much for being here and welcome back to the podcast.

   9. WKWes Kao4:36

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

   10. LRLenny Rachitsky4:40

       Very rare honor. Uh, 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. Uh, 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."

   11. WKWes Kao5:07

       Yeah.

   12. LRLenny Rachitsky5:08

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

   13. WKWes Kao5:32

       Absolutely.

2. 5:34 – 6:58

   Working with Wes

   1. WKWes Kao5:34

   2. LRLenny Rachitsky5:34

      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, and these are three different people.

   3. WKWes Kao5:52

      All right.

   4. LRLenny Rachitsky5:54

      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."

   5. WKWes Kao6:07

      Wow. (laughs)

   6. LRLenny Rachitsky6:09

      Okay? Okay, that's one.

   7. WKWes Kao6:09

      All right.

   8. LRLenny Rachitsky6:10

      "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?

   9. WKWes Kao6:46

      Those are really nice things. (laughs)

   10. LRLenny Rachitsky6:49

       Yeah.

   11. WKWes Kao6:49

       That's, that's amazing. I'm... Yeah, thank you so much.

   12. LRLenny Rachitsky6:52

       And these are by people across different companies, so...

   13. WKWes Kao6:54

       Cool.

   14. LRLenny Rachitsky6:54

       So, okay, so that was just to highlight (laughs) how good you are at this stuff.

3. 6:58 – 10:44

   The importance of communication

   1. LRLenny Rachitsky6:58

      And what we're gonna 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?

   2. WKWes Kao7:17

      I often see operators who explain things poorly and then are shocked and horrified when people are confused or, uh, there's skepticism, there's apathy, there's a lot of avoidable questions. And, uh, 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, um, I'm a big proponent of agency and, uh, realizing that we can only control our own behavior, um, 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 this skill of communicating?" And it absolutely is a skill.

   3. LRLenny Rachitsky8:11

      So what I'm hearing is, like, if you are 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, uh, a f- issue with your ability to communicate. It's probably not their, it's their fault.

   4. WKWes Kao8:27

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

   5. LRLenny Rachitsky8:38

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

   6. WKWes Kao8:46

      I think another big one that I teach in my course and really kick off with is, um, 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 wanna shine when they're presenting to senior leadership, but with everyone else, they're kind of calling it in. And I just don't think that you're gonna 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 times a quarter, and that's just not a lot of chance to practice. So, um, 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' time, or your manager's time, or your direct reports' time. So, that's something else that, um, I ask folks to keep in mind.

   7. LRLenny Rachitsky9:39

      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?

   8. WKWes Kao9:53

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

   9. LRLenny Rachitsky10:43

      Awesome.

4. 10:44 – 18:20

   Sales before logistics

   1. LRLenny Rachitsky10:44

      Okay. So I made a list of people's favorite tactics and frameworks and approaches that you've, that you teach, uh, 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, uh, let's just help people get better at these things.

   2. WKWes Kao10:58

      All right. Let's do it.

   3. LRLenny Rachitsky11:00

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

   4. WKWes Kao11:07

      Yes. So, uh, 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, what, you know, 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," uh, 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, uh, and to agree to do it, a- 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, um, you will likely, uh, get a slow response or just no response, right? We've all put a Slack message in a channel and got crickets and tumbleweed.Um, 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 the logistics tends to be a lot more effective.

   5. LRLenny Rachitsky12:22

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

   6. WKWes Kao12:26

      Yeah. So one of my clients, uh, is a head of operations, and she was trying to get the rest of her, uh, 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 gonna be motivating, it was gonna be, uh, it was gonna shine a light on folks. And she led with the logistics of which document to send, you know, to, 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 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, we're all supposed to do now. Like, yay, right? Um, and so she, she wasn't really getting a response, and that's because she dove straight into logistics, whereas what she could have done is start by selling folks, selling the other, uh, 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, uh, for them to feel motivated and to feel like the rest of the company really sees them and understands what they're doing, uh, and this is all, uh, something that, that, uh, is gonna 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 and fill it out this way and by this date," et cetera, et cetera.

   7. LRLenny Rachitsky13:59

      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 have time for all this context and background." Any advice on when to s- s- 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?

   8. WKWes Kao14:20

      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 (laughs) me about it again, like, I've 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 in 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. I'm talking about one to two minutes, even a couple sentences, and then transitioning into the main thing you want to talk about. So I am a huge proponent of doing that and, uh, 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.

   9. LRLenny Rachitsky15:24

      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.

   10. WKWes Kao15:30

       Mm-hmm.

   11. LRLenny Rachitsky15:30

       It's just a reminder, "Here's- here's why we think this is important." And I think that's such a good point, 'cause- 'cause a lot of times, it's like, uh, like a leader's looking at this thing you're asking them to do and you're like- they're like, "Why are we even- why- why am I spending time on this?" And just a reminder of like, "Okay, I see. I forgot this was gonna be- this is part of our strategy. This is a big- this has this much impact potential."

   12. WKWes Kao15:49

       Mm-hmm.

   13. LRLenny Rachitsky15:50

       And- or, "Here's how it could help our team be more efficient," so...

   14. WKWes Kao15:52

       Yeah.

   15. LRLenny Rachitsky15:52

       I like that.

   16. WKWes Kao15:52

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

   17. LRLenny Rachitsky15:54

       Mm. Is there- is there like a, I don't know, structure to this? Is it just like, why? Like, is there 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?

   18. WKWes Kao16:09

       Yeah. I think, um, 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 sentences. And then I also like asking, uh, or stating what I need from the other person upfront. So saying, you know, "Hey, we're here today because, uh, two weeks ago, we were reviewing the product flow and realized that there were a couple parts that were kind of confusing, so I took a stab at fixing those areas, rewriting the microcopy, and I want to present them to you today, see if you agree with these changes, and then we're gonna roll them out. Um, what I'm looking for from you is feedback on the changes and if you agree." So like, that was like 15 seconds, right? 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 certain kind of feedback.

   19. LRLenny Rachitsky16:59

       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 work- 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, uh, you need to kind of break through.

   20. WKWes Kao17:25

       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, uh, a 15-slide deck and execs would do that, and I'd be like, "Whoa, whoa, whoa." Like, "I have a- I have a whole sequence. I have a whole order." You know? And sometimes they would- they would give me buy in or make the decision by slide four, you know? And I'd be like, "Okay. Well," you know, "slide 13, I 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, okay? If my exec has already agreed, um, take the win and- and keep it moving, move on.

   21. LRLenny Rachitsky18:13

       Yeah. What's that quote? Like, if you've- if you've sold them, stop talking.

   22. WKWes Kao18:16

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

5. 18:20 – 24:31

   Being concise

   1. WKWes Kao18:20

   2. LRLenny Rachitsky18:20

      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?

   3. WKWes Kao18:30

      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 could have a 300-word memo that's meandering and long-winded, and 1,000-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. Cut to the chase. Main point, you know, put the main point at the top. Bottom line up 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 un-bury the lede unless you know what the lede is. And so, that, I found, is the bottleneck 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? Where like, you know exactly when people are gonna laugh, you know when they're gonna gasp or hold their breath, right? 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, uh, in a quick turnaround time, telling someone else about it, telling our team about it. And so, you are basically asking your brain to do a lot of different processes, uh, 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? And then trying to be, um, 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, uh, bring the conversation back to the most important points, uh, at- at being able to stay flexible, but also firm. Yeah, and- and- and preparation, I don't mean spending hours and hours preparing for a weekly meeting. Um, even a couple minutes really makes a huge difference. Most of us are so 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- are in that mental state. Um, 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 gonna go in there so much more focused and so much more able to be concise.

   4. LRLenny Rachitsky21:51

      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- why am I in this meeting? What do I- what do I want to get out of it? I- instead of, in the meeting, like, figuring it all out as you go, which, to your point, you're just gonna ramble and be like, "Oh, okay, here's what I actually want to say."

   5. WKWes Kao22:10

      Yeah. And what- what might I want to share in the meeting, too?

   6. LRLenny Rachitsky22:13

      Mm.

   7. WKWes Kao22:13

      You know, especially for more introverted folks, sometimes you need to decide beforehand that you wanna speak, and you wanna make sure you get a certain point across. So, even deciding that beforehand makes a huge difference.

   8. LRLenny Rachitsky22:25

      Yeah. I have found this, uh, 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. Uh, in writing, any- is there, like, any tactics you can share for someone to be a little more concise?

   9. WKWes Kao22:50

      I think the main tactic is to remind yourself to be concise.

   10. LRLenny Rachitsky22:54

       Hmm. (laughs)

   11. WKWes Kao22:55

       Um, and usually when I do that, I end up trimming 20%, at least, of what I wrote, tidying up some sentences. I also ask myself, how might I be, um, adding cognitive load to whatever it is that I'm saying? So, you know, is there a- 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, 'cause like, that's secondary." You know? And maybe you have your primary message in Slack, and then within the thread, add, you know, some of the secondary stuff, right? So, I find that most of us, it's- it's reminding yourself to be concise, and once you think of it, your brain naturally will see places where you can trim.

   12. LRLenny Rachitsky23:49

       There's a layer of advice under this that you're not saying that I'm gonna say, which is, actually look at the thing you wrote at least once before you share it. Because I- I used to be really bad at this. I'd just like, "Okay, I don't have time. I wrote this doc. Send it. Get feedback." All right, ... amount of time till I read this email, and I find just forcing yourself to look at it solves so much of this.

   13. WKWes Kao24:10

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

6. 24:31 – 27:30

   Books to help you become a better writer

   1. WKWes Kao24:31

   2. LRLenny Rachitsky24:31

      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 'cause people always ask me, "How did you, how did you learn to write?" I'm like, "I am not a writer. I don't know what I'm doing." But two books really helped me, uh, write more effectively, and one is specifically to help you write, uh, more concisely called On Writing Well.

   3. WKWes Kao24:50

      Mm-hmm. Mm-hmm.

   4. LRLenny Rachitsky24:50

      And I don't know if you've read that.

   5. WKWes Kao24:51

      Yeah.

   6. LRLenny Rachitsky24:52

      Okay, and it's basically like chapter after chapter of here's what you can cut, and he- 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 has, has changed. It's exactly the same message, and even is better with like 40% of the words cut."

   7. WKWes Kao25:12

      Is this by Sol Stein or s- or another author?

   8. LRLenny Rachitsky25:15

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

   9. WKWes Kao25:19

      Okay. Yeah. There's-

   10. LRLenny Rachitsky25:20

       But-

   11. WKWes Kao25:20

       There's a, there's a writing book by, um, Sol Stein that I absolutely love.

   12. LRLenny Rachitsky25:24

       Okay.

   13. WKWes Kao25:24

       And I feel like it might be called On Writing Well, but there also... I could see there being multiple books called On Writing Well. Um-

   14. LRLenny Rachitsky25:29

       There's also Writing W- Well, I think by Stephen King. That's like another one that people love.

   15. WKWes Kao25:33

       Mm-hmm. Mm-hmm.

   16. LRLenny Rachitsky25:33

       But there... On Writing Well is the one I really loved.

   17. WKWes Kao25:34

       Mm-hmm.

   18. LRLenny Rachitsky25:35

       'Cause it's very, like, tactical.

   19. WKWes Kao25:36

       Um, going back to something that, that you were saying earlier with, um-

   20. LRLenny Rachitsky25:39

       Mm-hmm.

   21. WKWes Kao25:40

       ... re-reading w- what you wrote, um, 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've included, there's gonna 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 o- who are all the people who are gonna come in contact with this message, who are going to refer to it and use it? And if I just take 30 more seconds to make sure that it's clean, how much can I unblock from their work?

   22. LRLenny Rachitsky26:34

       That's such a good point. I like that. (laughs) I love that term blast radius. It's such a good point, just like there's so much negative leverage in writing inefficiently and in- and 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 Zissner. There's Stein on Writing by Sol Stein-

   23. WKWes Kao27:02

       Ooh.

   24. LRLenny Rachitsky27:02

       ... which is what you said, you were talking about, and then Stephen King has a book called On Writing. (laughs) And I'm like-

   25. WKWes Kao27:08

       Yeah.

   26. LRLenny Rachitsky27:09

       ... "Yeah, I really can't see-"

   27. WKWes Kao27:10

       (laughs) Common title.

   28. LRLenny Rachitsky27:12

       ... a change. Not, uh, not ideal for SEO. But On Writing Well is the one that I love by William Zissner.

   29. WKWes Kao27:16

       Mm-hmm.

   30. LRLenny Rachitsky27:16

       There's also one called A Series of Sin- Of Short Sentences if you haven't seen that one. It's a really good wr- read too.
7. 27:30 – 32:05

   Signposting and formatting

   1. LRLenny Rachitsky27:30

      There's another framework/tactic that I've heard you recommend. It's called signposting. What is signposting?

   2. WKWes Kao27:38

      Signposting is using certain words, phrases, formatting, and an overall structure in your writing that helps guide your reader and, uh, signals what is coming in the rest of the post. So, this is especially helpful if you have a long memo. Uh, it adds structure to where we're going and, uh, what certain sections or 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 zoom to as a next step. Even first, second, third, kicking off a paragraph with that. Um, 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."

   3. LRLenny Rachitsky28:41

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

   4. WKWes Kao28:46

      Yeah. Gift. You wrote it.

   5. LRLenny Rachitsky28:48

      Gift, yeah, for like r- copywriting, and I l- I- these are basically power words for helping your brain see the structure and-

   6. WKWes Kao28:55

      Mm-hmm.

   7. LRLenny Rachitsky28:55

      ... get to the thing you wanna pay attention to, so I'll read back them, words you just used. For example, because, as a next step, and then first, second, third.

   8. WKWes Kao29:05

      Yeah. Yeah, you can use signposting, um, 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 wanna 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.

   9. LRLenny Rachitsky29:41

      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?

   10. WKWes Kao29:52

       I really hate excessive formatting. So, you know, I've seen memos where 30% of the note was bolded.

   11. LRLenny Rachitsky30:03

       (laughs)

   12. WKWes Kao30:03

       And that just negates the entire point of bolding 'cause if everything is bolded then none o- 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, uh, overuse bullets and sentence fragments, phrases in bullets, when they should use complete sentences that actually show the connective tissue between ideas, that show the logical flow of what it is that you're saying.And, you know, it's- it's- it feels faster and more concise to put bullets in- in 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- 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, 'cause 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. So that's like ............................ a great litmus test of, like, was that- w- was that idea fully thought out? 'Cause if it was, you should be able to really quickly turn it into a complete sente- uh, 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 and more skimmable. I'm just gonna throw a bunch of formatting and bullets, and turn, you know, turn everything into bullets, and- and it's not quite that easy of a solution.

   13. LRLenny Rachitsky31:40

       This is very much along the lines of the whole Amazon six-page memo where Jeff Bezos just kind of realized if he can't write it out as a long memo and explain yourself in prose, you- you don't actually know what you're saying.

   14. WKWes Kao31:53

       Mm-hmm.

   15. LRLenny Rachitsky31:53

       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.

   16. WKWes Kao32:00

       Mm-hmm.

   17. LRLenny Rachitsky32:01

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

8. 32:05 – 40:41

   How to develop and practice your communication skills

   1. LRLenny Rachitsky32:05

      a fragment of a sentence?

   2. WKWes Kao32:06

      Mm-hmm.

   3. LRLenny Rachitsky32:07

      I'm thinking about, as a listener, being like, okay, how do I actually get better at this? So maybe ta- let's take a tangent. I know that you hold- 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 do you ho- what's, like, a good way to start practicing these skills and know if what you're writing is getting better or as good? Is it, like, find a mentor, find someone that you think is a great writer and have them review stuff? Any tips there?

   4. WKWes Kao32:34

      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, um, 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 touch points of back and forth, does that shrink to two to three? Not every point of friction is gonna be avoidable, but a lot of it is if you get better at communicating. So I like watching for the reaction and, uh, how quickly 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, 'cause 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.

   5. LRLenny Rachitsky33:36

      So the advice here is just, uh, see how well your writing/meeting/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, eh, I don't really understand. There's, like, this spectrum of response, and what I'm hearing is just pay attention to if the- the speed to getting what you want is increasing in general.

   6. WKWes Kao33:59

      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, um, to get through to people. So, um, I would approach it with a- 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? Um, so yeah, so I- I really think it's about practicing. Um, 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, um, get overwhelmed, when you- when you're learning a new skill. And, uh, 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, um, and then getting, uh, 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, and, um, I always remind folks that you are building a new habit here, uh, and, you know, take it- be patient with yourself, take it step by step.

   7. LRLenny Rachitsky35:31

      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, uh, 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 had 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 in thinking, and just spending more time on documents, on 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 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, uh, I don't like this idea, and then it's like it all falls apart. So I guess any reactions to that?

   8. WKWes Kao36:29

      Yeah. All these little things compound and make a big difference. I...... 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 it. 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, 'cause every, you know, any piece of that process you thought wasn't, you know, wasn't worth, uh, spending time on and now this is just the, the quality of your work, and it's not as good as it could be. So, yes, like these might seem minor, but A, it compounds. Um, 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. 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, then we can do the hard work of getting better at those things.

   9. LRLenny Rachitsky38:42

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

   10. WKWes Kao38:51

       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, it, it is a little bit more time in the moment, but reaps a lot of benefits down the line.

   11. LRLenny Rachitsky39:25

       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, to 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, 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/lenny.

9. 40:41 – 42:23

   Slack communication

   1. LRLenny Rachitsky40:42

      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, the Slack channel at the company you worked at for old posts from Wes for inspiration for what to ask you, and she said zero- 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.

   2. WKWes Kao41:11

      Hmm. 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, to what I said earlier about, uh, watching for what's working, you know? There's, there's... Momentum is, is really encouraging.

   3. LRLenny Rachitsky42:01

      Hmm. And I, and I totally feel that if it starts, like if you start getting the things you want, that feels great. (laughs)

   4. WKWes Kao42:06

      Yeah, yeah, more.

   5. LRLenny Rachitsky42:07

      I feel like, "Okay, cool, there's a 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 on email.

   6. WKWes Kao42:15

      Mm-hmm. Very doable.

   7. LRLenny Rachitsky42:16

      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

10. 42:23 – 50:17

    Confidence in communication

    1. LRLenny Rachitsky42:23

       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 speak with leader-How, like, confident should I be about this is the answer, versus, like, "Here's a bunch of ideas. What do you think?" Where, what's your advice there?

    2. WKWes Kao42:41

       I find that people tend to naturally be on the spectrum, uh, 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. 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, y- you know, this way, because the rest of your team is- 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, uh, with your level of confidence. So, so that's for people who are overconfident. Um, it's equally a problem if you're under-confident. So I have some clients who, you know, their CEO asked them to, uh, share some recommendations with another team 'cause, you know, they've run something before. And so they share all this amazing information, 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 wanna 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 if..." You know? Like, we might lose a lot of money and time if you- if we don't take this idea, right? So again, speaking accurately is, um, so, so important.

    3. LRLenny Rachitsky44:56

       Is the simple way to think about then, kind of the- the right balances, 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?

    4. WKWes Kao45:11

       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, uh, with data if you have it. You know, you're n- not every situation you're gonna 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 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.

    5. LRLenny Rachitsky46:06

       Advice I got that really helped here for me was, uh, to try to not be super ... m- try not to be biased with how you frame everything. You have your, uh, 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, okay. Well, I can't really trust this 'cause I see you're just like, you clearly have an agenda." So it's a little bit like, have an agenda and a POV but be clear about what is actually true. Be accurate.

    6. WKWes Kao46:36

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

    7. LRLenny Rachitsky46:45

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

    8. WKWes Kao46:49

       Yeah. So in my course, I talk about not being a single-minded martyr. So 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, um, 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, uh, a recommendation she was making. So she, uh, 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 wanna 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 companywide goal is retention that year, that their biggest challenges and areas of opportunity were in retention, not necessarily in growth. And once she zoomed out and realized this, she was able to put her recommendation in context and realized 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 wanna work on it." You know, before that was- that was kind of her narrative. But once she zoomed out and- and realized she was being a single-minded martyr, um, 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 gonna keep advocating for it until I get a yes." Whereas really sometimes the best decision for the company is, "Not right now." 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, uh, 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, a more right-sized way of still, you know, advocating for your ideas, but, um, doing it with a bit more equanimity.

    9. LRLenny Rachitsky49:26

       And also just, uh, 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, uh, or revenue." And so that's just, I think a sub-goal, a sub-tactic there is just whenever you're pitching something, connect that to the goal of the person you're pitching to-

    10. WKWes Kao49:55

        Mm-hmm.

    11. LRLenny Rachitsky49:55

        ... so that they're like, "Oh, I see how this is gonna help me. That's great. Let's do it." Great advice. Uh, and I think this is something a lot of people run into is just, "Why aren't they listening to me? Why don't they want ... That's such a good idea."

    12. WKWes Kao50:06

        Mm-hmm.

    13. LRLenny Rachitsky50:07

        "They hate me. It's something ... Oh, I bet they hate me. They don't trust me." When it's just like, okay, this isn't a priority right now. Let's come back to it another time.

    14. WKWes Kao50:16

        Mm-hmm.

    15. LRLenny Rachitsky50:16

        Okay.

11. 50:17 – 54:00

    The MOO framework

    1. LRLenny Rachitsky50:17

       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 is MOO? What does it stand for, and what is it all about?

    2. WKWes Kao50:26

       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, we're on our back foot. When really, if you thought for even two minutes about, "What are obvious objections that I'm 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. Um, and so this is where knowing your own argument in and out, including counterarguments, becomes so important. So, knowing your counterarguments 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.

    3. LRLenny Rachitsky51:22

       When you hear you talk about this, it's like, "Obviously I should do this," but nobody ... Like very few people actually do this, like actually spend a couple minutes, "Okay, here's what I'm gonna pitch."

    4. WKWes Kao51:31

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

    5. LRLenny Rachitsky51:37

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

    6. WKWes Kao51:43

       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 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, this might be something we, we include at the end as 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.

    7. LRLenny Rachitsky52:49

       I think what's great ab- 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's probably gonna be this. Will it drive enough impact for the business? Oh, that's a great point. (laughs) Maybe I should not pitch this right now."

    8. WKWes Kao53:10

       Yeah. It definitely helps shape your own thinking. Um, I think communication and thinking are so much more interrelated than we think. You know, I think people think there's the thinking as phase one and then communicating the thinking, and the reality is a lot more intertwined. Uh, and, 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.

    9. LRLenny Rachitsky53:45

       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." That's ex- I know exactly that feeling.

12. 54:00 – 57:36

    Staying calm in high-stakes conversations

    1. WKWes Kao54:00

       Mm-hmm.

    2. LRLenny Rachitsky54:00

       Okay. So there's a couple more things that people have shared, uh, 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 if you disagree with someone. Any advice on that? Feels like you, you're really good at this.

    3. WKWes Kao54:18

       I think one thing that, um, 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 re- uh, area, just saying, "I'll get back to you," is sometimes a missed opportunity. 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 it up and I'll get 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, is now, you know, a bigger part of our business," et- et cetera. "Are you wondering if we are investing in mobile appropriately?" Or like, "Where's that," you know, "Where's that commission coming from," basically. Right? 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, uh, 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. Um, 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, um, 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.

    4. LRLenny Rachitsky56:48

       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, uh, 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 can 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-

    5. WKWes Kao57:28

       Yeah, I love that.

    6. LRLenny Rachitsky57:29

       ... like ref- reflect back their question, just like better understand what they're looking for.

    7. WKWes Kao57:32

       Mm-hmm. Mm-hmm.

    8. LRLenny Rachitsky57:34

       Awesome. Okay. Let's

13. 57:36 – 58:53

    Which tactic to start with

    1. LRLenny Rachitsky57:36

       go back to what I said we'd 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 to logistics and giving people the why. Signposting, using specific words to help people guide the, the dock 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, 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.

    2. WKWes Kao58:25

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

    3. LRLenny Rachitsky58:37

       Sweet. That's such an easy one to remember, just MOO. Okay, so stick a Post-it somewhere. When you're about to share something in Slack and ask someone for something, present at a meeting, send a strategy, 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.

14. 58:53 – 1:04:53

    Effective tactics for managing up

    1. LRLenny Rachitsky58:53

       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 around managing up. One of my most popular posts in the early days was advice for managing up and just how important it is. Uh, 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 under-appreciate how important it is to manage up, manage your manager, let's say?

    2. WKWes Kao59:18

       One of the most, uh, 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, uh, 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 realize that many senior people, uh, 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, 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 are gonna be dealing with more ambiguity, uh, and you're gonna 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're about to do and, uh, make sure that they're aligned. And so for me, realizing that managing up is something that, uh, is, is ongoing and that it l- it shifts and evolves and looks different, uh, as you go in your career, um, that was a, a big unlock for me.

    3. LRLenny Rachitsky1:00:44

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

    4. WKWes Kao1:00:54

       The biggest one is to share your point of view.So this, you know, some people are surprised by because they think I'm gonna 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, uh, 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 a solution, and then tell you what to do. Whereas if you instead said, "Hey, manager, here's what I think we should do. 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, uh, the amount of mental lift that they have t- they have to, uh, put forth. And so, sharing your point of view more readily, backing it up with evidence, that's an, 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. Um, you are actively looking around the corner, trying to solve problems, forming hypotheses in your mind, observing and noticing things. 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 could do.

    5. LRLenny Rachitsky1:03:04

       I was gonna ex- 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-

    6. WKWes Kao1:03:11

       Mm-hmm.

    7. LRLenny Rachitsky1:03:11

       ... 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," 'cause that's what... Like, if you, 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 exact- 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, 'cause that's putting your reputation on the line. So there's, like, a second order effect of it makes you actually spend more time on the thing and be clear about why you think this is a good idea and do more research. So, a lot of wins here.

    8. WKWes Kao1:03:53

       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, 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, uh, their junior people have, uh, often close contact with customers, with support tickets, with, you know, cleaning data, with, you know, a bunch of things where the manager would love to hear insights from that.

    9. LRLenny Rachitsky1:04:30

       And if you're finding not suc- if you're not having success with this, uh, if you're, if you're, like, hearing this and being like, "But it never worked 'cause 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.

    10. WKWes Kao1:04:51

        Mm-hmm.

15. 1:04:53 – 1:09:39

    Giving constructive feedback: strategy, not self-expression

    1. WKWes Kao1:04:53

    2. LRLenny Rachitsky1:04:53

       Okay. Let's see. We have a couple more really cool, uh, 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?

    3. WKWes Kao1:05:05

       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, you know, to tell them this feedback. And it would inevitably turn into a venting session, where I was, in the name of sharing the impact of what they did, uh, 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 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've 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. 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.

    4. LRLenny Rachitsky1:06:46

       Someone close to me in my life, uh, has very, uh, needs, is, is some- is working on this skill, which is, like there's just like a, "I want people to know how mess- they messed up. Uh, justice, I need this to be fair." And there's like a, 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 I, that's basically what you're saying, right, is like focus on the outcome you want to achieve, not like, uh, something that's useful, like some- something that will make you just feel better.

    5. WKWes Kao1:07:23

       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 is 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?" (laughs) Like, right? Like, and then, and then you're off, right? So yeah, getting that, getting that energy out I would say is 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.

    6. LRLenny Rachitsky1:08:23

       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 you'll be like, "Ugh, but I really want them to know this."

    7. WKWes Kao1:08:42

       There's a 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 are used to and certain ways of responding, and if that's, if you, if you believe that there is, uh, untapped upside, that like what, whatever you are at is kind of a local maximum, and that there's m- 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.

    8. LRLenny Rachitsky1:09:19

       This, um, resonates with Tobi Lutke when he was 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.

16. 1:09:39 – 1:16:36

    Delegating effectively while maintaining high standards

    1. LRLenny Rachitsky1:09:39

       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 gonna be as great. They want to just, "I just want this to be really good. I don't trust that it's gonna go as well as... I, if I did it my- my way, it would be great." So just advice on how to delegate effectively while maintaining high standards.

    2. WKWes Kao1:10:04

       Yeah. I have a framework called CEDAF, C-E-D-A-F.

    3. LRLenny Rachitsky1:10:08

       (laughs) Mm-hmm. I love all these acronyms. These are awesome.

    4. WKWes Kao1:10:09

       It's kind of like CEDAR but with an F at the end.

    5. LRLenny Rachitsky1:10:11

       Mm, CDAF.

    6. WKWes Kao1:10:11

       I need acronyms for myself. Like, all of these-

    7. LRLenny Rachitsky1:10:14

       (laughs)

    8. WKWes Kao1:10:14

       ... are, are really reminders for myself, 'cause I need a short way, uh, to remind myself. So, um, CEDAF stands for, the C is comprehension. So 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? Um, 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. Um, 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, and be excited about how this fits in to everything. So, E is for excitement. 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 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 when I'm really looking for that." Okay, perfect. Just tell them, you know? "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? 'Cause 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," or, "Oh, yeah, I, I didn't even really explain that well. 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 shortening 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, 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 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 wanna 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 CEDAF 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, uh, priorities this quarter, or to something else, right? So, um, it's a nice mental checklist.

    9. LRLenny Rachitsky1:13:49

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

    10. WKWes Kao1:13:56

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

    11. LRLenny Rachitsky1:13:59

        Upfront to save you tons of time later. Okay. Uh, okay, so as you describe this, I don't know if you're realizing this, but you're basically descri- 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. That's like exactly what you ... Like, it's basically, you're gonna 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, is, am I communicating this well? Comprehension. So CEDAF. Comprehension, is comprehension again just like, can I make this clear? Is that the way to think about that?

    12. WKWes Kao1:14:40

        Yeah. Can I make this clear? Does this person have everything they need to be able to accomplish-

    13. LRLenny Rachitsky1:14:45

        Okay.

    14. WKWes Kao1:14:45

        ... what I am asking them to do? Mm-hmm.

    15. LRLenny Rachitsky1:14:47

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

    16. WKWes Kao1:15:01

        Ooh.

    17. LRLenny Rachitsky1:15:01

        ... it does it better.

    18. WKWes Kao1:15:01

        Very interesting. Yeah. (laughs)

    19. LRLenny Rachitsky1:15:03

        It takes it more seriously. That's just so weird, right? It's like, I have a post about this and that's one other piece of advice, just to tell it why this is important. Okay. And 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.

    20. WKWes Kao1:15:16

        That, that is extreme.

    21. LRLenny Rachitsky1:15:17

        Okay.

    22. WKWes Kao1:15:17

        Hoo.

    23. LRLenny Rachitsky1:15:18

        It's ex- it's wild. Okay, so CEDAF. Comprehension, excited, de- uh, de-risk, think about ways you're g- you can de-risk, which is MOO, basically. What's the most-

    24. WKWes Kao1:15:27

        Mm-hmm.

    25. LRLenny Rachitsky1:15:27

        It's like a similar concept.

    26. WKWes Kao1:15:28

        Mm-hmm.

    27. LRLenny Rachitsky1:15:28

        Just like, think ahead to what wo- might go wrong. Uh, make sure you're aligned, which is, uh, quite important in the AI space. (laughs) Make sure you're aligned. And feedback. Get a quick feedback cycle. And it's interesting with, like, DeepResearch or some of these AI tools now, it's like, "I'm off for half an hour. See ya." And I imagine more and more of them will check in with you as it's going and ask you questions. I've, I used DeepResearch recently and it's really good at just like, "Okay, I'm gonna have five questions for you before I go off and do this work, just to clarify what you want."

    28. WKWes Kao1:15:57

        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 the, and then sometimes I'm like, "Do the whole thing. Just stop trying to conserve energy and just do th- I want you to do the whole thing." You know? Uh, but it, that's what it's doing. It's, it's breaking it into smaller chunks to de-risk that, you know, it's gonna use all this bandwidth to process this thing, and I'm gonna say, "Oh, that's not what I was looking for."

17. 1:16:36 – 1:19:59

    The swipe file: collecting inspiration for better communication

    1. WKWes Kao1:16:36

    2. LRLenny Rachitsky1:16:36

       I wanna come back to AI real quick, but, uh, 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 gonna find really valuable. Planting a seed. Okay, uh, before we get back to AI, you have this other concept that I love that I actually t- 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 it help you with? Why should people be doing this?

Episode duration: 1:33:38