Lenny's Podcast Transcripts

Transcript

Wes Kao[00:00:00)]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?

Lenny Rachitsky[00:00:22)]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?

Wes Kao[00:00:35)]I think the blast radius of a poorly written memo is way bigger than most people think. If you are 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

You have an awesome framework called MOO. Wes Kao[00:00:54)]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'm 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. Lenny Rachitsky[00:01:22)]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 conversation with Wes by George Bernard Shaw, "The single biggest problem in communication is the illusion that it has taken place." (00:01:51): By the end of this podcast if you listen to what Wes suggests, you'll 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,

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million monthly active users for free. Check it out at workos.com to learn more. That's workos.com.[00:03:36)]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. Wes Kao[00:04:36)]Thanks,

Lenny. I'm very honored to be a second-time guest. Lenny Rachitsky[00:04:40)]Very rare honor. No pressure, but I think this is going to 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 how high leverage the skill of communication is to product leaders, to leaders, just to 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. 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 communication, so I'm really excited to have you here and to help people become better communicators,

Absolutely. Lenny Rachitsky[00:05:34)]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?"

All right. Lenny Rachitsky[00:05:51)]And these are three different people. Okay, so first, "Wes single handedly raised the quality of the entire company's writing by like two X across the board. I always say the best writing course I ever took was working with Wes for a year."

Great. Lenny Rachitsky[00:06:10)]"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 a reasoning with every proposal in 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. Wes Kao[00:06:46)]Those are really nice things. That's amazing. Yeah,

thank you so much. Lenny Rachitsky[00:06:52)]And these are people across different companies,

Cool. Lenny Rachitsky[00:06:55)]Okay, so that was just to highlight of 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?

Wes Kao[00:07:17)]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. 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. Lenny Rachitsky[00:08:11)]So what I'm hearing is 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. Wes Kao[00:08:28)]Yeah, I would say so. You can't solve everything with improving your communication,

but you can increase the likelihood of getting what you want. Lenny Rachitsky[00:08:39)]Cool. Okay. Anything else along these lines of just things that are important to understand just broadly around communication, executive communication?

Wes Kao[00:08:46)]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. 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 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 I ask to keep in mind. Lenny Rachitsky[00:09:39)]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. 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?

Wes Kao[00:09:53)]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, 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 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 moving to the next step, whatever that might be,

communication is really in service of that end goal. Lenny Rachitsky[00:10:43)]Awesome. Okay. So I made a list of people's favorite tactics and frameworks and approaches that you teach,

and talking to folks that you've taught and folks that you've worked with. So I'm just going to go through a bunch and let's just help people get better at these things. Wes Kao[00:10:58)]All right,

let's do it. Lenny Rachitsky[00:11:00)]Okay. So the first is something you call sales, then logistics. What is that about?

Wes Kao[00:11:07)]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 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 than 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. And only then after they have bought in,

does it make sense to share the logistics.[00:11:57)]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 the logistics tends to be a lot more effective. Lenny Rachitsky[00:12:22)]Is there an example of that that might help illustrate that point or that approach?

Wes Kao[00:12:27)]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, 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 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.[00:13:20)]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 and fill it out this way and by this date," et cetera,

et cetera. Lenny Rachitsky[00:14:00)]I know that execs often want the opposite where they're just like, "Okay, I know, 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?

Wes Kao[00:14:20)]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 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 in a cold start and not kind of go two steps back one step forward.[00:14:55)]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'm a huge proponent of doing that and basically reminding people, why are we doing this? Why are we here today? Why does this matter?

And then getting into the meat. Lenny Rachitsky[00:15:24)]I love that. So basically 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 why we think this is important." And I think that's such a good point because a lot of times it's like a leader is looking at this thing you're asking them to do and 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 a part of our strategy, this has this much impact potential or here's how it could help our team be more efficient."

Wes Kao[00:15:52)]Yeah. And you can really do that in like 30

seconds. Lenny Rachitsky[00:15:56)]Is there like a, I don't know, structure to this? Is it just like why? 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." Starting like that? Anything along those lines?

Wes Kao[00:16:09)]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, "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 microcopy, 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?

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. Lenny Rachitsky[00:17:01)]I would love to hear it that way. I think there's like an implication here that maybe is worth sharing of just, a lot of this is about 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. 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. Wes Kao[00:17:25)]Yeah. So I call it the yes, yes, yes, next, next, next mindset where 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 a whole sequence, I have a whole order, you know? And sometimes they would give me buy 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 great graph I put together." Right? And what was really helpful for me was realizing that I should take the win. Okay, if five seconds already agreed, take the win and keep it moving,

move on. Lenny Rachitsky[00:18:13)]Yeah. What's that quote like? "If you've sold them, stop talking."

Wes Kao[00:18:16)]Right. Yes. Yeah,

you might talk them out of agreeing. Lenny Rachitsky[00:18:20)]Yeah. Okay. You mentioned being concise. Let's talk about that. You have some really good advice on just how to effectively be concise and not too concise. What's your advice there?

Wes Kao[00:18:31)]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 not equating concision with briefness I think is a really big one to understand.[00:19:05)]The second thing is a lot of advice about being concise, I think misses an important point. So we've all heard, "Don't bury the lead, cut to the chase." Main point, 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 can't unbury the lead unless you know what the lead is. And so that I found is the bottleneck to being concise. It's actually not really being clear of what you are thinking,

that's what's leading to being long-winded.[00:19:49)]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 going to laugh, you know when they're going to gasp or hold their breath, right? And why are you so good at telling that story and why are you so concise about it? Because you've told it a bunch of times, 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 are 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.[00:20:39)]And then trying to say something cohesive that makes sense, right? 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 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.[00:21:25)]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 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. Lenny Rachitsky[00:21:51)]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, actually think about why am I in this meeting? What do I want to get out of it? Instead of in the meeting figuring out a lot as you go, which to your point, you're just going to ramble and be like, "Oh, okay, here's what I actually want to say."

Wes Kao[00:22:10)]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. Lenny Rachitsky[00:22:25)]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?

Wes Kao[00:22:50)]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 is there a tighter, clearer, cleaner way that I can ask what I'm asking or present the information I'm presenting or 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 could trim this entire paragraph because that's secondary." And maybe you have your primary message in Slack, and then within the thread add some of the secondary stuff, right? So 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 trim. Lenny Rachitsky[00:23:50)]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. Lenny Rachitsky[00:24:00)]... really bad at this. I just like, "Okay, I don't have time. We wrote this doc, send it, get feedback. All right. Send this email. I don't have time to read this email."

And I find just forcing yourself to look at it solves so much of this. Wes Kao[00:24:10)]Oh, yes, yes, definitely. I was assuming before doing that, but you're right, some people might not be. And yes, definitely reading your own message first is huge. And yeah,

I find that even doing that you can often spot a lot of low-hanging fruit. Lenny Rachitsky[00:24:31)]Right. You'll find the typos and grammar issues and you'll be like, "Oh, I don't need this word." Along those lines, let me share two books. People always ask me, "How did you learn to write?" I'm like, "I'm not a writer, I don't know what I'm doing."

Yeah. Lenny Rachitsky[00:24:52)]Okay. And it's basically 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 screenshots of essays that students have written in his class and he's like, "Look at all those words you cut and nothing has changed. It's exactly the same message and even is better with 40% of the words cut."

Wes Kao[00:25:12)]Is this by Sol Stein or another author?

I don't have it... It's somewhere in my bookshelf. So we'll look it up. Wes Kao[00:25:19)]Yeah, there's a writing book by Sol Stein that I absolutely love. And I feel like it might be called On Writing Well,

but then also I could see there being multiple books called On Writing Well. Lenny Rachitsky[00:25:29)]There's also Writing Well I think by Stephen King, that's another one that people love,

but there On Writing Well is the one I really loved because it's very tactical. Wes Kao[00:25:37)]Going back to something that you were saying earlier with rereading what you wrote, I think the blast radius of a poorly written memo is way bigger than most people think. So 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. All 15 of these people are reading this being like, "Okay, what do I do with this?" (00:26:05): Whereas if you had just taken another look at it, those 15 people would be off to the races. They would've read your message and then known exactly what to do next or what their part was or what you were looking for from them. So I think about that a lot too. It's not just me writing this and sending it off. It's, "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? And if I just take 30 more seconds to make sure that it's clean, how much can I unblock from their work?"

Lenny Rachitsky[00:26:34)]That's such a good point. I like that, I love that term blast radius. It's such a good point. Just like there's so much negative leverage in writing inefficiently and inconcisely. If you spend like... Inconcisely? I don't know the word is there, but if you just spend 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 Zinsser. There's Stein On Writing by Sol Stein,

Yeah. Common title. Lenny Rachitsky[00:27:12)]Not ideal for SEO but On Writing Well is the one that I love by William Zinsser. There's also one called A Series Of Short Sentences if you haven't seen that one. It's a really good rate too. It's just how to write short sentences and just the power of just keeping sentences short,

which I struggle with. Wes Kao[00:27:27)]Yeah. Yeah,

I like that. Lenny Rachitsky[00:27:28)]Okay. Back to our agenda. There's another framework/tactic that I've heard you recommend. It's called signposting. What is signposting?

Wes Kao[00:27:38)]Signposting is 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 automatically 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."

Lenny Rachitsky[00:28:41)]These are power words for clarity. There's this whole concept of power words like, "free."

Wes Kao[00:28:47)]Yeah. "A gift."

Lenny Rachitsky[00:28:48)]"Gift." Yeah. For copywriting and 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."

Wes Kao[00:29:05)]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 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 some time as they were either listening to you or reading. Lenny Rachitsky[00:29:42)]Along those lines, I find I find formatting really helpful here, just bold and bullets. I know you have a pet peeve with too much formatting. How much is too much formatting?

Wes Kao[00:29:51)]I really hate excessive formatting. So, I've seen memos where 30% of the note was bolded. And that just negates the entire point of bolding because if everything is bolded then nothing 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.[00:30:33)]And it feels faster and more concise to put bullets 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. 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 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 brainpower.[00:31:15)]So that's I think a great litmus test of, "Was that idea fully thought out?" Because if it was, you should be able to really quickly turn it into a complete sentence. And many times, you actually aren't. So I see people like basically think, "Oh, I want to make this easier to read, more skimmable. I'm just going to throw a bunch of formatting and bullets and turn everything into bullets."

And it's not quite that easy of a solution. Lenny Rachitsky[00:31:41)]This is very much along the lines of the whole Amazon six-page memo where Jeff Bezos just realized, "If you can't write it out as a long memo and explain yourself in prose, you don't actually know what you're saying." And it's a really good filter for helping people actually crystallize and know themselves, "Okay, I see. I don't actually know what I'm doing here." And I love this is a microcosm of that. Can you just make a bullet point a real sentence versus a fragment of a sentence? (00:32:06): I'm thinking about as a listener being like, "Okay, how do I 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 a good way to start practicing these skills and know if what you're writing is getting better, is good. Is it find a mentor, find someone that you think is a great writer and have them review stuff? Any tips there?

Wes Kao[00:32:34)]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 friction, then that's 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? (00:33:08): 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 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 wasn't great. And keep trying,

basically. Lenny Rachitsky[00:33:35)]So the advice here is just see how well you're writing/meeting/suggestion goes, how well it does. And if it's not like there's the ideal immediately, "Yes, let's do it." And then there's the, "I don't really understand."

There's 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. Wes Kao[00:33:59)]Yeah, yeah. I don't think that there's any single shortcut on how to get better besides that. 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 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? If I frame it this way, do I get a different reaction? When I try this, am I able to cut through the noise more?" (00:34:39): Yeah. So I really think it's about 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. It's really easy when you are learning a new field or function to get overwhelmed 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 getting it better at that thing before moving on to the next thing.[00:35:19)]So that's like a really common thing I see in my course is people feeling overwhelmed. And I always remind folks that, "You are building a new habit here. And be patient with yourself, take it step by step."

Lenny Rachitsky[00:35:31)]There's a lot of stuff we're talking about here that a lot of people might be like, "This is so minor. What? I just bullet point sentences, be a little... Tell them the why at the beginning." (00:35:41): 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 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.[00:36:12)]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, "I don't like this idea." And then it's like it all falls apart. So I guess any reactions to that?

Wes Kao[00:36:29)]Yeah. All these little things compound and make a big difference. I often hear people think, "Well, 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 that. And then, but when you zoom out, that's like, "Well that's all your work then. This is literally everything you've touched. This is all your work output then."

because any piece of that process you thought wasn't worth spending time on and now this is just the quality of your work and it's not as good as it could be.[00:37:15)]So yes, these might seem minor but A, it compounds. And also B, all the "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's a lever that you can pull, that someone else thought, "Oh, we're hitting diminishing returns on that. I'm not going to 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 that the other person doesn't have.[00:37:56)]So yeah, 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. They'll try something once, a mediocre attempt and be like, "This channel doesn't work. This tactic doesn't work." It's like, "Really? Because it's working for a lot of other people who are getting really creative with it." (00:38:19): I'm not saying that everything has to work for you but for you to claim, "This thing just doesn't work," feels a little bit intellectually dishonest. It's more likely that your skill level, your creativity, your execution ability was not good enough. And that's fine. Let's admit that to ourselves because if we admit that,

then we can do the hard work of getting better at those things. Lenny Rachitsky[00:38:42)]It feels like if you really boil this down,

all the advice comes down to just spend a little more time on all these things you're putting out. Wes Kao[00:38:51)]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 is a little bit more time in the moment but reaps a lot of benefits down the line. Lenny Rachitsky[00:39:25)]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.I-O/lenny to get started for free and get six months of the team plan,

coda.io/lenny.[00:40:42)]You mentioned Slack. I have a great quote also about you that I didn't read that I'm just going to 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. Wes Kao[00:41:14)]Yeah, thank you. I will also say that 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 instant, it's not 100%, but over time I've realized that improving my communication has led to people receiving my ideas better. 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 and pay more attention to that. So that's going back to what I said earlier about watching for what's working. There's momentum is really encouraging. Lenny Rachitsky[00:42:01)]And I totally feel that. If you start getting the things you want, that feels great. I'd be like, "Okay, cool."

Wes Kao[00:42:08)]Yeah,

more. Lenny Rachitsky[00:42:09)]"Let's do more of that." Yeah, and again, it's like very minor things. It's like a couple more minutes on the Slack message,

Very doable. Lenny Rachitsky[00:42:17)]Yeah, which everyone can do. There's no 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. Apparently you have some really good advice on finding the right level of confidence in what you're saying. There's always this question of, "I come to this leader. How confident should I be about, 'This is the answer,' versus, 'Here's a bunch of ideas'?" What do you think? What's your advice there?

Wes Kao[00:42:41)]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 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." (00:43:12): 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 that this is absolutely 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 overreached with your level of confidence.[00:43:52)]So, that's for people who are overconfident. It's equally a problem if you're under-confident. So I have some clients who their CEO asked them to share some recommendations with another team because 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. Obviously, make your own decision. Do what you think is best. And if you want to just ignore everything, that's totally cool too." And it's like you just didn't have to say that. You could say, "Make your own decision, take all this into account,"

but you don't have to diminish to that degree.[00:44:31)]And so again, speaking accurately, if you have really strong reasons to recommend something to the cross-functional team, it's almost irresponsible to act like you are not really sure and it's just this random idea, "Hey, try it if you want to." We might lose a lot of money and time if we don't take this idea, right? So again, speaking accurately is so,

so important. Lenny Rachitsky[00:44:56)]Is a simple way to think about then 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."

Wes Kao[00:45:11)]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, with data, if you have it. 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. 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." (00:45:44): So you can talk about ideas with a lot more specificity when you share your thought process. And you can frame it all kicking off saying, "My initial thinking is," or, "Based on what we know, my hunch is, blank."

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. Lenny Rachitsky[00:46:07)]Advice I got that really helped here for me was to 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 if people notice that, they're like, "Oh, okay. 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,

Yeah. I think anytime people have to discount what you're saying because you are biased in this way is not great. Lenny Rachitsky[00:46:45)]Is there an example by any chance that highlights what you're describing here?

Wes Kao[00:46:49)]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 the recommendation to go through and is presenting a bunch of evidence, supporting that direction. 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 half of their engineer for two weeks.[00:47:36)]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, not necessarily in growth. And once she zoomed out and realized this,

she was able to put her recommendation in context. And realized that it's not just- Wes Kao[00:48:00)]... recommendation in context. And realize that it's not just I'm the only one who cares about this company. Everyone is a hypocrite. They say they believe this, but don't actually want to work on it. Before that was kind of her narrative, but once she zoomed out and realized she was being a single [inaudible 00:48:16], 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. 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. This doesn't actually fit our priorities right now, right? (00:48:42): Or maybe yes, but let's right size the level of investment. So it might look like half whatever the size of what that recommendation actually was, and having the maturity to realize that, to put your idea into context is huge. 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. If you prioritize what's best for the company, that helps you have a more right-sized way of still advocating for your ideas,

but doing it with a bit more equanimity. Lenny Rachitsky[00:49:26)]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. It makes sense. This is why leaders choose, here's what matters most. We got to do the things that are going to 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, I see how this is going to help me. That's great. Let's do it. Great advice." (00:50:01): And I think this is something a lot of people run into. It's just, "Why aren't 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." When it's just like, okay, this isn't a priority right now. Let's come back to it another time. Okay. I'm going to get to a couple more tactics and then I'm going to shift directions to talk about managers and being manager. You have an awesome framework called MOO. What is MOO? What does it stand for and what is it all about?

Wes Kao[00:50:26)]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 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'm likely to get when I share this, you often immediately come up with what some of those things are. So are you going to be able to anticipate every single objection? No. But can you anticipate the obvious ones? Absolutely. 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 have prepared in that way,

you're less likely to feel caught off guard. Lenny Rachitsky[00:51:23)]When you hear you talk about this, it's like, obviously I shouldn't do this, but very few people actually do this, actually spend a couple minutes, " Okay, here's what I'm going to pitch."

Wes Kao[00:51:31)]Even a couple seconds, really. Really, even a couple seconds,

your brain will think of something. Lenny Rachitsky[00:51:38)]Is there a story or an example of this that you share that highlights this idea of the power of MOO?

Wes Kao[00:51:43)]I use MOO multiple times a day, every day, every single day. 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? If I'm about to say this, the person may then say this to me. Well, if I take that into account,

I can volunteer that information upfront or I can frame it in a way where they're less likely to think that that's an issue.[00:52:19)]And so it's muscle memory for me at this point, and this might be something we include at the end is something to start with. But putting MOO on a post-it, Most Obvious Objection, what is someone likely to object about? And then just keeping that top of mind. It's a great way to train yourself 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. Lenny Rachitsky[00:52:50)]I think what's great about a lot of the tactics you're sharing is not only is it going to 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, the objection's probably going to be this. Will it drive enough impact for the business? Oh,

that's a great point. Maybe I should not pitch this right now. Wes Kao[00:53:10)]Yeah. It definitely helps shape your own thinking. I think communication and thinking are so much more interrelated than we think. 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 what you were planning to present and then you now have an opportunity to strengthen that pitch before you say it out loud. Lenny Rachitsky[00:53:45)]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 write it down." I know exactly that feeling. 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 if you disagree with someone, any advice on that,

it feels like you're really good at this. Wes Kao[00:54:17)]I think one thing that tends 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, 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 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. You can ask for a bit more information to be able to continue the conversation in that moment. So let's say that your exec says what percentage of users came from mobile last month and you don't have that number off the top of your head.[00:55:20)]So person A says, "Let me look into it 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 now a bigger part of our business, et cetera. Are you wondering if we are investing in mobile appropriately or 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. I call it the question behind the question, sometimes you get a question,

but underneath there's a deeper underlying concern.[00:56:10)]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. 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 every single thing prepared and the moment that I'm caught off guard,

everything goes to shit. Lenny Rachitsky[00:56:49)]Another tactic along these lines that's very similar to what you're describing, but 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 being like, let me just make sure I understand 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. Let me think about it." Or, "I have the quarterly number. Okay. That's what I know." So there's an interim step almost that I'll add into your piece of advice of just reflect back their question,

just better understand what they're looking for. Wes Kao[00:57:32)]Yeah,

I love that. Mm-hmm. Mm-hmm. Lenny Rachitsky[00:57:34)]Awesome. Okay, let's go back to what I said we do. 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 doc and not get overwhelmed. Finding the right level of confidence, having a POV, that sort of thing. Getting better, 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. Across those, which do you think someone should try to like, "Okay. Let me start here."

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. Lenny Rachitsky[00:58:37)]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 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 around 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 may be under appreciating how important it is to manage your manager,

let's say. Wes Kao[00:59:18)]One of the most common myths about managing up 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 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 are actually the best at managing up. That's partially how they got to be so senior in the first place. But also, 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.[01:00:09)]You are 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 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 make sure that they're aligned. And so for me, realizing that managing up is something that is ongoing and that it shifts and evolves and looks different as you go in your career,

that was a big unlock for me. Lenny Rachitsky[01:00:44)]Just that even 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. Wes Kao[01:00:54)]The biggest one is to share your point of view. So this 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 what you contributed. And that is a good idea, if you want to do it, you can do it. But I think 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. 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.[01:01:54)]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. 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." (01:02:36): 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. Lenny Rachitsky[01:03:04)]I was going to 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." 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 sounds great. Everyone wants that. So if you can do that, amazing. Who wouldn't want that? But then what'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 on the line. So there's 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. Wes Kao[01:03:53)]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 their junior people have often close contact with customers, with support tickets, with cleaning data,

with a bunch of things where the manager would love to hear insights from that. Lenny Rachitsky[01:04:32)]If you're not having success with this, if you're hearing this and be like, but it never worked, 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, sign post 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?

Wes Kao[01:05:05)]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. I used to be very conflict diverse,

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 my frustrations and all 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 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 not that bad or it was partially my fault too or whatever.[01:05:59)]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 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. Lenny Rachitsky[01:06:46)]Someone close to me in my life is working on the skill, which is there's just, "I want people to know how they messed up. Justice. I need this to be fair." And what I always recommend is just think about what you want to get out of this conversation, 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 is focus on the outcome you want to achieve, not something that's useful,

something that will make you just feel better. Wes Kao[01:07:23)]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. You might have a whole script, you're controlled, you're calm, and then you start talking and the other person raises an eyebrow and is 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?" Right? And then you're off, right? Yeah. 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. Lenny Rachitsky[01:08:23)]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 just need them to hear your mind. I just need you to know. And I think a lesson here is that may not be 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."

Wes Kao[01:08:42)]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. Most of us have certain patterns that we are used to and certain ways of responding, and if you believe that there is untapped upside that whatever you are at is kind of a local maximum and that there's better out there,

then that's where switching things up could be useful and not just doing everything that you've been doing and getting the same result that you might be getting. Lenny Rachitsky[01:09:19)]This resonates with Toby Lutke when he is doing 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 better than they think 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 spent 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. I just want this to be really good. I don't trust that it's going to go as well. If I did it my way,

Mm-hmm. I love all these acronyms. Wes Kao[01:10:09)]It's kind of like Cedar, but with an F at the end. I need acronyms for myself. All of these are really reminders for myself because I need a short way to remind myself. So 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. 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 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 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.[01:11:06)]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 a ton of time going in the wrong direction, filling out a hundred rows of the spreadsheet if 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 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, "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- Wes Kao[01:12:00)]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're picking up what I'm putting down? Because 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, "Okay, go off. Come back to me when you're done." So give people a chance to ask questions to see what parts are resonating, what parts they might be a little bit confused on. Usually, when I do this, it's amazing. Because my team member will say, "What did you mean by this part? How does this part fit in?" I'm like, "Oh my God, I totally forgot to mention this thing." Or, "Oh yeah, I didn't even really explain that well." Okay,

so let's go into that.[01:12:42)]And then F is feedback. 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, 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 finished 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, where do you want to go with this? Once you start, do you see any bottlenecks? (01:13:24): And so just really keeping that feedback loop super tight. I found that when I run through the CDAP acronym, there's usually one letter that I could amp up a little bit more like, oh, 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?

So it's a nice mental checklist. Lenny Rachitsky[01:13:49)]So much of your advice comes back to this idea that we've touched on a couple of times. We just spend a little bit more time upfront. Is that how you described it, a little more time upfront?

Wes Kao[01:13:56)]Yeah,

a little bit more time. A little bit more of an investment upfront. Lenny Rachitsky[01:13:59)]Upfront to save you tons of time later. Okay. So as you described this, I don't know if you're realizing this, but you're basically just helping people work better with AI and agents. 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. 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 CDAP. Comprehension is, again, can I make this clear? Is that the way to think about that?

Wes Kao[01:14:41)]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?

Lenny Rachitsky[01:14:47)]Okay. 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 it better. Wes Kao[01:14:47)]Oh, interesting,

yeah. Lenny Rachitsky[01:15:04)]It takes it more seriously. It's just so weird. I have a post about this, and that's one of the pieces of advice,

That is extreme. Cool. Lenny Rachitsky[01:15:18)]It's wild. Okay, so CEDF, comprehension, excited, de-risk, think about ways you can de-risk, which is moot, basically. What's the most? It's a similar concept. Just think ahead to what might go wrong. 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 deep research on 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 used deep research recently and it's really good at just like, okay,

let me have five questions for you before I go off and do this work just to clarify what you want. Wes Kao[01:15:58)]Yeah, I found that AI will often shorten the feedback loop and align with you as well. When you prompt it, when it comes back, it will not do the entire task for me, sometimes. It'll say, "I've done the first part of this. Does this sound right? Is this what you're looking for? If so, I will complete the next section." 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." But that's what it's doing, it's breaking it into smaller chunks to de-risk that 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."

Lenny Rachitsky[01:16:37)]I'm going 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. Before we get back to AI, you have this other concept that I love that I 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 it help you with? Why should people be doing this?

Wes Kao[01:17:03)]Yeah. So swipe files are really common for marketers, and I think other functions haven't caught on as much, but I think it is really, really useful. And basically a swipe file is collecting inspiration that you can refer back to later on. So 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, 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.[01:18:01)]I think there's so much happening around us all the time that your coworker says something smart and you're like, "Oh, that was nice," and then you keep moving on. But when you stop and pause and think, oh, that was really effective, 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. Lenny Rachitsky[01:18:38)]Something else about the swipe file,

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. It could be just whatever you're interested in. Wes Kao[01:18:52)]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 not capturing it,

it's easy to just move on to the next thing. Lenny Rachitsky[01:19:09)]Yeah, cool. And 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 or something, because I know a lot of people stick with it, is just start like a folder or a Notes, note, whatever you use for your note-taking, and just start throwing stuff in there. And it could be messy, right? It's just like,

throw it in. Wes Kao[01:19:27)]It can be super messy. I was going to say, my back end system is super messy and it's fine. 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, I open it. It's just on my home screen, I just add something. I'm not tagging anything, I'm not putting it in certain rows and filling information out. I'm just including it in a file, and if I want to go back and look at it,

it served its purpose. Lenny Rachitsky[01:19:58)]Awesome. Okay, so last question. AI, I'm going to just come back to this briefly. We have this segment on the podcast called AI Corner, 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 it's helped you become a better communicator? Is there anything you can share that might be helpful to folks?

Wes Kao[01:20:18)]Yeah. I love Claude. There are days when I talk to Claude for 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, "What would you say?" It's just not as good. Whereas if I say, "I am not sure about how to tell this person no, because I previously said yes and so I feel on the hook, but history has changed and so is there a nice way where I can be really respectful of our relationship and also make them feel seen and heard, but decline?" (01:21:19): So if I explain, "That's the problem I'm dealing with and here's what I would ideally like to be able to do," Claude comes back to something that's pretty good. And then from there I'll edit it to my voice because usually 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 go back and forth from there. Lenny Rachitsky[01:21:41)]Wes,

this is the most useful thing I've ever heard. Wes Kao[01:21:44)][inaudible 01:21:44].

Lenny Rachitsky[01:21:45)]I need this and I need this immediately, just nice ways to say no to stuff. This needs to be an extension that I can have in my browser, just, "Help me say no to this, please." Wow, such a great idea. Okay, good one. Okay, great. Wes, is there anything else? 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?

Wes Kao[01:22:11)]No, I feel like we covered a bunch of great frameworks, principles,

so lots for folks to get started. Lenny Rachitsky[01:22:18)]All the things. And 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 helped 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. Wes Kao[01:22:39)]All right,

Lenny Rachitsky[01:22:40)]Are you ready?

Let's do it. Lenny Rachitsky[01:22:42)]Okay. First question, what are a couple books that you recommend most to other people?

Wes Kao[01:22:46)]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, it's distracting. And I do the hardest things earlier in the day when you have more cognitive resources available. So that one's really good. Yeah,

those two. Lenny Rachitsky[01:23:31)]These are great. I completely get that phone thing. I'm just looking at my phone, I'm like, "Dang, get out of here. Just go away."

I think Arianna Huffington has a product you can buy that's 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. Wes Kao[01:23:54)]Oh,

that's cute. Lenny Rachitsky[01:23:55)]So cute,

I don't know if I need a separate bed for my phone. Lenny Rachitsky[01:24:01)]But it's like a ritual, I guess, and there's some theory behind it. Okay, next question. Favorite recent movie or TV show you really enjoyed?

Wes Kao[01:24:08)]I love Anything by Harlan Coben on Netflix. Basically, I don't even remember any specific movies or a TV series, but anything he puts out, he's an author and then 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 I don't remember any specific one, but if it's a Harlan Coben show,

I know it's going to be good. Lenny Rachitsky[01:24:46)]I'm looking at a list now I just Googled real quick. So it's all scary stuff, right?

Wes Kao[01:24:49)]Yeah, they're mystery thrillers, and I think he does a good job playing with time and revealing information over time. It's usually something about someone's past that is now coming to haunt them,

and so he'll skip between present day to the past and then slowly reveal stuff. And there's always a twist at the end. Lenny Rachitsky[01:25:11)]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?

Wes Kao[01:25:22)]I recently started using an electric toothbrush and it's been life-changing. So my husband got one and then a couple weeks later he gifted me one, and I was like, "Wow, this is actually really nice."

Lenny Rachitsky[01:25:34)]Are you a Sonicare person, Oral-B person, or something else?

Margins. Wes Kao[01:25:52)]I feel like every time I get a cleaning, the dentist is like, "So have you thought about, are you interested in Invisalign?" I'm like, "No." And so when they get a yes, I'm sure they're really excited, and then they lock you in, 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 horrified by how expensive these replacement heads were. Lenny Rachitsky[01:26:18)]But you got a free toothbrush. I think the Oral-B is what I use, but I think that's what the Wirecutter recommended, but it's so loud. I don't know. One of them is just really loud. I think it's the Oral-B, but it's better, apparently. I went with Wirecutter,

Ooh. Lenny Rachitsky[01:26:37)]... versus just the optimal efficient version. Anyway, let's keep going. Do you have a life motto that you often find useful in work or in life that you repeat yourself and share with folks?

Wes Kao[01:26:51)]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. Just assume it will take longer than you think and you'll be less stressed. Lenny Rachitsky[01:27:18)]That connects to everything we've been talking about. Just spend a little more time upfront to make it. And maybe if you spend more time front,

it'll take less time than you think. Wes Kao[01:27:25)]The other one is a riff on always be closing, like Glengarry Ross. "It's always be selling." This does not mean pawning your wares,

but rather putting forth effort into convincing the other person of whatever your recommendation is. Lenny Rachitsky[01:27:42)]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 just 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?

Wes Kao[01:28:07)]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. There's just certain things you have to do because it comes with the territory. Whereas when you are a solo operator 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 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, that's actually really,

really freeing.[01:28:54)]And so I would encourage folks to think about, what is the thing that you are extremely good at that people find super valuable, the part that you love doing most, if you could not do all the other stuff you don't want to do, and how can you think about doubling down on that?

Lenny Rachitsky[01:29:12)]That's such an important point. And the Claude 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, why the hell am I doing this? I can actually control where I spend time and why did I say yes to this?

Wes Kao[01:29:33)]I actually credit you with helping me come to this realization. I mentioned you on a podcast the other day about this because, do you remember when Maven was launching an important feature, I think it was our marketplace or something, and I had asked you if you wanted to go on Clubhouse to be part of the launch?

Lenny Rachitsky[01:29:56)]I remember that,

but I am sure I said no. Wes Kao[01:29:59)]Okay, yeah. You said no. You said no. And I was like, "Wow. Out of curiosity, what's the thought behind it?" And you said, I'm going to bastardize this, you could correct me, but you essentially said, "I don't really like doing live public speaking type things and I've been fortunate enough to build a career where I can write, I do my podcasts, and work only on the part that I love doing. And so I'm okay saying no to these other really interesting opportunities." And I remember at that time thinking it was so groundbreaking that you could say no to something that was legitimately a cool opportunity and be really confident about it because it wasn't your core competency. It wasn't the thing you are best at. And I've really kept that in mind when opportunities come my way of, am I excited about this? Is this what I'm really good at? Can I shine in this setting? Because when you are solo,

you get to choose the settings that you want to be in. Lenny Rachitsky[01:31:00)]That's such a cool story. I don't exactly remember that, but I am zero surprised at what I said. And the way I put it now, when folks invite me to stuff like this is I just find the ROI 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 than the podcast, the leverage is so much higher than just doing a talk because that takes so much time. So I just have this template now that basically says what I sent you, that is, that it helps. But it's tough. It's so hard to say no. Sometimes these opportunities are so interesting and the person is like, "Wait, what?" (01:31:37): Because I don't think the people asking you for stuff know that I'm getting 10 of them a day, and they're like, "Oh, he said no to my talk. He doesn't want to be on my podcast. What a jerk." That's what I think. I don't know if that's what they think. But anyway. Okay, that's great. Yes, and I think I just had a post about reaching a million subscribers to the newsletter, and actually had 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 can make money doing. That's the dream. And that's exactly what you have done as well. So thank you for being here,

Wes. I actually think we delivered on what I thought we would. I think this is going to be one of the most highest leverage conversations we've had.[01:32:21)]So two final questions. Where can folks find your course? I know you also do executive coaching. Where can folks learn more? And final question is just, how can folks be useful to you, Wes?

Wes Kao[01:32:33)]You can find out more at weskao.com. I linked 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 out about communication. So if you put any of these principles into practice,

I would love to hear about it. Lenny Rachitsky[01:32:53)]Awesome. 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?

Wes Kao[01:32:59)]Yeah,

bunch of platforms. Lenny Rachitsky[01:33:02)]All the places. Okay,

cool. Wes Kao[01:33:04)]Website, email, LinkedIn,

DM me. Lenny Rachitsky[01:33:05)]There we go. There we go. Wes,

thank you so much for being here. Wes Kao[01:33:08)]Yeah, thank you so much,

This was fun. Lenny Rachitsky[01:33:14)]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.