Persuasive communication and managing up | Wes Kao (Maven, altMBA, Section4)

1. 0:00 – 7:08

   Wes’s early career

   1. WKWes Kao0:00

      I think that most people assume that their boss has to manage them and they feel a little bit resentful that, you know, "Why should I manage my boss? Like, they're getting paid more. They are my manager. They have more responsibility." And you can continue to think that way and your career, you know, might be fine, but if you embrace that if you manage your boss, they're going to appreciate you much more, you're gonna get more opportunities, you're gonna have more trust with them. There's all these great things that happen when you decide to manage up.

   2. LRLenny Rachitsky0:34

      (instrumental music) Wes Kao is the co-founder of Maven, a cohort-based learning platform that I used to create my own course on product management. But even more interestingly, she's helped folks like Seth Godin start his AltMBA course, which is legendary. She's also helped people like David Perell, Tiago Forte, Scott Galloway, and even Morning Brew build their cohort-based courses. She's one of the smartest people I've ever met on the art of teaching and I've learned a ton from her. And in our chat, we cover a concept I love called the super specific who. We talk about the state change method and how using this idea, you'll run better meetings. We look at a bunch of advice for why you should spend time managing up and how to manage up effectively. We talk about a bunch of ways to write better, tips for saying no, and a bunch of other really interesting topics. I always have such a good time chatting with Wes and I hope that you learn as much from this chat as I did. And with that, I bring you Wes Kao. This episode is brought to you by Modern Treasury. Modern Treasury is a next generation operating system for moving and tracking money. They're modernizing the developer tools and financial processes for companies managing complex payment flows. Think digital wallets, via crypto on-ramps, ride sharing marketplaces, instant lending, and more. They work with high growth companies like Gusto, Hype, ClassPass, and Marqeta. Modern Treasury's robust APIs allow engineering to build payment flows right into your product while finance can monitor and approve everything through a sleek and modern web dashboard, enabling real-time payments, automatic reconciliation, continuous accounting, and compliance solutions. Modern Treasury's platform is used to reconcile over three billion dollars per month. They're one of the hottest young fintech startups on the market today, having raised funding from top firms like Benchmark, Altimeter, SVB Capital, Salesforce Ventures, and Y Combinator. Check them out at moderntreasury.com. This episode is brought to you by Berbix. Whether you're in the business of crypto or renting out vehicles or selling age-restricted goods, it's important to have the confidence that who you're selling to is who they say they are. With Berbix, businesses can quickly and easily verify someone's identity through their government-issued ID and real-time selfie. Unlike other identity verification software solutions, Berbix takes only seconds to verify an identity, helping you maximize conversion and mitigate fraud. With Berbix, you can grow revenue by instantly verifying a customer's driver's license, passport, or ID card. You can also deter fraud by customizing which transactions you want to accept or reject based on triggers like duplicate IDs, expiration dates, or a user session location. Get started quickly by setting up Berbix with no code, low code, or complete integration in as little as one afternoon. Visit berbix.com/start to get started. That's B-E-R-B-I-X dot-com slash start. Wes, I've learned so much from you over the years in so many different ways while building my course, through your writing, through your tweets, and generally, you're just a super fascinating human that I love this excuse to get to learn more about you and for listeners to learn more about you. And so with that, Wes, welcome to the podcast.

   3. WKWes Kao4:01

      Hey, Lenny. Great to be here.

   4. LRLenny Rachitsky4:03

      It's my pleasure. So just to set a little context about the Wes that we know today, your career path has been pretty untraditional for many of the guests that we've had on this podcast. And so I'd love to just hear a kind of a brief high-level overview of your career and kind of understand what made Wes the Wes that she is today.

   5. WKWes Kao4:23

      I started my career in corporate retail at the Gap headquarters in San Francisco. So I did a rotational training program, rotating between Old Navy, Banana Republic, Gap, and it was a great foundation in business fundamentals. You know, a lot of people talk about, "Should I, out of school, go to a bigger company or should I go to a startup?" So I kind of went to a, a bigger company and gradually have gone to smaller companies since then, until finally starting my own in the past 15 years. So, you know, I think the, the getting to see inside what a company that's, you know, been around for 40-plus years was like was, was really, really fantastic training and, uh, set me up for success for, for, you know, jumping into tech and, and other roles since then. After Gap, I went to a beauty company that was acquired by Shiseido, and then was at an ad tech company that was acquired by Snap, and then moved cross country from SF to New York to work with best-selling author Seth Godin, and that just changed my trajectory completely. It was just such a transformative experience getting to learn and work directly with, for three years, one of the best marketing minds and just most creative minds, I think, on the planet, uh, right now. And together, we co-founded the AltMBA, which I grew from just an idea between me and Seth to thousands of students, 45 countries, 500 cities, grew our team from just us two to 60-plus people all over the world. Uh, so it's just an amazing, amazing experience. And then after that, I consulted for a couple years working directly with other course creators who wanted to create their mini versions of the AltMBA. And from doing that, really proved out the idea that the format of court-based courses was something that was really special, that other experts in other industries, other functions could really leverage.Um, and then that led to starting Maven. Because when I was consulting and when I was doing AltMBA, you know, during those six, seven years, I realized how janky the tech stack was that everyone is using. And I was shocked that no one had tackled this problem of all of us course graders needing to, to, uh, toggle between half a dozen different tools just to make a live plus async course be able to work. And so when, when my co-founder, Gagan Biyani, and I got together, we were, uh, brainstorming, you know, what's the future of education and, and catching up, and we were just shocked that, you know, hey, why hasn't anyone tackled this yet? We should do this because we both really believe that core-based courses are the future, that more people are gonna want to teach these courses, but it's just too hard from a technical perspective now. But it doesn't have to be that way.

   6. LRLenny Rachitsky7:07

      Awesome.

2. 7:08 – 9:56

   How to land a job with Seth Godin

   1. LRLenny Rachitsky7:08

      I definitely want to chat a bit about Seth Godin. I've been such a huge fan of his for, I don't know, a decade. I used to subscribe to his newsletter, and I don't anymore because it's, like, an email every day and, like, it's overwhelming even though he made- he pointed out in one of his newsletters like, "Okay, just ignore it. Why would you be sad that I have so much content?" But it, it, it... yeah. Anyway, I unsubscribed recently.

   2. WKWes Kao7:27

      (laughs)

   3. LRLenny Rachitsky7:27

      But, uh, but I'm such a fan and so I'm so curious, one, how did you actually- how did you connect with him and how did that even happen? And then two, what is he like to work with?

   4. WKWes Kao7:36

      Yeah. Both very, very juicy questions. So the way that we connected was Seth had put out a blog post saying that he was looking for a special projects lead to help him figure out what to do next. So this was in 2014 when he had just sold off his last company, Squidoo, that he had been working on for, I think, eight years or so before that. So he was kind of ready for something new, at a crossroads, wanted some fresh inspiration, and I saw this blog post on a whim, and at that time I was, I was at that ad tech company in San Francisco, and I thought, "There are probably thousands of people who are gonna be applying to this, so I don't want to get my hopes up." I did want to move to New York. I feel like everyone in SF, you know, and California at some time wants to move to New York. And so I thought, "All right, I'm gonna toss my hat in the ring and not overthink it." And so the application required a video. So there's a written application and then there was a video. So Seth said, you know, "Take three minutes to talk about what you want to build, what you want to contribute, and what you want to learn." Some- something along those lines. And I did my video in one take. Normally, I would have done multiple takes, for sure, but here I just thought, you know, there's, there's a very little chance I'm gonna get this. And a couple days later, to my surprise, I get an email from Seth Godin. He's in my inbox and I'm just jumping up and down in my living room, you know, 'cause he's asked, "Hey, loved your video. Let's hop on a call for an interview." And of course, I, you know, write a very calm, professional response. And we did a couple rounds of interviews and I get the role. So I pack my life into six suitcases, get an apartment sight unseen in this little town right outside of New York City where Seth's office is. It's called Hastings-on-Hudson. And what initially started off as a six-month role eventually led to, to over three years, uh, working together and starting the AltMBA together. So that's how we, how we got connected. Very serendipitous. But my lesson there is don't take yourself out of the running before you get rejected. Like, don't reject yourself, basically. You know? Um, I think a lot of us have high standards and high expectations of ourselves, and it's almost like, "Oh, if I can't do the best application then I just shouldn't apply." You know, "If I don't have time to take five takes at this video, I just... it won't be good enough and so I just shouldn't do it." So for me, that was a great lesson in putting your best foot forward, but, but putting your foot forward.

   5. LRLenny Rachitsky9:55

      I love that.

3. 9:56 – 14:50

   What makes Seth Godin stand apart

   1. WKWes Kao9:56

      Um, yeah. So that was, that was how we, how we got connected. And then in terms of what it was like working with him, you know, I think, I think the, the Seth that people know externally can sometimes be different from the behind-the-scenes Seth. And that- I think that's true for all of us, by the way. Um, and so, you know, I think externally he can sometimes be a little bit of a, a vague Buddha, if you will. You know, he gives great, inspiring advice. His insights, I think, are amazing. Like, if you look at his blog, some people try to copy Seth's blog by writing short daily posts, but that is not the reason why Seth's blog is so good. Right? That, that is incidental that they are short and daily. They're- the reason why it works is because they are so insight-rich. And in person, he is even smarter and even sharper than he is in writing and online, which is so amazing. I'm just shocked by that because I feel like most people are the opposite. You know? It's like, you have time to curate what goes on your Twitter, your website. You have time to kind of, um, manicure this, you know, what you want people to think of you. But when you're live, you're just, you're there with the person. You know? Like, you're talking like normal people and you can really get a sense of how sharp or insightful or, or genuine someone is. And I think he's, he's even more genuine, even sharper, even funnier in person. So that's what he... you know, that was kind of high level. I think the other thing is that internally we had really high standards for what we would ship, which is a little bit different, I think, than what you might think if you were, if you were a Seth reader. You know? Because before I would read him and just do it essentially, right? Like, ship, put yourself out there, don't overthink it, and you might think that that means that there's a trade-off with quality. But the thing that I found so surprising about working together was that we often produced work, almost always, that was high quality, fast, and... What's that third thing of that triangle? Cheap. Or, like, not cheap, but, like-

   2. LRLenny Rachitsky11:56

      Mm-hmm. Yeah, yeah, price.

   3. WKWes Kao11:56

      ... affordable or, like, economical. Right? Like, usually it's like, "Oh, you only get two of these," or, or, you know, there's a trade-off between quality and speed. But we worked fast and we produced really great work. And so I think for me, it really raised the bar on everything for me and on strategies, on tactics, on expectations, on quality, speed. Um, I think the speed that we shipped... Before, I'd- I- you know, was at a Sequoia-backed-... Ad TechStarted and I thought, "Oh, like, I know what shipping fast is. Like, I was at a (laughs) startup," you know? And, and the speed that we shipped at, at Seth HQ was just beyond, like, it just blew away what I think normal people think of as, as, you know, fast, but it was also still so good. And so, I think that rigor and that, that refusal to accept anything but excellence was just so awesome and it just... It really spoke to me because I care a lot about craft. I think more people should care about craft. And I'm also kind of an obsessed person. Like, I have an obsessive personality and I just loved how Seth was kind of similarly obsessed. And so yeah, learned so much from him that I've taken with me obviously in, in, you know, building Maven now and, and everything that I do.

   4. LRLenny Rachitsky13:12

      Well, I have, I have 10 more questions I'd love to ask about Seth Godin, but I should probably try to get him on the podcast. (laughs)

   5. WKWes Kao13:19

      (laughs)

   6. LRLenny Rachitsky13:19

      What a, what a coup that would be. I have a Seth story actually I just remembered while you were talking. I saw him mention once that he replies to every email he gets, and so I emailed him-

   7. WKWes Kao13:29

      Yes.

   8. LRLenny Rachitsky13:29

      (laughs) 'cause I was such a-

   9. WKWes Kao13:30

      Just to check. (laughs)

   10. LRLenny Rachitsky13:31

       ... had such a crush. (laughs) Yeah, just to test, and he replied and he's like, "Why would I say this if I wasn't doing this? What benefit would that be for me?" (laughs) I was like, "Oh shit, I pissed him off."

   11. WKWes Kao13:40

       So funny.

   12. LRLenny Rachitsky13:41

       He hates me. (laughs)

   13. WKWes Kao13:42

       It's hilarious. (laughs)

   14. LRLenny Rachitsky13:44

       Oh, man. Okay, amazing. One last quick question. You also worked with Scott Galloway w- who's a very polarizing figure on Twitter at least, and you helped him create his courses. Maybe just one quick question on him. What's, what's he like and why do people dislike him so much on Twitter?

   15. WKWes Kao14:00

       Yeah. (laughs) I don't know about people disliking him. Uh, he definitely has spiky points of view, which I think are amazing. Um, uh, yeah, so Section 4, Scott Galloway's company, was one of the first clients I worked with after, after leaving ALT MBA, and I didn't work too closely with Scott. I worked really closely with, with his CEO, Greg Chave, and their exec team to design the sprint that's now their, their go-to course format. But yeah, I didn't work too closely with him directly.

   16. LRLenny Rachitsky14:27

       Okay, cool. (laughs) We won't get too deep there. Okay. So, what I wanna do with most of the time that we have together is to go into five big ideas, call it five big ideas from West Cow, concepts that, that you've shared in other places, that you've touched on in your writing and tweeting and things like that, that have struck and have stuck with me, and I suspect many other people, and just kind of go deeper on these ideas. Does that sound good?

   17. WKWes Kao14:49

       Sounds

4. 14:50 – 18:08

   Wes’s framework for better writing: the super-specific how

   1. WKWes Kao14:50

      great.

   2. LRLenny Rachitsky14:51

      Awesome. So the first idea I wanna chat about is something you called The Super Specific How, and you wrote a post about this, and it really clarified a lot of my thinking on writing, and the newsletter, and the podcast. And I find myself sharing this post and concept with other writers who are struggling a bit with their content. And so can you just explain this idea of The Super Specific How, and generally just how it can make folks better writers and thinkers?

   3. WKWes Kao15:18

      Yeah. The idea of The Super Specific How is that most writers, most course instructors spend too much time on the what and the why, and not enough time on how. So if you think about people who are reading your writing, most of them probably already agree with the general premise of what you're saying. Unless what you're saying is, is truly controversial, groundbreaking, or new to, to your audience, you don't need to spend too much time elaborating on, on the concept itself and why it matters. People really want to know, "How do I do this? How do I apply this to my own life? How do I think about the nuances when I'm applying this? What are examples that I can look at that help me better internalize how this really works?" So, a good example of this is if you're writing about product management and communication, let's say. So you don't want to spend too much time saying, talking about how communication is important for product managers, right? Like, most product managers already know that. Like, that's pretty 101. It's pretty basic. Instead, you want to spend that time talking about how to get buy-in when you don't have positional authority as a product manager, or how to turn chaos into order and be able to communicate effectively across multiple stakeholders, or how to communicate ideas where they're kind of assertions and hypotheses that might not work, but you need to put something forward to get the team going, right? These are all elements of communication that are juicier and more specific than just saying, you know, "Here's, here's why communication is important."

   4. LRLenny Rachitsky17:02

      Yeah, so a lot of it is cutting the backstory basically, right? And just like, get right to the meat of it.

   5. WKWes Kao17:07

      Yes.

   6. LRLenny Rachitsky17:07

      I found that exact... Yeah. E- ever since you wrote that, I'm like, "This is why, this is why a lot of my writing seems to work." 'Cause I don't, I don't... I try to cut the intro as much as possible and just get right to the meat of it.

   7. WKWes Kao17:17

      Yeah. I find in, sometimes in my writing, I'll write and then go back and cut a lot of the preamble. So, most people need less context setting and preamble than you might think, and I have a framework that I call start right before you get eaten by the bear.

   8. LRLenny Rachitsky17:33

      Hmm.

   9. WKWes Kao17:33

      And the idea is that if you're telling (laughs) a story about camping, don't start talking about going to REI to buy a Patagonia jacket and then booking the campsite, and the, the website had difficulties, and on the drive over, we stopped by this gas station. No one cares about all, all that, right? Like, start right before, you know, your friend left a Clif Bar out in their tent and you all almost got mauled by a bear, right? Like, get to the juicy part, and start, you know, a little bit of context right before you get to the juicy part, but, but that's the idea of start right before you get eaten by the bear, is cut out all that backstory

5. 18:08 – 21:45

   Writing and teaching without the BS

   1. WKWes Kao18:08

      scope creep.

   2. LRLenny Rachitsky18:09

      I like that. There's also this element to your thinking that you didn't touch on, which is kind of this... I think you call it the content hierarchy of bullshit. (laughs)

   3. WKWes Kao18:16

      Yes.

   4. LRLenny Rachitsky18:16

      Can you, can you speak to that?

   5. WKWes Kao18:18

      Yeah. Yeah. So if you imagine a pyramid triangle, at the bottom there's more room for BS, and at the very top of the triangle there's less room for BS. So what's at the bottom of that triangle?... Twitter, podcasts, short, you know, articles, right? It's basically situations that are one directional, where people can't really challenge what you're saying. Keynote speeches, another great one for, you know, lots, lots of room for BS (laughs) . So those are situations that, you know, they're more one directional. With Twitter at least, it's 280 characters, it's something short that you're saying that's a little bit of a mic drop. You just say it, you leave it there, and then you get to walk away without needing to defend it, without needing to share your rationale or think about counterpoints, and so there's more room for BS. Right? The format kind of encourages or allows it. Let's say it allows it. But as you move up the triangle, uh, the content hierarchy of BS, there's less and less room for BS. So long form, in-depth articles, less room for BS. Right? You have to defend the idea, you have to convince your reader. Books, also less room for BS. And at the top of the triangle, courses. One directional courses, like video courses on Udemy, LinkedIn Learning, but especially cohort-based courses where there is live and async interaction, there's very little room for BS. So if you think about a webinar or a keynote talk, or a book, it's, you know, you kind of say the thing and, and that's it. But in a court based course where your students are right there with you, where they can ask questions, when they can have conversation in the Zoom chat box, like if you're saying something that doesn't really make sense, there could be a whole conversation happening in Zoom chat saying like, "This doesn't make sense for XYZ reasons." Right? And so you have to be able to defend what is it that you're saying and make sure that what you're saying is rigorous. And I think that thinking about that content hierarchy of BS is, is great for holding ourselves to a higher standard, to make sure that we are not allowing ourselves (laughs) to spew BS just because the format might allow it. You know, a book for example, obviously the content of that book, the contents matter more than just the format, and so there are books that could be 10 page blog posts, and there are books where every page earns its real estate. So there's still a little bit of, you know, nuance in the hierarchy, but in general as you move up that hierarchy, there's less and less room for BS.

   6. LRLenny Rachitsky20:40

      I think this framework explains a bit why Twitter's so cringe to a lot of people, is these, like, threads that just sound so wise but, yeah, there's not a lot of depth to them if you really think about it and it's easy to sound smart. So one thing I'll add is, people are listening and they may be like, "Oh, of course, courses are at the top. Wes runs a course company." Uh, but having run a course and created a course, I 100% agree that there's just no room for BS in a course because, one, there's just so much content, there's so much time that you have to, like, cover, and so you can't just like, "Here's a wise thought, let's move on."

   7. WKWes Kao21:17

      Mm-hmm.

   8. LRLenny Rachitsky21:17

      You have to actually get into it and people hold you accountable to that kind of thing. And then, to your point, people are gonna ask questions and you're like, "Oh, shit. I don't... I... That's all I've got." (laughs)

   9. WKWes Kao21:26

      (laughs)

   10. LRLenny Rachitsky21:26

       "I have nothing more, nothing more to add. That's not gonna cut it." And so I totally agree with that, and that's why courses, I think, are so powerful and probably a, a much better way to learn than just reading a blog post or listening to a podcast if you really want to go deep on something. So I love that concept. Anything else you want to add on that idea before we move on to the next concept?

   11. WKWes Kao21:44

       Let's

6. 21:45 – 25:51

   State changes: how to keep your audience engaged when teaching

   1. WKWes Kao21:45

      go. Next concept-

   2. LRLenny Rachitsky21:46

      Okay. Let's do it.

   3. WKWes Kao21:47

      ... let's do it. (laughs)

   4. LRLenny Rachitsky21:47

      Okay. So when I was building my PM course with you, you blew my mind a number of times on how to actually teach effectively, and (laughs) one of the lessons you taught me was around the importance of creating state change in the talk, how to create state change. And so without giving it away, I'd love to just hear your thoughts on why, what is state change, why is it important, and just how does it help you not only give better talks, but also even better Zoom meetings?

   5. WKWes Kao22:13

      Yeah. If you think about most Zoom meetings or presentations, it's one person talking at you the entire time and everyone else has to listen silently. It's pretty hard to do that on Zoom where your, your camera's on, you're sitting, you know, you have to sit still, look straight ahead at the camera, control your face, and, like, make sure you look focused, and so it's really, it's really not surprising that most people find that very draining. You know, they want to turn off their cameras, they get distracted. So the idea behind what I call the state change method is that you should punctuate your monologues with state changes. So state changes are anything that shakes your audience awake and adds some variety. So it might be asking people to put something in the chat box. It might be switching from gallery view, where you see everyone kind of in that Brady Bunch grid, and switch over to screen share to share something and then switch back. It might be having someone else speak. It might be asking people to unmute themselves and go ahead and chime in. It might be putting people into breakout rooms so they can discuss amongst themselves and then come back and then do a popcorn where, you know, someone shares out and they popcorn to the next person, to the next person. So all these are examples of state changes that help your audience stay engaged with the material that you're presenting. And it's really, it's really in reaction to monologues. You know, like, I'm kind of imagining Salesforce with their no software sticker, if you think about no monologues, right? Like, try to avoid monologues as much as possible, because that puts your audience to sleep.

   6. LRLenny Rachitsky23:46

      What are examples of different states? You mentioned, uh, breakouts, chat, what other... what other sorts of things can you do? Especially on a Zoom, let's say, if we're running a meeting.

   7. WKWes Kao23:55

      Yeah. So we talked about breakouts, Zoom chat, um, switching from gallery view into screen share to show something and walk through it and then switch back. There's polls asking people, you know, before, before you reveal something you can ask, "What do you all think?" Right? "Go ahead and guess." So, you know, in the Maven Course Accelerator, the two week course that I teach on how to build a court based course, it's very meta, you know, I will ask people, "So what do you think the average attention span is for students?" So I could j- I could have just told people, like, "It's X." Right? But any time when you want to s- when you want to just share a piece of information, that's an opportunity for a potential state change. Have people guess, right? The more they engage and think about the problem themselves, the more that they are going to, to remember and also just-... interact with your material. So, I ask people to guess and then the answers range from an hour or 45 minutes to three seconds (laughs) . So it's, you know, it's, it's all over the place. The answer is two to four minutes, according to, to some research. So, you know, that's, that's a ripe opportunity for a state change. And the other way to think about it, I was talking to Nathan Barry from ConvertKit. He was saying that he loves the state change method too, and that anytime he does a presentation now, every three to five slides he'll put in a state change. So, the idea of every three to five minutes, every three to five slides, go ahead and put in a state change. We really want to turn this from an art into a science as much as possible, um, audience engagement. And if you just, kind of force yourself to look through your own material and say like, "Oh, like, have I done a state change these last couple of minutes?" If not, go in and throw one in. And more likely than not, when you look at that material at that, you know, at those intervals, you'll find something that lends itself really well to a state change.

   8. LRLenny Rachitsky25:37

      I'm feeling pressure to create some state change in this podcast.

   9. WKWes Kao25:40

      (laughs)

   10. LRLenny Rachitsky25:40

       Hey listeners, when was the last time you were in a meeting where there was some meaningful state change? Think about that for a moment.

   11. WKWes Kao25:47

       Love it. Yes. (laughs)

   12. LRLenny Rachitsky25:48

       Okay. We're pros. Who can't-

7. 25:51 – 29:27

   The data of “eyes light up” moments

   1. LRLenny Rachitsky25:51

      try, try to practice this lesson live. There's also this concept that you touch on called, I think it's called eyes light up concept.

   2. WKWes Kao25:58

      Mm-hmm.

   3. LRLenny Rachitsky25:58

      Or something like that. Okay, cool. Can you speak to that? 'Cause I think it relates to this idea of, of state change in meetings.

   4. WKWes Kao26:03

      Yeah. So the idea behind what I call eyes lighting up is that, you know, when you're talking to someone and you're explaining something, you're teaching them, you're sharing your startup idea or whatever, the normal response is people will want to be polite. So they'll nod, you know, and they'll say like, "Oh, okay, that's interesting." But there's usually a moment in the conversation where their eyes light up because they are genuinely actually interested in what you are saying at that moment. So, you as the presenter, as the, you know, salesperson or whatever that's pitching, you wanna make note of the moments when people's eyes light up because their face can't lie, right? Like, they can say, "Oh, yeah. Okay, that's interesting." It's, it's easy to kind of say that and be polite, but when someone's eyes light up, that's a sign that something that you said triggered a reaction in them, a visceral reaction. And I think s- so many of us, you know, we like to, to pretend that, "Oh, you know, I don't get enough data from people and, you know, this person said this, but what do they really mean?" And, and really I think that we're just being delusional. If we just acknowledge reality and like, "This person's, looks bored. They look bored." That is data, okay? Like, don't ignore that data, right? And then, "Oh, wait. There, I said this, this hot keyword or this phrase," right? "I, I explained something this way," and, and all of a sudden their face changed, their demeanor changed, they're leaning forward, they're wanting to catch what you're saying. Like, that's all data. So, so really the principle behind eyes light up is don't be a delusional in just taking people's, you know, what they're saying at face value. Really look at their face, look at the, you know, look for other clues, the, the excitement in their voice, and watch for these different eyes light up moments because those are great fodder for content that you might wanna write about, for the angle of your sales pitch, for how you might wanna explain something in the future. And really cut out all the parts that, that, you know, make people go dead in the eyes and just save the parts that make their eyes light up.

   5. LRLenny Rachitsky27:57

      Hey listeners, what kind of eyes lighting up behaviors can you, can you think of that show you somebody's really into your content?

   6. WKWes Kao28:05

      Yeah. Or when are times when, you know, in, in recent weeks when you've explained something or given a sales pitch and, and saw people's eyes light up. What were you saying in that moment? Think about that and jot that down.

   7. LRLenny Rachitsky28:17

      And so the skill here is, okay, for sales, that's interesting. So as a salesperson, it'll help you understand what part of your pitch resonates. I imagine for presentation prep, this is a useful skill. Obviously for building courses. Probably less useful for meetings, but I imagine there's also just like, "Oh, wow, this person got really excited when I shared this thing. Maybe spend a little more time on that idea."

   8. WKWes Kao28:38

      Yeah. I think it absolutely works for meetings.

   9. LRLenny Rachitsky28:40

      Mm-hmm.

   10. WKWes Kao28:40

       I think it works for internal meetings, for conversations even, with your cross-functional team members, with your boss, with your direct reports. You know, usually as you're explaining something, you can tell when y- even your manager is like, "Oh, yeah, that." Right? Or, like, you can kind of tell, like, there's, there's more energy in, in their response for certain parts. And when you think about it, you can find patterns of, "Oh, u- usually when I, when I share things with this person, you know, they tend to react well when I share these things. So why don't I trim out the other context that they don't really care about and focus on whatever, you know, made their eyes light up?" And it might be talking about numbers or it might be talking about upside or it might be talking about how little effort this is to try or whatever angle it is, it really gives you great data that you can kind of lean

8. 29:27 – 32:51

   What managing up can do for you

   1. WKWes Kao29:27

      into and flesh out more.

   2. LRLenny Rachitsky29:28

      You mentioned your manager, and that's a really good segue to our next topic, which is around managing up. If a feature ships but no one knows about it, did it really ship? Keeping customers and internal teams like sales, support, and marketing in the loop on what's changing across your product is surprisingly hard. First, you have to dig through tickets and pull requests just to see what's been done. Then you have to figure out what's relevant to each person, craft updates, and then share them across all of your channels. Multiply this by the number of things that ship every week, and that's basically a full-time job just to keep everyone updated on what's changing. That's why high-velocity product teams like Monte Carlo, Armory, and Popsicle use MakeLog. MakeLog makes it easy to see what's happening across tools like Jira, Linear, Asana, and GitHub, and then to write bite-sized updates which you can immediately share with your audience wherever they are, including within your app, on Slack, over email, and even on Twitter. No more long, boring, blog-style change log posts that slow you down. Just quick and easy updates that keep your users informed and happy. Try MakeLog for free today. Just visit makelog.com/lenny to get started. I think your most popular tweet you've ever tweeted-

   3. WKWes Kao30:42

      (laughs)

   4. LRLenny Rachitsky30:42

      ... is around the skill of managing up.And funny enough, I had a thread on managing up years ago, and it's also my most popular tweet thread ever. So (laughs) there's a lot of interest in this topic. And so I wanna ask you, why is managing up important? Why are people not doing it well? And how do you manage up effectively?

   5. WKWes Kao31:01

      Great questions. I think that most people assume that their boss has to manage them, and they feel a little bit resentful that, you know, "Why should I manage my boss? Like, they're getting paid more. They are my manager. They have more responsibility." And you can continue to think that way, and your career, you know, might be fine. But if you embrace that if you manage your boss, they're going to appreciate you much more, you're gonna get more opportunities, you're gonna have more trust with them, there's all these great things that happen when you decide to manage up. And I think, you know, more people are realizing that, you know, hey, as an individual contributor, even as a manager, we all kind of have bosses, right? So, you know, even as someone who leads people, you still need to manage up. It- there's no point in seniority where, as you climb the career ladder that, that it just doesn't matter anymore. And I think some, some people think that senior people don't need to manage up. Like, "Oh, once I'm, once I'm, you know, a director or VP, I don't need to manage up anymore. It's only something I need to do when, when I'm a coordinator or, you know, you know, an associate PM or something." But ironically, the most senior people are best at managing up. This is why they got promoted in the first place, because they were great at managing up to their bosses, to understand what was worries- worrying their bosses, what was keeping them up at night, so that they could take that off their plate. They were, you know, they're great at keeping their bosses in the loop on what's happening, so their bosses aren't constantly having to ask and, you know, pepper them with questions every day on, "Hey, how's this going?" Or, "What's the status of this?" Or, "Did we take care of this thing," right? They're proactive in communicating so their boss knows that certain things are taken care of. And so there's so many benefits that you can reap when you choose

9. 32:51 – 34:17

   How to manage up effectively

   1. WKWes Kao32:51

      to manage up.

   2. LRLenny Rachitsky32:52

      How do you suggest folks do it? I have, I actually have a tip, but, uh, is there something you- you have- you wanna share on that?

   3. WKWes Kao32:58

      Yeah. I think one really big way of doing that is keeping your boss in the loop on the kinds of decisions that you're making and what you're working on. It feels kind of almost blasé, like, "Well, duh," right? But- but actually, I think, I think we all know that we should do that. But the way that we execute, you know, I think sometimes your boss doesn't feel like they're in the loop, right? And so proactively giving the right amount of context for your manager to be able to weigh in on- on what you're doing and to be able to give feedback. I think that's- that's, you know, super, super important. And then, you know, thinking about the right level of context to give them, right? "Does your boss, uh, is this a reversible decision? Or is this one that, um, that is irreversible or- or difficult to reverse or expensive to reverse," right? Kind of using your sense of judgment so that you're not necessarily going to your boss for everything and telling them everything. Like, that's overwhelming for your manager who has a lot going on. It's really using your sense of judgment and good common sense to think about, "Okay, I wanna, you know, recommend that we do this thing. How do I share enough context about my thought process and rationale so that my boss has enough information to be able to push back if needed, or to be able to approve and

10. 34:17 – 36:19

    Lenny’s template for proactive communication

    1. WKWes Kao34:17

       know that I've gotten it taken care of?"

    2. LRLenny Rachitsky34:19

       Awesome. So to build on that, something I did for a long time that was really powerful, it's really simple, is I sent my manager a state of Lenny email every week, just titled The State of Lenny. And it had basically three sections, my priorities currently, blockers that I need their help with, and maybe that was the first thing that I put up just to make sure that they saw that, and then just things on my mind currently that week. And that, I think, is such a simple but such a powerful way to do exactly what you're talking about, keep people in the loop on what you're doing, make sure you're aligned on priorities, make sure things are getting unblocked, and also just avoid surprises as much as possible.

    3. WKWes Kao34:57

       Mm-hmm.

    4. LRLenny Rachitsky34:58

       Um, and so there's a little tip.

    5. WKWes Kao35:00

       I love that. I think the avoiding surprises is great. I think in a work context, surprises are generally not great. So I always say, you know, "Unless you're surprising me by bringing me a snack or something, like, don't surprise me." Like, actually, in my personal life too, I just- I don't like surprises. So I think especially in work, not throwing something over to your manager that, that just catches them off guard is, is good.

    6. LRLenny Rachitsky35:27

       I like that general rule, avoid surprises except for birthday parties and- and milestones. Yeah. That- that also touches on just a general rule I have of working is just overcommunicate. I find nobody's-

    7. WKWes Kao35:39

       Yes.

    8. LRLenny Rachitsky35:39

       ... ever like, "Just, Lenny, shut up. I don't wanna know about things." Like, it's always the opposite. "Why didn't I know about this?" Even if they don't pay attention, the fact that they have the chance to see it is alwa- always goes a long way.

    9. WKWes Kao35:51

       Yeah. I find especially in remote work too, erring on the side of overcommunicating is just, it ends up being the right level of communication. Like, you think you're overcommunicating, but to the recipient, it's actually just the right amount. And, you know, I've been surprised by how I thought everyone was aligned on a certain strategy or that we've, "Oh, we've already talked about this thing three times," and then realize that, "Oh, we actually weren't as aligned as I thought." So erring

11. 36:19 – 43:50

    The skills you need to communicate clearly through writing

    1. WKWes Kao36:19

       on the side of overcommunication is great. And I think also structuring your communication in a way where if someone already agrees with you or they get it, they can get the gist, but if someone doesn't get it, they can continue reading. So that kind of helps people spend their time well. You know? So I'll usually put the most important point at the top, the TL;DR if you will, the gist, and then I'll say, "Context:" and then that- there might be multiple paragraphs of context below for anyone who wants additional thinking on, "How did I get to this decision?" Or, "How did I, you know, how did I think about this?" But if they already agree with the decision and kind of...... know that context and they don't need to keep reading.

    2. LRLenny Rachitsky36:55

       I actually taught that format in, in my course. It, I think it was rooted in the military, where they're just like-

    3. WKWes Kao37:02

       Mm-hmm.

    4. LRLenny Rachitsky37:02

       ... their emails start with, "Bottom line, here's what you need to know, and then context, bullet point, bullet point, bullet point, bullet point." And so, it's a really simple way of just communicating things. Although, o- o- one student used that format with a potential customer, where it th- started off being, "Bottom line, here's where we're at," (laughs) and they're like, "Man, that's, that's aggressive."

    5. WKWes Kao37:21

       Yeah. (laughs)

    6. LRLenny Rachitsky37:22

       Or, or... (laughs) And so I had to adjust that-

    7. WKWes Kao37:24

       Yeah, yeah.

    8. LRLenny Rachitsky37:24

       ... to be a little softer. Okay. So I was gonna... (laughs) I had this beautiful segue, but, uh, anyway. You talked about communication, and that's a good segue to talking about writing, and you have a lot of great advice on writing and how to write well. We touched on a bit of this, of cutting out the backstory and being super specific with the how, but do you have any other advice for just writing in general? Because a lot of folks that listen to this are trying to write more, and you have some great stuff on this. So yeah, what do you... What can you share?

    9. WKWes Kao37:55

       Yeah. I think a lot of people learn writing from mimicking other people, and kind of learning by analogy, especially on Twitter or on social, which I think can... is useful to a certain point. But I also think that there's a lot of benefit in studying the craft of writing, you know, off of social. So one of the books that, that I've been recommending, and I think I'm jumping ahead to, potentially, a, a lightning round question, but, uh-

    10. LRLenny Rachitsky38:23

        Not allowed.

    11. WKWes Kao38:24

        ... it... (laughs) It's- it's a book called, It Was the Best of Sentences, It Was the Worst of Sentences by June Costa Grande, I think is her name, so we'll link this in the show notes. And another one is Better Business Writing by Harvard Business Press. They have a whole series on, you know, leadership, managing up, uh, writing, et cetera. And I recommend those two books, usually, to, to new team members who join, because they cover more of the, the craft of creating strong sentences, paragraphs, arguments, and thinking about the logic of what you're saying. A lot of times, when we write a sentence, there's actually already a point of view or, or, um... There's, there's a point of view baked in, but you don't want it to be an accidental point of view. Right? I was just talking to this... to my team member about this. She asked me to give her some feedback on something that she wrote, and the way that she had written her paragraph was leading for the reader. You know? It was... It was about an off-site that we have coming up, and she talked about whether we should change, you know, WeWork locations, something like that. So this is actually, like, super useful tactical stuff for Slack messages, you know, if you're DMing someone, if you're s-... if you're texting someone. Like, you can use these principles basically everywhere. And so she was... You know, it was a Slack message about, about changing WeWork locations, and the way that she had phrased it, the obvious conclusion was, "Oh, well, we, we should just stick with our current one." You know? And, and so I asked her, "Is that your recommendation? Because if it is, then great, 'cause you're kind of leading the reader to that, to that conclusion. But if it's not, you're asking a leading question that is skewing the results of this question." You know? And so it turned out that she was, she was kind of open. Like, she didn't really have an opinion, and so we thought, like, "Okay, how do we adjust this so that it'll get a more objective response?" And then we talked about it some more and thought, you know, "It's actually better if you do share a recommendation here. It's easier for the reader, so how do we then adjust it some more so that the recommendation is intentional within, within that paragraph?" So it's a little bit... I know it's, it's not quite a sound bite, but I see this a lot in, in people's writing, is that there's, there's these... either sentence structures that add more cognitive load to the reader or have a little bit of confusion, and it's, it's a technical issue, actually. It's, like, the, the which or some clause explains something directly before it, but they actually meant to... you know, meant for that clause to describe something, you know, ten words before at the beginning of the sentence. Right? It's kind of hard without a visual, but anyway, both of those books talk about the mechanics and the, the technical aspects of writing and the craft of writing really well. And I guess my spiky point of view is that more people should, should learn the craft of writing and the technical aspects of writing, not just, you know, look at what other people are doing to try to get audience engagement, but to actually improve your ability to precisely say what you mean and convey the level of conviction that you have, and not accidentally mislead people with your words because you didn't know that the way you wrote something could potentially mislead them.

    12. LRLenny Rachitsky41:29

        Got it. I actually got that same feedback that you gave this person once when I, uh, like, clearly had an opinion on what we should do as a team, and I, I gave pros and cons, and it was, like, very biased and clear what I thought we should do, and my manager's like, "Don't do that. Just try to be as unbiased as you can, or just tell me, 'Here's what you think we should do and here's why.'"

    13. WKWes Kao41:50

        Yeah.

    14. LRLenny Rachitsky41:50

        And so, it helped a lot.

    15. WKWes Kao41:51

        I, I love that, and I think, I think going... you know, pulling on the thread a little bit, it's because pros and cons lists... The, the structure of a pro and con list implies that you are giving equal weight to pros and cons, that you are accurately talking about pros and cons, right? Or objectively talking about them. So when you do pros and cons list, but they're skewed and you're leaving some things out of the cons list, it makes the reader suspicious and they can't trust you anymore, right? Whereas if you do a pros and cons list, but at the top you say, "My recommendation is X, here's the pros and cons of that," or, "Here are some risks associated with it," or whatever, you're building trust with your reader, because you were direct in saying, "Here's my recommendation, here's what I'm advocating for, and also, here are some downsides to that."

    16. LRLenny Rachitsky42:38

        Right. This also reminds me of the, uh, Minto pyramid, which I won't get too deep into, but the concept there is, in business, you often wanna start with, "Here's my conclusion, and then here's, here's why," versus-

    17. WKWes Kao42:50

        Mm-hmm.

    18. LRLenny Rachitsky42:50

        ... "Here's all the things I've done, here's all of my thinking, here's all my con-... all my, kind of, data points, and then now here's my conclusion at the end of that."In business, people are like, "Sh- just I'm bored. Just tell me-"

    19. WKWes Kao43:01

        Yeah.

    20. LRLenny Rachitsky43:01

        ... "what you think we should do, and then, and then help me understand why you got there."

    21. WKWes Kao43:04

        The worst, which happens a lot, is mixing all of those things with the action item or decision. So the action items and decisions are kind of interspersed randomly throughout a bunch of context, thought process, factors that you looked at, downside. It's like, it's all just interwoven and so your reader doesn't know which parts are FYIs or which parts are kind of background versus what is the thing that you want their response on. Like, what are you asking them to chime in on and what is the decision that, that we are, we're actually trying to make? So if you do add, you know, all the thought process, I think splitting it up and making it clear that you're splitting it up makes it so much more helpful for your reader.

    22. LRLenny Rachitsky43:46

        Awesome. And we'll link to all this stuff in the show notes, so don't feel like you have

12. 43:50 – 47:32

    How to protect your bandwidth (without having to say no to your boss)

    1. LRLenny Rachitsky43:50

       to remember all this. Okay, so this is, uh, a good time to get to our fifth section and our fifth topic, which is around the skill of saying no. I feel like this is such an under-taught skill. I heard that Tim Ferriss was working on a book called The No Book where he was gonna share all the ways he's learned to say no, but I think he shelved it for whatever reason. And I, I need advice on this 'cause I'm often asked for favors of all kinds, and I am not amazing at saying no without being... Uh, I try to be really nice about it, and it takes time. (laughs) And so I could use advice here, so I'm curious to hear your advice on saying no.

    2. WKWes Kao44:28

       Yeah. Saying no does not come naturally for me either, as kind of a, a recovering people pleaser. So I've thought a lot about how to say no in ways that feel warm and respectful and, you know, respect the other person. So I think there's, there's, uh, there's different ways to say no depending on the situation and your relationship with that person. So within work, for example, you know, saying no to, to your cross-functional team member or to your manager, right? Like, that's very different than saying no to someone who doesn't know you on the internet who is DMing you asking you to, to help them with something. And so, you know, with saying no with people that you have, let's say, long term dynamics with, uh, continuing dynamics like a manager or friend, et cetera, I usually like talking about the trade-offs of something. So this is something that I learned from Alex Peck, my coworker at, at Alt MBA, who's now CEO of Alt MBA. He was always great at this. So when we worked together, he was my design counterpart, and I would ask him like, "Hey, can you, you know, can you design this for me? Can you design that?" And, "Oh, you know, here's another thing I'm gonna throw over the wall to you," and he was always so good at saying no in a way that (laughs) like, felt good for me, the person who just asked him to do something. And I just thought like, "That's pretty different." 'Cause usually when people say no, I'm a little irked or, you know, a little miffed. So I thought like, "What is Alex doing that, that I can borrow from?" And it turns out that, that Alex would always talk about trade-offs. And he'd say, you know, "Wes, y- yes I can design this PDF for you. That means that the thing that I was gonna work on today, which was redesigning, you know, this page on the site, will have to wait until later this week," or, "This means that, you know, I'm gonna be deprioritizing this other thing. Does that sound good to you, or, like, do you want me to, you know, prioritize the original design project you wanted me to work on?" You know? And so for me hearing that, it, it felt like I was in control and able to, to help, help him prioritize basically. So it, it kind of, it went from being a conversation about yes or no, are you a helpful person or are you not, are you a team player or are you not, into, hey, like, how do we make sure that the important, right things get done? You know? And so it was gr- it's great for the person who you're saying no to, and it's also great for Alex because whenever he, we had those conversations, I always thought that he was really thoughtful about making sure that the most important projects that we want to work on stayed prioritized. So it's kind of, it's a little bit of a workaround. So you're not exactly saying no, but you're talking about trade-offs, which gets the, the result of the no, right? You're getting the, the... The reason why you want to say no is we don't have bandwidth to take everything on, um, but we feel weird about saying no to people because we're afraid that people are gonna, you know, think we're not, we're not cooperative or whatever. So, so by talking about trade-offs, you really get the outcome, which is you protect your bandwidth. You protect your bandwidth, you protect your mental health, you protect your, you know, ability to do great work without feeling overly stretched without actually even having to say the word no, which I just think is amazing.

13. 47:32 – 48:24

    How Lenny sets priorities and communicates them

    1. WKWes Kao47:32

    2. LRLenny Rachitsky47:33

       This is, uh, a concept, uh, related concept that a manager once taught me, which is essentially the same idea, and she called it prioritize and communicate. And the idea here is someone gives you something to do that's, it's not already on your plate. There's kinda, uh, there's kind of a two by two you can imagine in your head. There's, you can just prioritize it amongst your priorities and not communicate what you did and where it sits, or you could just communicate and not prioritize and that just means like, "Sorry, I don't have time for this right now." What you should do is prioritize it, "Here, it's gonna sit in number three on my priority list," and communicate, "This is gonna be third on my priority list. Does this seem reasonable to you? Would you agree? Should I do this sooner or no?" And that's a really good way of dealing with exactly what you're talking about. And so it's a little framework

    3. WKWes Kao48:18

       I love that.

    4. LRLenny Rachitsky48:19

       ...

    5. NANarrator48:20

       that I like.

    6. WKWes Kao48:20

       I love a good two by two matrix.

    7. LRLenny Rachitsky48:21

       (laughs)

    8. WKWes Kao48:21

       And that is a fantastic one. (laughs)

    9. LRLenny Rachitsky48:23

       There we go.

14. 48:24 – 53:07

    Lightning round!

    1. LRLenny Rachitsky48:24

       Sweet. Anything else you wanna touch on that topic before we move to our very exciting lightning round?

    2. WKWes Kao48:29

       Let's do the lightning round.

    3. LRLenny Rachitsky48:31

       Okay, here we go. (laughs) I need some sound effects I think. (laughs) But anyway, until then, okay, so I'm gonna ask you five questions and just tell me whatever comes to mind.And we'll go through it pretty quick. Sound good?

    4. WKWes Kao48:42

       Okay. Yes.

    5. LRLenny Rachitsky48:43

       Okay. You already knew this was coming. What's the book that you recommend most, you've recommended most in the past few months?

    6. WKWes Kao48:49

       The two craft of writing books that I had mentioned.

    7. LRLenny Rachitsky48:52

       Can you just remind us real quick while we're on there?

    8. WKWes Kao48:54

       Yes. It was The Best of Sentences, it was The Worst of Sentences-

    9. LRLenny Rachitsky48:57

       What a great title by the way.

    10. WKWes Kao48:59

        ... by Jude Costa-Grande. Yeah, so good. And then Better Business Writing by Harvard Business Review or Harvard Business Press.

    11. LRLenny Rachitsky49:05

        Awesome. I gotta read these. Okay, number two, what's a movie or show that you've recently watched and loved that maybe people haven't heard of?

    12. WKWes Kao49:13

        There's a show called Doctor Foster on Netflix that's, I think it's on Netflix, might be on Prime, it's a British kind of drama, crime, thriller that's super good. I love kind of, uh, mystery thrillers, so I've pretty much watched every single one out there, but I feel like many people haven't heard of this one, so if you're into that, check it out. Let me know, let me know what you think.

    13. LRLenny Rachitsky49:36

        Okay, amazing. I have not heard of that. Great, great choice. Okay, so I know you've taken a lot of courses. I forget how many. I, I know that's, uh, you're a course addict. So I'm curious, what's been your favorite course that you've taken?

    14. WKWes Kao49:47

        I really love Suzie Batize's course called AliveOS. Suzie is the, the founder and former CEO of Poo-Pourri. She's now chairman of Poo-Pourri. She grew her business, I think she started Poo-Pourri in her late 30s or 40s after, after multiple bankruptcies and she created this amazing course that, it's hard to describe. It's kind of, it's kind of about mindset and overcoming internal blockers so it's a little bit, you know, on the softer side, but I feel like it, it was just amazing community, amazing exercises that you go through with your small pod. It led to some really big breakthroughs, including starting Maven as a company.

    15. LRLenny Rachitsky50:25

        Oh.

    16. WKWes Kao50:25

        So at the end of, of, at the end of that eight-week course, I was kind of debating, you know, should I, should I do this or should I not? And with my small group, I worked through it, talked a lot about, you know, just subconsciously how I was feeling about it and stuff and it was really good. So AliveOS by Suzie Batize.

    17. LRLenny Rachitsky50:41

        And it's still going?

    18. WKWes Kao50:42

        Yeah, yeah.

    19. LRLenny Rachitsky50:42

        Amazing.

    20. WKWes Kao50:42

        She was one of my clients when I was consulting and, yeah, she's amazing.

    21. LRLenny Rachitsky50:45

        Okay. We're gonna link to that. While we're on this topic, how many courses would you say you've taken?

    22. WKWes Kao50:49

        Taken and built, a lot.

    23. LRLenny Rachitsky50:51

        (laughs)

    24. WKWes Kao50:52

        Dozens. Dozens that have had hundreds of cohorts within, you know-

    25. LRLenny Rachitsky50:57

        Oh.

    26. WKWes Kao50:57

        ... each course. So-

    27. LRLenny Rachitsky50:57

        Yeah.

    28. WKWes Kao50:58

        Um, yeah.

    29. LRLenny Rachitsky50:59

        Okay.

    30. WKWes Kao50:59

        So lots of courses.

Episode duration: 53:07