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

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 going to get more opportunities. you're going to have more trust with them. There's all these great things that happen when you decide to manage up.

Wes Kao is the co-founder of Maven, a cohort-based learning platform that I use to create my own course on product management. But even more interestingly, she's helped folks like Seth Godin start his alt MBA 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 Calm. 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, fiat crypto on-ramps, ride-sharing marketplaces, instant lending, and more. They work with high-growth companies like Gusto, Pipe, ClassPass, and Marketo. 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 $3 billion 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 moderntrasury.com this episode is brought to you by Burbix. Whether you're in the business of crypto or renting out vehicles or 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 VeriCred, businesses can quickly and easily verify someone's identity through their government-issued ID and real-time selfie. Unlike other identity verification software solutions, VeriCred takes only seconds to verify an identity, helping you maximize conversion and mitigate fraud. With VeriCred, 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 user session location. Get started quickly by setting up VeriBIX with no code, low code, or complete integration in as little as one afternoon. Visit veribix.com/start to get started. That's B-E-R-B-I-X.com/start. 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.

Hey, Lenny, great to be here.

It's my pleasure. So just to set a little context about the West 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 West the West that she is today.

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. 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 bigger company and gradually have gone to smaller companies since then until finally starting my own in the past 15 years. So I think that the Getting to see inside what a company that's been around for 40 plus years was like was really, really fantastic training and set me up for success for jumping into tech 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 bestselling 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 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. So it was just an amazing, amazing experience. And then after that, I consulted for a couple of 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. and then that led to starting Maven. Because when I was consulting and when I was doing all 10 BA, 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 creators needing to toggle between half a dozen different tools just to make a live plus async course be able to work. And so when my co-founder Gagan, Bhavya, and I got together, we were brainstorming, you know, what's the future of education 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 going to 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. Awesome. 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 it's overwhelming, even though he pointed out in one of his newsletters, like, okay, just ignore it. Why would you be sad that if so much content? But anyway, unsubscribed. 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 does he like to work with? 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 at that ad tech company in San Francisco. And I thought there are probably thousands of people who are going to 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, in California at some time wants to move to New York. And so I thought, all right, I'm going to toss my hat in the ring and not overthink it. And so the application required a video. So there's written application and there's 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. 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 a very little chance I'm going to get this. And a couple of 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, because he's asked, Hey, loved your video. Let's hop on a call for an interview. and of course I 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 called Hastings on Hudson. And what initially started off as a six month role eventually led to over three years working together and starting the Alt 10 Bay 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. Don't reject yourself, basically. 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 it just shouldn't apply. If I don't have time to take five takes of this video, 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 putting your foot forward.

I love that.

Yeah, so that was how we got connected. And then in terms of what it was like working with him, I think the Seth that people know externally can sometimes be different from the behind the scenes Seth. And I think that's true for all of us, by the way. And so I think externally he can sometimes be a little bit of a vague Buddha, if you will. He gives great inspiring advice. His insights, I think, are amazing. 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. That is incidental that they are short and daily. The reason why it works is because they're so insight rich. And in person, he is even smarter and even sharper than he is in 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 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 genuine someone is. And I think 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 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. I think the speed that we shipped before, I was at a Sequoia backed at Techstars and I thought, oh, like I know what shipping fast is, like I was at a startup, you know, and, and the speed that we shipped at, at Seth Hui was just, beyond. Like it just blew away what I think normal people think of as fast, but it was also still so good. And so I think that rigor and that refusal to accept anything but excellence was just so awesome. And it really spoke to me because I care a lot about craft. I think more people should care about craft. 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.

Wow. I have, I have 10 more questions I'd love to ask about Seth Cohned, but I should probably try to get him on the podcast. What a, what a coup that would be. I have a Seth story actually, I just remembered while you were talking, I I saw him mention once that he replies to every email he gets. And so I emailed him because I was such a- Just a check. I had such a crush. Yeah, just a chest. 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? I was like, oh shit, I piss people off. It's so funny.

He hates me.

It's hilarious. Oh man. Okay. Amazing. One last quick question. You also work with Scott Galloway, 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 he like? And why do people dislike him so much on Twitter?

I don't know about people disliking him. He definitely has spiky points of view, which I think are amazing. Yeah. So section four, Scott Gallopy's company was one of the first clients I worked with after leaving AltMBA. And I didn't work too closely with Scott. I worked really closely with with his CEO, Greg Shav and their exec team to design the sprint that's now their go-to course format. But yeah, I didn't work too closely with him directly.

Okay, cool. We won't get too deep there. Okay. So what I want to do with most of the time that we have together is to go into five big ideas. You call it five big ideas from West Cow concepts 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?

Sounds great.

Awesome. So the first idea I want to chat about is something you call 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?

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 truly controversial, groundbreaking, or new to your audience, you don't need to spend too much time elaborating 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 then just saying, you know, here's, here's why communication is important.

Yeah. So a lot of it is cutting the back story basically, right? And just like get right to the meat of it. I found that exact, yeah, 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.

Yeah, I find that 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. And the idea is that if you're telling a story about camping, don't start talking about going to REI to buy a Patagonia jacket and then booking the campsite and the website had difficulties. And on the drive over, we stopped by the gas station. I think no one cares about all that, right? Like start right before, you know, your friend left a cliff 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 we get to the juicy part. But that's the idea of start right before you get eaten by the bear. It's cut out all that backstory scope creep.

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. can you speak to that? 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. So those are situations that, you know, they're more one directional with Twitter at least. It's 200 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, the content hierarchy of BS, there's less and less room for BS. So long form in-depth articles, less room for BS. 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. If you think about a webinar, a keynote talk, or a book, you kind of say the thing and that's it. But in a core-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, if you're saying something that doesn't really make sense, there could be a whole conversation happening in Zoom chat saying, this doesn't make sense for XYZ reasons. And so you have to be able to defend what it is that you're saying and make sure that what you're saying is rigorous. And I think that thinking about that content here, BS is, is great for holding ourselves to a higher standard to make sure that we are not allowing ourselves to spew BS just because a 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.

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 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 again, just like, here's a wise thought. Let's move on. 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. You're like, oh shit, I don't, that's all I got. I have nothing more to add. That's not gonna cut it. And so I totally agree that, and that's why courses I think are so powerful and probably 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?

Let's go. Next concept.

Let's do it.

Let's do it.

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 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?

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 camera's on, you're sitting, you have to sit still, look straight ahead at the camera, control your face, and make sure you look focused. And so it's really not surprising that most people find that very draining. 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 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.

What are examples of different states? You mentioned breakouts, chat, what other sorts of things can you do, especially on a Zoom, let's say, for running a meeting?

Yeah. So we talk about breakouts, Zoom chat, 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 you reveal something, you can ask, what do you all think? Go ahead and guess. So, you know, in the Maven course accelerator, the two week course that I teach on how to build a core 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 have just told people, like it's X, right? But anytime 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 remember and also just interact with your material. So I asked people to guess, and then the answers range from an hour or 45 minutes to three seconds. So it's all over the place. The answer is two to four minutes, according to some research. So that's a ripe opportunity for state change. And the other way to think about it, I was talking to Nathan Barry from ConvertKit. He was saying that he loves 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 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 in the last couple of minutes? If not, go ahead 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.

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

Love it. Yes.

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

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 salesperson, whatever that's pitching, you want to 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 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 so many of us, We like to pretend that, oh, I don't get enough data from people and this person said this, but what do they really mean? And really, I think that we're just being delusional. If we just acknowledge reality and this person looks bored, they look bored. That is data. Don't ignore that data. And then, oh wait, there, I said this hot keyword or this phrase, or I explained something this way, 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 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 excitement in their voice and watch for these different eyesight up moments because those are great fodder for content that you might want to write about for the angle of your sales pitch, for how you might want to explain something in the future and really cut out all the parts that make people go dead in the eyes and just say the parts that make their eyes light up.

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

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

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 share this thing, maybe spend a little.

More time on the idea. I think it absolutely works for meetings. I think it works for internal meetings, for conversations. When you're explaining something, you can tell when you, 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 the response for certain parts. And when you think about it, you can find patterns of, oh, 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 into and flesh out more.

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 changelog posts that slow you down. Just quick, quick and easy updates that keep your users informed and happy. Try Make Log for free today. Just visit makelog.com/lenny to get started. I think your most popular tweet you've ever tweeted 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 there's a lot of interest in this topic. And so I want to ask you, why is managing up important? Why are people not doing it well? And how do you manage up effectively?

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 going to get more opportunities. You're going to have more trust with them. There's all these great things that happen when you decide to manage up. And I think more people are realizing that, hey, as an individual contributor or 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. There's no point in seniority where, as you climb the career ladder, that it just doesn't matter anymore. And I think some people think that senior people don't need to manage up. Like, oh, once I'm a director or VP, I don't need to manage up anymore. It's only something I need to do when I'm a coordinator or, 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 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 do 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 to manage up.

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

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 actually, I think we all know that we should do that, but the way that we execute, 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 what you're doing and to be able to give feedback, I think that's super, super important. And then thinking about the right level of context, to give them, right? Does your boss, is this a reversible decision or is this one that is irreversible or difficult to reverse or expensive to reverse, right? 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 want it 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 know that I've gotten it taken care of?

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 what you're doing. Make sure you're aligning priorities. Make sure things are getting unblocked and also just avoid surprise as much as possible. And so there's a little tip.

I love that. I think the avoiding surprises is great. I think in the 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 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 just catches them off guard is good.

I like that general rule, avoid surprises except for birthday parties and milestones. Yeah, that also touches on just the general rule I have of working is just over communicate. I find nobody's ever like, just Lenny shut up. I don't want to 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 always goes a long way.

Yeah, I find especially in remote work too, erring on the side of over communicating is just it ends up being the right level of communication. Like you think you're over communicating, 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 airing on the side of over communication 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 TLDR, if you will, the gist, and then I'll say context colon, 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.

I actually taught that format in my course. I think it was rooted in the military where they're just like, 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 one student used that format with a potential customer where it started off being bottom line, here's where we're at. And they're like, man, that's aggressive. And so I had to adjust that to be a little softer. Okay. So I was gonna, I had this beautiful segue, but 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 can you share?

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 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 lightning round question, but not allowed. 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, writing, et cetera. And I recommend those two books usually to new team members who join because they cover more of 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 there's a point of view baked in, but you don't want it to be an accidental point of view. I was just talking 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 about an offsite that we have coming up. And she talked about whether we should change, you know, we work location, 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 texting someone, like you can use these principles basically everywhere. And so she was, you know, it was a Slack message about changing work locations. And the way that she had phrased it, the obvious conclusion was, oh, well, we should just stick with our current one. And so I asked her, is that your recommendation? Because if it is, then great, because you're kind of leading the reader to that conclusion. But if it's not, you're asking a leading question that is skewing the results of this question. And so it turned out that she was kind of open. She didn't really have an opinion, and so we thought, 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 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 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 witch or some clause explains something directly before it, but they actually meant to, you know, meant for that clause to describe something, you know, 10 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 technical aspects of writing and the craft of writing really well. and I guess my spiky point of view is that more people should learn the craft of writing and the technical aspects of writing, not just 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.

Got it. I actually got that same feedback that you gave this person once when I clearly had an opinion on what we should do as a team. And I gave pros and cons and it was 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.

Yeah. I love that. And I think going, you know, pulling on the thread a little bit, it's because pros and cons lists, 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 pros and cons of that, or here's some risks associated with it, 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. Right. This also reminds me of the Minto Pyramid, which I won't get too deep into, but the concept there is in business, you often want to start with, Here's my conclusion. And then here's, here's why versus here's all the things I've done. Here's all my thinking. Here's all my, all my kind of data points. And then now here's my conclusion at the end of that. And business people are like, just, I'm bored. Just tell me what you think we should do. And then, and then help me understand why you got there.

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. Awesome. And we'll link to all this stuff in the show notes, so don't feel like you have to remember all this. Okay, so this is a, 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 Note Book. Where he was going to share all the ways he's learned to say no. But I think he shelved it for whatever reason. And I need advice on this because I'm often asked for favors of all kinds and I am not amazing at saying no without being, I try to be really nice about it and it takes time. And so I could use advice here. So I'm curious to hear your advice on saying no.

Yeah, saying no does not come naturally for me either as kind of a, a recovering people pleaser. So I 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 a, 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 help them with something. And so, you know, with saying no with people that you have, let's say long term dynamics with 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 AltMBA, who's now CEO of AltMBA. 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 design this for me? Can you design that? And oh, here's another thing I'm going to throw over the wall to you. And he was always so good at saying no in a way that felt good for me, the person who just asked him to do something. And I just thought, that's pretty different. Because usually when people say no, I'm a little irked or a little miffed. So I thought, what is Alex doing that I can borrow from? And it turns out that Alex would always talk about trade-offs. And he'd say, Wes, yes, I can design this PDF for you. That means that the thing that I was going to work on today, which was redesigning this page on the site, we'll have to wait until later this week. Or this means that I'm going to be de-prioritizing this other thing. Does that sound good to you? Or do you want me to prioritize the original design project you wanted me to work on? You know, and so for me hearing that, it felt like I was in control and able to help him prioritize basically. So 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's great for the person who you're saying no to, And it's also great for Alex because whenever we have 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 result of the no, right? You're getting the, the reason why we want to say no is we don't have bandwidth to take everything on, but we feel weird about saying no to people because we're afraid that people are going to, 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.

This is a concept or related concept that a manager once taught me, which is essentially the same idea. And she called it proritize and communicate. And the idea here is someone gives you something to do that's, it's not already in your plate. There's kind of, there's kind of a two by two. You can imagine 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 going to sit in number three in my priority list and communicate. This is going to be third in my priority list. Does this seem reasonable to you? Would you agree? Should I do this sooner or not? And that's a really good way of dealing with exactly what you're talking about.

And so it's a little framework. I love that. I love a good two by two matrix.

And that is a fantastic one. There we go. Sweet. Anything else you want to touch on that topic before we move to our.

Very exciting lightning round?

Let's do the lightning round. Okay. Here we go. I need some sound effects, I think. 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? Okay. You already knew this was coming. What's the book that you recommend most? You've recommended most in the past few months.

The two craft of writing books that I mentioned.

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

Yes. It was the best of sentences. It was the worst of sentences. What a great title. Casagrande. Yeah. So good. And then. Better Business Writing by Harvard Business Review.

Or Harvard Business Press. Awesome. I got to 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? There's a show called Dr. 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 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 what you think.

Okay. Amazing. I have not heard of that. Great choice. Okay. So I know you've taken a lot of courses. I forget how many. I know that's a you're a course addict.

So I'm curious, what's been your favorite course that you've taken? I really love Susie Batis's course called Alive OS. Susie is the founder and former CEO of PooPari. She's now chairman of PooPari. She grew her business. I think she started PooPari in her late 30s or 40s after multiple bankruptcies. And she created this amazing course that it's hard to describe. It's kind of about mindset and overcoming internal blockers. So it's a little bit on the software side, but I feel like it was just amazing community, amazing exercises that you go through with your small pod. It led to some really big breakthroughs. I'm going to link to that.

While we're on this topic, how many courses would you say you've taken?

Taken and built a lot, dozens, dozens that have had hundreds of cohorts within, you know, each course. So, yeah, yeah.

Okay.

Lots of courses that you said course addict.

So, yeah. Okay. What's your favorite Maven course right now to give a little plug to Maven?

Oh, probably Amanda Nidivdad's course on content marketing. It's called Content Marketing 201. I haven't taken this, but I've heard really good things about Mirali Nika's course on breaking into technical product management. She's a technical PM with a PhD at Meta right now. She was at Google before. Her courses, fantastic.

Awesome. Okay, final question.

What's your least favorite fruit? Probably grapes. But when they're frozen, they're kind of like little popsicles, so they're not too.

Bad when they're frozen, but probably grapes.

Wow. And it's a surprising answer. Very contrarian. Oh, okay.

I love that that's my most. Maven HQ.

You can find me at MavenHQ. on Twitter or @maven.com or @weskao and weskao.com and in terms of listeners, if any of you are interested in creating your own course and sharing your expertise and your knowledge online, definitely check out our Maven Course Accelerator. It's a free two-week course that teaches you everything that you need to know about building a course.

What a founder pitching the company Twitter handle versus her own. Wes, thank you so much for being here. It's a blast. and I'm excited for people to listen to this.

Thanks, Lenny.

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.