Aug. 28, 2022

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

Wes Kao has worked with Seth Godin (where she co-founded the altMBA and served as executive director), David Perell on his Write of Passage course, Professor Scott Galloway on Section4, and Morning Brew. Currently, she’s the co-founder of Maven, a cohort-based learning platform where I taught my own course. Wes is passionate about telling stories that stay true to the creator’s intentions while keeping your audience listening. In today’s episode, you will learn how to use state changes to keep your audience engaged, how to communicate more clearly by focusing on the how more than the why, how to manage up for success, and how to communicate your priorities to set a boundary.

Where to find Wes Kao:

• Website:

• Twitter:

• LinkedIn:

Where to find Lenny:

• Newsletter:

• Twitter:

• LinkedIn:

Thank you to our wonderful sponsors for making this episode possible:

• Modern Treasury:

• Berbix:

• Makelog:


• The Super Specific How: How to make your cohort-based course more rigorous:

It Was the Best of Sentences, It Was the Worst of Sentences: A Writer’s Guide to Crafting Killer Sentences:

Guide to Better Business Writing (HBR Guide Series):

• Seth Godin’s blog:

The Minto Pyramid Principle: Logic in Writing, Thinking, and Problem Solving:

Doctor Foster:

• Suzy Batiz:

• Amanda Natividad’s Marketing 201 course:

• Dr. Marily Nika’s course:

In this episode, we cover:

[03:39] Wes’s early career

[07:08] How to land a job with Seth Godin

[09:56] What makes Seth Godin stand apart

[14:50] Wes’s framework for better writing: the super-specific how

[18:08] Writing and teaching without the BS

[21:45] State changes: how to keep your audience engaged when teaching

[25:51] The data of “eyes light up” moments

[29:27] What managing up can do for you

[32:51] How to manage up effectively

[34:17] Lenny’s template for proactive communication

[36:19] The skills you need to communicate clearly through writing

[43:50] How to protect your bandwidth (without having to say no to your boss)

[47:32] How Lenny sets priorities and communicates them

[48:24] Lightning round!

Production and marketing:

Get full access to Lenny's Newsletter at


Wes Kao (00:00):

I think that most people assume that their boss has to manage them and they feel a little bit resentful that, why should I manage my boss? They're getting paid more. They are my manager. They have more responsibility.

Wes Kao (00:14):

And you can continue to think that way and your career 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.

Lenny (00:36):

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 have ever met on the art of teaching and I've learned a ton from her.

Lenny (01:01):

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.

Lenny (01:36):

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Lenny (03:42):

Wes, I have 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.

Wes Kao (04:01):

Hey, Lenny. Great to be here.

Lenny (04:03):

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 brief, high level overview of your career and understand what made Wes the Wes that she is today.

Wes Kao (04:23):

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.

Wes Kao (04:39):

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 went to a bigger company and gradually have gone to smaller companies since then until finally starting my own in the past 15 years.

Wes Kao (04:55):

So I think that 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.

Wes Kao (05:11):

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.

Wes Kao (05:26):

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.

Wes Kao (05:42):

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.

Wes Kao (05:59):

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 cohort-based courses was something that was really special, that other experts in other industries, other functions could really leverage.

Wes Kao (06:19):

And then that led to starting Maven because when I was consulting and when I was doing altMBA, during those six, seven years, I realized how janky the tech stack was that everyone was 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.

Wes Kao (06:44):

And so when my co-founder Gagan Biyani and I got together, we were brainstorming what's the future of education and catching up. And we were just shocked that, hey, why hasn't anyone tackled this yet? We should do this because we both really believe that cohort-based courses are the future that [inaudible 00:07:02] 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.

Lenny (07:07):

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 an email every day and it's overwhelming, even though he pointed out in one of his newsletters, okay, just ignore it. Why would you be sad that I have so much content? But yeah, anyway I unsubscribed recently, but I'm such a fan. And so I'm so curious, one, how did you connect with him and how did that even happen? And then two, what is he like to work with?

Wes Kao (07:37):

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.

Wes Kao (07:57):

So he was 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 and 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.

Wes Kao (08:25):

And so the application required a video, so there was a written application and then there was a video. So Seth said, "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.

Wes Kao (08:39):

And I did my video in one take. Normally I would've done multiple takes for sure, but here I just thought there's a very little chance I'm going to 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 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.

Wes Kao (09:06):

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 over three years working together and starting the altMBA together.

Wes Kao (09:24):

So that's 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 I 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.

Lenny (09:55):

I love that.

Wes Kao (09:57):

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 that 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.

Wes Kao (10:22):

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 are so insight rich.

Wes Kao (10:39):

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. It's like you have time to curate what goes on your Twitter, your website. You have time to manicure this, what you want people to think of you, but when you are live, you're there with the person, 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.

Wes Kao (11:12):

So 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 a Seth reader. Because before I would read him and just do it, essentially, ship, put yourself out there, don't overthink it.

Wes Kao (11:34):

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 not cheap, but affordable or economical. Usually it's like, oh, you only get two of these or there's the trade-off between quality and speed, but we worked fast and we produced really great work.

Wes Kao (12:06):

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 ad tech startup and I thought, oh, I know what shipping fast is, I was at a startup.

Wes Kao (12:26):

And the speed that we shipped at Seth HQ was just beyond. 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 and I'm also kind of an obsessed person. I have an obsessive personality and I just loved how Seth was similarly obsessed. And so yeah, learned so much from him that I've taken with me obviously in building Maven now and everything that I do.

Lenny (13:12):

Wow. I've 10 more questions I'd love to ask about Seth Godin, but I should probably try to get him on the podcast. What a coup that would be. I have a sad story actually. I just remembered while you were talking, I saw him mentioned once that he replies to every email he gets. And so I emailed him because-

Wes Kao (13:30):

Just to check.

Lenny (13:31):

... I had such a crush. 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?" I was like, "Oh shit, I pissed him off.

Wes Kao (13:40):

So funny.

Lenny (13:40):

He hates me.

Wes Kao (13:43):

It's hilarious.

Lenny (13:44):

Oh man. Okay. Amazing. One last quick question. You also worked 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?

Wes Kao (14:00):

Yeah, I don't know about people disliking him. He definitely has spiky points of view, which I think are amazing. Yeah. So Section4, Scott Galloway's company was one of the first clients that I worked with after leaving altMBA, and I didn't work too closely with Scott. I worked really closely with his CEO, Greg Shove 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.

Lenny (14:27):

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 could call it the five big ideas from Wes Kao, concepts that you've shared in other places that you've touched on your writing and tweeting and things like that have struck and have stuck with me and I suspect many other people, and just go deeper on these ideas. Does that sound good?

Wes Kao (14:49):

Sounds great.

Lenny (14:51):

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?

Wes Kao (15:18):

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.

Wes Kao (15:44):

Unless what you're saying is truly controversial, a ground-breaker, 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?

Wes Kao (16:09):

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 talking about how communication is important for product managers. Most product managers already know that. That's pretty 101, it's pretty basic.

Wes Kao (16:29):

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 there're assertions and hypotheses that might not work, but you need to put something forward to get the team going. These are all elements of communication that are juicier and more specific than just saying, here's why communication is important.

Lenny (17:02):

So a lot of it is cutting the backstory basically and just get right to the meat of it.

Wes Kao (17:06):


Lenny (17:09):

Ever since you wrote that, I'm like, this is why a lot of my writing seems to work because I try to cut the intro as much as possible and just get right to the meat of it.

Wes Kao (17:18):

I find 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 this gas station.

Wes Kao (17:48):

No one cares about all that. Start right before your friend left a Clif Bar out in their tent and you all almost got mauled by a bear. Get to the juicy part. And serve a little bit of context right before you get to the juicy part, but that's the idea of start right before you get eaten by the bear is cut out all that backstory scope creep.

Lenny (18:09):

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

Wes Kao (18:16):


Lenny (18:16):

Can you speak to that?

Wes Kao (18:18):

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 articles. It's basically situations that are one directional where people can't really challenge what you're saying. Keynote speech is another great one for lots of room for BS. So those are situations that they're more one directional.

Wes Kao (18:49):

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 counter points, and so there's more room for BS, right? The format encourages or allows it. Let's say it allows it.

Wes Kao (19:09):

But as you move up the triangle of 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.

Wes Kao (19:37):

So if you think about a webinar or a keynote talk or a book, you say the thing and that's it, but in a cohort-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 X, Y, Z reasons." And so you have to be able to defend what it's that you're saying and make sure that what you're saying is rigorous.

Wes Kao (20:07):

And I think that thinking about that content hierarchy of BS 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. 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 nuance in the hierarchy, but in general, as you move up that hierarchy, there's less and less room for BS.

Lenny (20:40):

I think this framework explains a bit why Twitter's so cringe to a lot of people is these threads that just sounds 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.

Lenny (20:52):

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." 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 because there's so much time that you have to cover. And so you can't 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.

Lenny (21:21):

And then to your point, people are going to ask questions and you're like, "Oh, shit, that's all I got. I have nothing more to add." That's not going to cut it. And so I totally agree. 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 go deep on something. So I love that concept.

Lenny (21:41):

Anything else you want to add on that idea before we move on to the next concept?

Wes Kao (21:44):

Let's go. Next concept.

Lenny (21:45):

Okay, let's do it.

Wes Kao (21:46):

Let's do it.

Lenny (21:47):

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 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 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?

Wes Kao (22:14):

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.

Wes Kao (22:42):

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 in that Brady Bunch grid and switch over to screen share, to share something and then switch back.

Wes Kao (23:07):

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 someone shares out and they popcorn to the next person to the next person.

Wes Kao (23:22):

So all these are examples of state changes that help your audience stay engaged with the material that you are presenting. And it's really in reaction to monologues. I'm kind of imagining Salesforce with their no software sticker. If you think about no monologues, try to avoid monologues as much as possible because that puts your audience to sleep.

Lenny (23:46):

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?

Wes Kao (23:56):

So we talked 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. Before you reveal something, you can ask, what do you all think? Go ahead and guess.

Wes Kao (24:13):

So in the Maven Course Accelerator, the two week course that I teach on how to build a cohort-based course, it's very meta, I will ask people, so what do you think the average attention span is for students? So I could have just told people it's X, but anytime, when you want to just share a piece of information, that's an opportunity for a potential state change.

Wes Kao (24:35):

Have people guess. 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 ask people to guess, and then the answers range from an hour or 45 minutes to three seconds. So it's just all over the place. The answer's two to four minutes, according to some research. So that's a ripe opportunity for state change.

Wes Kao (25:00):

And the other way to think about it, I was talking to Nathan Barry from ConvertKit, he was saying that he loves stage 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 stage change.

Wes Kao (25:17):

We really want to turn this from an art into a science, as much as possible, audience engagement. And if you just force yourself to look through your own material and say, "Oh, 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 those intervals, you'll find something that lends itself really well to a state change.

Lenny (25:37):

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.

Wes Kao (25:47):

Love it. Yes.

Lenny (25:49):

Okay. We're pros. Okay, I'm going to try to practice this lesson live. There's also this concept that you touch on, I think it's called eyes light up concept or something like that.

Wes Kao (25:58):


Lenny (25:59):

Okay, cool. Can you speak to that, because I think it relates to this idea of state change in meetings?

Wes Kao (26:03):

Yeah. So the idea behind what I call eyes lighting up is that 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 and they'll say, "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.

Wes Kao (26:31):

So you, as the presenter, as the salesperson or whatever, that's pitching, you want to make note of the moments when people's eyes light up because their face can't lie. They can say, "Oh yeah. Okay, that's interesting." It's easy to 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.

Wes Kao (26:54):

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 key word or this phrase or I explained something this way and all of a sudden, their face change or demeanor change, they're leaning forward, they're wanting to catch what you're saying, that's all data.

Wes Kao (27:27):

So really the principle behind eyes light up is don't be delusional in just taking people's, what they're saying at face value. Really look at their face, look for other clues, the excitement in their voice and watch for these different eyes light 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 you 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.

Lenny (27:57):

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

Wes Kao (28:05):

Or when are times 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.

Lenny (28:17):

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 share this thing, maybe spent a little more time on that idea.

Wes Kao (28:38):

I think it absolutely works for meetings. I think it works for internal meetings, for conversations, even with your cross-functional team members, with your boss, with your direct reports. Usually as you're explaining something, you can tell when even your manager is like, "Oh yeah, that." Or you can tell there's more energy in the response for certain parts.

Wes Kao (29:01):

And when you think about it, you can find patterns of, oh, usually, when I share things with this person, 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 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. Whatever angle it is, it really gives you great data that you can lean into and flesh out more.

Lenny (29:28):

You mentioned your manager and that's a really good segue to our next topic, which is around managing up.

Lenny (29:35):

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.

Lenny (29:47):

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 PopSQL use Makelog.

Lenny (30:09):

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, to get started.

Lenny (30:39):

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?

Wes Kao (31:01):

Great questions. I think that most people assume that their boss has to manage them and they feel a little bit resentful that, why should I manage my boss? They're getting paid more. They are my manager. They have more responsibility. And you can continue to think that way and your career 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 (31:38):

And I think more people are realizing that, hey, as an individual contributor, or even as a manager, we all have bosses. So 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.

Wes Kao (31:58):

And I think some people think that senior people don't need to manage up like, oh, once I'm a director of VP, I don't need to manage up anymore, it's only something I need to do when I'm a coordinator or 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.

Wes Kao (32:29):

They're great at keeping their bosses in the loop on what's happening so their bosses, aren't constantly having to ask and 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? 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.

Lenny (32:52):

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

Wes Kao (32:58):

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 are working on. It feels almost blase like, well, duh, 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. 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.

Wes Kao (33:32):

And then thinking about the right level of context to give them, is this a reversible decision or is this one that is irreversible or difficult to reverse or expensive to reverse? Using your sense of judgment so that you're not necessarily going to your boss for everything and telling them everything. 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 to 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?

Lenny (34:19):

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.

Lenny (34:44):

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 about what you're doing, make sure you're aligned on priorities, make sure things are getting unblocked, and also just avoid surprise as much as possible. And so there's a little tip.

Wes Kao (35:00):

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, unless you're surprising me by bringing me a snack or something, don't surprise me. Actually, in my personal life too, 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.

Lenny (35:27):

I like that general rule, avoid surprises, except for birthday parties and milestones. That also touches on just a 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." 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.

Wes Kao (35:51):

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. You think you're over communicating, but to the recipient, it's actually just the right amount. And I've been surprised by how I thought everyone was aligned on a certain strategy or that, oh, we've already talked about this thing three times and then realized that, oh, we actually weren't as aligned as I thought.

Wes Kao (36:18):

So erring on 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 helps people spend their time well.

Wes Kao (36:34):

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 think about this. But if they already agree with the decision and know that context, then they don't need to keep reading.

Lenny (36:56):

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.

Lenny (37:11):

Although one student used that format with a potential customer where they started off being bottom line, here's where we're at and they were like, "Man, that's aggressive." And so I had to adjust that to be a little softer. Okay.

Lenny (37:26):

So 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?

Wes Kao (37:55):

I think a lot of people learn writing from mimicking other people and 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 off of social. So one of the books that I've been recommending, I think I'm jumping ahead to potentially a lightning round question, but-

Lenny (38:23):

Not allowed.

Wes Kao (38:25):

... it's a book called It Was the Best of Sentences, It Was the Worst of Sentences by June Casagrande, 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 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.

Wes Kao (39:00):

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.

Wes Kao (39:21):

It was about an offsite that we have coming up and she talked about whether we should change a WeWork location, something like that. So this is actually super useful, tactical stuff for Slack messages, if you're DMing someone, if you're texting someone, you can use these principles basically everywhere.

Wes Kao (39:37):

And so it was a Slack message about changing WeWork 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 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.

Wes Kao (40:03):

And so it turned out that she was 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 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 that paragraph?

Wes Kao (40:26):

I know it's not quite a soundbite, but I see this a lot in people's writing is that there's these either sentence structures that add more cognitive load to the reader or have a little bit of confusion, and it's a technical issue actually. It's like the which or some clause explains something directly before it, but they actually meant for that clause to describe something 10 words before at the beginning of the sentence, right?

Wes Kao (40:53):

It's 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.

Lenny (41:29):

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." And it helped a lot.

Wes Kao (41:51):

I love that. And I think 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 or objectively talking about them.

Wes Kao (42:09):

So when you do a pros and cons list, but they're skewed and you are leaving some things out of the cons list, it makes the reader suspicious and they can't trust you anymore, 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 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."

Lenny (42:38):

Right. This also reminds me of the mental 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 why, versus here's all the things I've done, here's all my thinking, here's all my data points, and then now here's my conclusion at the end of that. In business, people are like, "I'm bored. Just tell me what you think we should do and then help me understand why you got there."

Wes Kao (43:04):

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 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 we're actually trying to make? So if you do add 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.

Lenny (43:46):

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 good time to get 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 going to share all the ways he's learned to say no, but I think he shelved it for whatever reason.

Lenny (44:11):

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.

Wes Kao (44:28):

Yeah. Saying no does not come naturally for me either as a recovering people pleaser. So I thought a lot about how to say no in ways that feel warm and respectful and respect the other person. So I think there's different ways to say no, depending on the situation and your relationship with that person.

Wes Kao (44:50):

So within work, for example, saying no to your cross-functional team member or to your manager, 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.

Wes Kao (45:05):

And so with saying no with people that you have, let's say long term dynamics with, continuing dynamics, like a manager or a 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.

Wes Kao (45:27):

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.

Wes Kao (45:51):

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, will have to wait until later this week." Or, "This means that I'm going to be deprioritizing 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?"

Wes Kao (46:21):

And so for me hearing that it felt like I was in control and able to help him prioritize, basically. So 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, how do we make sure that the important right things get done?

Wes Kao (46:43):

And so it's great for the person who you're saying no to and it's also great for Alex because whenever 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.

Wes Kao (46:56):

So it's a little bit of a work around. So you're not exactly saying no, but you're talking about trade-offs, which gets the result of the no. The reason why you 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 think we're not cooperative or whatever.

Wes Kao (47:16):

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 ability to do great work without feeling overly stretched, without actually even having to say the word no, which I just think is amazing.

Lenny (47:33):

This is a concept or a 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 not already in your plate, there's 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 going to sit in number three in my priority list, and communicate it, this is going to be third on 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 that's the little framework [inaudible 00:48:19]-

Wes Kao (48:18):

I love that. I love a good two-by-two matrix and that is a fantastic one.

Lenny (48:23):

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

Wes Kao (48:30):

Let's do the lightning round.

Lenny (48:31):

Okay. Here we go. I need some sound effects, I think, but anyway, until then. Okay, so I'm going to ask you five questions and just tell me whatever comes to mind and we'll go through it pretty quick. Sound good?

Wes Kao (48:43):

Okay. Yes.

Lenny (48:44):

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

Wes Kao (48:50):

The two craft of writing books that I had mentioned.

Lenny (48:52):

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

Wes Kao (48:54):

Yes. It Was the Best of Sentences, It Was the Worst of Sentences by June-

Lenny (48:58):

What a great title by the way.

Wes Kao (48:59):

... Casagrande. Yeah, it's so good. And then Better Business Writing by Harvard Business Review or Harvard Business Press.

Lenny (49:06):

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.

Wes Kao (49:13):

There's a show called Doctor Foster on Netflix. I think it's on Netflix, it might be on Prime. It's a British kind of drama, crime thriller that's super good. I love 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.

Lenny (49:36):

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 you're a course addict. So I'm curious, what's been your favorite course that you've taken?

Wes Kao (49:47):

I really love Suzy Batiz course called Alive OS. Suzy is 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 multiple bankruptcies. And she created this amazing course that it's hard to describe. It's kind of about mindset and overcoming internal blockers.

Wes Kao (50:12):

So it's a little bit on the softer 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, including starting Maven as in the company. So at the end of that eight week course, I was debating, should I do this or should I not? And with my small group, I worked through it, talked a lot about just subconsciously how I was feeling about it and stuff. And it was really good. So Alive OS by Suzy Batiz.

Lenny (50:41):

And it's still going?

Wes Kao (50:42):

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

Lenny (50:45):

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

Wes Kao (50:49):

Taken and built? A lot, dozens. Dozens that have had hundreds of cohorts within each course, so yeah.

Lenny (50:59):

Wow, okay. That's a lot.

Wes Kao (50:59):

So lots of course.

Lenny (51:00):

It's an expensive hobby.

Wes Kao (51:01):

I love that you said course addict.

Lenny (51:02):

Okay, what's your favorite Maven course right now to give a little plug to Maven?

Wes Kao (51:08):

Ooh, probably Amanda Natividad's course on content marketing. It's called Content Marketing 201. Or, I haven't taken this, but I've heard really good things about Marily 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 course is fantastic.

Lenny (51:30):

Awesome. Okay. Final question, what's your least favorite fruit?

Wes Kao (51:33):

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.

Lenny (51:41):

Wow. A surprising answer. Very contrarian.

Wes Kao (51:43):

Oh, okay.

Lenny (51:43):

You're just like-

Wes Kao (51:46):

I love that, that's my most contrarian spiky point of view is that I dislike grapes.

Lenny (51:49):

Might just be. It's just like a explosion of flavor and sugar. Okay, well, we've reached the end of our chat. Wes, if it wasn't obvious, this was incredibly fun. I had so much fun chatting and learning from you. Two final questions. Where can folks find you online, learn more about you and or Maven, and then how can listeners be useful to you?

Wes Kao (52:08):

You can find me at @MavenHQ on Twitter, or at, or @wes_kao and 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 to week course that teaches you everything that you need to know about building a course.

Lenny (52:31):

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

Wes Kao (52:42):

Thanks Lenny.

Lenny (52:44):

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 See you in the next episode.