Aug 28, 2022 · 53m · lennys-podcast
Persuasive communication and managing up | Wes Kao (Maven, altMBA, Section4)
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this interview, educator and Maven co-founder Wes Kao breaks down actionable frameworks for persuasive workplace communication, strategic upward management, and engaging cohort-based education. She shares tactical techniques to cut irrelevant backstory, structure written arguments with bottom-line clarity, manage audience attention, and negotiate trade-offs effectively.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Lenny holds 30.9% of the talking time here. How this is scored →
Lenny as informed peer 4.2 Guest teaching 5.2 Guest disagreement 1.2 Lenny pushing back 0.2
speaking balance: gold is Lenny, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 26:55 Rejecting polite feedback as delusion
Wes forcefully challenges listeners who ignore audience body language, calling it delusional to rely on polite verbal agreement when facial expressions reveal boredom.
Hardest push from Lenny ▶ 28:35 Questioning 'eyes light up' utility in meetingsLenny pushes back gently on Wes's framework, wondering whether reading 'eyes light up' cues is actually applicable in ordinary internal meetings compared to sales or teaching.
Biggest teaching moment ▶ 18:20 The Content Hierarchy of Bullshit breakdownWes articulates why low-friction broadcast media allow unvetted assertions, educating the host on how interactive cohort courses force rigorous thinking.
Lenny holds their own ▶ 34:19 Lenny's 'State of Lenny' management systemLenny demonstrates his own operational expertise by detailing the structured 3-part weekly email template he used to manage up and prevent organizational surprises.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Lenny as informed peer | Guest teaching | Guest disagreement | Lenny pushing back | Why |
|---|---|---|---|---|---|---|
| Wes Kao's Career Journey and Founding Maven | 3 | 4 | 0 | 0 | Lenny opens by setting context around Wes's career path. Wes walks through her foundational background from Gap to Seth Godin and co-founding Maven without any conflict. | |
| Working with Seth Godin and AltMBA High Standards | 3 | 5 | 1 | 0 | Wes breaks down what working with Seth Godin is really like, dispelling surface assumptions about his daily blogging and explaining their refusal to compromise on speed versus quality. | |
| Seth Godin Email Anecdote and Scott Galloway Collaboration | 5 | 5 | 1 | 0 | Wes explains 'the super specific how' and her 'eating by the bear' storytelling framework. Lenny validates the framework with his own newsletter writing experience. | |
| The Content Hierarchy of Bullshit | 4 | 6 | 2 | 1 | Wes defines the 'Content Hierarchy of Bullshit', explaining why short-form content enables shallow ideas while cohort courses force accountability. Lenny adds his PM course experience to reinforce her point. | |
| Big Idea 2: The State Change Method in Meetings and Talks | 4 | 6 | 1 | 0 | Wes presents the state change method for presentations and Zoom meetings. Lenny enthusiastically attempts to apply it live by breaking the fourth wall with the podcast audience. | |
| The Eyes Light Up Concept: Reading Audience Signals | 3 | 6 | 2 | 1 | Wes discusses watching for 'eyes light up' moments as objective audience feedback and warns against being delusional about polite responses. Lenny questions its applicability in internal meetings, which Wes expands upon. | |
| Sponsor Message: MakeLog | 6 | 5 | 1 | 0 | Wes and Lenny discuss managing up and proactively communicating context. Lenny offers his own concrete system ('the state of Lenny' weekly email) and military communication framing. | |
| Big Idea 4: The Craft of Writing and Clear Thinking | 5 | 6 | 2 | 0 | Wes argues for studying the mechanical craft of sentence construction rather than copying Twitter templates, sharing an example of fixing a leading Slack message. Lenny connects this to the Minto Pyramid Principle. | |
| Big Idea 5: The Skill of Saying No via Trade-offs | 6 | 5 | 1 | 0 | Wes shares Alex Peck's trade-off technique for saying no constructively. Lenny matches her insight with a 2x2 matrix framework on prioritizing versus communicating. | |
| Lightning Round: Books, Shows, Courses, and Contrarian Views | 3 | 4 | 1 | 0 | A relaxed lightning round covering book recommendations, niche thriller series, AliveOS course experience, and Wes's contrarian dislike of grapes. |
Statements from this episode (16)
Kao: altMBA expanded to thousands of students across 45 countries
“Together we co-founded the Alt MBA, 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.”
Kao: Cohort-based courses are the future of education
“We both really believe that core based courses are the future that we're 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.”
Kao: Godin's Blog Succeeds on Insight Density, Not Posting Frequency
“Some people try to copy Seth's blog by writing short daily posts, but that is not the reason why Seth's blog is so good, right? That, that is incidental that they are short and daily. They're the reason why it works is because they're so insight rich”
Kao: Writers and instructors focus too much on why versus how
“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.”
Kao: Audiences need much less preamble than creators think
“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.”
Kao: One-directional content formats allow more low-substance claims
“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 …”
Kao: Cohort-based courses force instructor rigor through real-time student scrutiny
“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. Like if you're saying something that doesn't really make sense, there could be a whole conversation happ…”
Kao: Presenters should punctuate monologues with state changes to sustain attention
“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 add some variety.”
Kao: Presenters should insert a state change every three to five minutes or slides
“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.”
Kao: Track involuntary audience engagement rather than polite verbal agreement
“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 …”
Kao: Senior leaders reach top roles because they excel at managing up
“Ironically, the most senior people are best at managing up. This is why they got promoted in the first place, because they were great at managing up to their bosses to understand what was Worries worrying their bosses, what was keeping them up at night so that…”
Kao: Over-communicating in remote work is actually the right amount for recipients
“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.”
Kao: Writers should study technical mechanics, not just mimic viral formats
“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 you know, look at what other people are doing to try to get audience engagement, but to actually improve your ability to pre…”
Kao: Biased pros-and-cons lists destroy trust; state recommendations upfront
“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…”
Kao: Interspersing action items within background context confuses readers
“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…”
Kao: Communicating trade-offs protects bandwidth without saying no directly
“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 …”