Lenny's PodcastPersuasive communication and managing up | Wes Kao (Maven, altMBA, Section4)
CHAPTERS
- 0:00 – 4:03
Why managing up accelerates your career (and why people resist it)
Wes opens with the core premise: your boss won’t (and can’t) perfectly manage you, and proactively managing up creates trust, opportunity, and leverage. She reframes managing up from “unfair extra work” into a strategic career skill that benefits both you and your manager.
- •Common resentment: “My boss should manage me” vs. treating managing up as a career advantage
- •Managing up builds trust and earns more autonomy and opportunities
- •Reframing: managing up is useful at every level, not just for junior roles
- 4:03 – 7:36
Wes Kao’s unconventional path: from Gap to altMBA to founding Maven
Wes walks through her career arc—starting at Gap’s corporate rotational program, moving through acquisitions, then making a pivotal leap to work with Seth Godin. She explains how building altMBA and later consulting for course creators revealed the need for better infrastructure, which became Maven.
- •Early foundation in business fundamentals from a large company (Gap)
- •Multiple roles at smaller companies and acquisitions (Shiseido, Snap)
- •Co-founding and scaling altMBA globally
- •Consulting validated cohort-based learning as a repeatable model
- •Maven born from frustration with a fragmented “janky” course tech stack
- 7:36 – 9:56
How Wes landed the job with Seth Godin: applying before you’re ‘ready’
Wes shares the serendipitous story of responding to Seth’s blog post seeking a special projects lead. Her takeaway is practical: don’t disqualify yourself prematurely—submit the application even if it’s not perfect.
- •Seth’s public job post and the application that required a short video
- •Wes did the video in one take and applied anyway
- •“Don’t reject yourself before you get rejected” as a career principle
- •Taking action creates luck and unexpected trajectory shifts
- 9:56 – 14:51
What makes Seth Godin stand out: insight density, speed, and high standards
Wes describes the gap between Seth’s public persona and behind-the-scenes execution. She emphasizes his unusually high “insight-per-sentence,” plus the ability to ship fast without compromising quality—raising her personal bar for craft and rigor.
- •Seth is sharper in person than in writing—rare compared to most creators
- •His blog works because it’s insight-rich, not merely short/daily
- •High standards paired with extreme shipping velocity
- •Quality-speed tradeoff isn’t always inevitable when craft is obsessive
- 14:51 – 17:17
Better writing through the “Super Specific How” (cut the what/why)
Wes introduces her writing/teaching framework: most creators over-invest in context and persuasion and under-invest in actionable mechanics. Great content assumes the audience already buys the premise and focuses on the nuanced “how” with examples and application guidance.
- •Most audiences already agree with your ‘what’ and ‘why’
- •Readers crave application: nuance, steps, examples, decision tradeoffs
- •Use specificity (e.g., how to get buy-in without authority) to add value
- •Aim to reduce preamble and increase actionable density
- 17:17 – 18:18
Eliminating fluff: “Start right before you get eaten by the bear”
Wes shares a memorable editing heuristic: cut the long lead-up and start where the story becomes meaningful. The goal is to remove “backstory scope creep” so the audience reaches the compelling moment quickly.
- •Skip irrelevant setup details and begin near the core tension
- •Editing often means deleting more context than feels comfortable
- •Use the bear metaphor to pressure-test where the story should start
- 18:18 – 21:47
The “content hierarchy of BS”: formats that demand rigor
Wes explains how different media formats tolerate different levels of vagueness. One-directional, short-form platforms allow more unchallenged assertions, while interactive teaching—especially cohort-based courses—forces precision because learners can question you in real time.
- •More BS tolerated in Twitter, keynotes, and short one-way content
- •Less BS in long-form articles and books where arguments must hold up
- •Least room for BS in live, interactive cohort-based courses
- •Use the hierarchy to hold yourself to a higher rigor standard
- 21:47 – 26:03
The state change method: keep Zoom meetings and teaching engaging
Wes introduces “state changes” as deliberate interruptions to monologue mode that re-engage attention and reduce Zoom fatigue. She offers a practical cadence—every few minutes or slides, switch the interaction mode to reset attention.
- •Zoom monologues are draining; state changes add variety and participation
- •Examples: chat prompts, polls, screen share toggles, different speakers
- •Breakout rooms + share-outs/popcorn to increase engagement
- •Rule of thumb: add a state change every 3–5 slides/minutes
- 26:03 – 30:42
Using “eyes light up” moments as behavioral data
Wes argues that people’s faces provide honest feedback even when their words are polite. Tracking the moments when someone visibly perks up gives you evidence for what resonates—useful for sales pitches, meetings, and how you frame ideas internally.
- •Polite nodding isn’t signal; genuine excitement is
- •Look for leaning forward, energy shift, and animated responses
- •Treat boredom/excitement as real data, not ambiguity
- •Use patterns to refine future messaging and focus on what lands
- 30:42 – 32:52
Managing up, part 1: why it matters at every seniority level
Wes and Lenny move from audience-reading to workplace influence. Wes explains that the most senior people are often the best at managing up—anticipating what worries their leaders and keeping them informed—because it’s a promotion-relevant skill, not a junior workaround.
- •Managing up isn’t optional at higher levels; it becomes more important
- •Senior operators remove worries from their boss’s plate
- •Proactive updates prevent constant status pings and build confidence
- •Core outcome: more trust, autonomy, and better opportunities
- 32:52 – 37:55
Managing up, part 2: proactive updates + structured communication (templates)
They get tactical: keep your boss in the loop with the right amount of context, calibrated to decision reversibility and risk. Lenny shares his weekly “State of Lenny” email template, and Wes adds guidance on TL;DR-first writing that lets busy readers dive deeper only if needed.
- •Share decisions and rationale at an appropriate detail level
- •Use judgment: not everything needs escalation; irreversible decisions do
- •Weekly manager update template: priorities, blockers, and things on your mind
- •Avoid surprises; remote work usually requires ‘overcommunication’
- •Format tips: TL;DR first, then labeled context for skimmability
- 37:55 – 44:28
Writing skills for work: clarity, intent, and trustworthy recommendations
Wes recommends learning the craft of writing beyond social-media mimicry. She discusses how subtle phrasing can unintentionally lead readers, create cognitive load, or erode trust—especially with biased “pros/cons” lists—so recommendations should be explicit and the structure should separate decisions from background.
- •Study writing mechanics (sentences/structure), not just engagement tactics
- •Avoid accidental POVs; be intentional about recommendations
- •Pros/cons lists imply objectivity—bias makes readers suspicious
- •Business writing best practice: conclusion first, then supporting logic
- •Separate decisions/action items from context to reduce confusion
- 44:28 – 48:31
Protecting your bandwidth: saying no by talking trade-offs
Wes shares a people-pleaser-friendly approach to declining requests: shift the conversation from ‘no’ to prioritization and trade-offs. By making the cost visible (what slips if this gets added), you preserve relationships while still defending focus and capacity.
- •Different ‘no’ strategies for work relationships vs. internet requests
- •Trade-off framing: “Yes, but this other priority moves”
- •Turns a moral judgment (‘helpful or not’) into a prioritization discussion
- •Lenny’s related framework: ‘prioritize and communicate’ with a simple 2x2
- 48:31 – 53:07
Lightning round + where to find Wes and Maven
They close with quick personal recommendations (books, shows, courses), plus a brief plug for Maven and Wes’s online presence. Wes highlights a favorite course she took (AliveOS) and shares where listeners can learn more or explore building a course via Maven’s free accelerator.
- •Writing book recs: *It Was the Best of Sentences, It Was the Worst of Sentences*; *Better Business Writing*
- •Show rec: *Doctor Foster*
- •Favorite course taken: AliveOS (Suzie Batiz) and its impact on starting Maven
- •Maven course shout-outs and Wes’s handles/websites for follow-up
