Wes Kao (Maven, Seth Godin, Section4)28 August 2022

Persuasive communication and managing up

8Frameworks

14Insights

Episode overview

Wes Kao explains how writers and teachers can replace broad premises and lengthy backstory with a “super specific how,” then use deliberate state changes to sustain attention. She argues that managing up means proactively supplying appropriate context, communicating priorities, and preventing surprises. The conversation also covers precise business writing and a trade-off-based way to decline work without damaging collaborative relationships.

Key ideas

Focus writing and teaching on specific application, nuance, and examples rather than overexplaining what something is or why it matters.
Start a story immediately before its consequential moment, cutting preamble that does not help the audience understand the payoff.
Punctuate presentations and Zoom meetings with state changes such as chat prompts, polls, screen sharing, new speakers, and breakout rooms.
Observe moments when listeners’ eyes light up and use those reactions as data for refining content, pitches, and internal communication.
Manage up by keeping managers informed, matching the amount of context to the reversibility and importance of a decision, and avoiding surprises.
Lead business communication with the conclusion or recommendation, then separate optional context from decisions and action items.
When declining new work, explain the priority trade-offs and let the requester help choose what should move.

Transcript available · source text is retained privately and is not published

Frameworks in this episode

Influence5 steps

Eyes Light Up

Track the moments faces change, then cut everything that doesn't produce them.

Read →

Leadership5 steps

Managing Up by Calibrated Context

Proactively give your boss exactly enough context to weigh in — scaled to reversibility.

Read →

Communication5 steps

Recommendation-First Writing

Lead with the call, label the context, and never hide a point of view inside a neutral-looking pros-and-cons list.

Read →

Productivity5 steps

Saying No by Trading Off

Never say no. Say yes, name what it displaces, and hand the prioritisation back.

Read →

Communication3 steps

Start Right Before You Get Eaten by the Bear

Open your story one beat before the juicy part — everything earlier is backstory scope creep.

Read →

Communication3 steps

The Content Hierarchy of BS

Rank formats by how much they let you get away with — then hold yourself to the top of the pyramid.

Read →

Communication4 steps

The State Change Method

Punctuate every monologue with something that shakes the audience awake, every 3-5 minutes.

Read →

Communication5 steps

The Super Specific How

Cut the what and the why; spend your word count on the how nobody else will teach.

Read →

People & resources mentioned

Attributed to the moment in the episode. Timestamps are approximate.

People · 14

Thiago ForteMentionsmentioned
“she's also helped people like David Perell Thiago Forte Scott Galloway”
▶ Watch at ~0:30approx.
Seth GodinMentionsSeth is an absolute Legend he's published 21 books including 18 International bestsellers
“she's helped folks like Seth Goden start his alt MBA course which is legendary”
▶ Watch at ~0:30approx.
Scott GallowayMentionsmentioned
“she's also helped people like David Perell Thiago Forte Scott Galloway”
▶ Watch at ~0:30approx.
David PerellMentionsDescribed podcasting as maximizing usefulness per minute without removing humanity.
“she's also helped people like David Perell Thiago Forte Scott Galloway”
▶ Watch at ~0:30approx.
Wes KaoMentionsWes co-created the AltMBA program with Seth Godin. She co-founded a company called Maven.
“and with that I bring you Wes Cal”
▶ Watch at ~1:00approx.
Lenny RachitskyMentionstoday we've got another very special compilation episode something I've been pulling on more and more with the podcast and the newsletter
“hey Lenny great to be here”
▶ Watch at ~4:00approx.
Seth GodinMentionsSeth is an absolute Legend he's published 21 books including 18 International bestsellers
“moved cross country from SF to New York to work with bestselling author Seth Goden”
▶ Watch at ~5:00approx.
Greg ShoveMentionshis CEO Greg shove
“I worked really closely with with his CEO Greg shove and their exec team to design the Sprint”
▶ Watch at ~14:00approx.
Nathan BarryMentionsmentioned
“I was talking to Nathan Barry from convertkit he was saying that he loves State change method too”
▶ Watch at ~25:00approx.
Tim FerrissMentionsCited for his fear-setting framework and as an influence on Paul Millerd's five-episode podcast experiment.
“I heard that Tim Ferris was working on a book called The no book”
▶ Watch at ~44:00approx.
Alex PeckMentionsmy cooworker at at altmba who's now CEO of altmba
“this is something that I learned from Alex peek my cooworker at at altmba who's now CEO of altmba”
▶ Watch at ~45:00approx.
Suzy BatizMentionsthe founder and former CEO of poopery she's now chairman
“Susie is the the founder and former CEO of poopery she's now chairman”
▶ Watch at ~49:30approx.
Marily NikaMentionsmarily teaches the most popular course on Maven on AI and product management she's currently product lead at meta
“merily Nika's course on breaking into technical product management she's a technical PM with a PhD at meta”
▶ Watch at ~51:00approx.
Amanda NatividadMentionstheir VP of marketing the new VP of marketing Amanda and timidad
“probably Amanda nad's course on content marketing”
▶ Watch at ~51:00approx.

Resources · 25

MavenCoinedwebsite · Maven
“Wes cow is the co-founder of Maven a cohort-based learning platform”
▶ Watch at ~0:30approx.
Modern TreasuryMentionscompany
“this episode is brought to you by modern treasury”
▶ Watch at ~1:30approx.
BerbixMentionscompany
“this episode is brought to you by verbick”
▶ Watch at ~2:30approx.
GapMentionscompany
“I started my career in corporate retail at the Gap headquarters in San Francisco”
▶ Watch at ~4:00approx.
Banana RepublicMentionscompany
“I did a rotation training program rotating between Old Navy Banana Republic Gap”
▶ Watch at ~4:00approx.
Old NavyMentionscompany
“I did a rotation training program rotating between Old Navy Banana Republic Gap”
▶ Watch at ~4:00approx.
altMBACoinedcourse · Seth Godin
“together we co-founded the altmba which I Grew From just an idea between me and Seth to thousands of students”
▶ Watch at ~5:30approx.
Section4Mentionscompany · Scott Galloway
“section four Scott Gallow company was one of the first clients I worked with after after leaving altmba”
▶ Watch at ~14:00approx.
ZoomUsessoftware · Zoom Video Communications
“State changes are anything that shakes your audience awake and adds some variety”
▶ Watch at ~22:30approx.
ZoomMentionssoftware · Zoom Video Communications
“it might be putting people into breakout room so they can discuss amongst themselves”
▶ Watch at ~23:00approx.
ConvertKitMentionscompany · Nathan Barry
“I was talking to Nathan Barry from convertkit he was saying that he loves State change method too”
▶ Watch at ~25:00approx.
MakelogRecommendscompany · Makelog
“try make log for free today just visit make log.com Lenny to get started”
▶ Watch at ~30:30approx.
It Was the Best of Sentences, It Was the Worst of SentencesRecommendsbook · June Casagrande
“it's a book called it was best of sentences it was the worst of sentences by June KAS Grande”
▶ Watch at ~38:00approx.
The Pyramid PrincipleMentionsbook · Barbara Minto
“this also reminds me of the MTO pyramid which I won't get too deep into”
▶ Watch at ~42:30approx.
The No BookCoinedbook · Tim Ferriss
“I heard that Tim Ferris was working on a book called The no book”
▶ Watch at ~44:00approx.
NetflixMentionscompany · Netflix
“there's a show called Dr Foster on Netflix that's I think it's on Netflix might be on Prime”
▶ Watch at ~49:00approx.
Better Business WritingRecommendsbook · Harvard Business Review Press
“and then Better Business writing by Harvard Business review or Harvard Business press”
▶ Watch at ~49:00approx.
Doctor FosterRecommendstv show
“there's a show called Dr Foster on Netflix that's I think it's on Netflix might be on Prime”
▶ Watch at ~49:00approx.
Live OSRecommendscourse · Suzy Batiz
“I really love Susie bz's course called live OS”
▶ Watch at ~49:30approx.
Poo-PourriCoinedcompany · Suzy Batiz
“Susie is the the founder and former CEO of poopery she's now chairman”
▶ Watch at ~49:30approx.
Breaking into Technical Product ManagementRecommendscourse · Marily Nika
“I've heard really good things about merily Nika's course on breaking into technical product management”
▶ Watch at ~51:00approx.
Content Marketing 201Recommendscourse · Amanda Natividad
“probably Amanda nad's course on content marketing it's called content marketing 2011”
▶ Watch at ~51:00approx.
Maven Course AcceleratorRecommendscourse · Maven
“definitely check out our Maven course accelerator it's a free twoe course”
▶ Watch at ~52:00approx.
MavenMentionswebsite · Maven
“you can find me at Maven HQ on Twitter or maven.com”
▶ Watch at ~52:00approx.
Lenny's PodcastCoinedpodcast · Lenny Rachitsky
“you can find all past episodes or learn more about the show at Lenny podcast.com”
▶ Watch at ~53:00approx.

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Insights & moments

The myth-busts, hot takes, explainers, and tools worth keeping.

Myth Buster· 1

Myth Buster11:30

You Don't Always Have to Trade Quality for Speed

The common belief is you can only pick two of quality, speed, and cheap. Wes says working with Seth surprised her because they consistently produced high-quality work fast, breaking the assumed tradeoff. It raised her bar on what shipping fast while staying excellent actually looks like.

The usual assumption is a hard tradeoff between quality and speed
Working with Seth, they almost always produced high-quality work fast
The shipping speed exceeded what she'd seen even at a prior startup
A refusal to accept anything but excellence coexisted with speed

“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…”
Wes Kao · 11:30

“but we worked fast and we produced really great work”
Wes Kao · 12:00

#craft#productivity#quality

Hot Take· 2

Hot Take40:30

Study the Craft of Writing, Don't Just Copy Twitter

Wes's spiky point of view is that most people learn writing by mimicking others on social media, when they'd benefit far more from studying the actual craft: sentences, paragraphs, arguments, and logic. The goal is to precisely say what you mean and convey conviction without accidentally misleading readers.

Learning by analogy on Twitter is useful only to a point
Studying craft improves your ability to say precisely what you mean
A sentence often carries an accidental point of view you didn't intend
Leading questions and misplaced clauses add cognitive load and can mislead

“and I guess my spiky point of view is that more people should should learn the craft of writing and the technical aspects of writing…”
Wes Kao · 41:00

#writing#craft#communication

Hot Take41:30

A Biased Pros-and-Cons List Makes You Untrustworthy

Wes argues that a pros-and-cons list implies equal, objective weighting, so a skewed one that omits real cons makes readers suspicious and erodes trust. The better move is to state your recommendation up front and then honestly list the downsides and risks of that recommendation.

The pros-and-cons format implies objective, equal weighting
A skewed list that hides cons makes the reader suspicious
State your recommendation first, then give pros, cons, and risks of it
Being direct about downsides actually builds trust

“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…”
Wes Kao · 42:00

#communication#writing#decision-making

Explainer· 1

Explainer30:30

Why Even Senior People Have to Manage Up

Wes challenges the resentment many feel about managing their boss, arguing that embracing it earns more trust, opportunities, and appreciation. She notes everyone has a boss regardless of seniority, and that the most senior people got promoted precisely because they were best at managing up.

Many people resent managing up, feeling it's the boss's job to manage them
Embracing managing up builds trust and unlocks more opportunities
There is no seniority level where managing up stops mattering
Senior people are best at it: they anticipate what worries the boss and keep them in the loop proactively

“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…”
Wes Kao · 31:00

“but ironically the most senior people are best at managing up this is why they got promoted in the first place”
Wes Kao · 32:00

#managing-up#career#leadership

Story· 4

Story04:00

Why Wes Kao Started Her Career at Gap, Not a Startup

Wes explains her untraditional path: she began in corporate retail at Gap headquarters, rotating through Old Navy, Banana Republic, and Gap. She frames this deliberate choice of a big, 40-plus-year-old company as foundational business training that later set her up for tech and startups.

Started in a rotation training program across Old Navy, Banana Republic, and Gap
Chose a large established company over a startup out of school, then moved progressively smaller
Seeing inside a 40+ year old company was strong training in business fundamentals
Later moved through companies acquired by Chanel-adjacent beauty and Snap before Seth Godin and Maven

“I started my career in corporate retail at the Gap headquarters in San Francisco”
Wes Kao · 04:00

#career#fundamentals#retail

Story07:30

How Wes Landed the Seth Godin Role by Not Rejecting Herself

Wes saw Seth Godin's blog post seeking a special projects lead and applied on a whim, filming the required video in a single take because she assumed she'd never get it. She got the role, which became three-plus years and the co-founding of altMBA. Her lesson: don't take yourself out of the running before you're actually rejected.

Seth posted publicly in 2014 looking for someone to help him figure out what to do next
Wes did her application video in one take, assuming thousands would apply
A six-month role turned into 3+ years and co-founding the altMBA
The lesson: high self-standards make people pre-reject themselves before applying

“don't reject yourself basically”
Wes Kao · 09:30

#career#confidence#seth-godin

Story10:00

What Seth Godin Is Really Like Behind the Scenes

Wes contrasts the public 'vague Buddha' Seth with the behind-the-scenes version, saying he is even sharper and more genuine in person than online. She also corrects a common imitation error: copying Seth's short daily blog format misses the point, since the posts work because they're insight-rich, not because they're short.

Seth is even smarter, sharper, funnier, and more genuine in person than in writing
Copying his short daily blog format misses why it works
The format being short and daily is incidental; the insight density is the reason
Internally they held very high standards for what they would ship

“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”
Wes Kao · 10:00

“in person he is even smarter and even sharper than he is in writing and online”
Wes Kao · 10:30

#seth-godin#writing#craft

Story44:00

How to Say No by Talking About Trade-offs

Wes learned from her altMBA colleague Alex Peck a way of declining requests that still felt good to the asker. Instead of a flat no, Alex framed trade-offs: yes, I can do this, which means this other thing waits, does that work? It protects your bandwidth and keeps the important work prioritized without ever saying no.

Works best with people you have ongoing relationships with (managers, teammates, friends)
Frame the request against what it would displace, then let them choose
The asker feels in control and involved in prioritizing
You get the outcome of a no, protecting bandwidth, without saying the word

“so you're not exactly saying no but you're talking about trade-offs which gets the the result of the no”
Wes Kao · 46:30

#saying-no#prioritization#communication

Tool· 3

Tool34:00

The 'State of Lenny' Weekly Email to Your Manager

Lenny shares a simple managing-up habit: a weekly email to his manager titled 'the state of Lenny' with three sections. It kept priorities aligned, surfaced blockers for help, and avoided surprises, doing exactly what Wes recommends for keeping a boss in the loop.

Send your manager a short weekly status email
Three sections: current priorities, blockers needing their help, and things on your mind
Lead with blockers so the manager sees them first
Keeps priorities aligned, unblocks work, and avoids surprises

“I sent my manager a state of Lenny email every week just titled the state of Lenny”
Lenny · 34:00

#managing-up#communication#tools

Tool48:30

Two Books Wes Recommends for the Craft of Writing

Wes recommends two books she gives new team members to learn the mechanics of strong sentences, paragraphs, and arguments: 'It Was the Best of Sentences, It Was the Worst of Sentences' by June Casagrande, and 'Better Business Writing' from Harvard Business Review.

'It Was the Best of Sentences, It Was the Worst of Sentences' by June Casagrande
'Better Business Writing' by Harvard Business Review press
She gives these to new team members to teach writing craft
They cover sentence, paragraph, argument mechanics and logic, not social-media tactics

“it was the best of sentences it was the worst of sentences a great Kasa Grande”
Wes Kao · 48:30

#books#writing#recommendations

Tool49:30

The Course That Led Wes to Start Maven

Wes names Susie Batiz's 8-week course 'LivE OS' as her favorite course taken. Batiz, founder of Poo-Pourri after multiple bankruptcies, built a mindset-focused program that produced breakthroughs for Wes, including the decision to start Maven, worked through with her small pod.

Favorite course: 'LivE OS' by Susie Batiz, founder of Poo-Pourri
It's about mindset and overcoming internal blockers
Small-pod exercises drove real breakthroughs over the 8 weeks
It directly influenced her decision to start Maven

“it led to some really big breakthroughs including starting Maven as a company”
Wes Kao · 50:00

#courses#mindset#recommendations

Takeaway· 3

Takeaway35:00

Don't Surprise Your Manager (Unless It's a Snack)

Wes argues that in a work context surprises are generally bad, and a core benefit of keeping people in the loop is avoiding catching your manager off guard. The only good surprises are snacks, birthday parties, and milestones.

Work surprises are generally not good
Keeping your boss informed prevents catching them off guard
Acceptable surprises: snacks, birthday parties, milestones
Applies in personal life too

“so I always say you know unless you're surprising me by bringing me a snack or something like don't surprise me”
Wes Kao · 35:00

#managing-up#communication

Takeaway35:30

What Feels Like Overcommunicating Is Usually Just Right

Lenny and Wes agree that erring toward overcommunication is almost always correct. Nobody complains about being told too much; the usual complaint is 'why didn't I know about this?' In remote work especially, what feels like overcommunicating lands as just the right amount for the recipient.

People rarely object to receiving too much information
The common complaint is being left out, not over-informed
Giving people the chance to see something goes a long way even if they don't read it
In remote work, perceived overcommunication is often the correct level

“I find nobody's ever like just let me shut up I don't want to know about things like it's always the opposite why didn't I…”
Lenny · 35:30

“you think you're overc communicating but to the recipient it's actually just the right amount”
Wes Kao · 36:00

#communication#remote-work#managing-up

Takeaway36:00

Put the TL;DR First, Then Label the Context

Wes structures messages so the most important point sits at the top, followed by an explicit 'Context:' section. Readers who already agree can stop; those who want the reasoning keep going. She traces the format to military 'bottom line up front' writing, with a caveat that it can read as too blunt with customers.

Lead with the gist / TL;DR at the very top
Follow with an explicit 'context' section for anyone who wants the reasoning
Lets agreers skip ahead and skeptics keep reading, saving everyone's time
Rooted in military 'bottom line' emails; soften it for external/customer audiences

“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”
Wes Kao · 36:30

#writing#communication#managing-up

Key ideas

Frameworks in this episode

Eyes Light Up

Managing Up by Calibrated Context

Recommendation-First Writing

Saying No by Trading Off

Start Right Before You Get Eaten by the Bear

The Content Hierarchy of BS

The State Change Method

The Super Specific How

People & resources mentioned

People · 14

Resources · 25

Insights & moments

⚡Myth Buster· 1

You Don't Always Have to Trade Quality for Speed

◆Hot Take· 2

Study the Craft of Writing, Don't Just Copy Twitter

A Biased Pros-and-Cons List Makes You Untrustworthy

✶Explainer· 1

Why Even Senior People Have to Manage Up

❝Story· 4

Why Wes Kao Started Her Career at Gap, Not a Startup

How Wes Landed the Seth Godin Role by Not Rejecting Herself

What Seth Godin Is Really Like Behind the Scenes

How to Say No by Talking About Trade-offs

✦Tool· 3

The 'State of Lenny' Weekly Email to Your Manager

Two Books Wes Recommends for the Craft of Writing

The Course That Led Wes to Start Maven

▲Takeaway· 3

Don't Surprise Your Manager (Unless It's a Snack)

What Feels Like Overcommunicating Is Usually Just Right

Put the TL;DR First, Then Label the Context

Myth Buster· 1

Hot Take· 2

Explainer· 1

Story· 4

Tool· 3

Takeaway· 3