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

Persuasive communication and managing up

8Frameworks
14Insights

Frameworks in this episode

Influence5 steps

Eyes Light Up

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

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Leadership5 steps

Managing Up by Calibrated Context

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

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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.

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Productivity5 steps

Saying No by Trading Off

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

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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.

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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.

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Communication4 steps

The State Change Method

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

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Communication5 steps

The Super Specific How

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

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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