Wes Kao (coach, entrepreneur, advisor)06 April 2025

Become a better communicator: Specific frameworks to improve your clarity, influence, and impact

9Frameworks

15Insights

Episode overview

Lenny Rachitsky and Wes Kao explain how clearer verbal and written communication increases the likelihood of buy-in, sound decisions, and forward movement. Kao presents practical frameworks including sales before logistics, signposting, the most obvious objection, strategy not self-expression, and CEDAF delegation. They emphasize preparation, accurate expressions of confidence, audience empathy, short feedback loops, and modest upfront effort that prevents larger downstream confusion. The discussion also covers managing up, swipe files, and using Claude as a drafting and thought-partnership tool.

Key ideas

Communication is a learnable means to an outcome, so when an audience is confused or unconvinced, first examine how the message could be clearer and more compelling.
Sell the reason, business benefit, and problem being solved before presenting logistics; briefly state what input or decision you need.
Concision is economy of words rather than mere brevity, and preparation is the most reliable way to identify the core point before speaking or writing.
Use signposting words and restrained formatting to expose structure without forcing readers to infer the connective tissue between fragmented bullets.
Before presenting, identify the most obvious objection and understand counterarguments as well as the case for your recommendation.
Manage up by offering a point of view supported by evidence, logic, examples, or first principles instead of transferring the entire thinking burden to a manager.
Give feedback strategically for the desired behavior change, after processing emotional frustration elsewhere, rather than using the conversation for self-expression.
Delegate with CEDAF: ensure comprehension, create excitement, derisk likely failures, confirm alignment, and shorten the feedback loop.

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

Frameworks in this episode

Communication3 steps

Answer the Question Behind the Question

When caught without a number, answer the adjacent question and surface the real concern.

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Leadership5 steps

CEDAF Delegation Framework

A five-part checklist for delegating without lowering your standards — to humans or AI.

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Leadership3 steps

Manage Up by Sharing Your Point of View

Bring your manager a recommendation to react to, not an open question to solve.

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Communication3 steps

MOO — Most Obvious Objection

Spend two minutes pre-empting the objection you'll obviously get, and stop feeling blindsided.

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Influence4 steps

Sales Then Logistics

Sell the why before you explain the how, or your ask gets crickets.

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Communication3 steps

Signposting

Use structural cue-words to guide the reader through your writing without heavy formatting.

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Influence4 steps

Speak Accurately (Avoid the Single-Minded Martyr)

Match your stated confidence to your actual evidence — neither overreach nor over-hedge.

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Leadership3 steps

Strategy Not Self-Expression

Feedback's goal is behavior change, so cut everything that doesn't serve it — usually 90%.

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Self-Mastery3 steps

The Swipe File

Capture examples of communication that work — the act of collecting trains your eye.

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People & resources mentioned

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

People · 11

Wes KaoMentionsWes co-created the AltMBA program with Seth Godin. She co-founded a company called Maven.
“Today my guest is Wes Ko. Wes co-created the AltNBA program with Seth Goden.”
▶ Watch at ~1:00approx.
Seth GodinMentionsSeth is an absolute Legend he's published 21 books including 18 International bestsellers
“Wes co-created the AltNBA program with Seth Goden.”
▶ Watch at ~1:00approx.
George Bernard ShawCoinedThere's a quote that came to mind after I stopped recording this conversation with Wes by George Bernard Shaw.
“There's a quote that came to mind after I stopped recording this conversation with Wes by George Bernard Shaw.”
▶ Watch at ~1:30approx.
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
“Wes, thank you so much for being here and welcome back to the podcast.”
▶ Watch at ~4:30approx.
William ZinsserCoinedSo, there's on writing well by William Zissner.
“So, there's on writing well by William Zissner.”
▶ Watch at ~26:30approx.
Stephen KingCoinedthere's a book called on writing by Stephen King
“Stephen King has a book called on writing.”
▶ Watch at ~27:00approx.
Joan DidionCoinedThere's a quote I have highlighted on this podcast a number of times that I love that is exactly along these lines by Joan Ddian.
“There's a quote I have highlighted on this podcast a number of times that I love that is exactly along these lines by Joan Ddian.”
▶ Watch at ~53:30approx.
Albert EinsteinMentionsThere's that great Einstein quote about insanity being repeating things that you're doing, expecting a different outcome.
“There's that great Einstein quote about insanity being repeating things that you're doing, expecting a different outcome.”
▶ Watch at ~1:08:30approx.
David RockCoinedAnother one is Your brain at work by Dr. David Rock.
“Another one is Your brain at work by Dr. David Rock.”
▶ Watch at ~1:22:30approx.
Andy GroveCoinedBusiness leader cited for distinguishing competency from motivation.
“One is High Output Management by Andy Grove, which is a classic.”
▶ Watch at ~1:22:30approx.
Harlan CobenRecommendsI love anything by Harlon Coin on Netflix.
“I love anything by Harlon Coin on Netflix.”
▶ Watch at ~1:24:00approx.

Resources · 31

altMBACoinedcourse · Seth Godin
“Wes co-created the AltNBA program with Seth Goden.”
▶ Watch at ~1:00approx.
MavenCoinedwebsite · Maven
“She co-founded a company called Maven, which I often collaborate with, which makes it easy for people to host live cohort-based courses.”
▶ Watch at ~1:00approx.
Executive Communication and InfluenceCoinedcourse · Wes Kao
“She recently left Maven to launch her own course on executive communication and influence.”
▶ Watch at ~1:30approx.
NotionMentionssoftware · Notion Labs
“you get a year free of Perplexity Pro, Superhum, Notion, Linear, and Granola.”
▶ Watch at ~2:00approx.
GranolaMentionssoftware · Granola
“you get a year free of Perplexity Pro, Superhum, Notion, Linear, and Granola.”
▶ Watch at ~2:00approx.
LinearMentionssoftware · Linear
“you get a year free of Perplexity Pro, Superhum, Notion, Linear, and Granola.”
▶ Watch at ~2:00approx.
Lenny's NewsletterMentionsnewsletter · Lenny Rachitsky
“Also, if you become a yearly subscriber of my newsletter, you get a year free of Perplexity Pro, Superhum, Notion, Linear, and Granola.”
▶ Watch at ~2:00approx.
SuperhumanMentionssoftware · Superhuman
“you get a year free of Perplexity Pro, Superhum, Notion, Linear, and Granola.”
▶ Watch at ~2:00approx.
Perplexity ProMentionssoftware · Perplexity AI
“you get a year free of Perplexity Pro, Superhum, Notion, Linear, and Granola.”
▶ Watch at ~2:00approx.
Google DocsMentionssoftware · Google
“Zanzibar, which was originally designed for Google to power Google Docs and YouTube.”
▶ Watch at ~2:30approx.
YouTubeMentionswebsite · Google
“Zanzibar, which was originally designed for Google to power Google Docs and YouTube.”
▶ Watch at ~2:30approx.
WarrantMentionssoftware · Warrant
“Work OS also recently acquired Warrant, the fine grain authorization service.”
▶ Watch at ~2:30approx.
ZanzibarCoinedsoftware · Google
“Warrant's product is based on a groundbreaking authorization system called Zanzibar, which was originally designed for Google to power Google Docs and YouTube.”
▶ Watch at ~2:30approx.
VantaRecommendssoftware · Christina Cacioppo
“Get $1,000 off Vanta when you go to vanta.com/lenny.”
▶ Watch at ~4:00approx.
SlackUsessoftware · Slack Technologies
“We've all put a Slack message in a channel and got crickets and tumble weed.”
▶ Watch at ~12:00approx.
On Writing WellRecommendsbook · William Zinsser
“one is specifically to help you write more concisely called on writing well.”
▶ Watch at ~24:30approx.
On WritingMentionsbook · Stephen King
“Stephen King has a book called on writing.”
▶ Watch at ~27:00approx.
Several Short Sentences About WritingRecommendsbook · Verlyn Klinkenborg
“There's also one called a series of sing of short sentences. If you haven't seen that one it's a really good rate too.”
▶ Watch at ~27:00approx.
CodaUsessoftware · Coda
“I personally use KOD every single day to manage my podcast and also to manage my community.”
▶ Watch at ~39:00approx.
ClaudeUsessoftware · Anthropic
“I love Claude. Uh, there are days when I talk to Claude for like three or four hours prompting as a thought partner.”
▶ Watch at ~1:20:00approx.
ChatGPTMentionssoftware · OpenAI
“how will this help me get more out of Claude and ChatgBT.”
▶ Watch at ~1:22:00approx.
High Output ManagementRecommendsbook · Andy Grove
“One is High Output Management by Andy Grove, which is a classic.”
▶ Watch at ~1:22:30approx.
Your Brain at WorkRecommendsbook · David Rock
“Another one is Your brain at work by Dr. David Rock.”
▶ Watch at ~1:22:30approx.
NetflixUsescompany · Netflix
“I love anything by Harlon Coin on Netflix.”
▶ Watch at ~1:24:00approx.
The Harlan Coben CollectionRecommendstv show · Harlan Coben
“There's a page the Harland coin collection on Netflix that we'll link to that has all this stuff.”
▶ Watch at ~1:25:00approx.
Oral-B electric toothbrushUsesproduct · Oral-B
“It's Oral B, but I've not tried any other brand.”
▶ Watch at ~1:25:30approx.
InvisalignUsesproduct · Align Technology
“That was one that um my our dentist gifted my husband this electric toothbrush because he did Invisalign.”
▶ Watch at ~1:25:30approx.
Glengarry Glen RossMentionsfilm
“The other one is a riff on always be closing by Glenn Gary Ross.”
▶ Watch at ~1:27:00approx.
weskao.comRecommendswebsite · Wes Kao
“You can find out more at wesko.com. I linked to my course to my coaching from my main page.”
▶ Watch at ~1:32:30approx.
LinkedInUseswebsite · LinkedIn
“I also post on LinkedIn as well, so you can follow me there.”
▶ Watch at ~1:32:30approx.
Lenny's PodcastMentionspodcast · Lenny Rachitsky
“You can find all past episodes or learn more about the show at lennispodcast.com.”
▶ Watch at ~1:33:00approx.

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Insights & moments

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

Myth Buster· 1

Myth Buster18:30

Being concise isn't about word count, it's economy of words

A common mistake is equating concision with brevity. Wes reframes concision as the density of insight per word, not the absolute word count, so a short memo can be meandering while a long one can be tight.

Concision is about economy of words and density of insight, not raw brevity
A 300-word memo can be long-winded; a 1,000-word memo can be tight
Being too concise is its own pet peeve when it strips out needed substance

“being concise is not about absolute word count. It's about economy of words. It's about the density of the insight that you're sharing.”
Wes Kao · 18:30

“you can have a 300word memo that's meandering and long-winded and a thousandword memo that is tight and concise.”
Wes Kao · 18:30

#writing#concision#communication

Hot Take· 3

Hot Take25:30

The blast radius of a poorly written memo is bigger than you think

Wes frames a sloppy Slack message or memo as having a large 'blast radius' because every reader has to decipher it and generate back-and-forth. Spending 30 extra seconds to make it clean unblocks everyone downstream.

A confusing message to 15 people multiplies into 15 people's worth of confusion and back-and-forth
A clean message lets everyone read it and immediately know their next step
Think about everyone who will come in contact with the message, not just yourself writing it

“I think the blast radius of a poorly written memo is way bigger than most people think.”
Wes Kao · 25:30

“if you had just taken another look at it, um those 15 people would be off to the races”
Wes Kao · 26:00

#writing#slack#leverage#communication

Hot Take30:00

Over-formatting and bullet fragments are often a lazy crutch

Wes pushes back on excessive bolding and bullet fragments. If everything is bolded, nothing is highlighted; and forcing a fragment into a full sentence is a litmus test that often reveals you didn't actually know what you meant.

Bolding 30% of a note negates the point of bolding entirely
Sentence fragments make the reader decipher and guess your meaning, so it nets out slower
Turning a fragment into a complete sentence tests whether the idea was fully thought out
Echoes Amazon's six-page memo: if you can't write it in prose, you don't know what you're saying

“if everything is bolded, then none of nothing is is being highlighted, right?”
Wes Kao · 30:00

“if you had to turn your sentence fragment into a full sentence a lot of times like it actually is harder than you think because…”
Wes Kao · 30:30

#writing#formatting#clarity#communication

Hot Take37:30

The alpha is in the 'boring' basics everyone quits too early

Wes argues the big, obvious things are already being done by everyone, so there's little alpha there. The edge is in the basic skills people dismiss as too minor, where they claim diminishing returns far too early and there's still juice to squeeze.

Everyone already does the big things, so there's little alpha in them
Unglamorous skills people think are 'too basic' are an underused lever
People claim the point of diminishing returns way too early, in communication and in tactics generally
Often it's not that a channel or tactic doesn't work, but that execution wasn't good enough

“all the quote unquote big things everyone else is already doing. So there's not a lot of alpha in that.”
Wes Kao · 37:30

“I find that people claim the point of diminishing returns way too early.”
Wes Kao · 38:00

#skills#career#competitive-edge#communication

Explainer· 2

Explainer19:30

You can't cut to the chase until you know what the chase is

Wes says advice like 'don't bury the lead' assumes you already know your core point, which is usually the real bottleneck. The reliable fix for rambling is unglamorous preparation, even just 30 seconds to a minute before a meeting.

Aphorisms like 'cut to the chase' assume you know your core point, which you often don't
Long-windedness usually signals unclear thinking, not verbosity
In meetings your brain is listening, processing, and forming a response in real time, so preparation offloads that
Even 30 seconds to ground yourself before a meeting sharply improves concision

“you can't cut to the chase unless you know what the chase is.”
Wes Kao · 19:30

“the only solution I found consistently to being concise is preparation. It's not a very glamorous solution by any means”
Wes Kao · 20:30

#concision#preparation#meetings#communication

Explainer55:00

When you don't know the answer, don't default to 'I'll get back to you'

Instead of reflexively saying 'let me get back to you,' Wes suggests answering in the general direction of the question with what you do know, then probing why they're asking. Repeated questions on the same topic often signal a deeper, subconscious concern, the 'question behind the question.'

'I'll get back to you' is safe but often a missed opportunity if you know the domain
Offer an adjacent data point you do have, then validate why they're asking
Repeated questions on one topic usually signal a deeper underlying concern
It's your responsibility to surface that hidden question, since the asker may not know it's there

“just saying I'll get back to you is sometimes a missed opportunity.”
Wes Kao · 55:00

“sometimes you get a question but underneath there's a deeper underlying concern and many times people don't even know that it's there”
Wes Kao · 56:00

#communication#meetings#executive-communication#questions

Story· 1

Story46:30

The single-minded martyr: why your great idea keeps getting ignored

Wes describes a growth-acquisition client who couldn't get cross-functional headcount for her project and assumed everyone was a hypocrite. Once she zoomed out and remembered the CEO's company-wide goal was retention, not growth, she saw she was a 'single-minded martyr' and could right-size her proposal to the company's real priorities.

A single-minded martyr pushes their agenda and resents skeptics
The client's project didn't fit the CEO's stated company goal of retention
Junior people fixate on getting a yes; sometimes the best answer for the company is 'not now'
Do what's best for the company, not what's best for your career, team, or wins
If your pitch isn't aligned with current priorities, it won't be prioritized, and that's rational

“always do what's best for the company, not necessarily what's best for me, my career, my team, my wins.”
Wes Kao · 49:00

“More junior people are like, I need a win. Like I need to get a yes for this proposal and I'm going to keep advocating…”
Wes Kao · 48:00

#influence#prioritization#strategy#career

Tool· 2

Tool1:20:00

How Wes uses Claude as a multi-hour thought partner

Wes shares that she sometimes talks to Claude for three or four hours as a thought partner, and pastes in tricky emails for a draft reply. The key: sharing her own point of view makes the output far better than just asking 'what would you say?'

She uses Claude for initial drafts and to bounce ideas off of, sometimes for hours
She pastes in emails she's unsure how to answer and asks for a draft reply with direction
Giving the AI your point of view and constraints beats a blank 'what would you say?'
She edits the output to her voice since it's often too formal, then iterates with Claude again

“there are days when I talk to Claude for like three or four hours prompting as a thought partner.”
Wes Kao · 1:20:00

“I found that sharing my point of view makes the output way better. If I just give it something and say like what would you…”
Wes Kao · 1:20:30

#ai#claude#productivity#writing

Tool1:22:30

Wes Kao's book recommendations on writing and management

Across the episode Wes recommends books that shaped her writing and management thinking: On Writing Well by William Zinsser for concision, plus lightning-round picks High Output Management by Andy Grove and Your Brain at Work by David Rock for managing attention and cognitive resources.

On Writing Well by William Zinsser: tactical, chapter after chapter of what you can cut
High Output Management by Andy Grove: a management classic
Your Brain at Work by Dr. David Rock: understand your brain and attention to allocate mental resources
After reading Your Brain at Work, Wes hides her phone from view and does the hardest tasks earlier in the day

“One is High Output Management by Andy Grove, which is a classic. Another one is Your brain at work by Dr. David Rock.”
Wes Kao · 1:22:30

#books#writing#management#productivity

Takeaway· 6

Takeaway07:30

If people don't understand you, start by asking how you contributed

Wes Kao argues communication is a learnable skill, and the highest-leverage place to start is your own agency. Instead of blaming an audience for confusion, skepticism, or apathy, ask how you might be contributing and how you could explain things more clearly or compellingly.

Operators often explain things poorly, then are shocked by confusion or pushback
You can only control your own behavior, so improve the input you control
Reframe from blaming others to 'how can I be clearer and anticipate their questions?'
Communication absolutely is a skill that can be improved with reps

“instead of blaming other people for not understanding me, I think about how could I explain this more clearly?”
Wes Kao · 07:30

#communication#mindset#agency#leadership

Takeaway09:00

Practice like it's game day: don't save your best only for execs

Many operators save their sharpest communication for senior leadership and coast with everyone else. Wes argues you can't get enough reps to master executive communication if you only practice it with executives, since most people present to execs only once a month.

People 'shine' for senior leaders but coast with peers, reports, and cross-functional teammates
You only present to execs a couple times a quarter, which is too few reps to improve
Treat every stakeholder as important, because they are
If you don't want to waste your CEO's time, don't waste your teammates' time either

“I see a lot of operators who save their best behavior for executives only.”
Wes Kao · 09:00

#communication#practice#executive-communication#habits

Takeaway17:30

The 'yes yes yes next' mindset: take the win and stop talking

Executives often buy in by slide four of a 15-slide deck, but presenters keep going through their planned sequence. Wes learned to read that 'yes yes yes, next next' signal, take the win, and keep it moving rather than risk talking them out of the agreement.

Execs operate in a 'yes yes yes next next' mindset and often decide early
Once you've won the decision, don't push through your remaining slides
Continuing after a yes risks talking your audience out of agreeing

“take the win and and keep it moving. Move on.”
Wes Kao · 18:00

“You might you might talk them out of agreeing.”
18:00

#executive-communication#persuasion#presentations

Takeaway43:00

Speak accurately: match your words to your actual conviction

Wes says both overconfidence and underconfidence are problems, and the fix is speaking accurately about your level of conviction and evidence. Stating a hunch as fact can waste real headcount and dollars; diminishing a strong recommendation is equally irresponsible.

Saying 'this is X' or 'this will X' differs from 'this could X' or 'this might increase the likelihood of X'
Overconfident people state hypotheses as fact and mislead teams into real spend
Underconfident people undercut strong recommendations with 'ignore everything I said'
Pair a clear point of view with accurate labeling of what's proven vs. a hunch

“You can avoid a lot of problems if you speak accurately about your level of conviction and about the actual amount of evidence that you…”
Wes Kao · 43:00

“It's okay for something to be an initial hunch. Say it's an initial hunch.”
Wes Kao · 43:00

#communication#confidence#decision-making#influence

Takeaway59:30

Managing up never ends, it gets more important as you get senior

Wes busts the myth that managing up is a junior-only skill you outgrow. It became more important the more senior she got, because senior roles deal with ambiguity and mandates rather than well-defined tasks, and the highest-leverage way to manage up is sharing your point of view.

Many assume managing up fades with seniority; the opposite is true
Senior roles get ambiguity and mandates, not problems on a silver platter, which requires alignment
The best way to manage up is being vocal with your point of view, not just recapping tasks
'Here's what I think we should do, where do you see gaps?' reduces your manager's cognitive load
Sharing your POV signals you're a rigorous, strategic thinker, and even junior people can do it

“managing up, I not only had to manage up, it actually became more important.”
Wes Kao · 59:30

“Hey manager, here's what I think we should do. How does that sound? Where do you see gaps? Am I thinking in the right direction?”
Wes Kao · 1:01:30

#managing-up#career#leadership#communication

Takeaway1:28:30

Going solo: craft your work around a narrow slice you're best at

Reflecting on leaving in-house operating roles to go solo, Wes describes the freedom to craft her business around only the narrow slice she's best at and loves. That, plus the confidence to say no to genuinely cool opportunities outside her core competency, is what makes it freeing.

In-house roles come with obligations you can't fully control
Solo work lets you build around only your strengths where there's market demand
The 'narrow slice' you're best at is actually freeing, not limiting
Saying no to legitimately interesting opportunities outside your core competency is the enabling skill

“I could craft my business, my work around only the part that I'm best at and that can be a narrow ass slice. Like that's…”
Wes Kao · 1:28:30

#career#solo#focus#saying-no

Key ideas

Frameworks in this episode

Answer the Question Behind the Question

CEDAF Delegation Framework

Manage Up by Sharing Your Point of View

MOO — Most Obvious Objection

Sales Then Logistics

Signposting

Speak Accurately (Avoid the Single-Minded Martyr)

Strategy Not Self-Expression

The Swipe File

People & resources mentioned

People · 11

Resources · 31

Insights & moments

⚡Myth Buster· 1

Being concise isn't about word count, it's economy of words

◆Hot Take· 3

The blast radius of a poorly written memo is bigger than you think

Over-formatting and bullet fragments are often a lazy crutch

The alpha is in the 'boring' basics everyone quits too early

✶Explainer· 2

You can't cut to the chase until you know what the chase is

When you don't know the answer, don't default to 'I'll get back to you'

❝Story· 1

The single-minded martyr: why your great idea keeps getting ignored

✦Tool· 2

How Wes uses Claude as a multi-hour thought partner

Wes Kao's book recommendations on writing and management

▲Takeaway· 6

If people don't understand you, start by asking how you contributed

Practice like it's game day: don't save your best only for execs

The 'yes yes yes next' mindset: take the win and stop talking

Speak accurately: match your words to your actual conviction

Managing up never ends, it gets more important as you get senior

Going solo: craft your work around a narrow slice you're best at

Myth Buster· 1

Hot Take· 3

Explainer· 2

Story· 1

Tool· 2

Takeaway· 6