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

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

9Frameworks
15Insights

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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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