🎥 Watch the full episode here

📆 Published: April 6th 2025 🕒

Estimated Reading Time: 4 mins. Time saved: 90 mins! 🔥

Executive Communication: The Career Accelerant Most People Underestimate

🎙️ Pod Shots - Bitesized Podcast Summaries

Remember, we've built an ever-growing library of our top podcast summaries. Whether you need a quick refresher, want to preview an episode, or need to get up to speed fast – we've got you covered. Check it out here

🎯 From Rambling Emails to Career-Defining Clarity: The Communication Playbook That Raised Company Writing Quality 2X

"Wes single-handedly raised the quality of the entire company's writing by like 2X across the board. I always say the best writing course I ever took was working with Wes for a year." That's just one testimonial about Wes Kao, who co-created the Alt-MBA with Seth Godin, co-founded Maven, and now teaches one of the platform's most popular courses on executive communication.

But here's what most people get wrong: they think communication skills matter less as you get more senior. The opposite is true. As Boz, Meta's CTO, famously wrote: "Communication is the job." And the more senior you become, the more ambiguous your mandate, the more critical these skills become.

This conversation matters because there's a quote by George Bernard Shaw that captures the workplace perfectly: "The single biggest problem in communication is the illusion that it has taken place." Most of us think we're communicating clearly. We're not. And it's costing us promotions, buy-in, and impact.

📊 OVERALL SUMMARY

Wes Kao has spent her career mastering the art of executive communication—first at the Alt-MBA with Seth Godin, then as co-founder of Maven, and now teaching thousands of operators how to communicate with clarity and influence. Her frameworks have helped people get promoted faster, secure buy-in from skeptical executives, and transform how entire companies write and present.

What makes Wes's approach different:

She doesn't teach generic "communication tips." She teaches tactical frameworks you can use immediately—MOO (Most Obvious Objection), CEDAF (for delegation), "sales then logistics," and "strategy not self-expression" for feedback. These aren't fluffy concepts. They're battle-tested patterns that work in Slack messages, strategy docs, and high-stakes presentations.

The core insight: Most communication problems aren't about talent or charisma. They're about preparation, structure, and empathy. Wes's advice boils down to spending a little more time upfront (sometimes just 30 seconds) to save hours of confusion, back-and-forth, and misalignment later.

Key themes:

• Concision isn't brevity – A 1,000-word memo can be tighter than a 300-word one if every sentence earns its place

• Managing up gets harder, not easier – Senior people are the best at it because they have to be

• The blast radius of bad writing is massive – One unclear Slack message to 15 people creates 15 confused people

• Preparation is the only shortcut – Even 30 seconds before a meeting transforms your clarity

• Communication is a means to an end – The goal isn't to sound smart; it's to get the outcome you want

This episode is packed with immediately actionable tactics for anyone who writes emails, runs meetings, or needs to convince people of anything.

🎓 Why Communication Matters More Than You Think

Here's the myth Wes believed early in her career: "I'll have to manage up when I'm junior, but eventually I'll outgrow it." She was wrong. The more senior she got, the more important communication became.

Why? Because senior roles come with ambiguity. Your manager isn't handing you well-defined tasks anymore. You're getting mandates like "make this number go up" or "create this division." You need to manage up to ensure alignment, share your thinking, and make sure you're not going in the wrong direction for three months.

Colleagues who've worked with Wes describe her impact:

• "Wes never just throws things out there. She's precise with her use of language, meticulous about examining her own ideas before bringing them in front of others."

• "Wes includes reasoning with every proposal and context behind all her recommendations so everyone around her learns an order of magnitude faster."

• "Zero half-baked thoughts, 100% complete sentences, perfect punctuation, clear takeaways at the top of every message."

Wes's philosophy: "If I'm not getting the reaction I'm looking for, how might I be contributing to that?" Instead of blaming others for not understanding, she asks: How could I explain this more clearly? How can I be more compelling? How can I anticipate their questions?

Key Takeaways:

• Communication skills become MORE important as you get senior, not less

• If people aren't buying in, look at your communication first before blaming them

• Practice like it's game day—don't save your best communication for executives only

• Communication is a means to an end: the goal is getting the outcome you want

💼 Sales, Then Logistics

One of the most common mistakes Wes sees: jumping straight into logistics before securing buy-in. People overestimate how much their audience has already bought into the idea.

The mistake looks like this: You send a Slack message explaining which document to fill out, what format to use, and the deadline—without explaining why anyone should care. The result? Crickets. Or slow, reluctant responses.

Example: A head of operations wanted her executive team to share weekly wins to motivate the company. She led with logistics: which doc, what time, what format. It felt like another checkbox on an already overwhelming to-do list. No one responded.

The fix: Start with sales. "We're doing this because it's a chance to shine a light on your team members doing amazing work. This will motivate them and help the rest of the company see what you're accomplishing." Then share the logistics.

Even with executives who say "just get to the point," you still need 30 seconds of framing. Why are we here? Why does this matter? What do I need from you? That's not fluff—it's context that helps them listen more effectively.

Key Takeaways:

• Don't assume people have bought in just because they agreed two weeks ago

• Sales notes are different from logistics notes—know which one you're writing

• Even executives need 30 seconds of "why" before diving into "how"

• Framing upfront prevents the "cold start" problem in meetings

✂️ Being Concise (Without Being Brief)

Wes's pet peeve: people equating concision with brevity. "Being concise is not about absolute word count. It's about economy of words—the density of insight you're sharing."

You can have a 300-word memo that's meandering and a 1,000-word memo that's tight and concise. The difference? Every sentence in the 1,000-word version earns its place.

The real bottleneck to concision: Not knowing what your core point is. You can't "cut to the chase" unless you know what the chase is. You can't "unbury the lead" unless you know what the lead is.

Think about your go-to story—the one you've told dozens of times. You know exactly when people will laugh, gasp, or lean in. Why? Because you've told it so many times that you know all the beats. At work, we're rarely talking about the same thing repeatedly. We're processing new information in real-time while trying to explain it clearly.

The solution: Preparation. Even 30 seconds before a meeting makes a huge difference. Most of us are so back-to-back that we're still unwinding from the last Zoom call 30 seconds into the next one. If you take one minute to ground yourself—Why am I in this meeting? What do I want to share?—you'll be infinitely more concise.

For writing: Remind yourself to be concise. When Wes does this, she trims at least 20% of what she wrote. Ask yourself: How might I be adding cognitive load? Is there a tighter, clearer way to say this?

Key Takeaways:

• Concision = economy of words, not word count

• The bottleneck is knowing your core point, not finding shorter words

• Preparation is the only consistent solution—even 30 seconds helps

• Rereading your own message before sending catches 20%+ of unnecessary words

🗺️ Signposting: Power Words for Clarity

Signposting uses specific words, phrases, and formatting to guide your reader and signal what's coming next. It's especially helpful in long memos.

Wes's favorite signposting words:

• "For example" – signals you're about to show an example

• "Because" – signals you're sharing logic and rationale

• "As a next step" – people's eyes automatically zoom to this

• "First, second, third" – structures paragraphs without needing bold/italics

These are power words for clarity. In copywriting, power words like "free" and "gift" grab attention. In communication, signposting words help your brain see structure and focus on what matters.

Verbal signposting: "The most important part to pay attention to is..." or "The part we were most surprised by is..." or "The part that customers loved most is..."

You're not just adding structure—you're grabbing people's attention back if it's strayed.

Key Takeaways:

• Signposting words guide readers without relying on formatting

• Works in writing (memos, emails) and verbally (presentations, demos)

• "For example," "because," "as a next step" are your best friends

• Signals what's coming so people can listen/read more effectively

🎨 Formatting: Don't Overdo It

Wes hates excessive formatting. She's seen memos where 30% of the text is bolded. "That negates the entire point of bolding. If everything is bolded, nothing is highlighted."

The bullet point trap: People overuse bullets and sentence fragments thinking it makes things more concise. But fragments often force your reader to decipher and interpret what you meant. Net-net, it takes longer.

Bullets can also be a crutch. If you can't turn your sentence fragment into a full sentence, you probably don't fully understand your own idea. Trying to write a complete sentence forces you to use brainpower—and reveals gaps in your thinking.

This is the Amazon six-page memo philosophy: if you can't write it out in prose, you don't actually know what you're saying. It's a filter for crystallising your thinking.

Key Takeaways:

• Use formatting more sparingly than you think—if 30% is bolded, nothing stands out

• Bullet points can hide incomplete thinking

• If you can't turn a fragment into a full sentence, your idea isn't fully formed

• Complete sentences show the connected tissue between ideas

🎯 Finding the Right Level of Confidence

People tend to fall into two camps: overconfident or under-confident.

Overconfident people state hypotheses as facts. "This will increase retention by 20%." Really? Or is it "This could increase retention" or "This will increase the likelihood of improving retention"? Speak accurately. Your team is listening at face value and might spend real headcount and dollars pursuing something you oversold.

Under-confident people diminish their recommendations. A CEO asks them to share advice with another team. They share amazing insights, then end with: "But you can ignore everything I just said. Do what you think is best." You don't have to say that. If you have strong reasons to recommend something, it's almost irresponsible to act like you're not sure.

The single-minded martyr problem: Wes had a client on the growth team who couldn't get headcount for her project. Everyone said they believed in it, but no one would lend her half an engineer for two weeks. As they talked, she revealed the CEO had said the company-wide goal was retention, not growth.

She was being a "single-minded martyr"—so focused on her agenda that she couldn't see the bigger picture. Once she zoomed out, she could right-size her proposal to fit company priorities.

Key Takeaways:

• Speak accurately about your level of conviction—don't state hypotheses as facts

• Don't diminish strong recommendations by saying "ignore this if you want"

• Put your proposal in context of company priorities, not just your team's goals

• Maturity means knowing when the right answer is "not right now"

🐄 MOO: Most Obvious Objection

MOO stands for Most Obvious Objection. It's Wes's favourite framework and she uses it multiple times a day.

The idea: We're often surprised by questions in meetings, feeling blindsided. But if you thought for even two minutes about obvious objections you're likely to get, you'd immediately come up with several.

Can you anticipate every objection? No. But can you anticipate the obvious ones? Absolutely.

How to use MOO: Before you share something—whether it's a Slack message, strategy doc, or presentation—ask yourself: What might someone object to? What questions will they have? Then address those upfront or frame your message to preempt them.

This is a mental filter that trains you to think a couple steps ahead. If I say this, they might say that. If I take that into account, I can volunteer that information upfront or frame it so they're less likely to see it as an issue.

Key Takeaways:

• Anticipate obvious objections before presenting—even two minutes helps

• Addressing objections upfront prevents you from being caught off guard

• MOO trains you to empathize with your audience

• Put it on a Post-it: "What's the Most Obvious Objection?"

🧊 Keeping Your Cool in Real-Time Conversations

High-stakes conversations throw people off, especially when asked a question they don't know the answer to. Most people panic or default to "Let me look into it and get back to you."

That's fine—it's better than making something up. But if you're experienced and confident in your domain, just saying "I'll get back to you" is a missed opportunity.

Better approach: Answer a similar question in the direction you think they're asking about, then validate.

Example: Your exec asks, "What percentage of users came from mobile last month?" You don't have that number off the top of your head.

• Person A: "Let me look into it and I'll get back to you."

• Person B: "I don't have that number off the top of my head, but in the last quarter it's been 60-70% and it's grown over the past year, so mobile is now a bigger part of our business. Are you wondering if we're investing in mobile appropriately?"

Person B continues the conversation, provides useful context, and uncovers the question behind the question.

The question behind the question: Sometimes people ask surface-level questions, but there's a deeper concern underneath. If you're getting multiple questions on the same thing, probe deeper. "Where's this question coming from?" or "Are you concerned about X?"

Another tactic: Reflect back their question. "Let me make sure I understand—you want to know monthly retention for...?" This buys you time to think, shows you're listening, and helps clarify what they actually want.

Key Takeaways:

• Don't default to "I'll get back to you"—answer in the general direction if you can

• Find the question behind the question by probing for deeper concerns

• Reflect back their question to buy time and clarify what they want

• Continuing the conversation in the moment is often more valuable than perfect data later

📈 Managing Up: It Gets More Important, Not Less

The myth: "I'll have to manage up when I'm junior, but I'll outgrow it." The reality: Managing up becomes more important as you get senior.

Why? Because the more senior you are, the less your manager gives you well-defined tasks. You're dealing with ambiguity. You need to manage up to ensure alignment, share your thinking, and avoid going in the wrong direction for months.

The highest-leverage way to manage up: Share your point of view.

When you ask your manager, "What should we do?" you're putting cognitive load on them. They have to think about the problem, craft solutions, and tell you what to do.

Instead: "Here's what I think we should do. How does that sound? Where do you see gaps?" You give them something to build off of, reducing their mental lift. You also show you're an active, rigorous thinker who's looking around corners.

This works for junior people too: You don't need the perfect answer. Share what you're noticing. "I've noticed this problem popping up in a couple places. Here's what I think might be happening." When you share a report, don't just send the data—point out insights and takeaways.

Managers want this. Junior people often have the most visibility into customer issues, support tickets, and data. If you're not speaking up, your manager doesn't have that visibility.

Key Takeaways:

• Managing up becomes MORE important as you get senior, not less

• Share your point of view instead of asking "What should I do?"

• Reduces cognitive load on your manager and shows strategic thinking

• Junior people can do this too—share what you're noticing and observing

💬 Giving Feedback Well: Strategy, Not Self-Expression

Wes's framework for feedback: Strategy, not self-expression.

By the time we give feedback, we've usually been frustrated for a while. Wes used to be conflict-averse, so she'd wait until she couldn't hold it in anymore. Then she'd schedule a one-on-one and it would turn into a venting session—sharing all her frustrations and how the person harmed her.

This was counterproductive. The person either felt demoralised or got defensive, wanting to argue about how it wasn't that bad or was partially her fault too.

The better way: Think about motivating behaviour change. That's the goal. So trim everything that doesn't contribute to that goal. Keep only the 10% that will make the person want to change and help them understand the benefit to them and others.

Before the conversation: Get the energy out. Vent to your therapist, partner, or friend. Otherwise, you bring that energy into the conversation and it doesn't take much to set you off. The person raises an eyebrow, acts incredulous, and you snap.

Key Takeaways:

• Goal is behavior change, not venting or making them feel bad

• Trim 90% of what you want to say—keep only what motivates change

• Get the venting energy out before the conversation (therapist, friend, partner)

• Going in clear and grounded sets a positive emotional tone

🎯 Delegating with High Standards: CEDAF

Wes's framework for delegation: CEDAF (like "cedar" with an F at the end).

C = Comprehension: Have I given this person everything they need to understand what I want them to do? Logins, context, what the end result should look like.

E = Excitement: Am I explaining this in a way that makes it as exciting as it could be? Even boring tasks can be exciting if you explain why it matters to the project or the company.

D = De-risk: Am I de-risking obvious risks? If you're worried they'll spend hours going in the wrong direction, have them do 10 rows of the spreadsheet first, see how long it takes, then regroup. If you think they might misunderstand, say: "You might think I mean X, but I actually want Y."

A = Align: Am I giving them a chance to speak up and make sure we're aligned? Don't just explain and say "go." Give them space to ask questions. Often they'll say, "What did you mean by this part?" and you'll realize you forgot to mention something crucial.

F = Feedback: How can I shorten the feedback loop? Instead of waiting a week, check in after a day. Or even better, brainstorm a couple things they want to do at the end of the initial conversation. Get a sense of their direction before they go off and build.

Bonus insight: This framework also works for delegating to AI agents. Comprehension, excitement (context), de-risk, align, feedback—it's the same process.

Key Takeaways:

• CEDAF: Comprehension, Excitement, De-risk, Align, Feedback

• Shorten the feedback loop as much as possible, then shorten it again

• De-risk by having them do a small portion first before going all-in

• This framework works for delegating to people AND AI agents

📂 Swipe Files: Training Yourself to Notice What Works

A swipe file is a collection of inspiration you can refer back to later. Marketers use them for copy, landing pages, and ads. Wes has an Apple Notes file called "Smart Things People Have Said."

She doesn't actually go back and look at it often. The value is in the act of adding to it—it trains her to notice when something is working well.

"There's so much happening around us all the time. Your coworker says something smart and you're like, 'Oh, that was nice,' and then you keep moving on. But when you stop and pause and think, 'Oh, that was really effective. Let me add it to my file,' you're also thinking about why it was effective and whether you can borrow it."

What to collect: Quotes, phrases, screenshots of cool designs, strategy docs, conversion flows, anything you're interested in. It can be super messy. Wes doesn't tag anything or organise it. She just adds it to a file.

Key Takeaways:

• Swipe files train you to notice what works, even if you never look back at them

• Collect phrases, designs, docs, flows—anything that resonates

• It can be messy—the value is in the act of capturing, not organising

• Helps you analyse and break down why something was effective

💡 CONTRARIAN INSIGHTS (Quick Hits)

• Managing up gets harder, not easier – Senior people are the best at it because they have to be; it doesn't go away

• Concision isn't brevity – A 1,000-word memo can be tighter than a 300-word one if every sentence earns its place

• The blast radius of bad writing is massive – One unclear Slack message to 15 people creates 15 confused people and hours of back-and-forth

• Preparation is the only shortcut – Even 30 seconds before a meeting transforms your clarity and concision

• Bullet points can be a crutch – If you can't turn a fragment into a full sentence, your idea isn't fully formed

• Trim 90% of your feedback – The goal is behaviour change, not venting; keep only what motivates change

• Everything takes longer than you think – Add buffers for yourself in launches, errands, career building, and skill development

• You can craft your career around a narrow slice – As a solo operator, you can focus only on what you're best at and love doing

• Communication and thinking are intertwined – "I don't know what I think until I write it down" (Joan Didion)

• CEDAF works for AI too – The same delegation framework applies to prompting AI agents effectively

🔗 Links Referenced

• Wes Kao's Website: https://weskao.com

• Lenny's Podcast: https://www.lennyspodcast.com

• Full Episode: https://www.youtube.com/watch?v=BIvVGhy_VxU

• Maven (Wes's Course Platform): https://maven.com

• Books Mentioned:

  • High Output Management by Andy Grove

  • Your Brain At Work by Dr. David Rock

  • On Writing Well by William Zinsser

  • Stein On Writing by Sol Stein

  • On Writing by Stephen King

This article is part of the Pod Shots series, transforming podcast conversations into actionable insights for busy product leaders, tech founders, and investors. For more summaries, visit our library.

That’s a wrap.

As always, the journey doesn't end here!

Please share and let us know whether you liked this separate Pod Shot, or whether you’d rather stick with your usual programming….. 🚀👋

Alastair 🍽️.