Confidence Calibration

Wes Kao is an entrepreneur, coach, and advisor. She co-founded the live learning platform Maven, backed by First Round and a16z. Before Maven, Wes co-created the altMBA with best-selling author Seth Godin. Today, Wes teaches a popular course on executive communication and influence. Through her course and one-on-one coaching, she’s helped thousands of operators, founders, and product leaders master the art of influence through clear, compelling communication. Known for her surgical writing style and no-BS frameworks, Wes returns to the pod to deliver a tactical master class on becoming a sharper, more persuasive communicator—at work, in meetings, and across your career.

What you’ll learn:

1. The #1 communication mistake leaders make—and Wes’s proven fix to instantly gain buy-in

2. Wes’s MOO (Most Obvious Objection) framework to consistently anticipate and overcome pushback in meetings

3. How to master concise communication—including Wes’s tactical approach for brevity without losing meaning

4. The art of executive presence: actionable strategies for conveying confidence and clarity, even under pressure

5. The “sales, then logistics” framework—and why your ideas keep getting ignored without it

6. The power of “signposting”—and why executives skim your docs without it

7. Exactly how to give feedback that works—Wes’s “strategy, not self-expression” principle to drive behavior change without friction

8. Practical ways to instantly improve your writing, emails, and Slack messages—simple techniques Wes teaches executives

9. Managing up like a pro: Wes’s clear, practical advice on earning trust, building credibility, and aligning with senior leaders

10. Career accelerators: specific habits and tactics from Wes for growing your influence, advancing your career, and standing out

11. Real-world communication examples—Wes breaks down real scenarios she’s solved, providing step-by-step solutions you can copy today

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Brought to you by:

• WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs

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• Coda—The all-in-one collaborative workspace

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Where to find Wes Kao:

• LinkedIn: https://www.linkedin.com/in/weskao/

• Website: https://www.weskao.com/

• Maven course: https://maven.com/wes-kao/executive-communication-influence

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Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

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In this episode, we cover:

(00:00) Introduction to Wes Kao

(05:34) Working with Wes

(06:58) The importance of communication

(10:44) Sales before logistics

(18:20) Being concise

(24:31) Books to help you become a better writer

(27:30) Signposting and formatting

(32:05) How to develop and practice your communication skills

(40:41) Slack communication

(42:23) Confidence in communication

(50:17) The MOO framework

(54:00) Staying calm in high-stakes conversations

(57:36) Which tactic to start with

(58:53) Effective tactics for managing up

(01:04:53) Giving constructive feedback: strategy, not self-expression

(01:09:39) Delegating effectively while maintaining high standards

(01:16:36) The swipe file: collecting inspiration for better communication

(01:19:59) Leveraging AI for better communication

(01:22:01) Lightning round

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Referenced:

• Persuasive communication and managing up | Wes Kao (Maven, Seth Godin, Section4): https://www.lennysnewsletter.com/p/persuasive-communication-wes-kao

• Making Meta | Andrew ‘Boz’ Bosworth (CTO): https://www.lennysnewsletter.com/p/making-meta-andrew-boz-bosworth-cto

• Communication is the job: https://boz.com/articles/communication-is-the-job

• Maven: https://maven.com/

• Sales, not logistics: https://newsletter.weskao.com/p/sales-not-logistics

• How to be more concise: https://newsletter.weskao.com/p/how-to-be-concise

• Signposting: How to reduce cognitive load for your reader: https://newsletter.weskao.com/p/sign-posting-how-to-reduce-cognitive

• Airbnb’s Vlad Loktev on embracing chaos, inquiry over advocacy, poking the bear, and “impact, impact, impact” (Partner at Index Ventures, Airbnb GM/VP Product): https://www.lennysnewsletter.com/p/impact-impact-impact-vlad-loktev

• Tone and words: Use accurate language: https://newsletter.weskao.com/p/tone-and-words-use-accurate-language

• Quote by Joan Didion: https://www.goodreads.com/quotes/264509-i-don-t-know-what-i-think-until-i-write-it

• Strategy, not self-expression: How to decide what to say when giving feedback: https://newsletter.weskao.com/p/strategy-not-self-expression

• Tobi Lütke’s leadership playbook: Playing infinite games, operating from first principles, and maximizing human potential (founder and CEO of Shopify): https://www.lennysnewsletter.com/p/tobi-lutkes-leadership-playbook

• The CEDAF framework: Delegating gets easier when you get better at explaining your ideas: https://newsletter.weskao.com/p/delegating-and-explaining

• Swipe file: https://en.wikipedia.org/wiki/Swipe_file

• Apple Notes: https://apps.apple.com/us/app/notes/id1110145109

• Claude: https://claude.ai/new

• ChatGPT: https://chatgpt.com/

• Arianna Huffington’s phone bed charging station (Oak): https://www.amazon.com/Arianna-Huffingtons-Phone-Charging-Station/dp/B079C5DBF4?th=1

• The Harlan Coben Collection on Netflix: https://www.netflix.com/browse/genre/81180221

• Oral-B Pro 1000 rechargeable electric toothbrush: https://www.amazon.com/dp/B003UKM9CO/

• The Best Electric Toothbrush: https://www.nytimes.com/wirecutter/reviews/best-electric-toothbrush/

• Glengarry Glen Ross on Prime Video: https://www.amazon.com/Glengarry-Glen-Ross-James-Foley/dp/B002NN5F7A

• 1,000,000: https://www.lennysnewsletter.com/p/1000000

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Recommended books:

• On Writing Well: The Classic Guide to Writing Nonfiction: https://www.amazon.com/Writing-Well-Classic-Guide-Nonfiction/dp/0060891548/

• Stein on Writing: A Master Editor of Some of the Most Successful Writers of Our Century Shares His Craft Techniques and Strategies: https://www.amazon.com/Stein-Writing-Successful-Techniques-Strategies/dp/0312254210/

• On Writing: A Memoir of the Craft: https://www.amazon.com/Writing-Memoir-Craft-Stephen-King/dp/1982159375

• Several Short Sentences About Writing: https://www.amazon.com/Several-Short-Sentences-About-Writing/dp/0307279413/

• High Output Management: https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884

• Your Brain at Work: Strategies for Overcoming Distraction, Regaining Focus, and Working Smarter All Day Long: https://www.amazon.com/Your-Brain-Work-Revised-Updated/dp/0063003155/

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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

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Lenny may be an investor in the companies discussed.

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