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
—
Brought to you by:
• WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs
• Vanta—Automate compliance. Simplify security
• Coda—The all-in-one collaborative workspace
—
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
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
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
—
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
Popular Podcasts
Stuff You Should Know
If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.
Dateline NBC
Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com
The Burden
The Burden is a documentary series that takes listeners into the hidden places where justice is done (and undone). It dives deep into the lives of heroes and villains. And it focuses a spotlight on those who triumph even when the odds are against them. Season 5 - The Burden: Death & Deceit in Alliance On April Fools Day 1999, 26-year-old Yvonne Layne was found murdered in her Alliance, Ohio home. David Thorne, her ex-boyfriend and father of one of her children, was instantly a suspect. Another young man admitted to the murder, and David breathed a sigh of relief, until the confessed murderer fingered David; “He paid me to do it.” David was sentenced to life without parole. Two decades later, Pulitzer winner and podcast host, Maggie Freleng (Bone Valley Season 3: Graves County, Wrongful Conviction, Suave) launched a “live” investigation into David's conviction alongside Jason Baldwin (himself wrongfully convicted as a member of the West Memphis Three). Maggie had come to believe that the entire investigation of David was botched by the tiny local police department, or worse, covered up the real killer. Was Maggie correct? Was David’s claim of innocence credible? In Death and Deceit in Alliance, Maggie recounts the case that launched her career, and ultimately, “broke” her.” The results will shock the listener and reduce Maggie to tears and self-doubt. This is not your typical wrongful conviction story. In fact, it turns the genre on its head. It asks the question: What if our champions are foolish? Season 4 - The Burden: Get the Money and Run “Trying to murder my father, this was the thing that put me on the path.” That’s Joe Loya and that path was bank robbery. Bank, bank, bank, bank, bank. In season 4 of The Burden: Get the Money and Run, we hear from Joe who was once the most prolific bank robber in Southern California, and beyond. He used disguises, body doubles, proxies. He leaped over counters, grabbed the money and ran. Even as the FBI was closing in. It was a showdown between a daring bank robber, and a patient FBI agent. Joe was no ordinary bank robber. He was bright, articulate, charismatic, and driven by a dark rage that he summoned up at will. In seven episodes, Joe tells all: the what, the how… and the why. Including why he tried to murder his father. Season 3 - The Burden: Avenger Miriam Lewin is one of Argentina’s leading journalists today. At 19 years old, she was kidnapped off the streets of Buenos Aires for her political activism and thrown into a concentration camp. Thousands of her fellow inmates were executed, tossed alive from a cargo plane into the ocean. Miriam, along with a handful of others, will survive the camp. Then as a journalist, she will wage a decades long campaign to bring her tormentors to justice. Avenger is about one woman’s triumphant battle against unbelievable odds to survive torture, claim justice for the crimes done against her and others like her, and change the future of her country. Season 2 - The Burden: Empire on Blood Empire on Blood is set in the Bronx, NY, in the early 90s, when two young drug dealers ruled an intersection known as “The Corner on Blood.” The boss, Calvin Buari, lived large. He and a protege swore they would build an empire on blood. Then the relationship frayed and the protege accused Calvin of a double homicide which he claimed he didn’t do. But did he? Award-winning journalist Steve Fishman spent seven years to answer that question. This is the story of one man’s last chance to overturn his life sentence. He may prevail, but someone’s gotta pay. The Burden: Empire on Blood is the director’s cut of the true crime classic which reached #1 on the charts when it was first released half a dozen years ago. Season 1 - The Burden In the 1990s, Detective Louis N. Scarcella was legendary. In a city overrun by violent crime, he cracked the toughest cases and put away the worst criminals. “The Hulk” was his nickname. Then the story changed. Scarcella ran into a group of convicted murderers who all say they are innocent. They turned themselves into jailhouse-lawyers and in prison founded a lway firm. When they realized Scarcella helped put many of them away, they set their sights on taking him down. And with the help of a NY Times reporter they have a chance. For years, Scarcella insisted he did nothing wrong. But that’s all he’d say. Until we tracked Scarcella to a sauna in a Russian bathhouse, where he started to talk..and talk and talk. “The guilty have gone free,” he whispered. And then agreed to take us into the belly of the beast. Welcome to The Burden.