Mastering the Art of Teaching, Writing, and Managing Up: Lessons from Wes Kao¶

What do Seth Godin, Scott Galloway, and the future of online education have in common? Wes Kao. In a recent episode of Lenny’s Podcast, Wes Kao—co-founder of Maven and an expert in cohort-based courses—shared her journey, frameworks for better writing and teaching, and actionable advice for managing up and communicating effectively at work. Whether you’re a course creator, a manager, or simply someone looking to level up your writing and communication, this episode is packed with insights you won’t want to miss.

Introduction: Who is Wes Kao?¶

Wes Kao is a powerhouse in the world of online education. After starting her career in corporate retail at Gap, she worked with industry giants like Seth Godin (co-founding the legendary altMBA), consulted for top creators, and eventually launched Maven—a platform that makes it easier for experts to run cohort-based courses. Her unorthodox career path and obsession with craft have made her a sought-after authority on teaching, writing, and organizational effectiveness.

“I care a lot about craft, and I think more people should care about craft.” — Wes Kao

From Corporate Retail to Seth Godin’s Right Hand¶

Wes’s journey is a testament to the power of saying yes to unexpected opportunities. She described how a serendipitous application to Seth Godin’s call for a “special projects lead” led her to co-create the altMBA, impacting thousands of students worldwide.

Key Takeaway: Don’t self-reject. Put your foot forward, even if you don’t feel perfectly prepared.

“Don’t take yourself out of the running before you get rejected. Don’t reject yourself.” — Wes Kao

Working with Seth Godin, Wes learned the importance of high standards, speed, and rigor—producing “high quality, fast, and economical” work. She noted that Seth is even sharper and more genuine in person than he appears online.

The Super-Specific How: A Framework for Better Writing¶

One of Wes’s most impactful concepts is the “super-specific how.” Most writers and teachers focus too much on the what and why, but the real value is in the how.

Cut the backstory: Get straight to the actionable advice.
Be specific: Instead of generalities, offer concrete steps and examples.
Start right before you get eaten by the bear: Begin your story or lesson at the most interesting, relevant moment.

“Most people need less context setting and preamble than you might think.” — Wes Kao

The Content Hierarchy: Where BS Can Hide¶

Wes introduced a “content hierarchy” pyramid: - Bottom: Twitter, podcasts, keynotes—more room for unchallenged statements (“BS”). - Top: Cohort-based courses—students can ask questions in real-time, so there’s little room for fluff or inaccuracies.

“In a cohort-based course... you have to be able to defend what you’re saying and make sure that what you’re saying is rigorous.” — Wes Kao

The State Change Method: Keeping Audiences Engaged¶

Whether you’re teaching a course or running a Zoom meeting, Wes advocates for frequent “state changes”—deliberate shifts in activity or engagement to keep attention high.

Examples of state changes: - Ask participants to respond in the chat. - Switch between gallery view and screen sharing. - Use polls or breakout rooms. - Invite others to speak or share.

“Punctuate your monologues with state changes. Anything that shakes your audience awake and adds some variety.” — Wes Kao

She also highlighted the importance of noticing “eyes light up” moments—those times when your audience is visibly more engaged. Use these cues to refine your content and focus on what resonates.

Managing Up: Why and How¶

Managing up isn’t just for junior employees; it’s a key skill at every level.

Why it matters: Proactively managing your relationship with your boss builds trust, opens up opportunities, and helps avoid surprises.
How to do it: Keep your manager in the loop with regular, structured updates (e.g., a weekly “State of Lenny” email outlining priorities, blockers, and what’s on your mind).
Overcommunicate: Err on the side of too much communication—especially in remote work.

“The most senior people are best at managing up. This is why they got promoted in the first place.” — Wes Kao

Pro Tip: Use frameworks like “bottom line up front” (BLUF) and provide context for those who want to dig deeper.

Wes encourages writers to go beyond copying popular formats on Twitter or LinkedIn and to study the actual craft of writing.

Be precise: Avoid accidental bias or confusion in your writing.
Structure matters: Start with your recommendation or main point, then provide supporting context.
Build trust: If you present pros and cons, be transparent about your recommendation.

“More people should learn the craft of writing and the technical aspects of writing—not just look at what other people are doing to try to get audience engagement.” — Wes Kao

The Art of Saying No (Without Saying “No”)¶

For people pleasers, saying no can be tough. Wes suggests reframing the conversation around trade-offs:

Instead of a flat “no,” explain what saying “yes” would mean deprioritizing.
Invite the requester to help decide on priorities.

“By talking about trade-offs, you really get the outcome, which is you protect your bandwidth...without actually even having to say the word no.” — Wes Kao

Lightning Round: Recommendations and Contrarian Opinions¶

Most recommended books: See list below.
Favorite Maven courses: Amanda Natividad’s “Content Marketing 201” and Marylee Nicasio’s “Breaking into Technical Product Management.”
Least favorite fruit: Grapes (unless frozen!).

Conclusion: Raising the Bar on Teaching, Writing, and Work¶

Wes Kao’s frameworks and insights are a masterclass in intentionality—whether you’re writing, teaching, or collaborating at work. The main takeaways:

Focus on the super-specific how in your writing and teaching.
Keep your audience engaged with frequent state changes.
Manage up by proactively communicating and avoiding surprises.
Study the craft of writing, not just the formats.
Protect your bandwidth by discussing trade-offs, not just saying “no.”

If you’re interested in creating your own cohort-based course, check out Maven’s free Course Accelerator. And remember: don’t self-reject. Take the leap—you might just end up changing your own trajectory.

Books Recommended in the Podcast¶

It Was the Best of Sentences, It Was the Worst of Sentences by June Casagrande
Recommended for mastering the craft of writing clear, effective sentences.
Better Business Writing by Harvard Business Press
A practical guide for improving business communication and writing skills.

Inspired by Wes Kao’s appearance on Lenny’s Podcast. For more, follow Wes on Twitter or visit maven.com.

Podcast: Persuasive communication and managing up | Wes Kao (Maven, altMBA, Section4)