Table of Contents
Learn game-changing communication strategies from Wes Kao, co-founder of Maven and former partner to Seth Godin. Discover the "super specific how" framework for better writing, state change methods for engaging audiences, proven techniques for managing up effectively, and how to protect your bandwidth without saying no. Essential skills for anyone wanting to communicate more persuasively and advance their career.
Key Takeaways
- Focus on the "super specific how" rather than what and why - Most people already agree with your premise; they want to know exactly how to apply it to their situation
- Use state changes every 3-5 minutes to keep audiences engaged - Break up monologues with chat interactions, polls, breakouts, and screen sharing to prevent cognitive fatigue
- Managing up is the secret to career advancement - Senior people are best at managing up because it got them promoted; proactive communication builds trust and opportunities
- Watch for "eyes light up" moments to identify what resonates - People's faces can't lie; use these signals to refine your content, sales pitches, and presentations
- Protect bandwidth by discussing trade-offs, not saying no - Frame requests in terms of what gets deprioritized rather than refusing outright
- Content hierarchy of BS: courses have the least room for nonsense - Live cohort-based courses force accountability and rigor that other formats allow you to avoid
- Write with intentional perspective, not accidental bias - Be deliberate about your point of view and recommendations rather than accidentally leading readers
Timeline Overview
Wes's early career (00:00) - Career progression from Gap headquarters through beauty and adtech companies to working with Seth Godin
How to land a job with Seth Godin (07:08) - Applied to Seth's special projects role with one-take video, moved cross-country for six-month role that became three years
What makes Seth Godin stand apart (09:56) - High standards for quality while shipping fast, obsessive attention to craft, and genuine authenticity
Wes's framework for better writing: the super-specific how (14:50) - Most readers already agree with your premise; spend time on practical implementation details and nuanced examples
Writing and teaching without the BS (18:08) - Twitter and keynotes allow more BS; cohort-based courses with live interaction demand rigor and accountability
State changes: how to keep your audience engaged when teaching (21:45) - Use chat, polls, breakouts, screen sharing, and other interactions to prevent audience fatigue and maintain engagement
The data of "eyes light up" moments (25:51) - Watch for visceral reactions that indicate true engagement versus polite nodding; use this data to refine messaging
What managing up can do for you (29:27) - Builds trust, creates opportunities, and helps bosses understand your value; ironically, senior people are best at it
How to manage up effectively (32:51) - Keep boss informed on decisions, provide appropriate detail for reversible vs irreversible choices, avoid surprises
Lenny's template for proactive communication (34:17) - Three sections: current priorities, blockers needing help, and things on mind; simple but powerful alignment tool
The skills you need to communicate clearly through writing (36:19) - Learn technical aspects of sentence construction, argument logic, and intentional perspective rather than mimicking others
How to protect your bandwidth (without having to say no to your boss) (43:50) - Frame new requests in terms of what gets deprioritized; turns yes/no into collaborative prioritization
How Lenny sets priorities and communicates them (47:32) - Don't just prioritize or just communicate; do both to ensure alignment and manage expectations
Lightning round! (48:24) - Book suggestions, favorite courses, and surprisingly contrarian fruit preferences
Wes's Early Career
Wes Kao's path demonstrates the value of starting with solid business fundamentals. Beginning at Gap headquarters in San Francisco, she completed a rotation program across Old Navy, Banana Republic, and Gap - providing crucial foundation in business operations before transitioning to smaller companies and eventually founding her own.
This progression from large corporate environments to startups to entrepreneurship gave her exposure to different scales and challenges, ultimately preparing her for the unique opportunity to work with Seth Godin and co-found the altMBA.
Landing the Seth Godin Opportunity
The story of how Wes connected with Seth Godin illustrates a crucial career principle: "Don't reject yourself before getting rejected." When Seth posted about looking for a special projects lead, Wes applied despite assuming thousands would compete.
Her approach was refreshingly authentic - she created her application video in one take, resisting the perfectionist urge to do multiple versions. This authenticity, combined with her willingness to take risks (moving cross-country for a six-month role), led to over three years of collaboration and the co-founding of altMBA.
Key lesson: Put your best foot forward, but actually put your foot forward. Many people talk themselves out of opportunities before even trying.
What Makes Seth Godin Exceptional
Working directly with Seth revealed insights that external observers might miss:
Sharper in person than in writing - Most people are the opposite, having time to curate their online presence. Seth's real-time insights and conversational sharpness exceeded even his polished blog content.
High standards without sacrificing speed - The typical quality/speed/cost triangle didn't apply. They consistently produced high-quality work fast, challenging the assumption that speed requires quality trade-offs.
Obsessive attention to craft - This aligned with Wes's own personality and raised her standards across strategy, tactics, and execution.
This experience demonstrates that working with exceptional people can fundamentally raise your own standards and capabilities.
The Super Specific How Framework
Most writers and course creators spend too much time on what and why, not enough on how. Unless your topic is truly controversial or groundbreaking, your audience probably already agrees with your general premise.
The Problem
Writers often provide too much context and backstory before getting to practical application. This "scope creep" bores readers who want actionable insights.
The Solution
"Start right before you get eaten by the bear" - Cut everything except essential context right before the valuable part. If telling a camping story, don't start with shopping at REI or booking the campsite; start when your friend left food out and attracted bears.
Application to Product Management
Instead of explaining why communication matters for PMs (obvious), focus on:
- How to get buy-in without positional authority
- How to turn chaos into order across multiple stakeholders
- How to communicate hypotheses that might not work but need team momentum
This framework forces you to provide specific, actionable value rather than general platitudes.
Content Hierarchy of BS
Wes's content hierarchy reveals where different formats allow or discourage intellectual rigor:
High BS Tolerance (Bottom of Pyramid)
- Twitter threads: 280 characters, mic-drop format, walk away without defending
- Keynote speeches: One-directional, limited audience challenge
- Podcasts: Conversational but limited real-time pushback
Medium BS Tolerance
- Long-form articles: Must defend ideas and convince readers
- Books: Require sustained argument and evidence
Low BS Tolerance (Top of Pyramid)
- One-directional courses: Video content on platforms like Udemy
- Cohort-based courses: Live interaction, real-time questions, immediate accountability
The highest level - cohort-based courses with live student interaction - forces maximum rigor because students can challenge ideas in real-time through chat, questions, and discussion.
Key insight: Choose your content format deliberately, understanding how much intellectual rigor it demands and allows.
State Change Method
Traditional presentations and Zoom meetings often involve one person talking while everyone else listens silently - extremely draining, especially in virtual environments.
The Problem
Monologues put audiences to sleep. People struggle to:
- Sit still and look engaged on camera
- Control facial expressions for extended periods
- Maintain focus without interaction
The Solution: State Changes Every 3-5 Minutes
- Chat interactions: Ask people to respond in Zoom chat
- View switching: Move between gallery view and screen sharing
- Polls: Have audience guess before revealing information
- Breakout rooms: Small group discussions with report-backs
- Popcorn sharing: Sequential sharing where each person calls on the next
Practical Implementation
Nathan Barry suggests putting a state change every 3-5 slides in presentations. Force yourself to review material at regular intervals and insert interaction opportunities.
Example: Instead of just telling students the average attention span is 2-4 minutes, ask them to guess first. Answers range from hours to seconds, making the reveal more memorable.
Eyes Light Up Moments
People's faces reveal genuine interest more than their words. While someone might politely say "that's interesting," their eyes lighting up indicates visceral engagement.
Recognition Skills
Watch for:
- Facial expression changes: From polite attention to genuine interest
- Body language shifts: Leaning forward, increased alertness
- Voice changes: More energy and enthusiasm in responses
- Follow-up questions: Spontaneous deeper inquiry
Applications
- Sales pitches: Identify which parts truly resonate vs. polite listening
- Content creation: Note which topics generate genuine excitement for future writing
- Presentations: Expand on sections that create visible engagement
- Meetings: Recognize when ideas truly land with stakeholders
Key principle: Don't be delusional about lukewarm responses. Bored looks are data - use them to identify what doesn't work and double down on what creates genuine excitement.
Managing Up Fundamentals
Most people assume their boss should manage them and feel resentful about "managing up." This perspective limits career growth and misses the strategic value of proactive relationship management.
Why Managing Up Matters
- Trust building: Bosses appreciate employees who keep them informed
- Opportunity creation: Well-managed relationships lead to better assignments
- Career advancement: Senior people excel at managing up - it's how they got promoted
- Universal skill: Everyone has a boss at some level, making this perpetually relevant
Core Principles
- Proactive communication: Share decisions and rationale before being asked
- Right level of context: Distinguish between reversible and irreversible decisions
- No surprises: Keep leadership informed of potential issues early
- Trade-off awareness: Help bosses understand resource allocation decisions
The State of [Name] Email Template
Weekly emails with three sections:
- Current priorities: What you're focused on this week
- Blockers needing help: Specific areas where manager input/support needed
- Things on mind: Additional context, concerns, or opportunities
This simple format ensures alignment, prevents surprises, and demonstrates proactive thinking.
Clear Written Communication
Study Craft, Not Just Tactics
Most people learn writing by mimicking social media posts, but this approach has limitations. Studying actual writing craft provides better foundation for:
- Sentence construction: Technical aspects of clear communication
- Argument logic: How to build persuasive reasoning
- Intentional perspective: Deliberate rather than accidental point of view
Recommended Resources
- "It Was the Best of Sentences, It Was the Worst of Sentences" by June Casagrande
- "Better Business Writing" by Harvard Business Press
Common Writing Problems
Accidental leading: Writing that unintentionally guides readers toward conclusions you don't intend.
Example: Asking "Should we change our office location?" in a way that implies staying is better, when you actually want objective input.
Solution: Be intentional about your recommendation level and make it explicit.
Structure for Business Communication
- Lead with conclusion: "My recommendation is X"
- Provide reasoning: "Here's why I think this..."
- Address downsides: "Here are risks to consider..."
- Separate context: Clearly distinguish background info from action items
This structure (similar to MINTO pyramid) respects busy readers who want conclusions first, with supporting detail available for those who need it.
Protecting Bandwidth Through Trade-off Discussions
The Problem with Traditional "No"
Saying no to requests often feels:
- Uncooperative or unhelpful
- Like you're avoiding work
- Potentially damaging to relationships
The Trade-off Approach
Instead of yes/no framing, discuss what gets deprioritized:
Traditional response: "Sorry, I don't have bandwidth for that right now."
Trade-off response: "Yes, I can design that PDF for you. That means the website redesign I was planning to work on today will have to wait until later this week. Does that sound good, or should I prioritize the original design project?"
Benefits of This Approach
- Maintains relationships: You're not refusing to help
- Enables informed decisions: Requester understands full impact
- Demonstrates thoughtfulness: Shows you're managing priorities strategically
- Shifts conversation: From "helpful vs unhelpful" to "what's most important"
Prioritize and Communicate Framework
When receiving new requests:
- Prioritize it: Determine where it fits in your current work queue
- Communicate placement: "This would be third on my priority list"
- Confirm alignment: "Does this timing work, or should we adjust priorities?"
This approach protects bandwidth while maintaining collaborative relationships.
Practical Implications
For Writers and Content Creators:
- Cut backstory ruthlessly - Start right before the valuable part
- Focus on specific how-to details rather than general concepts
- Choose content formats that match your rigor level - Don't hide behind low-accountability formats
- Watch for eyes-light-up moments to refine messaging
For Presenters and Teachers:
- Build in state changes every 3-5 minutes to maintain engagement
- Use interaction to make content memorable rather than just informative
- Pay attention to genuine vs polite audience responses
- Design courses for accountability if you want to develop rigorous thinking
For Career Development:
- Manage up proactively at every level - it's a skill that compounds over time
- Communicate with intentional structure - lead with conclusions, provide context separately
- Send regular status updates to build trust and prevent surprises
- Frame new requests as trade-off decisions rather than yes/no choices
For Team Communication:
- Be explicit about your recommendations rather than accidentally biasing
- Separate background context from action items in written communication
- Use the MINTO pyramid structure for business writing
- Discuss priorities collaboratively when bandwidth is limited
Conclusion
The overarching theme of Wes's advice is intentionality - being deliberate about how you communicate, structure content, manage relationships, and protect your ability to do great work. These aren't just tactics but fundamental approaches to professional effectiveness that compound over time.
