Seth Wylie reveals why successful AI transformation starts with the people already experimenting - not training programs or executive mandates.

**🔑 KEY INSIGHTS:**

- Why mandatory AI training kills experimentation before it starts

- The one question that gets everyone talking: "What have you been experimenting with this week?"

- How to connect grassroots innovation to executive priorities

- Why executives are disconnected from AI tools (and what to do about it)

- Building "AI Clubs" that people actually want to join

- Creating psychological safety for awkward first attempts

**⚡ SETH'S APPROACH:**

Find the experimenters already on your team → Create space for them to share → Let insights bubble up naturally → Then add training when there's momentum

"Companies need to harvest the experimentation that's already happening, not mandate what should be happening."

**⏰ TIMESTAMPS:**

**01:00** - Meet Seth Wylie: AI Transformation Expert & Acapella Singer

**08:32** - Finding Signal: How to Spot AI Innovation in Your Organization

**10:45** - **The Magic Question: "What Have You Been Experimenting With This Week?"**

**13:18** - Why Executives Are Disconnected from AI Tools

**14:11** - What Companies Get Wrong: Training Before Mindset

**18:08** - Leadership by Example: When CEOs Use AI for Poetry

**19:26** - The Translation Problem: Executive vs. Individual Priorities

**20:23** - Emergence Capital's Offsite Success Story

**28:36** - Organizational Structure Changes for AI Transformation

**32:22** - Creating Value Categories: ROI vs. Engagement vs. Innovation

**34:48** - The Spreadsheet Story: How Leaders Kill Innovation and The Power of Executive Curiosity

**37:10** - **Seth's Favorite Tool: AI for Self-Knowledge**

**40:29** - Amy's Claude Projects Discovery (Life-Changing!)

**42:19** - Wrap-up & Gratitude

**💼 LEADERSHIP CORNER**

**42:47** - Question: Should I Dive Into AI Tools or Let My People Mature First?

**43:03** - Meg's Take: Get Context First, Model Curiosity Over Perfection

**44:56** - The Learning Paradox: Being Bad at Things Builds Empathy

**47:15** - Practical Advice for AI Leadership Balance

**53:58** - Final Thanks & Sign-off

🎵 **BONUS:** Seth performs an acapella song live on the show!

**📚 RESOURCES:**

New York Times: CEOs Adopt AI: https://www.nytimes.com/2025/08/16/business/ceos-adopt-ai.html

Meg's AI Fluency Blog: https://www.megbear.com/post/stop-wasting-time-on-ai-fluency-projects

Emergence Capital Offsite: https://www.linkedin.com/posts/jakesaper_at-emergence-capitals-investment-team-offsite-activity-7328060051531747328-v3on/

Reshuffle Book: https://amazn.so/Rrd62oi

**🔗 CONNECT:**

Seth: https://www.linkedin.com/in/sethwylie/

Leadership Questions: [email protected]

Instagram: https://www.instagram.com/megandamyshow/

LinkedIn: https://www.linkedin.com/company/the-meg-amy-show

#AITransformation #BottomUpInnovation #AIStrategy #OrganizationalChange #Leadership #Innovation #AIAdoption #BusinessTransformation #WorkplaceInnovation #AIExperimentation