The CEO's AI Playbook: What I Teach YPO Chapters

When I speak to YPO chapters about AI, I see the same pattern: rooms full of successful CEOs who know AI matters but don’t know where to start. They’ve read the articles. They’ve heard the pitches. What they need is a practical playbook from someone who’s actually done it.

Here’s the condensed version of what I share.

The Reality Check

YPO members collectively influence trillions in revenue. AI literacy at this level has outsized impact. But most CEO-level AI education is too theoretical. “AI will change everything” is not a strategy.

What CEOs need is: “Here’s what to do Monday morning.”

The Three Frameworks

1. Slowinski’s Pyramid - Where to start. Start with repetitive tasks nobody wants to do (support, data entry, email). Then tackle skill gaps (coding, design, analysis). Then compress urgent deadlines. Always start at the base.

2. The Weds.ai Method - How to build culture. Weekly mandatory AI sessions on real problems. 4 hours building + 1 hour demos. The demo creates accountability, competition, and exposure. No hiding. No excuses.

3. CEO-Led Adoption - Who leads it. You. Not your CTO. Not a consultant. The CEO must use AI daily, share mistakes publicly, and spend 10-25% of time on AI evangelism. Self-led adoption takes 1-2 years. Delegated adoption takes 5+.

The Numbers

From our transformation at Trilogy:

• 4x revenue per headcount
• 80% of customer support AI-handled
• Code reduced from 3M to 125K lines
• Board deck prep: full day to 90 minutes

These results took 3 years. But the foundation was built in the first 90 days.

What I See in YPO Rooms

The 20% who are already doing it light up during the session. They want to compare notes, share challenges, and push further.

The 60% who are interested leave with a specific 90-day plan. Most follow through because the peer accountability of YPO keeps them honest.

The 20% who are skeptical usually come around after seeing a live demo. When I build something useful for their specific business in 10 minutes using AI, the abstract becomes concrete.

The Workshop Formats

I offer three formats for YPO chapters:

The 5-5-5 Workshop (90 min): 5-minute hook, 50 minutes live demos, 25 minutes hands-on practice, 10 minutes action commits.

AI Strategy Roundtable (2 hours): Landscape briefing, member case studies, small group discussions, action items.

AI Deep Dive (half-day): Full strategy session + hands-on lab + networking + governance discussion.

The Invitation

If you’re a YPO member or chapter leader, bring this conversation to your chapter. The earlier your members start, the bigger the advantage. AI transformation is a compounding investment - every month of delay narrows the window.