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Free Lesson
Get Leadership to See AI Reality
30 min
May 11, 2026 12:00 PM
Virtual (Zoom)
In this video
What you'll learn
Reframe the "Can't we just?" conversation
Turn vague AI requests into structured decisions using six questions that work in any leadership meeting.
Align on any AI request in under five minutes
Assess any AI request in minutes using a Cynefin-based framework — and respond with facts, not frustration.
Move from AI hype to coherent strategy
Connect any AI request back to diagnosis, guiding policy, and coherent action — the three elements of real strategy.
Push back without killing the conversation
Say no, or not yet, to an AI request in a way that keeps you credible and builds on the relationship.
Why this topic matters
Every exec review contains the same request: Can't we just use AI? Most approaches teach you to work better under that pressure. This one teaches you to change the conditions — shifting leadership from capability thinking ('can we do this?') to strategy ('should we do this, and what does it cost us?') before it derails your team
You'll learn from
Randy Silver
Product & Leadership Coach (ex Amazon, HSBC), co-host of The Product Experience
Previously at
