Back-Pocket Questions
For awkward pauses, one-word answers, or when a topic needs a reset.
Let me push on that — if you had to bet your own money on where AI creates the most durable value in your industry over the next three years, where does it go?
Who in this room do you think is furthest ahead on AI? What makes you say that?
What’s the question about AI that you’re afraid to ask out loud in your own organization?
Has anyone in this room changed their mind about something significant in the last six months because of what you’ve seen from AI?
If the AI investment cycle turns out to be a bubble — and some cycles do — what’s the tell?
What’s the most important thing you’ve personally done to build your own AI fluency? Not your team’s. Yours.
We’ve talked a lot about what AI can do. What can it not do — what has surprised you about where it falls short?
👉 [To someone quiet] You’ve been listening. What’s landing wrong for you in this conversation?