Suggested questions

1What was the moment you realized that mid-sized companies were actually at a disadvantage with AI compared to much larger enterprises?

2When a leadership team says, “We know AI matters, but we don’t know where to start,” what does that usually look like inside the business?

3You’ve worked inside startups, consultancies, and large organizations—what changes when a company tries to bolt AI onto existing processes instead of rethinking how the work gets done?

4Can you walk us through an early engagement where a company expected quick AI wins, and what surprised them once they actually started using it?

5A lot of executives worry about investing too early and backing the wrong tools—what have you seen happen when companies wait too long instead?

6You were building AI products before the current wave of hype—what did those early limitations teach you about where AI actually creates real value today?

7In operationally heavy industries like e-commerce or financial services, where do teams usually feel the friction most before AI enters the picture?

8When companies start using AI to interact with their own data, how does decision-making tend to change inside leadership teams?

9What’s a common internal process you’ve seen that leaders assume is “just part of the job,” but turns out to be far more optional once AI is involved?

10Looking ahead a few years, what do you think work will feel like inside companies that adopted AI thoughtfully versus those that treated it as a series of experiments?