• What’s one “manual” business practice you believe will disappear in the next 5–10 years?

• Can you share a moment when automation freed your team to do better work? How does automation create space for creativity or kindness?

• When did you first feel like a CEO or realize you weren’t there yet? Story behind that

• What advice would you give to operators, marketers, or specialists moving into CEO roles, and why?

• How can a first-time CEO build trust with the Board? What are your top three recommendations?

• How can automation reduce bias by standardizing decisions?

• What leadership challenges are unique to SaaS or fintech companies, and why?

• What myths about automation still exist, and why are they myths? Are common beliefs like “automation destroys jobs,” “automation is only for large enterprises,” “automation is primarily a technology problem,” and “automation removes the human element” actually true? Why or why not?

News and Updates

• What book(s) or article(s) did you read this past month that stayed with you? What takeaways do you have?

• What event(s), talks or experiences did you attend this past month that stayed with you? What takeaways do you have?

• What podcast(s) did you listen to this past month that stayed with you?