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Questions Executives Should Ask the Interviewer

The questions you ask reveal how you think. At the executive level, sharp, strategic questions signal leadership and help you evaluate whether the role is right. Here are the questions worth asking — and why.

Digby R. Kerr
By Digby R. Kerr, Wharton-educated executive, author of 16 published books, founder of Kerr University™. About 35 years in global business.

Questions that show strategic thinking

'What does success look like in the first year?' 'What's the biggest challenge facing this team?' 'How does this role fit the company's three-year plan?' These show you think about outcomes and the bigger picture.

Questions that evaluate the role

You're interviewing them too. 'Why is this role open?' 'What happened to the last person in it?' 'How would you describe the leadership culture?' Real answers tell you whether to take the job.

Avoid the throwaway questions

Skip questions you could Google or that focus on perks. At the executive level, thin questions undercut you. Ask things that only an insider could answer — it signals seriousness and depth.

Frequently asked questions

What questions should executives ask interviewers?

Strategic ones about first-year success, the team's biggest challenge, and how the role fits the company's plan — plus why the role is open.

Why do the questions I ask matter?

They reveal how you think and signal leadership — as much as your answers do.

What questions should I avoid?

Anything you could Google or that focuses only on perks.

Can coaching help me prepare questions?

Yes — we build your list. Book a free 30-minute class.

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