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Questions to Ask Your Executive Mentor

The quality of mentoring you get depends on the questions you ask. Great questions unlock a mentor's most valuable experience. Here are the ones that turn a good session into a career-changing one.

Digby R. Kerr
By Digby R. Kerr — Wharton MBA, author of 12 books, founder of Kerr University™. 35+ years leading global business.

Questions about their decisions

'What's a decision you got wrong, and what did it teach you?' 'How did you handle X when you were in my position?' Learning from a mentor's real choices — especially the mistakes — is where the gold is.

Questions about your blind spots

'What do you see holding me back that I might not?' 'If you were me, what would you focus on next?' These invite the honest, outside perspective you can't get on your own.

Questions about the path ahead

'What separates the people who make it to the next level from those who don't?' 'What should I be doing now that I'll wish I'd started earlier?' Forward-looking questions turn experience into your roadmap.

Frequently asked questions

What questions should I ask my mentor?

Ask about their real decisions and mistakes, your blind spots, and what separates people who reach the next level.

What's the best mentoring question?

'What do you see holding me back that I might not?' — it unlocks honest, outside perspective.

How do I prepare for a mentoring session?

Bring two or three specific, forward-looking questions tied to your real situation.

How do I start mentoring with Kerr University?

At Kerr University™ mentoring is always 1-on-1 with Digby R. Kerr, flexible around your schedule, affordably priced, with 24/7 WhatsApp access and free certificate courses included. Book a free 30-minute session.

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