It’s the questions they probably won’t expect that will give you the greatest insight.

Question: What’s an out-of-the-box question to ask my business mentor?

What Question Should I Be Asking?

“There are lots of questions I like to ask in order to gain insight and knowledge from a business mentor. You should ask them what they think you should be asking. What might you be overlooking in your strategy or approach? Is there something you haven’t thought of that they would like to share with you? Sometimes you just don’t know what you don’t know.”

What Set You on the Path to Pursue Your Career?

“Ask for their “a-ha” moment. I’ve found those inciting incidents to be pretty revealing.”

What’s the Most Significant Regret You Have About Your Career?

“People are often laser-focused on getting advice about running their startup, but it pays to remember that these people are still human beings who make mistakes. How someone responds to this question can tell you a lot about who they are, and about how you might deal with your own failures in the future.”

What Did You Learn by Failing?

“Ask your mentor about a time when he or she failed, why they failed and what they learned from that experience. Learning from personal failure is hard; learning from other people’s failures is much more efficient.”

What Are My Greatest Attributes?

“I remember feeling frustrated and overwhelmed after starting my business in a new city. Long story short, my new mentor told me at the time — based on our first visit — that I would definitely excel and explained the reasons why. And I did. I maximized on that conversation and always remember that honest pep talk. Sometimes other people see things in us that we don’t.”

What Is One Thing You Would Go Back and Change?

“It doesn’t matter if it’s a personal or business situation. Everyone has one, and the answer is usually eye-opening.”

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