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14 Great Questions Every Entrepreneur Should Ask

A while ago, I stumbled across an article in Inc. magazine entitled “100 great questions every entrepreneur should ask.” The questions were submitted by a variety of business leaders and business writers, and while all were pretty good, predictably, some were better than others. So I picked out a few that I thought were particularly impactful to share with you. Most of these questions I have paraphrased for clarity. I offered comments on some, but not all. To see my picks, please continue reading below.

14 Great Questions Every Entrepreneur Should Ask

1. What one word comes to mind when our customers, employees, and vendors think of us?

In other words, what one word do you hope defines you in your marketplace? It’s a significant part of your brand. If you were Apple, that word might be “innovation.” If you were Mercedes Benz, that word might be “quality.” What’s your one word and what are you doing to nurture and protect it?

2. If you sold your company tomorrow, what’s the first thing the new owner would change?

3. Do you personally speak with your top customers on a regular basis?

4. Who uses our product or service in ways we never expected?

5. “What would have to be true for the option on the table to be the best possible choice?”   ~ Roger Martin, professor, Rotman Business School

This question is particularly useful when you’re trying to choose between a variety of diverse options. It forces you to examine the underlying assumptions that support each option.

6. Is the way in which we allocate resources consistent with our strategy?

If you have a growth strategy in place, are your people’s regular activities consistent with that strategy? Or are they more consistent with a business-as-usual strategy?

7. What do customers dislike about doing business in our industry? What can we do to be the opposite of that?

8. “If our company went out of business tomorrow, would anyone who doesn’t get a paycheck here care?”         ~ Dan Pink, author

This is another way of asking if your business is still relevant. Have your products, services, and business methods kept pace with your customers’ evolving needs?

9. What happens here when people fail? Do we treat failure as a learning experience or as an occasion for disciplinary action?

If you want your people to be creative, innovative, and to have the courage to try new things, you can’t slap them down when their efforts don’t produce the results they hoped for.

10. “Do your employees have the opportunity to do what they do best every day?”                ~ Marcus Buckingham, author

The vast majority of employees would tell you they do not have the opportunity do what they do best every day. In your hiring practices, do you differentiate between the skills a candidate has learned over time vs. the natural talents he or she was born with? And do you try to put the people you hire in positions where they can make the best use of their talents?

11. “What successful thing are we doing today that may be blinding us to new growth opportunities?”         ~ Scott D. Anthony, managing partner, Innosight

Success can kill creativity and innovation. It can breed a let’s-just-keep-doing-what-we’re-doing-and-not-rock-the-boat mentality.

12. “What potential megatrends could make our business model obsolete?”            ~ Michael A. Cusumano, professor, MIT

And a companion to the question above –

“How can we become the company that would put us out of business?”          ~ Danny Meyer, CEO of Union Square Hospitality Group

A little paranoia can be a good thing. You should always keep a weather eye out for technological, social, political, and competitive changes that could make you rethink the way you do business.

13. What is it like to work for my company?

Do your employees feel challenged and engaged at work? Or do they feel stressed out and unappreciated? Or more to the point, do you care how they feel?

14. “What prevents me from making the changes I know will make me a more effective leader?”             ~ Marshall Goldsmith, leadership coach and author

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