Top 40 questions every entrepreneur should ask


Have you ever imagined Superman and Batman in a face-off to determine which one is better? When it comes to the best innovation tool, the same scenario could be applied to questions and answers. And although this isn’t a competition between questions and answers, the prize for such a “theoretical” battle would have to be awarded to questions. Why? Well, questions are the spark that ignites your imagination. They reveal paths that may not have been considered at first or they may even avert some catastrophes.

As a result, Michael Pope and I decided to compile a list of the best 40 questions entrepreneurs should ask themselves and their teams. We decided to reach out to entrepreneurs and revisit the best business books out there. The answers to the following questions will almost certainly impede you from remaining passive given the fact that they require not only reflection, but also action.

The main reason why an entrepreneur should ask himself these questions is that the inquiry may trigger divergent thinking that, in turn, leads to a non-obvious solution. By asking the right question, people are free to come up with new ideas and solutions. If you think you can come up with a good question you have utilized in your company, we welcome you to add it to our list. Given the fact that “rigid mindsets” are often dangerous things, please read this list with an open mind.

1. “Who are you going to put out of business, and why?”Brad Feld, managing director, Foundry Group

2. “Instead of going to current contacts for new ideas, what if you reconnected with dormant contacts – the people you used to know? If you were going reactivate a dormant tie, who would it be?” – Adam Grant, author and professor at Wharton

3. “What should we stop doing?” – Peter Drucker, management expert and author

4. “Do we have bad profits?” Jonathan L. Byrnes, author and senior lecturer at MIT
Byrnes states that, “Some investments look attractive, but they also take the company’s capital and focus away from its main line of business.”

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

6. “What are the implications of this decision 10 minutes, 10 months, and 10 years from now?”Suzy Welch, author

7. “Who, on the executive team or the board, has spoken to a customer recently?”James Champy, author and management expert

8. “How do you encourage people to take control and responsibility?”Dan Ariely, professor, Duke University

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

10. “If I had to leave my organization for a year and the only communication I could have with employees was a single paragraph, what would I write?”Pat Lencioni, author and founder of The Table Group
Lencioni explains, “Determining the substance of this paragraph forces you to identify the company’s core values and strategies, and the roles and responsibilities of those hypothetically left behind.”

11. “What do we stand for – and what are we against?”Scott Goodson, co-founder of StrawberryFrog

12. “Who have we, as a company, historically been when we’ve been at our best?”Keith Yamashita, author and founder of SYPartners

13. “Among our stronger employees, how many see themselves at the company in three years? How many would leave for a 10 percent raise from another company?”Jonathan Rosenberg, adviser to Google management

14. “Do we have the right people on the bus?”Jim Collins, author and management consultant

15. “Do we aggressively reward and promote the people who have the biggest impact on creating excellent products?” – Jonathan Rosenberg

16. “What do we need to start doing?”Jack Bergstrand, CEO, Brand Velocity

17. “How can we become more high-tech but still be high touch?” – James Champy, author and management expert

18. “How would our PR, marketing, and social media change if we did not use outside agencies?”Guy Kawasaki, founder, Garage Technology Ventures and Alltop
Kawasaki explains, “Let’s see what happens when a company can’t abdicate these functions to hired guns. I’d bet that employees, because they know and love their product more than any agency, can do a much better job at less expense to boot.”

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

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

21. “Are we relevant? Will we be relevant five years from now? Ten?”Debra Kaye, innovation consultant and author

22. “What happens at this company when people fail?”Bob Sutton and Jeff Pfeffer, Stanford professors

23. “Do your employees have the opportunity to do what they do best everyday?”Marcus Buckingham, author

24. “Do we say “no” to customers for no reason?”Matt Dixon, author and executive director of research at CEB
You may have created your customer policies at a time when you lacked resources, technology wasn’t up-to-snuff, or low service levels were the industry norm. Have those circumstances changed? If so, your customer policies should change too.

25. “Do you see more potential in people than they do in themselves?” – Adam Grant

26. “Do you, as a leader, bounce back quickly from setbacks?”Bob Rosen, executive coach and author

27. “Did my employees make progress today?”Teresa Amabile, author and Harvard Business School professor
Amabile explains, “Forward momentum in employees’ work has the greatest positive impact on their motivation.”

28. “What is your BATNA (best alternative to a negotiated agreement)?” – Roger Fisher and William Ury, negotiation experts

29. “What are the rules and assumptions my industry operates under? What if the opposite were true?”Phil McKinney, innovation expert

30. “If our customer were my grandmother, would I tell her to buy what we’re selling?” – Dan Pink

31. “Why should people listen to you?”Dave Ulrich and Norm Smallwood, co-founders, The RBL Group

32. “Do I know what I’m doing? And who do I call if I don’t?”Erin Pooley, business journalist

33. “What was the last experiment we ran?”Scott Berkun, author

34. “Are you satisfied with your current role? If not, what is missing from it?” – Charles Handy, author and management expert

35. “What stupid rule would we most like to kill?”Lisa Bodell, CEO, FutureThink

36. “Who do we want out customers to become?” – Michael Schrage, professor, MIT

37. “Who are four people whose careers I’ve enhanced?” – Alex Gorsky, CEO, Johnson & Johnson

38. “How will we build a 100-year startup?”Phil Libin, CEO, Evernote

39. “What’s the best design framework for an organization in a post Industrial-Age if the top-down, command and control model is no longer relevant?” – Traci Fenton, CEO, Worldblu

40. “What did we miss in the interview for the worst hire we ever made?” – Alberto Perlman, CEO of Zumba Fitness


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