Do you keep 50% of your time unscheduled?

This sounds like a strange question—in fact, for those of us with back-to-back meetings and to-do lists a mile long, it might sound downright silly.

But if you’re a manager, leader, or entrepreneur, it’s one worth pondering. As Dov Frohman explains in his book, Leadership the Hard Way, leaders with sufficient “slop” in their schedules can reflect on lessons they’ve learned and strategize for the future in a way that people with jam-packed schedules simply can’t.

This is just one of the incredibly insightful questions posed in Inc.’s compilation of “100 Great Questions Every Entrepreneur Should Ask”—a list featuring successful business leaders’ recommendations on what leaders of the future should be asking themselves regularly. While the quotes in the list can help entrepreneurs think through everything from competitive strategy to product innovation, we thought that some of the best tidbits were helpful takeaways for managers at any company and any level.

Here’s a quick a roundup of our (adapted) favorites from the list—to ask yourself today.

  1. What is it like to work for me?
  2. What prevents me from making the changes I know will make me a more effective leader?
  3. If no one would ever find out about my accomplishments, how would I lead differently?
  4. Did my employees make progress today?
  5. 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?
  6. What did I miss in the interview for the worst hire I ever made?
  7. How is the way I think and process information affecting my organizational culture?
  8. Do my employees have the opportunity to do what they do best every day?
  9. Do I see more potential in people than they do in themselves?
  10. Why should people listen to me?
  11. How do I encourage people to take control and responsibility?
  12. Do I know what I’m doing? And who do I call if I don’t?



As Warren Berger, author of A More Beautiful Question, explains, asking good questions and doing so often “opens people to new ideas and possibilities.” So, no matter where you are or where you’re headed, make time to do so regularly. The answers—and, more importantly, what you do with them—will take you far.


Photo of man with questions courtesy of Shutterstock.