Special feature for “My Quest for the Best” listeners

Ten questions to help you be a more effective leader

To those who’ve come here by way of Bill Ringle’s podcast “My Quest for the Best,” welcome! Here is an exclusive post for you, pulling together some of the most effective Leadership questions from my new book, The Book of Beautiful Questions: The Powerful Questions That Will Help You Decide, Create, Connect, and Lead. The book has dozens of “leadership questions” (and hundreds of questions overall), but the following are my “top 10” in terms of helping you clarify your vision and mission as a leader.

When it comes to leadership questions, start with the why’s—fundamental ‘why’ questions, pertaining to motivation, rationale, and purpose. Aspiring leaders often don’t spend enough time considering whether there is a greater purpose driving their leadership aspirations—or clarifying what that purpose might be. The demands of leadership now are so great that unless one is driven by a sense of purpose that transcends personal ambition—and unless one enjoys the actual day-to-day work of engaging with and leading others—the pursuit may not prove satisfying or sustainable in the long run.

  1. Start by asking, Why do I want to lead this endeavor or these people—and why would they want me to lead them?

It’s a two-part question. And the answer to first part of the question should also work for the second part. For example, if your answer to part one is, “I feel I’ve earned the top spot,” or, “I need the pay raise,” that doesn’t work well for the second part (why people would want you to lead them). But if your answer is more along the lines of, “I want to create a great organization that will inspire people to reach their full potential,” that works for both parts of the question.

  1. Am I willing to step back in order to help others move forward? Many aspiring leaders are rising stars and high-performers, but their success as a leader depends more on helping others achieve success.
  2. Do I have the confidence to be humble? The balance is to be humble enough to admit you don’t have all the answers—while being confident that you can help the organization to figure them out.
  3. Do I seek to create an organization in my own image? If the answer is ‘yes,’ that could be a problem. Too many leaders surround themselves with similar people, depriving the organization of the diverse thinking needed to be successful today.
  4. If we disappeared tomorrow, who would miss us? This speculative question helps clarify why you matter and to whom. (Another good question along these lines: What do we do that others can’t or won’t? It helps clarify your organization’s strengths and uniqueness.)
  5. How might we be not just a company but a cause? Today, every organization is expected to contribute something worthwhile—to employees, local communities, and the world. Ask what your organizations for—and also what it’s against.
  6. What should we stop doing? This comes from the legendary management expert Peter Drucker, who urged leaders to practice “systematic abandonment”—constantly moving away from projects, products, or initiatives that are no longer helping the organization to move forward.
  7. What is the one thing I can do that would make everything else easier or unnecessary? A favorite question from the real estate giant Gary Keller, this “focusing question” should be asked at the start of any new challenge or project.
  8. How can we become the company that would put us out of business? This question invites you to envision a future rival: What might this predator look like, and why would it have an advantage over us? Having figured that out, you can think about how to make yourself more like the predator. (Hat tip to the restauranteur Danny Meier for sharing this question).
  9. What’s going on out there—and how can I help? Perhaps the most important question any leader can ask. It requires getting out of the corner office and circulating, inquiring about the various challenges people are facing—and offering your support. One caveat: only ask the question if you’re sincere about actually providing help as requested.

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