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10 Questions Every Leader Is Afraid to Ask but Should

December 8, 2021 Molly Fletcher

Molly Fletcher recently appeared at the 22nd annual Women in Leadership Institute™, before an audience of 2,600+ women leaders from top organizations. She electrified the stage with her personal stories as a trailblazing sports agent and inspired us to effectively and thoughtfully advocate for ourselves and our teams in a way that builds meaningful relationships. In her latest blog, she shares 10 questions every leader is afraid to ask—but should. Check out her tips below and set yourself up for success in 2022 and beyond.

And, if you’re looking for even more from Molly, grab your own on-demand pass to the Women in Leadership Institute, which allows you to experience Molly’s keynote and other incredible content on your schedule through January 31, 2022.

What leader doesn’t want to be more trusted and more effective? To get there, you must find your blind spots so you can resolve them intentionally to become a stronger leader. It takes openness, vulnerability and fearlessness to have this kind of curiosity.

Many leaders are afraid to ask tough questions, but trust me, your leadership and team will benefit. That’s why I strongly believe that every leader should ask themselves these 10 questions and carefully listen to the answers.

  1. Is there a critical conversation I have been avoiding that I need to make happen this week? Remember the best way to make a problem get worse is to not address it.
  2. Am I taking over meetings, preventing my team members from contributing and growing? A great leader is a great supporter.
  3. Did I send one email to someone who wouldn’t expect it from me, thanking them for being on our team with specific feedback on their gifts? Gratitude is a great fuel source for them and you.
  4. Is my team coming to me for feedback? When communication breaks down, it’s on you to take action.
  5. Do I tell the truth even when stressed? Honesty is a cornerstone of leadership.
  6. Do my actions line up with my words? Integrity is easily compromised, and authenticity is the foundation of trust.
  7. Do I have a healthy balance between being rational and being emotional? Remember the power of a wise mind.
  8. Have I stepped outside of my office to do something, see something, read something or listen to something that has nothing to do with my work? Perspective is needed as a leader.
  9. Am I making statements when I could be asking questions? Curiosity-based leadership is the point of this exercise.
  10. Have I called a loved one to tell them that I love them, thank them for their support or simply check in? Remember that your actions to those who matter most in your life make you a leader worth following too.


Your Game Changer Takeaway

Try printing this list, or the one question that resonates the most, to keep within view. Find a trusted source who will give you authentic feedback. The discomfort you may feel temporarily will be worth the long-term gain.

Molly Fletcher is the author of The Energy Clock: 3 Simple Steps to Create a Life Full of ENERGY—and Live Your Best Every Day. Register now for the On-Demand Women in Leadership Institute to experience Molly’s dynamic keynote on negotiation tactics—and hear from Magic Johnson, Sheila Marcelo and other exceptional leaders.

Dark haired woman watches from audience of conference event

Women in Leadership Institute

NOV. 1–4, 2022 | Orlando, Florida, or Virtual
A 4-day immersive learning experience designed to equip women leaders with actionable strategies to overcome the hurdles women often face in the workplace.

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