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10 Questions Every Leader Is Afraid to Ask but Should

February 20, 2023 Molly Fletcher

Molly Fletcher, trailblazing sports agent, author and expert negotiator, returns to the Linkage Leadership Insights Blog with her latest insights—and we are thrilled to share that Linkage is partnering with Molly to bring you The Advancing Women Leaders Game Changer Negotiation ProgramAvailable in person or virtually for a cohort of up to 25 women leaders in your organization, this program empowers women to take the next step on their leadership journeys.

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. Bring Molly’s actionable and practical negotiation program to women leaders at your organization. Learn more about The Advancing Women Leaders Game Changer Negotiation Program.

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Women in Leadership Institute

NOV. 13–16, 2023 | 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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