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Martin Itzkow, FRSA

Inspiring dialogue, learning, and positive change

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Home › Coaching Leaders, Individuals and Teams › Questions that Leaders Must Ask Themselves
Questions that Leaders Must Ask Themselves

Questions that Leaders Must Ask Themselves

May 10, 2022 by Martin |

I am quite intrigued about the kind of important questions leaders may ask themselves when they have the time and reflective practice to grow their leadership wisdom and keep their implicit, and conscious biases in check.

This is my discernment of the range of questions leaders from all walks of life are wrestling with in one way or another. These questions and others give voice to the future practice of leading oneself to lead others.

Here are some questions that I will continue to add from time to time. If you have a question to post on my website, please send it to me.

Proposed Questions:
  1. How does one know that the organization hasn’t become heartless? To be truthful, how much heart is demonstrated every day in your relationship building with all staff?
  2. How does current leadership teach leading self and others, to others throughout the organization?
  3. How much of my emotions, both felt and unfelt, influence the quality of my decision-making?
  4. How does a leader view the purpose and the value of creating or supporting organizational silos?
  5. How would a leader judge the maturity of the organization’s leadership team?
  6. How does the leader’s adult development pathway impact the quality of the decision-making, the treatment that staff feel, and the stability of the organization?
  7. What are the current leadership biases impacting the organization’s leadership?
  8. How does a leader maximize his/her potential while focusing attention on the staff and their need to grow and develop (find meaningful learning opportunities)? (In an environment of chaos, stress and the need to maintain harmony in a person’s life)
  9. How do you as a leader know that you are demonstrating the leadership your staff expects from you? Three areas of MUSTS for leaders:1 – Do you know (their talents, skills and strengths that they value and not you, and what they love about their work with your organization) the people that work for you? 2 – Do you see and hear your staff? and 3 – Do you care for them? (How do you know?)
  10. Why do I believe that as a leader I have all the right answers?
  11. When do I vanish into a task? Why is this important to know?
  12. Where and when am I aware of what is informing me now?
  13. What do you believe people expect of you? How do you know?
  14. What nourishes me in my work life that is different than in my life?
  15. As a leader focusing attention on DEI, how do you demonstrate a genuine desire to understand what it is like inside your organization to be powerless or marginalized?
  16. How have you contributed and possibly still do for others to experience discriminatory behaviour in your organization, at all levels?
  17. How have you come to realize that the organization needs to become more diverse, equitable, and inclusive?
  18. How can you make your organization truly a better place for everyone?
  19. How much of our experience of others in our organizations demonstrate pity or sympathy rather than empathy or true compassion? This asks about our awareness of our blind spots.

Filed Under: Coaching Leaders, Individuals and Teams, Dialogue and Engagement, Leadership

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About Martin Itzkow

Martin Itzkow, FRSA, is a convener of deep change, based in Winnipeg, MB, Canada.

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