The Smart Work


Call to Action

The Pit


Ten-Step Guide for Exploring Mature Leadership
Conversation Questions



Leadership Maturity Conversation Questions


1) What is your personal definition of a leader? What are the characteristics of that person? Develop a “leader’s job description.” Name some leaders in today’s world. Discuss how they fit your characteristics for leadership.

2) What story or stories are dominant in your life and/or your organization right now? Are they compelling to you? Why?

3) Does the telling of the story have to be verbal? Can it be situational? Can it be acted out? How can it be told “over and over,” in many different ways so that it is embedded in the organization? What might those ways be?

4) What stories does your organization hold about the nature of leadership? Are they stories you believe?

The Call

5) When do you know something is actually a “call”? How do you know a call should be listened to? How does it manifest itself in you? In those close to you? In leaders you admire?

6) What do you think the source of the call is for most people? Is it a gift? What are some examples of clarity or compassion in calls you have seen?

The Hero/Leader

7) What’s the difference in your mind between being a hero and a leader? Are they synonymous? Must you be both, or is one a step on the way to the other?

8) Should leadership be a solitary journey? Is that even possible? Who should go along? Contrast Peter Pan and Nelson Mandela (or the mature leader of your choice). Who went with them? What is the difference in their leadership from a follower’s perspective?

The Journey

9) Does the hero always complete the journey? Is she a failure if she doesn’t? Can she pass off her leadership role to other potential leaders along the way? Is the breakdown or failure most likely to be one of the monsters? Internal? External? For what reasons?

10) Would you describe your organization’s culture as autonomy-focused, connection-focused or balanced? How would you describe yourself in terms of the autonomy/connection balance? If they are significantly different, what are the consequences of that? What are the benefits and costs of being in that position?

The Monsters

11) In what domain do you think you personally face the most monsters? Name them. In what domains do you think your organization faces the most monsters? Name them. Which are the worst? Are the personal and organizational monsters different? How should they be addressed?

12) Describe a difficult situation your organization currently faces. What are the monsters in that scenario? Imagine that you represent intellectual, emotional, moral and spiritual wisdom. Give your organization advice about how to handle those monsters from each of the four domains.


13) Did you ever have a “wormhole” experience? Do you know others who did? What happened? What triggered it? What was the end result? What changed? For better or worse?

14) Are you prepared to accept your leadership role in the organization? Can you let go of doing everything yourself? Are you ready and willing to live under the microscope? Can you live with or function with not having answers?

The Return

15) Describe maturity:
a) For yourself.
b) For your boss
c) For your organization
d) For your country.

16) As a leader, whether in your own life or in an organization, what truths do you think you speak? What hope do you point to? Are there things you stop yourself from saying or hoping?

17) To what would you like to return at the end of your current leadership journey? To whom? What would you like to give back?

18) Write your own living leadership story in 4-5 paragraphs. Then write a paragraph or two that tells where you would like the story to go next. Read these stories to one another and comment in this format:
a) What I appreciated about this story was…
b) What I learned from this story was…
c) What I still wonder about this story is…

19) What is your one big hope for yourself and for this organization? What are the new conversations that will help us achieve this hope?

20) Based on our conversations, what needs to change in this organization? How do we want it to be? Where are we now? What do we need to do more of, better or differently in order to get there?

21) Based on our conversations, what commitments need to be made in order to change? (Remembering that the only person you can change is yourself.) By whom and by when? Are we willing to make them? What competing commitments do we hold that might derail us?

22) If modeling, being the change you want to see, is the most powerful form of influencing others to change, what changes in your own behavior can you publicly commit to or ask to be held accountable for? Who, within your own sphere of influence, do you hope to impact by such changes? How will they know you have changed? How will you know they have changed?