Photo by Fernando Rodrigues on Unsplash

Shadow and Leadership

  • What drives us to do what we do?
  • Why do good people do bad things?
  • What is our relationship with power and status?

How do We Recognize Our Shadow?

  • Insecurity about identity and self-worth
  • The belief that the world is a hostile place
  • Functional Atheism (the belief that ultimate responsibility for everything rests with us)
  • Fears (especially fear of chaos and uncertainty)
  • Denial of death and fear of failure

Shadow Tracking: How, Where, and When Does Shadow Show Up?

  • How do you handle failure?
  • How do you handle conflict? (How did your family handle conflict?)
  • How do you handle chaos and uncertainty?
  • What is your greatest fear?
  • What was not talked about when you were growing up?
  • What behavior do you judge yourself the most for?
  • When you think about the people you admire the most, what traits do they have that make you admire them?
  • What are the challenges you are facing at work, with colleagues, and/or at home?
  • What trait or traits are you most critical about in your teammates, partner, friends, family, or community?
  • What role do you tend to play in relationships?
  • When you are defensive, shut down, or reactive when engaging with people, what are you believing about yourself?

CEO Shadow Casting — An Exercise.

  1. List the virtues and values that are of paramount importance for your organization.
  2. List their opposites.
  3. List the undesirable characteristics of your organization. These may include undesirable behaviors or attitudes exhibited by all or some of your organization. Consider, also, characteristics you’re aware of, and those mentioned by others that you may not have witnessed yourself.
  4. Thinking of the two which evoke the strongest reactions:
  5. Are either of these undesirable qualities personally unsettling or eliciting a particularly strong reaction in you?
  6. Are either of these qualities linked to anything you’ve listed in #2?
  7. Are either of these qualities in any way similar to patterns of behavior you’ve experienced repeatedly in your relationships outside the company?
  8. Are either of these similar in any way to behavior or attitudes you have that: Undermine your own best self or shoot yourself in the foot? Cause yourself familiar grief? Evoke fear, which may seem familiar, blocking or stunting your own growth?
  9. If you responded “Yes” to any of the questions in #4, or feel that you may somehow carry responsibility, write down the quality as a potential Shadow quality you may be unintentionally cultivating in your own organization.
  10. Journal on how you may be complicit in fostering these attitudes or behaviors in your organization. What are possible responses for change?

Ready for more Shadow Work?

  • Reboot: Leadership and Art of Growing Up, by Jerry Colonna
  • Why Good People Do Bad Things, by James Hollis
  • Shadow Dance, by David Richo



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Allison Schultz

Co-founder and coach @RebootHQ. Lifting up the wisdom of the equines for leaders of today so we can return to our truest self.