25 CEOs List 20 Things that Keep them up at Night

I had dinner last evening with 25 CEOs. Before dinner, each one answered the question,

“What keeps you up at night?”


Here’s a sampling from the conversation.

  1. Growing small and sticking to our core mission.
  2. Biased media creating mis-perceptions.
  3. Dealing with government regulation.
  4. Seeking input from others.
  5. Instability of political environments.
  6. Getting culture right.
  7. Recruiting and retaining talent that can face great challenges.
  8. Choosing and executing on the things that will make the greatest difference.
  9. Developing, delivering, and executing on an effective strategic plan.
  10. Connecting with customers.
  11. Sharing the work.
  12. Being viewed as trustworthy.
  13. Aligning talent with opportunity.
  14. Navigating transparency.
  15. Crafting a future while following a founder.
  16. Initiating and participating in the right conversations.
  17. Aligning resources with the strategic plan.
  18. Facing the challenge of change.
  19. Developing leaders.
  20. Getting it right when people ask for advice.

Personal leadership:

I thought about the question on a personal level. What keeps me up at night is being the kind of leader I expect others to be.

It’s easy to expect things from others and lose sight of living up to those same expectations.

One way to spot a tendency to expect more from others than you expect from yourself is to listen to your frustrations and complaints about others. Do the frustrations you feel about others speak to inconsistencies in your own behaviors?

  1. Do you expect others to act with boldness when you aren’t giving clear direction?
  2. Are you expecting others to be transparent when you are self-protective?
  3. Do you expect others to receive constructive feedback with gratitude when you brush it off?
  4. Do you expect managers to communicate with their teams when you huddle in your office?
  5. Are you expecting people to come to you for advice when you make up your mind without seeking input?

From a leadership point of view, what keeps you up at night?

Which items on the list of 20 seem most relevant to you?