The Question No One Asks Leaders

It was a moment of authenticity that I’ll never forget.

I was shocked when General Dempsey, retired Chairman of the Joint Chiefs of Staff said, “The question I wish people would have asked me is, ‘How do you feel?’” (In the interview room at the World LEADERS Group.)

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A few months ago, a successful CIO shared the story of listening to his CEO talk through an issue. The CIO, toward the end of the conversation, asked, “How do you feel about that?”

The CEO just started talking. Before they hung up, he said, “Thank you.”

No feelings:

I joke about being a stoic New Englander. We don’t have feelings.

Leaders who don’t have feelings look down on those who do.

Maybe you think feelings are for weak leaders. In the rush to deliver results and solve problems, feelings are left at the door. You may think it doesn’t matter how you feel. Do your work.


Feelings matter because emotion is energy.

When you rule out emotion, you throw cold water on emotional energy. Even when emotion is dark, finding a path forward reignites energy.


Connect with others by providing space for them to express emotion.

  1. Don’t feel the need to dampen joy because people don’t see all the problems you see.
  2. Ask, “What’s making you feel so joyful?”
  3. Don’t feel the  need to solve emotion when it’s dark.
  4. Ask, “What’s behind your frustration?”
  5. Affirm what you hear. “I see how you could feel that way.”

Bonus: Show respect when you see vulnerability in others.

Before asking leaders how they feel:

  1. Build trusting relationships. Don’t ask the boss about her feelings on your first day.
  2. Embrace a listening ear. I hate it when someone tries to fix my feelings.
  3. Demonstrate the ability to keep secrets.

What suggestions and/or warnings do you have about asking leaders how they feel?