The Leader’s Toolkit: Questions That Unlock Truth in One-on-Ones

“Tell me one thing you really like about the organization, and one thing that frustrates you about the company?”

“Tell me what you do here, that’s not in your job description, that you think is really critical?”

“Tell me something you think I don’t know, that you think I should know, that is important?”

These questions come from The Corner Office, a former New York Times column by Adam Bryant, where he interviewed CEOs about how they lead. They remain as apt today as ever for senior executives looking to spark honest conversations in one-on-one interactions.

Other leadership thinkers have expanded this questioning approach. In Reinventing Leadership, Robert Townsend and Warren Bennis, and in The Hard Thing About Hard Things, Ben Horowitz, recommend CEOs ask questions such as:

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