“Tell me one thing you really like about the organisation, 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:

• What made you mad today?

• What took too long?

• What was wasted?

• What was misunderstood today?

• What job took too many people or too many steps?

• If we could improve in any way, how would we do it?

• What’s the number-one problem with our organisation?

• What’s not fun about working here?

• Who is really excelling in the company? Who do you admire?

• If you were me, what changes would you make?

• What don’t you like about the product?

• What’s the biggest opportunity we’re missing?

• What are we not doing that we should be doing?

• Are you happy working here?

• Tell me something I don’t want to hear – it’s OK to give me bad news.

The Key: Trust Before Truth

The questions only work if people believe you genuinely want the answers, and if they trust they won’t be punished for being candid.

Own the Conversation

Implementation idea:

Select three to five of the above questions and test them in your one-on-ones this month. Notice which questions spark the most insight. Refine your list and make them part of your standard leadership toolkit.