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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Fooling Ourselves: The One Question Every Leader Should Ask

A number of years ago, I asked members of my Mastermind group** to respond to the following question:

“How do I fool myself by holding a perception that is lesser or greater than reality?”

I posed this question because I know I have blind spots about how others perceive me.

Understanding how I come across – through the eyes of trusted colleagues – helps me avoid fooling myself about my impact.

Here’s the text of the email I sent after that Mastermind group meeting:

Subject: Thanks in advance / How do I fool myself by holding a perception that is lesser or greater than reality?

Hi Everyone,

At our last Mastermind meeting I asked Alan, John and Don to help me out. I asked them to consider this question about me:

“How do I fool myself by holding a perception that is lesser or greater than reality?”

…and to email me their thoughts.

I invite you Peter & Ian to do the same. I asked the guys to be as direct as possible.

The reason I’m seeking this feedback is because I know I have blind spots about how I come across or blind spots about how I am perceived by others.

For example: I may perceive myself as being inspiring, while another person might perceive me as overwhelming.

Knowing more about how others perceive me will help me understand myself better. Then I can take action – if warranted – to adjust how I behave, think, etc.

Be assured: whatever you say, I won’t take it personally. All of your perceptions are valid.

Thanks for considering this and for any feedback you provide.

Cheers,

Michael K

In addition to feedback about my vitality and energy I projected, one person offered a gem I was unaware of. Namely:

That I came across as a bit of a know-it-all.

Since then, I often acknowledge this perception early in my client work. I might say:

“I know I can come across as a know-it-all. I want to assure you I definitely don’t believe I know everything about this topic – though I’m always striving to improve.”

There are formal tools (like 360-degree feedback instruments) designed to give insight into how others see us. But these can be cumbersome, time-consuming, and often fraught.

By contrast, when asked of someone you trust, this “How do I fool myself?” question can provide valuable, actionable feedback –  quickly and directly.

**(A Mastermind group is a group of like-minded people (in my case solo business owners) who meet regularly to help each other in a particular venture or interest. Here is a link to a PDF by Jack Canfield on how to set up and run a Mastermind group).

Own the Conversation

In the next seven days, take a risk:

Send your own adapted “How do I fool myself?” request email to someone you trust.

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P.S.Here’s a prior post of mine, that might interest with advice from jazz great, Theolonius Monk, titled Thelonious Monk and memorable speaking