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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Your first meeting, as a leader of a new team, is crucial

“(Bryant) What were some early moves you made, in terms of culture, in your current role?

(Kenny) From Day 1, I wanted to establish that it was a culture of respect and generosity and truthfulness, and that we were going to work together to solve problems.

On my first day, I met all the employees at a quarterly ad sales meeting The first presentation started – and this was January 2012 – and we had just come off a big quarter because of Hurricane Irene.

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Get promoted more quickly, by solving problems

Below is a powerful vignette – contained in the book, The Leap to Leader by Adam Bryant  – on what you need to do, to be promoted.

Finally, if you want to move up quickly,

develop a reputation as a problem-solver.

Companies have problems. Bosses have problems. Be ready to take on those problems—or “challenges,” if that’s what you’d prefer to call them—and you will move up quickly.

Companies have problems. Bosses have problems. Be ready to take on those problems, and you will move up quickly

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Executives: Can YOU Be Compassionate and DEMANDING?

‘Lucien Alziari, the chief human resources officer at Prudential Financial, captures this paradox in an approach he uses to give feedback to his team. “I tell them right up front, ‘Look, I grew up with tough love and you’re going to experience tough love,’” Alziari said. “It’s really important that you remember both sides of that phrase, because if you’re just experiencing tough, it’s going to feel like the dark side of the moon. But know that I’ve got your best interest at heart, and the only reason I’m doing this is because I believe in you and I want you to be even better than you are.” This is a quote from a great S+B article, Can you master the inner game of leadership by Adam Bryant and Kevin Sharer.

There are many other gems in the article such as:

“That was sort of an epiphany for me,” Leondakis said. “I thought that being tough-minded and decisive and all those qualities and traits that I thought I was supposed to exhibit meant that I couldn’t show compassion.  “Since then, I’ve met just about every CEO who runs a big company. The ones I’m most impressed with do not seem packaged. They have this sense of peace, this self-awareness, that says, ‘I understand who I am.” “For every expert who urges you to “lead from the front,” you can find another who insists that the best approach is to “lead from behind.” “The best approach is to let people know about the big challenges (ideally paired with a plan for addressing them) while not overwhelming them.“ “CEOs need to be able to sense the mood — to, in effect, “read the weather” — in meetings or as they walk the hallways or visit stores and factory floors.”

Own the Conversation

If you have time the article (about 3400 words) is well worth reading. If you don’t have time to read the article, let me suggest you ask yourself these questions:
  • How well can I read a room – and what’s one thing I could do to improve my ‘room reading’?
  • When is it best to lead from the front versus leading from behind – and what is my preference?
  • In what situations can I be verbose and overwhelm people – and how might I avoid verbosity?

Five SURE FIRE ways to UP your LISTENING Game

“You can’t have an agenda,” Joel Peterson, the chairman of JetBlue Airways and founder of Peterson Partners, an investment firm, told me. “When you have your own agenda when you’re listening to someone, what you’re doing is you’re formulating your response rather than processing what the other person is saying.

You have to really be at home with yourself. If you have these driving needs to show off or be heard or whatever, then that kind of overwhelms the process. If you’re really grounded and at home with yourself, then you can actually get in the other person’s world, and I think that builds trust.” 

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Are YOU demonstrating AMBIGUOUS leadership?

People will believe your certainty. They may not know if an idea is good or not. But they will believe how certain you are, that it is a good idea.

When you are certain you need to project certainty.

I’ve seen million dollar deals sunk

because the person pitching came across as uncertain – when it was clearly the right thing to do. And it’s not about bluffing. Trying to convince someone of something when you’re not certain about it.

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Do you MAKE this MISTAKE in the BOARDROOM?

“Few things seem to get CEOs riled up more than lengthy PowerPoint presentations. It’s not the software they dislike: that’s just a tool. 

What irks them is the unfocused thinking

that leads to overlong slide presentations.

Do you make the mistake of unfocused thinking prior to your boardroom presentations?

There is wide agreement it’s a problem: “death by PowerPoint” has become a cliché.”

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Are you a ‘PRE-PACKAGED’ leader?

Recently I read a terrific article about the newly appointed CEO of The Ford Motor Company, Jim Hackett. The article was written by Jerry Useem, in a 7/3/19 Australian Financial Review, Review Magazine edition, entitled: Why Ford hired a furniture maker as CEO. 

This article is well-worth reading. A comment in it that made be pause and think was this. “If you look at business history, the winners are almost always those that get their user experience right”.

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