When the new boss asks you 'the question'

It's one of the trickiest questions of a career, and it's fraught with danger.

There’s nothing like a CEO transition to make everybody nervous. When a new leader comes in, especially one from the outside, fear and excitement tend to pervade the organization, and the rumor mill suddenly shifts into overdrive.

There are always winners and losers on the management team. And there is inevitably an excruciating waiting period while the new boss decides who’s in and who’s out. It is during this awkward purgatory when one must prepare for what I like to call "the question."

"The question" is always the same, though the wording might be slightly different. It takes place when the new boss sits down, asks you about yourself and your role, and then shares some observations. Then, it arrives.

"What do you think of Helen?" Or Roberto. Or Sarah. Or Malcolm. Or any other member of the management team.

It’s one of the trickiest questions of a career, and it’s fraught with danger. On one hand, the new boss is truly interested in your evaluation of another member of the senior team. They want to know how that person is perceived, what his or her strengths and weaknesses are, and the value they bring to the firm.

On the other, they might just be testing you to see if you are a team player or how political you are. Are you eager to throw a colleague under the bus? Are you honest and forthright with your answer – or are you hedging and trying to get a feel for what the right answer might be. Finally, they might just want to see how smart, confident, and insightful you are. Is your answer based on objective data or personal feelings, and is your insight helpful to a new leader.

In essence, the question is a test of your integrity, and a foreshadowing of the kind of relationship you’re going to have with the new boss. During one such transition, I was asked to meet the new boss for dinner at an airport hotel, as we were both in town for a management meeting. I had met privately with him before, but it had been all business.

The dinner was an opportunity to relax and get acquainted. And for the first 30 minutes, all was good. We schmoozed about family, vacations, travel, and the adjustment to a new firm. Then he unleashed "the question."

"What do you think of Brian? What do you think of Anita? What do you think of Jim?"

I fielded these as best I could. I tried to be honest, unemotional, candid, and forthright. The boss gave no indication of what he thought of my answers. Then he said something odd. "What do you think about Spetner?" he asked.

I assumed he was making a joke about me, so I said: "Spetner – what a loser! He doesn’t add any value."

The new boss looked concerned and a little shocked. "Really?" he said. "You don’t think he adds any value to the North American operations?"

I then realized he was referring to another colleague whose last name was Spencer. I was mortified. Not only had I just unwittingly trashed my colleague, but it appeared the new boss of the company did not
even know my name.

I sputtered and apologized for the bad joke, and explained the negative comments about Spencer. We then both had a nice laugh, but I wasn’t sure if I had blown it or not. As it turned out, I had a long and productive relationship with the boss, and he was a fabulous leader for our organization. Turns out, he just wasn’t so good with names.

Don Spetner is a senior corporate adviser with Weber Shandwick. He was previously CCO and CMO for Korn/Ferry International. He can be reached at donspetner@gmail.com. 

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