The CEO of my company is asking me questions and fishing for info about my boss. Am I supposed to share what I see happening?

My boss reports to the CEO of the company. The CEO is asking for my direct opinion on several things. What do I do? How much do I tell the CEO about what’s going on?

-Senior Executive at a Fortune 500 Company

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Dear Senior Executive,

It’s awesome that a leader is asking people how they are doing and how things are going. The more people give and receive feedback the better things will be.

On this flip side, this can also be a dangerous if you share things that you haven’t first shared with your boss. Nobody minds when you give positive feedback. But if someone asks you what could be better and you share something someone else could improve, it shouldn’t come a surprise.

In the best of all worlds, everything is being done to help everyone, the top boss, your boss, and you. Sometimes, there can be ulterior motives and people can be on a fishing expedition. You have to be careful of that. You can ask the CEO if your boss is aware of this discussion. (If the answer is no, it tells you something.) You can say that you’re happy to share your impressions but feel uncomfortable doing so without your boss’s knowledge that you’re talking. This is a little like references and back-channel references ; when you share bad news about someone else and haven’t discussed it first, it’s probably not appropriate.

If this isn't an impromptu meeting, you can let your boss know about the meeting and discuss what you are planning to share. No one is a little kid here—everyone is a senior executive—and there shouldn’t be secrets kept. Many places have confidential skip level interviews and those work when the existence of those meetings is open, and everyone can be honest. In a case where you have information that’s constructive for the company but potentially negative for a person, be honest but don’t look to throw someone under the bus.

I want to acknowledge that these situations can be awkward. It reminds me of a time when I had a manager who was very direct with me about what I could and couldn’t do. Once, before he went out of town, he told me about a situation happening and instructed me not to engage with it he was away. Sure enough, as soon as he left, the acting manager approached me and ordered me to do it. I replied that my boss left clear instructions that I was not to carry this out.

“Do you know what term insubordination is,” he asked.

“Yes,” I replied.

“Well, you are being insubordinate to me and that’s a fireable offense,” he said. “Get out of here and we’ll figure out what to do with you later.”

At the time, I was 26 and I didn’t know what to do. Nothing happened from it, and I didn’t get fired.

I understand these things can be tricky to navigate and full of nuance. Always take the high road with everything you do. Put this through that filter and you’ll do the right thing.

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