Bad Boss Story: CEO Double Life

Source: Street interview

"I worked at a company in upstate New York. And my boss was in upstate New York. But we also did business in Washington DC and he had a whole second family in Washington DC.

Depending on which city I was in, I had to go out to dinner with him and his wife and kids in both cities, but make sure I never mentioned the other family or anything while I was with him. And it was a very awkward situation for several years.

What brought it to a head was he had to have surgery up in New York. His wife from DC called me to find out how he did and I told her and she said, well, how do you know that? And I said, well, they told me at the hospital and she said, they would never tell you you're not family who told you how he did? And she kept harassing me, I finally said, you know what his wife up here did. And that was the end of it.

I knew that I would never tolerate it again. I would say: this is not how I live my life and I can't be part of living your life this way. It was a horrible situation. He was a very senior guy in the company and he ended up losing his job over it.

It was an ugly time. But I learned what not to do. You never put anybody in situation you wouldn't want to be in. I think I have the happiest employees in the world. We have a booming company in New York and we got the happiest people."

👀 Our Take:

Forcing employees to cover personal deception is a deep breach of trust. It’s emotional labour they didn’t consent to and corrodes workplace culture. Leaders who blur personal ethics with professional expectations rarely last.

🧠 Could this have been avoided?

Yes. Clearer boundaries between personal and professional life — plus a culture where staff can safely say “no” — would have stopped this.

That’s why we built the Work Personality snapshot — a 60-second quiz that helps people reflect on their style, strengths, and blind spots at work.

→ Find out what kind of boss you’d be

📹 Watch more street interviews