Dear Tell All: I’m about a half-year into a new job at a local company and have an unusual relationship forming with the boss.
I was intimidated by the guy from the minute I got there. He’s in his 40s and has worked at our company for most of his career, climbing the ladder to the top. He’s incredibly professional and commanding. Everybody in the office respects him, despite the fact that he’s not personally close to any of our colleagues. He maintains a proper distance from employees, to the point of coldness.
As for me, I’m in my late 20s and am self-conscious about being one of the few women in my department. Though I have a different supervisor, I occasionally report directly to the boss in one-on-one meetings. I always prepare hard for these meetings, hoping to make a good impression and contribute meaningfully to the company.
About two months ago, a weird thing happened. I asked my boss a harmless personal question at the end of our meeting, just to make conversation, and he let his guard down. He confided in me about his concerns at work and at home. I did what I normally do in such situations: listened to his stories, asked him questions and showed sympathy.
Since then, our one-on-one meetings have become increasingly personal. He tells me about his problems and asks me about mine, occasionally dishing about others in the management team. I enjoy our growing closeness and am almost certain this is not leading to a proposition. For all his troubles at home, my boss seems essentially happy with his wife and dotes on his kids.
On the other hand, I find myself feeling uneasy as I keep our new intimacy a secret from coworkers. In the hallways and at group meetings, my boss treats me with the same aloofness that he does everyone else.
I keep telling myself there’s nothing wrong with developing a satisfying friendship, even in this unorthodox relationship. Am I giving myself bad advice?
On Probation
Dear On Probation: I think you’ve answered your own question by seeking the help of an advice columnist. Deep down you know there’s something fishy about this relationship, no matter how hard you try to convince yourself that it’s fine.
Here are the red flags: The age differential. The power differential. The creepy sexual politics, no matter what you say about his “essentially happy” marriage. The inappropriate dishing about the management team.
That uneasiness you feel about your boss’ intimacy behind closed doors compared to his aloofness in public? Ignore it at your peril.
You describe this guy as “incredibly professional,” On Probation, but your letter makes me doubt it. Even though he’s the boss and you are (I assume) on probation at this company, you need to be the one to act professionally. Stick to business in your one-on-one meetings. If he doesn’t take the hint, run to human resources.
It’s true that blowing the whistle on your boss won’t endear you to him. But I’m guessing the word “endearment” appears nowhere in your job description.
Do you have a question about life or love in Madison?
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