A reader writes:

I have a strong working relationship with my boss, the owner of the company I work at. We clicked instantly in my initial interview, get along well, and he is consistently impressed by my work. Most importantly, I think he values me because I’m not afraid of difficult conversations, and I’m the only person in company leadership willing to tell him when I disagree with him or when I think he’s making a mistake.

As one of the few women in leadership in a very male-dominated industry, I’m used to weirdness in my relationships with male bosses. Typically, they will take credit for my work, or publicly treat me like a secretary or assistant while privately relying on me to do the majority of their role. My current boss has never done anything like this, although he often seeks my advice. It’s probably one of the healthier and more functional working relationships I’ve ever had with a manager.

But I do have one odd problem. Sometimes I will initiate a conversation with my boss that is difficult or fraught — stuff like one of the other senior managers interfering in a project and refusing to let go, or explaining that my boss made a decision that has negatively impacted the company and needs a different resolution. These conversations usually go well, although he is always saddened to hear he’s done something that people found frustrating or hurtful, and he definitely does not enjoy giving his senior leadership negative feedback. And if any of these situations affect me, it impacts him even more because of how much he values me. I’m good at keeping these conversations productive and professional, but at the end of really difficult ones he has a habit of telling me he loves me as part of saying goodbye (we all work remotely, and these meetings are virtual).

I am not someone who uses the “L-Word” liberally! I say it to my close family members and two or three close friends. I do not think my boss is attracted to me or means it in even a slightly romantic way when he tells me he loves me. Instead, I think he feels emotionally vulnerable: I get the sense I might be the only person in his whole career who’s been comfortable giving him direct and constructive critical feedback, and he’s seeking validation that our relationship is still strong in spite of the difficult conversation. As such, if I were to say “That’s weird” or “Please stop telling me you love me” in the moment, I’m concerned it would negatively impact our relationship and cause him to feel even more vulnerable and sad. But if I bring it up out of the blue, it feels like making a weirdly big deal out of something that could conceivably be a slip of the tongue (three or four times now).

Should I just let this weird quirk go? What do I say in return? He’s never pressed the issue. So far he’s always said something like “Have a great afternoon! Love you!” and I’ve just ignored the second part and gone with a cheerful but awkward-feeling “You too!”

It’s definitely strange, right?

– I don’t love you

Yes, it’s strange! (Although not unheard of.)

Some people are more free with the L-word, even in a business context. It sounds like he trusts you to take it in the spirit he intends it in — not as “I like you romantically” or “at moment I may make a pass at you” or “you are dearer to me than my wife” but as “you are very important to me professionally and as a fellow human and I appreciate and value you.”

But it’s unusual for a work context … and ideally he would have noticed your discomfort the first time and not repeated it.

As for what to do: If you’re not terribly bothered by it, it’s fine to just let it go. You can convert it in your head to “I appreciate and value you” and shrug it off as a weird, even amusing quirk from someone you have a strong relationship with.

But if it does bother you, it’s okay to say something! I hear you on not wanting to make him feel bad, but the next time he says it, you could take that as an opening to say, “I know you mean that in a completely professional sense, but I don’t toss that word around much and it makes me feel a little awkward. Maybe just say you appreciate me!” That way you’re not calling him weird or saying he’s out of line or that he can never express that he values you, but you’re conveying, “Here’s where my boundaries are and here’s what would make me comfortable.”

#boss #telling #loves #Manager