How To Kill An Unwanted Office Flirtation

flirting_employee_slide1_annaIllustrated by Anna Sudit.
I was promoted to management in a small business fairly recently. I'm female in my early twenties and most of my staff are males in their thirties. Most of the guys have gone through a phase where they casually flirt with me then move on.
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One guy doesn't seem to be moving on. He asks really personal questions, and I know he has a steady girlfriend. Every time he flirts with me, I have politely shut him down.
Other than that, he’s a model employee. But, harmless or not, his flirting makes me really uncomfortable. Our company is too small to have an HR department. Jim's performance review is coming up, and I feel like I should broach this subject with him. Am I overreacting? How do I ask him to stop flirting with me when he may not even realize he's doing it in the first place?
Don't save this up for his performance evaluation. For one thing, performance evaluations shouldn’t contain surprises. Also, this is going to be a lot less awkward for both of you if you address it as it comes up, rather than in a separate conversation later. If addressing it in the moment doesn’t work then, yes, you’ll need to escalate it to a bigger conversation. But you have a good chance of solving this in a way that will be easier on both of you if you call it out when it’s happening.
That means you’re going to need to work on being direct in the moment. For instance, the next time he asks why you’re single or what you look for in a relationship, say, “I’d really rather not discuss my personal life at work. But I’m looking forward to hearing about how your call with ABC Corp went.”
You’ll notice that this example ends with bringing up a work topic. That’s because correcting his boundaries is likely to go down more easily if you move quickly into a work-related interaction, so that you can model what your professional relationship should look like, and demonstrate to him that he doesn’t need to be embarrassed because you’re not dwelling on it. Your goal here, after all, is not just to shut down his inappropriate questioning but also to have an effective professional relationship with him.
Ideally, doing this a couple of times should be enough to send him the message that he needs to cut out this whole line of conversation. And if that happens, he might have simply been a clueless guy who didn’t realize how inappropriate his behavior was.
However, if it continues, then you’re dealing with someone who’s willing to disregard direct instructions to stop. That’s significantly more problematic, and if that’s the case, you need to escalate your approach. For instance: “Jim, I’ve asked you to stop asking about X or commenting on my relationship status, but you’re continuing to do it, anyway. What’s going on?” In other words, handle it the way you would with any other work issue where you’d directly asked him to stop and found that the behavior was continuing. Don’t feel like you have to put this in a different category just because it’s flirting.
While you might feel awkward about having to say any of this at all, keep in mind that he’s the one forcing your hand here. After all, if he were respecting normal professional boundaries, you wouldn’t need to point out that he’s crossing them.

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