Q: Someone I recently started supervising at work after a re-org is showing an alarming desire to be “best friends” with me rather than respect appropriate boss/subordinate boundaries.

She tries to turn every contact between us personal and has even started texting me on weekends about nonwork matters. She constantly compliments me about how “wise and wonderful” I am. When I steer her back onto work topics, she doesn’t pay attention.

I believe this is 50 percent manipulation (she feels she’ll get an easier life at work if she engages my friendship) and 50 percent personal baggage. At one point, she spontaneously broke into tears about how her mother “ignores” her in favor of other siblings, so I think she has some serious Mommy issues and has decided I’m a good candidate to be her surrogate mother.

Can you advise me on how to establish professional boundaries? She has some performance issues that need to be addressed, and I need her to really hear and understand that I will have to make decisions as a boss and will not base them on personal connections. How can I confront this without triggering more drama?

A: In personal relationships, we need our friends and loved ones to provide a sympathetic shoulder to cry on and to let us vent without pushing solutions. Good friends overlook flaws and don’t keep count of mistakes; they make themselves available for private, intimate discussions.

With your sycophantic subordinate, you need to do the exact opposite of all these things.


“I can see you’re upset. I’ll give you some time to gather yourself.”

“That sounds like a difficult situation. Have you considered talking to a professional about it? We have an Employee Assistance Program that is completely confidential.”

“I appreciate that you enjoy working on this team. But there are some issues with your performance that we need to discuss.”

Your response to weekend texts: *crickets*

And avoid one-on-one time. When it’s time for a serious discussion, have someone from HR present to witness the conversation and to keep the focus on her performance. If she ambushes you in your office and tries to pin you down for personal chatter, cut her off politely: “I’m sorry, I don’t have time to chat. Did you have a work matter I can help with?” If she’s having an emotional breakdown, stand up and invite her to walk with you to HR for a confidential conversation.

It may feel cold to respond this way to someone who’s “just being friendly.” But even best friends know how to respect each other’s boundaries — especially at work. The weaker her respect for boundaries is, the firmer your boundaries have to be. And whether she realizes it or not, you can do her more good as a boss than as a buddy. If your recent re-org included layoffs, she may be feeling insecure about surviving another round; honest feedback that helps her improve her performance could help her replace neediness with confidence.

If she ends up becoming the competent, independent employee you need, you may eventually be able to have a friendlier, more relaxed rapport with her. Until then, your work relationship is your only relationship.