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Should Your Work Friends Include Your Assistant?

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Should Your Work Friends Include Your Assistant? 2019 Update: Administrative Professionals’ Day is April 24, 2019. You can check out our most recent thread on what we’re getting for our assistants on Administrative Professionals’ Day here

Do you socialize with your assistant or secretary? Do you consider him or her to be among your work friends? Or do you keep your relationship with staffers friendly but avoid turning it into an actual friendship? If the relationship has swung too far towards “friendship,” how do you bring it back to “collegial”? Reader N wonders…

How do you reformalize a working relationship with your secretary? I work in law and I have been cognizant about not talking down to my secretary, who is also a young female. I have noticed recently she has interpreted this to mean we are “friends,” which is fine. Recently, she has seemed to step up her attitude, and does not make requests of me politely. I don’t want my niceness mistaken for passiveness or that she does not need to respect me the way she does others who were not as nice.

Hmmmn… tough question, Reader N! With Administrative Professionals Day observed this Wednesday it’s a good time to revisit the issue. In general, I think it’s fine to be friendly with staffers and other subordinates, but the closer the relationship gets, the more complicated it gets. One reader wrote to us a while ago where she was the only female lawyer, and the group of female secretaries was being very welcoming — in that case, where she already had an uphill battle to be/feel accepted with the other lawyers, I think she was right to keep her distance.  Outside of that circumstance, friendship with subordinates can also be complicated because if the assistant screws up, needs redirection or criticism, or just generally needs firmer deadlines and oversight, all of that is easier to do with an arm’s length, professional relationship, without adding more intense emotions of doubt and betrayal (“but I thought we were friends” / “why is my friend betraying me”). (We had a great discussion on whether a boss should be respected vs. liked just last year.)

As to reader N’s question, how can you bring an office friendship with an assistant back to a collegial relationship? I’m curious to hear what the readers say here, but I think the answer is “very carefully.” My $.02 tips:

  • Be wary of public/private distinction. If it’s just the two of you and she’s trying to be sassy or cute, or is allowing her bad mood to show through to you, that’s one thing and, I think, common between two people who work together. If you feel whatever she’s doing is undermining you in front of clients, supervisors, or subordinates, though, you need to sit her down and talk to her in a formal setting, i.e. sitting in your office sitting opposite your desk, or in a conference room across the table — definitely not at lunch or said casually while working side-by-side on something.  (You may want to loop in HR before you say anything to her.) If whatever she’s doing is really annoying to you and out of line, even if it’s in private, you may want to say something to her also.
  • Keep all talk related to the office. If you’ve told her anything about your personal life, assess if you’ve told her too much — she’s not your therapist, she’s your assistant. Tell her what you need to to give her context (“my family may be calling a lot today because my grandmother is ill; please patch them through immediately if you can”), but stop it at a few sentences.  If she’s telling you too much about her personal life, try to shut it down and steal some tips from our chatty boss discussion. For example, send something to the printer as soon as she comes in your office so you can escort her out and walk down the hallway with her to get it.
  • If you see her outside the office, keep your relationship collegial. Keep any personal discussion to 2-3 sentences.  I think this applies whether it’s an office happy hour, or if you happen to have some shared activity outside of work (e.g., spin class, or a kids’ soccer team, or something), in which case it’s fine to talk about the activity at hand for whatever time is needed. Especially since Reader N is trying to dial the relationship back from Friend to Coworker, I would avoid any outings where it’s just the two of you — i.e., if you’ve been going out to lunch or for drinks together, lay off that behavior.

Ladies, what are your thoughts? Where is the line between collegial/too friendly — and how do you dial it back if someone’s stepped over the line?  Do you think it’s harder/easier to manage friends? (In other news: for those of you with assistants, what are you getting for your assistant for Administrative Professionals’ Day this year?  Here’s a link to our last discussion on that topic.) 

Further reading:

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