Should Your Work Friends Include Your Assistant?

Should Your Work Friends Include Your Assistant? 2018 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:



  1. Greenbelt :

    Does anyone have any restaurant recommendations for Greenbelt, Maryland? Looking for a place to take a client.

    Thanks in advance!

  2. At one of my jobs, my secretary-paralegal was an instant kindred spirit. We became fast friends because we just hit it off as people. I would never consider preventing a genuine relationship from forming because of the boss-subordinate relationship. I find that as a busy adult new friends are really hard to come by, and when the opportunity presents itself, it should be embraced.

    The OP’s question is a little different because there’s a “respect” issue, but as to that, I don’t think it’s generally our job as people or professionals to police someone else’s attitude. If you act professionally, that is how you will be judged by others, and as between you and the assistant, asking for or demanding outward expressions of deference or respect is not a sign of power. And there is really no way to do it without sounding like a status-obsessed jerk. Any individual instance of rudeness should be addressed in the moment (or when appropriate), if it needs addressing, but that’s the same no matter what the power dynamic.

  3. I am friends with a member of my support staff. I have all personal conversations in person, and send formal requests via email when it is more like an “assignment.”

    On a related note, I was dismayed recently to hear some male partners/counsel criticizing (among themselves) a more junior female attorney for being too friendly with her secretary. I think it was based on a perception that the female attorney wasn’t taking her time in the office seriously.

  4. Executive secretary here!

    I would prefer to be friendly rather than friends with anyone who has significant supervisory powers. “Friendly” certainly includes a little idle chat, the occasional group work lunch, etc, but actual friendship gets too confusing. Also, frankly, I don’t want to have to deal with differences in our values – I don’t want you to judge my politics or personal habits when we work together, and I don’t want to be in a position to judge yours. And we live very different lives – I make much less money, have a less socially respected position and probably have less job security than you. My retirement picture is very different; my housing is different; the travel I can afford is different. It can be unpleasant to try to maintain a friendship in the face of these differences, particularly if I am required to pretend familiarity with things I can’t afford, or to cover up the fact that I can’t afford them.

    I’d say that I’m on a more “work friends” basis with people who rarely have work for me and have very little say in how I spend my time. I would not object to being real-life friends with these people if the situation came up, but it’s not something I’m going to pursue.

    I would much prefer to be treated with a little formality as a skilled assistant rather than muddying the waters with a “friendship” that can only be very unequal.