Ask Your Boss: I am Going on Vacation Either You Let Me or Not!

“I have an employee that on several occasions since she started here almost three years ago gets very defensive and combative at times. It seems to happen when I’ve had to speak firmly to her or inform her of something she doesn’t like the answer to. The most recent was when she came in and told me what days she’s taking for vacation (without previously getting the ok, and I also found that she had already booked tickets) I let her know she did not have sufficient vacation to cover the days. Next thing you know, she’s telling me I’m rude, this has happened in the past. She informed me she already booked the tickets and she’s going with no pay regardless. I let her know I was not being rude just giving her the information. She told me I’m supposed to be her friend and I should have asked what she was doing. I told her that I’m her office manager. She then used the f word. This is not the first time this has happened.”

Have you told her how she makes you feel? Have you talked to her in the past that she comes across as a jerk and a huge pain in the ass? I assume you have talked to her (for you own sanity!) about it because if you have not, then you will have to start NOW. No more delays.

I can see a few issues in your situation (to be honest, there is a whole bag of pretty shitty issues here):

  1. you are friends with an employee whom you also manage;
  2. your employee does not recognize your authority as a manager nor does she respect you as her friend (but the latter is personal, and I will leave it up to you to deal with that);
  3. there is a huge insubordination issue;
  4. oh, and don’t forget the “f” word. No one, and let me repeat it again, NO ONE, should speak like this to their manager (or anyone really.)

I am sure you have already thought about this: you don’t need a friend like her, AND you don’t need an employee like her either. I am usually not that harsh or mean or evil, but in this situation you need to let her go. However, it is easier said than done.

This is what I recommend or, let’s say, this is what I would do if I were you:

  1. I would write down our conversation (the one you described to me.) I love keeping notes because they come in handy when it comes to firing people.
  2. I would talk to this woman, and tell her that you do not appreciate her language, her attitude, her conduct and her work ethics. I would then proceed to explain that as her manager I have to write her up for insubordination and disrespect.
  3. I would hand her our organization’s policies and procedures regarding scheduling time off. I would calmly tell her that she has not asked for the time off and has not followed the outlined procedures (I would highlight the steps in the procedures for her – people like to see highlighted stuff.) I would advice her to re-visit our policies and procedures.
  4. I would lay out my expectations as her manager (also, preferably in writing) and state very clearly what I would like her to change and by when. I would give her a month to correct her behavior if I wanted to keep her working for me, and two weeks if I wanted to replace her.
  5. A side note: what is your time off policy? Our policy is that you cannot take unpaid time off. It might be considered grounds for termination. On a personal note: you should not give a shit if she booked a trip and bought tickets already. Her vacation was not approved. It is not your problem. It is on her.
  6. I would watch her like a hawk and start writing her up for every mistake she makes. Somehow, I suspect she is not a stellar employee.

Managers do not have to be friends with their employees. In fact, it is better for everyone not to be friends! I was burned a few times myself, and had to cut out a couple of friends because they could not accept me as their manager and a friend.

Remember, you need to assert yourself as a manager. It is not the most pleasant aspect of our work, but what else can we do, right? Sometimes I want to throw a binder into someone’s head. Sometimes I want to swear like a sailor, and splash coffee into someone’s face. But then I remember who I am and what I represent, and things do not look too bad after that. You have the power. Use it!

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