How do I handle this bad work dynamic?

If your assistant is venting to someone else, but insisting to you that nothing is wrong, then I see three possibilities:

1. You are the problem she’s venting about. Or…

2. The problem involves something that she thinks would lower your opinion of her (or cause her problems in the workplace) if you knew about it, Or…

3. The problem is something she thinks you wouldn’t be sympathetic to her concerns about.

Honestly, I don’t know that there’s really anything you can or should do about it. If she insists nothing’s wrong, you can’t make her tell you. And going after the other support staff person without some pretty solid knowledge that she’s definitely creating a negative work environment strikes me as both dicey and unfair. If the other person is giving your assistant counsel that you wouldn’t agree with, that doesn’t necessarily mean she’s doing anything wrong…

You have a very bad dynamic going on.

1. Do not discuss your assistant or her behavior with another employee.

2. Stop listening to the support person except about her own performance or duties. Stop her instantly if she tries to talk to you about anything else. Warn her to confine her conversation with other employees to her duties.

3. Separate their hours and see if that improves the situation.

4. Once you have instituted these steps, try and talk to the assistant again. Ask her, specifically, if you have done anything to upset her.

To answer some of the questions above; yes I do think she is venting about me, I wouldn’t go to lunch with them and a past employee.

The communication is really only between the two of them, for instance, the support staff person asked for more hours, realizing they socialize too much I asked that she keep that to a minimum. The first thing she does is going to my assistant and tells her I said, they both talk too much.

@marinelife I really don’t do that, I’m odd man out on this triangle. It’s when my assistant wants to vent that she goes to the support staff person. The support staff person receives it and all of a sudden it feels like I’m odd man out. I’m the boss, so I realize that may be part of the territory. But I have come to be aware that the support staff person is a bad judge of what’s going on and is advising my assistant based on her perspective and without any further communication back to me. I think, in a perfect world, what she should do is tell my assistant to address issues with me. If it persists I may separate their hours. There is a lot of analysis in what I do and I can’t have distractions of this nature.

I think what you need to do is sit down with both of them and remind them that your personal policy is to have open dialogue. Remind them both that they are there to work. If either one has a work problem they should not be discussing them openly with other employees.

It sounds to me like you’re trying to micro-control what your employees talk about to a completely unrealistic level. To be blunt, if they don’t like you, you can’t force them to not talk about why they don’t like you. It’s not like they’re discussing company confidential information inappropriately or something. They’re complaining (to each other) about the boss’s decisions.

If it’s making their work unacceptable, then address the unacceptable work (and don’t worry about why you think the work is becoming unacceptable). If you just don’t like the complaining, grow a thicker skin, or make decisions they don’t want to complain about.

Here’s a possibility that has not been mentioned. Is she pregnant?
Did her behavior change radically in a very short t9ime? How recent a hire is she?

I believe there was someone here who interviewed and accepted a position with a company but did not mention her pregnancy, even though she had every intention on leaving. I’m not saying it happens often or if this is the case. It is simply a possibility.

@derekfnord I hear you. Most of this is in my head where I’m trying to sort it out. I’ve kept my mouth in check and only took issue when work is affected. Thanks for shoting straight.

@Season_of_Fall You can let the Support Person go without cause. Her employment is at will.

Sounds like a lot of juvenile stuff going on.
Maybe I missed something but is this not a business? Are they doing their jobs properly? This is the first important question.
If you are a manager or supervisor you can’t be their friend or worry about going to lunch or not as an issue.
Focus on the tasks and business needs. Do they do there job and get done what they need to.
Past that, you may be able to help keep them focused and stop the behind the back stuff, but leave that to HR if they are not performing.
Skip the drama and get the work done.

It sounds to me like you have a habit of crossing boundaries that you shouldn’t be crossing. If you’re the manager, and these are support staff, you should be going to lunch with your peers, and the support staff should be hanging out together. By the virtue of the power you have over their jobs, they are not your peers. Not to say that you can’t be a nice person or a good manager to work for, but it’s not their job to like you; it’s their job to do the work that you give them, and your job to provide opportunities to learn new things, take responsibility and grow their skills.

Where did I say I was going to lunch with them? I didn’t and that is what caused issue. I am just trying to sort out what’s critical and what’s not. Should I correct it, ignore it, ect. It is affecting work flow. The support staff person is a bad influence, but not to a degree I can name or call her out on.

Do you have one-on-ones with your staff? I meet with my manager once every two weeks, for 30 minutes, go over my projects, discuss difficulties, and if there were to be something that needed addressing, it would be addressed in the one-on-ones. You could address the situation not on a personal level, but in terms of professional development. Every meeting ends with him asking what he can do to help me work more efficiently. I have nothing in common with him as a person and I don’t agree with all of his decisions, but he is a good manager to work for, because it’s always only about the work.

The point on the lunch was I think stating that you should not even have this as a worry.
If a support person has issue with it, it is their issue and you have to rise above it. Sounds like the support person is certainly an issue to manage through.
There will always be this kind of thing to one degree or another. This is the hardest part of Managing people. Find out what they bring to the table and help them flourish at work. Help motivate them positively and find ways to build teamwork.
For me, I would find a project or task where they had to work together and earn some respect for what they are there for.
Sink or swim and monitor.

The support person is lying to me in front of my assistant and the assistant is going with it. I haven’t caught her red-handed yet. I had a good heart to heart with my assistant yesterday, but today when the support person was in, after support person left, I asked my assistant how it was going I got a glassy eyed, it’s fine. I understand that I cannot micro manage how other people feel and all but it pisses me off to watch the respect of my personal assistant undermined by this bull crap. The more that happens the more I am assigning blame to my personal assistant for going with this. It sucks to watch someone subversively screw up a year’s worth of training.

Part of the problem is the support person probably senses that I am over her. So combine the facts that she is announced she is leaving with she knows I would like her gone, and she probably feels no obligation to be respectful and not stir trouble up. So the hinge question is do I get rid of her earlier or let it play out.

At this point I would like to let her go and leave my assistant the option to follow her out the door. If I let this continue wouldn’t this risk undermining respect for me across the board? Surely there is some pivot point where a business relationship with an employee has soured enough that it is not worth continuing.

@Season_of_Fall Being a good manager is not to find fault or assign blame.
People are people and I hardly think there is anything sinister going on that you need to control.
I may have missed something but what does “I am over her” mean?

By standing firm ground and not playing into it will gain you more respect than letting it annoy you.

In business you can’t take things personally. Back to the statements prior of there is not much you can do if she is doing her job and no breaking any company rules.