When Bosses Cry: Dealing With Problem Employees

To be clear, “When Bosses Cry” is not a new version of an old Prince song. I just thought it was time to talk about things from a boss’ perspective. Especially problem employees — or what I sometimes like to call “very special people” (VSPs). They can bring even the best boss to tears!

I get lots of visits to this blog from searches looking for help with awful bosses. And problem bosses of all kinds. And there are certainly plenty of lousy bosses who make their employees lives miserable. We’ve talked about them before and will again.

But just for now, I’d like to talk about a different kind of problem … good bosses who have to deal with problem employees. Their very own VSPs.

Richard’ “special” problem employees

Let’s turn first to someone I’ll call Richard, who manages a government office. Richard is one of the kindest, most caring people I know. And he spends a lot of time thinking about how to make sure he’s doing what he can to address employee concerns and needs. Even the small stuff many bosses would ignore.

But he has a few VSPs who recently have been finding problems with everything he asks them to do and seem to have ganged up on him. This is an especially busy period and the time he has to devote to them means he is pulled away from critical business tasks.

And so he also can’t give his other staff the support he’d like. The VSPs just keep hammering away at him to give them what they want, without even stopping to think about the rest of the department.

“Me me me!” says Sarah’s VSP

Sarah also manages some VSPs. She works for a large organization, but her department is severely understaffed. She asked one of her VSPs to take on some extra duties and devoted lots of time and effort to providing him ample training and support materials.

And she met with the rest of her staff to make sure the VSP had their support. But the VSP threw up roadblocks at every turn and is basically finding excuses not to do the job. He was happy with his fairly light workload and doesn’t want that to change.

Change red light for problem employees

In Richard’s case, in addition to the heavy workload, there has been a lot of major changes in the agency. Even though their department is still untouched, I’m sure the uncertainty is felt by all. In addition, they recently moved to a different location.

These are prime conditions for VSPs to begin acting out. Uncertainty, change, and pressure-filled days can cause people who are insecure to begin with to feel threatened, frightened, and/or ignored.

So often acting out gives them the attention they need. But it can also be about not wanting too much attention or extra work (like in Sarah’s situation). Very often, if VSPs are too hard to deal with, they get to be left alone in their own little corner.

VSP behavior can also be an attempt (conscious or unconscious) to deflect any possible blame toward their boss or co-workers. By planting the seeds of “they done me wrong” they may feel they are then protecting themselves from blame.

And there are real personal problems

Of course, sometimes being difficult is a result of things in their own life that are not going well and so they lash out at the most immediate target: their boss. I remember once when I was managing a man going through a non-amicable divorce. He repeatedly “forgot” to handle things I asked him to do and also insisted on saying “yes dear” when I asked him to do anything.

Now we’ve all experienced tough times and probably seen it come out in the way we deal with others at work. If it isn’t a permanent condition, this only makes you a TVSP (temporary very special person), which is much easier to deal with.

In the case of the divorced man, he actually wound up going to some support groups where he learned a lot about himself and how he deals with people in his life. He eventually apologized to me and turned himself into a (mostly) reformed TVSP.

It’s a lot like having a problem child

Most of the time, the solution isn’t that easy. Dealing with VSPs can make a boss’s life a living hell. And, finding a way to work with the VSP (especially where firing is not an option) may involve several attempts and a combination of methods.

It’s a lot like having a problem child. There is no one method that works in every case. And to add to the “fun”, a problem employee may be carrying their own set of childhood baggage, where you may trigger their long-held parentally-associated feelings.

Tips for working with problem employees

There are too many different variations of VSPs to give you a handy-dandy set of “how-to” suggestions. Still, here are some thoughts that might be useful depending on the VSP type or situation:

• Remember to treat VSPs and all staff with the same high expectations. Studies have shown that people rise or fall to the level at which they are treated. That doesn’t mean that anything short of perfection is not accepted — we all need room to make mistakes and not everyone can be as good as your star employee. But it helps for a person to know you have faith in them. Some VSPs come from a background of low expectations and low self-esteem, but that doesn’t mean they can’t eventually learn some new tricks.
• When speaking with a VSP who is showing anger, keep the conversations clear and simple. Focus the discussion as much as possible on the topic at hand. Try to get specific answers to help you fully understand where s/he is coming from and then end the discussion with a few very clear action items. (One note: If the person is screaming, then of course it’s not a good time to have any conversation.)
• If the VSP is someone who wants to do a good job but feels unappreciated or underutilized, make sure you take time to let the person know you’d like to find a way to make this job work better for them. Find out if there are some skills they feel they are missing or if there is anything you can do to help them feel more comfortable. Some people just need specific, manageable tasks (and appropriate training and coaching) that build their skills to where you need them to be.

More ideas that might work

• People who refuse to do their work and want to be left alone need to be given a clear understanding in writing of what it is you need them to do and how they will be measured. They also need to know there will be consequences. And then, if they don’t do their work you have to start writing them up and working to get them out. This is only for the really tough cases and should be a last resort. Yes … I know it takes time and energy, but so does dealing with this person day in and day out — plus it’s really awful for staff morale.
• VSPs can sometimes function well and improve if you find some “wins” for them by assigning them tasks they have a good chance of succeeding at. Often praise and approval and the feeling that they are good at what they do help them move up to the next level.
• Regular, constructive feedback and coaching can help many VSPs. And sometimes just asking them how they are and letting them know you see them as a person and not just a worker bee.
• Regularly assess the workload and abilities of your whole staff. You may need to make some changes to prevent the situation Sarah had with her underworked VSP. Some VSPs have a way of slowly extricating themselves from obligations.

Just a few more things you might try

• Sometimes assigning the VSP to a new manager and maybe even giving the VSP a new set of responsibilities can help. Knowing their interests and aptitudes can work to your advantage. I know one VSP who took on a very limited but important set of responsibilities and is now doing well – with only occasional VSP episodes.
• Possibly it would help to resocialize the VSP by enlisting the help of others in your department to mentor the person and/or maybe even get them involved in some special activities or office social event. If possible, ask the person to help plan an office event like a one-time volunteer activity or even bowling!
• If all else fails and you can’t fire people for whatever reason, create a small unit of VSPs and find some research or special projects for them to do. Those who are ready to come back to the real world get to rejoin the other units if they want. (This also works where you can fire people. VSPs, who are usually quite sharp, are aware that departments to the side are easy targets of budget-cutting. Sometimes a motivating factor for change!)

A bit more about problem employees

I could go on with this, but for now I think you get the idea. Bosses have a lot to deal with. And they aren’t all ogres. Some actually are pretty nice people who are just looking for ways to keep the place running smoothly. But a few VSPs can throw the whole operation out of balance.

While there is no one-size-fits-all solution, please remember that bosses are people too. If you’re a VSP, how about making today “give your boss a break” day? Remember, you could be a boss one day too.

And if you are the boss of problem employees … please know I feel your pain. And you are not alone. Good luck finding some things that help. And if you do find some, please let us know.

(with apologies to Prince)

He’s never satisfied (He’s never satisfied)
Why do we scream at each other?

This is what it sounds like
When bosses cry.

About the author…

Ronnie Ann, founder of Work To the Wise and Work Coach Cafe, bases her real-world advice on her many years as an organizational consultant where she helped interview and hire people, added to a certificate from NYU in Career Planning & Development, as well as her many adventures as a serial job seeker.

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