How to deal with difficult employees

How to deal with difficult employees

"Why aren't those contracts finished yet?"

Jim's stomach felt like it developed a vacuum inside. Jenny, his co-worker, had a bad morning once again.

"You told me about them yesterday, Jenny. You know how long they take".

"You just have to work longer hours! After all, your afternoons are always free."

That wasn't true and she knew it. But Jim knew she didn't care.

So he let it go.


Life was hell for everyone around Jenny. She struggled to get custody over her 4-year old son and it didn't look good for. People had to understand and take her attitudes without complaining.

She was going through a hard time, after all.

Jenny's behavior got worse over the months. Once she realized no one dared to call her out, she lost all remaining motivation to hold back her frustrations.

Dealing with difficult employees like Jenny

As a boss, you’re likely familiar with Jenny's sugar-sweet side. She's on her best behavior around you. Or maybe Jenny is a high-performer and you fear you'll lose productivity.

Whatever the case may be, you know something is wrong. You hear complaints about her over and over again. You can feel the heaviness in the air. She's wearing a mask that comes off when you're not around.

We can only hide our issues for a short while. Eventually, they all come out somehow.

Shot this through a shop window in Barcelona. They had marvellous masks on display and the chaotic arrangement fascinated me.
Masking away issues only works for a short while.

Some bosses try to get out of this mess by addressing the whole crows. We’re all familiar with the old pep-talk about sticking together. We're all covering for each other and the boss has our backs.

Well, a good speaker might mesmerize an audience for a day but it won't take care of difficult employees like Jenny.

She will still be there, poisoning the air day in and day out. She might be nice to the boss, even agree with the speaker and be fired up about the future.

But Monday always comes and she will be back to her destructive default-behavior.

Convincing ourselves

Our minds like to come up with little lies in these situations. There are so many things on your plate, right? They are adults, after all, and you’re not a babysitter.

It’s up to us to believe those lies or not. We can even make up arguments in our minds to support them. It gets easier the more we push it away and let it fester. And over time, it even feels insignificant because we ignored it for so long.

But the truth is that we’re chickening out. We’re afraid of confronting our difficult employees. Even more, we’re afraid of handling the situation the wrong way.

That fear is justified. There are many ways this could blow up in our faces. We could come off as too weak or too strong, choose the wrong words, destroy team dynamics, cause people to leave and maybe even jeopardize our jobs.

Yet it’s your responsibility as the leader to protect your people.

Confrontations are an opportunity to prove your loyalty to your team. Yes, you got skin in the game and you’re more than just talk. It gives people the chance to see if their trust is well-placed.

It doesn’t have to be perfect. But it has to be done.

Confronting correctly

So you decide to take action and sit Jenny down.

Congrats on your courage and leadership.

Let’s go through a couple of guidelines that will help you navigate the conversation.

It's important that you start by describing specific instances of Jenny’s behavior. Don’t just talk about the general impression people have of her. After all, she might not even be aware of the havoc she's creating.

Presenting the situation as neutral as possible will allow you to show her behavior without judgment. She won't feel attacked, which is why you should not lead with the complaints you received.

Always give her the benefit of the doubt. It's very likely at this point that she can still turn things around. Be open, specific and go into the conversion with an open mind. Be armed with more than one scenario in case you feel stuck or hung up on details.

If you tell her directly about the complaints you received you just put her into survival mode and activated her amygdala. That means she's on high alert and can't think straight.

Now, it's either fight or flight and she won't be rational anymore. Emotions will bubble over and she'll talk about the first thing that pops into their mind. So remember: Don’t make her afraid.

Don't make difficult employees panic.
Don't make difficult employees panic. There is no good outcome.


The conversation with Jenny can either lead to promises of improvement or total rejection.

The latter makes the solution straightforward because you have to think of about the unity in your team.

You have to do the hard thing and let her go.

But she'll likely promise to improve. That's great but it's only the first step.

Now you have to establish concrete expectations. You can't allow her situation to become an excuse for her behavior. It would give her your backing to spread her mood in the office. It would have been better had you not talked to her at all.

But just as with your team, Jenny needs to trust you. Show a lot of empathy during the conversation. It's important that she knows she can come to you. It's important she knows that you understand her situation.

It's even possible that you help her within your means. Maybe she needs time off, a lighter workload or different responsibilities. If she's willing to change, you can give her the right tools. But she has to understand that she’s the one who has to work on her inner life.

If she's willing to work with you, it's important to establish clear goals.

Since we all see the world through different filters make sure you’re both on the same page. Repeat her thoughts in your own words.

Finally, put your conclusions down into writing. It will hold her accountable and won't leave her any wiggle room with your expectations.

You can always refer back to the exact points you agreed upon. Make sure she has access to it at all times.

Trust in your leadership

Your decisions as a boss impact the lives of those who work for you. Ignoring a situation with any difficult employee and hoping it will go away is a decision in itself.

You might not hear about it anymore but the ramifications will spread like cancer throughout your team.

As a leader, you are responsible for them. They need to feel safe in their environment to enjoy their work and put their hearts into it.

Ignore trouble among your staff and you've misused your role as the leader and protector of your team. You'll lose a great amount of trust and all you'll be left with is the authority of your position.

Don't make the mistake of thinking your team will get it. Or even ignore it and forget about it.

They will remember.

Show them that you care about them. Show them you are worthy of their trust.

Confront difficulties and conquer their hearts.

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