5 Tips for Dealing with Difficult Employees

João Monteiro
4 min readDec 31, 2020

“You manage things; you lead people.”

– American computer scientist, Grace Hopper.

Dealing with difficult employees is part of every leader’s journey. It isn’t fun, and it’s not something any leader looks forward to. But knowing how to navigate these tough situations is a necessary skill every leader must have. Unlike projects and initiatives, you’ve got to remember — you manage things; you lead people. As an entrepreneur and CEO, I’ve thought back on this advice a lot when dealing with difficult employees.

I have collected the best tips over the years for dealing with difficult employees and I want to share them here with you.

1) Assess the situation

First things first. You’ve got to understand what is happening. Assess the situation. How is your employee behaving differently and what is causing the shift?

Trust me — I know from experience. Leaders have a lot going on, and a problem employee just adds to that list. It can be easy to think, “This guy is just slacking off because he doesn’t care.” Or “What does it matter? It isn’t affecting anything too much.”

But what’s really going on? And won’t it matter if something goes wrong because of a problem you ignored? I know you’re busy — we all are. But this is something you can’t ignore. Do a little bit of critical thinking and investigation.

Don’t just pretend like the issue isn’t happening, or it could get the best of you. Do what’s best for your company and your employees.

2) Communicate and give feedback

I’ve said it before, and I’ll say it again. Communication is key.

You’ve done your homework — observed and paid attention. You have accepted that there is a problem. Now’s time to do something about it. Talk it out with your difficult employee(s).

Hear them out. Make sure that they feel comfortable sharing and let them talk. Give them a private space to share what’s been going on and how things are looking from their perspective.

This step is critical for three reasons.

One, just by having this conversation, you’re letting your employee know that there is trouble in paradise. There’s a chance they might not have been aware of the problem, themselves. Two, you get to hear their side of things. This might come as a surprise to them, but the opportunity to speak freely on what has been affecting their performance could reveal things to both of you. And three, you get to say something.

We don’t have to become psychologists, but sometimes we should use their business tools. For instance, the Johari Window Model is a really useful tool utilized by business professionals and leaders globally.

Basically, the idea is pretty simple. It’s a tool that can help managers give feedback, and help employees receive feedback. It’s specifically made to help people learn more about themselves, so you can see how it’s perfect for this type of situation. It is divided in these 4 sections:

Johari Window Model

  • OPEN — Things about you that others know, and you are aware of
  • BLIND SPOTS — Things about you that others know, and you are not aware of
  • HIDDEN — Things you keep secret or private from others
  • UNKNOWN — Things you have yet to discover about yourself that nobody knows

A lot of times when we have problems with employees, their issues are either open or blind spots, but they can be related to things that are hidden.

Talk these things through and be specific.

Have you noticed something that your employee doesn’t seem aware of? That might be their blind spot. Have they talked about something their coworkers are complaining about? That’s something that’s open.

Communicating and using helpful business tools like the Johari Window Model to provide detailed feedback can teach your employees to admit their problems and work on fixing them together.

3) Keep track and be diligent

Leaders don’t take pleasure in firing people. It’s not a great part of our job.

When we hire someone, we expect them to be able to do the job they’re being paid to do. So, when it looks like they are underperforming or having difficulties, that is not a good sign of happy times ahead.

But just because firing people isn’t something we enjoy doing, it doesn’t mean it isn’t a necessary part of our job sometimes. The right way to know if you should let someone go is to keep a record of their behavior.

The best way to move forward steps after 1 & 2 is to hold your employee accountable. Keep track of their behavior. Make note of it and be consistent. Sometimes you need to make hard choices to do what’s best for your company and employees.

4) Be part of the solution, not the problem

Whatever you do, don’t be part of the problem. Complaining about your difficult employee to your other employees is not the solution.

Instead, keep your priorities in order. Remember that helping your employee helps your business. Focus on your business’s health as a whole and try not to get lost in office drama. Spreading toxicity will only add salt to the wound. Don’t make it worse.

5) Be a support system, but know when it’s time to say goodbye

You’re a leader, not your employees’ therapist or a life coach.

You manage things; you lead people. Ultimately, even the best managers cannot control their employees.

Do your best to support your difficult employees. Keep lines of communication open and help them to recognize and work on their difficulties. Besides this, there is not much else you can do from your end.

If communicating, giving feedback, and being a resource to your employees are not working to solve the issues, then it may be time to say goodbye. Make sure you have gone through every protocol with your HR department before you fire an employee.

I hope you’ve found these tips useful.

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