[ this post is the third part of the difficult people series, if you missed the first 2, check out the one on dealing with a bad boss, and the one on handling pesky peers that don’t work for you ]

One of the hardest parts of any job is working with difficult people. No matter how much we wish they would just change and make our lives easier, that’s not the most effective strategy for getting things done in the face of a difficult coworker.

When you’re a manager, you’re responsible for a lot – not the least of the success and satisfaction of the people on your team. But not everyone makes it easy. Today let’s take a look at how to handle a difficult employee.

When I first became a manager, it took me a long time to figure out the kind of manager I was going to be. I struggled with wanting to be friends with everyone on my team, but also wanting to be taken seriously by everyone above and below me, and it was a while before I found the balance that worked for me.

And while I was figuring out my role and career,

the whole time I was also managing a team of several people who I was supposed represent and lead. A lot of managers (especially new ones) are so busy trying to do everything expected of them as manager that dealing with a bad employee is the last thing they want to do.


It can be overwhelming to run a team or department, and demands come from all sides. When an employee is causing problems, there are plenty of people who get overwhelmed and don’t know what to do, or who decide they just don’t want to deal with it at all.

But you are a manager. Your whole job is to make every single person on your team successful by helping them do the best work and strengthen their career. To be an effective manager, you have to face a struggling employee head on – not only for their sake, but for the sake of the rest of your team. A problem employee can send bad vibes through an otherwise awesome team and make everyone’s lives more difficult.

What’s the best way to manage an employee who’s causing a negative stir?  Below are some strategies that have worked for me and those around me.

sometimes those who challenge you the most teach you the best

Every big problem starts as a small one

Ignoring a problem and hoping it gets better on its own is rarely a good strategy. According to the

Labor Law Compliance Center official website, when you notice problems starting to arise with a particular employee (or group of employees), it’s really important to pay attention to it right away.</p><p dir=”ltr”>Everyone has bad days, and everyone makes mistakes, so you don’t necessarily need to intervene every single time someone lets a project slip or says something negative in a meeting. But you do need to take note, and be aware if the problem continues.</p><p dir=”ltr”>If you notice, though, that things are getting worse or an employee is consistently repeating the same bad behavior, you do need to step in. Think about it: people don’t act like jerks because it’s fun or they think it will make things better. More often, bad behavior stems from things like insecurity and lack of trust – like when a new boss comes in or there’s another change in the organization or process. A blowup at a meeting probably has less to do with that one thing they’re yelling about, and more to do with how that one thing exemplifies the underlying problem they have with you (or the organization).


So first you need to find out what it is that’s causing them to behave in a harmful way. Understanding a person’s motivations unlocks your power&nbsp;to do something about it.  Think of it like root cause analysis, things are unlikely to improve if you don’t address the underlying cause.

Unfortunately, most managers aren’t equipped with special super powers that allow them to read their employee’s minds. So that means you’re going to need to have a conversation.

Communication is your best friend

The best way to find out what’s bothering someone is to ask. When you ask people to explain what is causing their issue, the real reason may surprise you; you’re not inside their head, so your assumptions about their problems can be way off.

That’s why it’s best to make it possible for them to just tell you, without leading them (intentionally or not) to tell you something you want to hear. One thing I’ve learned in doing a ton of interviews is that you’ve got to learn to frame questions in a way that removes the other person’s incentive to give you the answer they think you want. Job candidates (and employees) want your approval, and most will try to craft their responses to conform to what you want. Create a situation in which their fear of saying the wrong thing can go away, and they can speak truthfully.

The best way to do this with a bad employee is to frame the conversation as an opportunity for you to get to know each other better, and to remind them that your goal is to help and support them.

Keep it non-confrontational; my goal in dealing with problems on a team is to keep everything neutral or positive. Instead of walking up and saying, “Hey, you have an attitude. What’s the deal?”, start the conversation by demonstrating your interest in them.

Ask them what they like about their work. Ask how things are going for them, and how they feel about their career. It’s also a good opportunity for you to tell them more about yourself too. Emphasize how passionate you are about the work your company is doing, and how important your team is to that work.

Explain a bit about your role in relationship to them: you’re there to help them, to unblock them, and to make their work life easier. If you or the employee is new, let them know that you’re going to keep working *for* them and that trust will build the longer you guys are working together.

I’ll go on to ask what I can do in the future to keep problems like this one from happening again. It’s completely possible that you made a call on a new process or said something offhand in a meeting that was actually a huge deal to the people you manage. The more you know about these things when they happen, the better you can do. Let them know you want to hear from them, because you want to make things better.

I’ve done things like this before, and have been surprised to hear from an employee that something I thought was a good idea really wasn’t working. You’re not there in the trenches with them every day, so be open to the fact that your “great idea” might actually be causing problems for the people on your team. And then (and perhaps most importantly) be willing to fix it.

Having the conversation

Before you ever get around to the real meat of the conversation you want to have with a struggling employee, there are a bunch of subtle things you can do to help build trust and make it possible for them to open up to you about their issues.

For example, I find that putting yourself in a position so that you’re on the same level as them is extremely helpful. You might try finding a project where you and that person can work on something together, or you can try asking them for help on something in your domain.

Tell them, “I was just going over the new feature your team submitted, and I thought this part was so awesome.” Then ask, “Can you tell me more about how you made it work?” Giving them the opportunity to tell you about their good work builds trust, and helps them to see you as someone genuinely interested in them and their career. This is also a great way to get at small problems before they become big ones, and can nip a potential situation in the bud.

If you need to discuss a larger issue head on, keep the situation and place as neutral as possible. I like to take them out to lunch or coffee, so you’re out of the confines of the office and on neutral territory. Dynamics are different out in the real world. It’s easier to see your boss as someone you can talk to instead of “the person in charge” when you’re not in the same place their problems are occurring.

When you’re ready to head out for the meeting, pick them up at their desk instead of making them come to you. Keep it on their turf; the boss’ office can be an intimidating place for some.

Everything you can do to seem less like a tyrannical authority figure is in your best interest. Talk to them like a person, stay engaged, and listen close.

Let cooler heads prevail

In the heat of the moment, a lot of nasty things can get said. Unless it’s absolutely necessary for you to speak up right there, at that moment about a problem, always try to save your conversation with a problem employee until everyone’s calmed down a bit.

Not only will you save the both of you from speaking out of anger, but you’re much more likely to get a positive result than you would trying to talk to someone who’s boiling over. An angry person isn’t interested in letting you help them. Someone who’s had a chance to cool off more likely will be.

Letting a problem cool off is also a great chance for you to get an outside opinion. I once had an employee make a really negative comment to me, and in the moment, I was upset but figured he meant well and just misspoke. When I was talking this situation over with a friend after work, though, they gave me insight into what that person could have meant.

It was a great chance to see the issue from another person’s perspective, and allowed me to discuss the problem with the employee by seeing it a little more clearly from their point of view (and for more on this check out this book Difficult Conversations – my friend Erin recommended it and it gives you a whole new look on context and intentions). Remember, we’re not mind readers, so if you need it, ask for help to walk in the other person’s shoes.


One of my favorite sayings is this: you have two ears and only one mouth, so you’re supposed to listen twice as much. Helping a bad employee get back on track and be successful is all about communicating with them well and letting them help you help them.

If you’ve had a success repairing a relationship with an employee, or have other tips or references, please share them in the comments.  

– Read related: Buddy Punch Time Clock.

Related Posts: