How to Deal With Difficult Employees

As a career manager or even a first-time manager, the chance of encountering difficult employees is, unfortunately, very high. You need to prepare yourself in advance to handle the situation without causing additional problems. Even if you're one of the lucky managers who doesn't have a chronically cranky member on the team, there will always be That One Person who, while not generally difficult to work with, has their moments of stubbornness and inflexibility.

How do you manage difficult team situations without coming off as the bad guy? Read our tips in this infographic for properly identifying and addressing difficult employees, and check out our tips for how to deal with difficult employees

A Manager's Guide to Working with Difficult Team Members

What is a problem employee?

A problem employee is, simply put, someone who is causing problems in the workplace. Some problems are more obvious than others — disrespect, gossiping, and stealing could be some examples.

But showing up consistently overwhelmed, upset, or cranky are less obvious. We typically think of these as moods that can’t be helped, not behavior that can negatively impact others. When serious life changes occur, we must show empathy while also addressing the problem so that work doesn’t suffer too. 

Little behaviors can add up over time. Running late to every meeting, willfully ignoring task status updates in the project management platform, or simply neglecting to respond to emails in a timely manner are all examples of a problem employee. 

And it’s not just affecting them. One employee’s bad attitude or emotional ups and downs may have a ripple effect on your entire workplace culture. Whether it’s missed deadlines or self-sabotage, this employees’ actions will no doubt impact everyone else on the team. 

How to deal with difficult employees as a new manager

When a business has a hard time working with an employee, it can drain productivity and make the work environment hostile. How to handle a difficult employee can be addressed through a variety of strategies and procedures.

In the worst-case scenario, if your company has a consistently hard time motivating and managing one of its employees, then you may need to offboard them. This can improve the performance and morale of the other workers.

But as a new manager, firing difficult employees should not be your first port of call. As you get the lay of the land, you may discover that letting people go isn’t a smart move, and there are other ways to address their behavior.

If you’re not happy with certain behavior, don’t just go along with it. Instead, set expectations that are consistent with your company’s policies and the standards you have for yourself. This will help employees copy what you do as you lead by example. 

If the change doesn’t work, try communicating the next steps. Good managers will set specific consequences if the situation still isn’t improving. 

Tell difficult employees that they can still turn it around by identifying the consequences of continuing to behave in a way that negatively impacts the rest of the team. From there, monitor progress and help them achieve their new behavioral goals. 

Remember, problem-solving is all about collaboration. Employees resent an “us against them” work culture but will appreciate you partnering with them to solve the issue. 

Good managers will ensure that every possible step has been taken to retain an employee before termination is used as a last resort. They make sure they’ve done all they can before taking that final step. 

Top tips for managing a difficult employee

Insubordinate employees can disrupt a workplace and kill productivity. Getting them to behave properly can help managers improve their performance. Use one or more of these actionable tips to come up with your own game plan for dealing with difficult employees:

Be professional

It’s important to avoid making the conversation too personal. The goal is to find a way to move forward and not to create more confrontation.

Openly communicate

Having a two-way conversation with a challenging employee can help you identify the root cause of their behavior and address it. Instead of attacking them, focus on the issues that have been identified. Then, reinforce your message by asking the employee to explain their actions. There may be a reason why this employee has been acting out, and perhaps you can work together to address it and stop the behavior.

Ask questions

There may be other factors that contribute to their negative behavior. Some might be outside of work. But you may be surprised to find that others are totally within your control and you can easily help the problem employee solve these problems. 

Use examples

It can be hard to give harsh feedback, but it is important to provide clear and specific examples of the problematic behavior that has occurred. This can help lower the employee's defensiveness and improve their performance.

Record everything

When you witness poor performance or problematic behavior, record it in writing so you can keep track of it and remember all of its details. This is good practice so that if the situation is escalated, you have all the evidence and information ready to defend your position..

Get help

The human resources team can help you identify the issue, discuss the steps you need to take, and provide a course of action.

Work together

Set a timeline for improvement and clearly state expectations. Having the employee sign the plan will help ensure that the plan is followed and that the evaluation framework is used to measure success.

If your plan for improvement doesn’t work, you may end up with a failed strategy. The easiest way to set clear consequences is by sending a warning letter or revoking their employment contract.

Extend grace

Give your employees time to improve their behavior. During this time, monitor their progress and keep track of any issues that might be affecting their ability to meet the agreed-upon timeline.

Isolate them

If the situation is not immediately fixable, consider separating a disruptive employee from the other team members to prevent their behavior from spreading. Doing so can help keep the employee from causing problems for the other team members.

Take responsibility

Whether you intend to or not, there may be something you are doing that has influenced bad behavior among difficult employees. Take responsibility for the situation and try to resolve it in a way that works for both parties.

How do you deal with difficult employees in a virtual environment?

First, it’s important to realize that it’s harder to humanize employees we only interact with online. Sometimes, when an employee is struggling, we stop paying attention to what's happening around them. Understanding the implicit bias we may have toward remote colleagues is the first step to resolving conflicts with them. 

Second, communication that is as specific as possible is critical in a virtual environment. Give employees clear, behavioral feedback. It's not uncommon for most managers to spend months or even years criticizing their poor performers without offering anything concrete for them to work on.  

Great managers know how to be concise and constructive. This approach helps lower the other person's defensiveness and gives them the information they need to improve. It does two key things: it lowers the other person's defensiveness and helps them improve at the same time. 

Third, managers should document their workflow for dealing with difficult employees. In a physical office, there are always other people around to witness behavior and provide guidance. In a virtual office, unless specific individuals are invited to the call, you’ll mainly interact with this employee one-on-one to resolve this issue. 

So when dealing with problematic remote employees, make a list of the key points and actions that you need to take to improve the situation. Record what you do and say to this employee, along with meeting dates, times, and formats. 

This will help you identify areas of weakness in your own management style and allow you to make better decisions next time. It will also protect you from any accusations a disgruntled employee may choose to make. 

When everything is written down, it’s easier to remember and analyze, especially when the situation is emotionally charged. 

How to improve the behavior of a difficult team member

If the problem persists, it will cause more damage to your team. This is why it is important to know how to solve it. 

Not sure how to put this all into practice? Follow these steps for how to deal with difficult employees in a way that maintains and even strengthens your relationships:

Step 1: Label it

The key to solving problems before they get out of hand is to label it early on. If you notice a behavior that is negative more than once, be sure to consciously observe that employee moving forward. If the action happens consistently, that's when you know you have a problem to solve.

Step 2: Start tracking

Using a simple spreadsheet or project and task history in Wrike, make a note of how often the behavior occurs and the severity of it. 

For example, if an employee is consistently late on their deadlines, you can track whether or not they are turning in work the next day or the following weeks. You can also use your project management software to add context to the task and how it impacted the rest of the project. 

By using your project management software to add context, you can get to the root of the problem faster. Continuing this example, even if an employee is consistently late, there might be a bottleneck from a different employee who's actually causing the holdup. 

You can also look to see if the workload is distributed evenly. If not, be sure to redistribute and communicate your observations along with your solutions for moving forward. Chances are, your employees are just overwhelmed and will greatly appreciate the gesture.

However, if the difficult employees really are to blame for the behavior and you see it showing up over several weeks or months, you know you have to do something about it.

Step 3: Identify patterns

We all go through rough patches, but there might be patterns that emerge from your observations. It's good to note them whenever they come up. That way, when you're having a conversation with your employee, you have more insight into what may be exaggerating or promoting that behavior. 

For example, if your remote employee is late to meetings every Thursday but on time every other day of the week, it may be a sign that they have a responsibility outside of work that is preventing them from arriving on time on this specific day of the week. 

Whether it's picking up a child from school or attending a meeting for a different project that typically runs over time, you'll be able to either move the meeting to accommodate or work with the employee to find an alternative solution.

Step 4: Plan solutions

Typically the simplest answer is always the best. In the short term, having a discussion and coming up with a plan is a great way to solve small issues. 

You can also plan long-term solutions for how to address the behavior. That includes setting up a meeting with an HR rep present, keeping notes on what you want to discuss during the meeting, and offering the employee an opportunity to discuss any personal issues that might be coming up for them in private ahead of time. 

You may even find that the behavior is starting to become a pattern but is not quite yet a big enough problem to escalate the situation. If that's the case, then give the person a heads up in a private meeting or via email that you notice something is different. 

If you choose to email them, communicate this in a helpful tone. Ask if you can assist in any way.

Step 5: Communicate expectations

Even if you share your initial plan in your meeting, it's good to reiterate your expectations both in person and in writing. Make sure that the wording is clear and not vague. Have your employee sign off on the expectations with a formal signature or by reiterating their understanding of it.  

Keep in mind when working with a large remote team that personalities and cultural differences often come into play when communicating sensitive information like this. Look for ways that your unconscious bias might be affecting the interaction. Remember to lead with kindness and helpfulness while also being firm on what is expected moving forward.

Step 6: Monitor progress

Dealing with a difficult employee isn't a set-it-and-forget-it type of project. Instead, you'll need to monitor progress over time. 

Once you've laid out your plan and the employee has begun to execute it, make sure you check in and ask if they need any additional assistance from you. They might have questions or find that the plan makes sense on paper but not in action. If that's the case, adjust as needed. 

Make sure you choose a KPI for this project just like you would any other. That way, you can monitor the ups and downs as you go. Once you see consistent improvement, make a note to check in less often but still keep an eye on it in future months or quarters. 

And once your employee has changed their behavior, make sure that you acknowledge and celebrate them. Show them how much you appreciate them working with you on this. 

Not only will it improve the work environment for your entire team but it might also improve their quality of life. 

Keep in mind that some difficult employees are only difficult because they aren't being managed well. Without clear communication and empathy, it can be challenging to tell the difference. 


When dealing with a difficult employee, the ideal outcome is for you to work together to develop a solution that both parties agree on. Partner with Wrike to help get all your employees on the same page and monitor their behavior over time. Start your free two-week trial today. 

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