Turning Tension into Teamwork: Strategies for Managing Difficult Employees

Workplaces are full of different personalities, work habits, and viewpoints, and every company has its fair share of… let’s say tricky individuals. Whether it’s a colleague with a knack for passive-aggressive remarks, a boss who explodes over minor issues, or a team member who remains unresponsive, these people can truly test our resilience.

In this blog post, we’re going to break down what makes someone a “difficult employee,” explore how engagement ties into negative behavior, and share some practical tips for managing sensitive situations.

Who Are Difficult Employees, and Why Do They Appear?

Difficult employees come in many forms, but have you ever stopped to think about why these “challenging” behaviors pop up in the first place? In most cases, it has less to do with the individual and more to do with the company as a whole.  Poor communication, lack of support, and unclear expectations are just a few internal HR problems that might be off within just any organization. And there’s more to it! Let’s look at five common types of difficult employees and try to understand how to manage them effectively.

The Chronic Complainer

This employee always has something to grumble about, whether it’s the coffee machine being on the fritz, their workload being too heavy, or even the office temperature being just a tad too cold.

Though some individuals naturally gravitate towards negativity, typically chronic complainers are more than just pessimists. Many of them believe their voices aren’t being heard in the workplace; others feel overwhelmed or powerless in their roles. They also might think that sharing grievances will make them more relevant in conversations or highlight their importance within the team.

Managing chronic complainers:

1. Listen Actively: Give them your full attention and acknowledge their feelings. This doesn’t mean you have to agree with them, but showing that you care can go a long way in diffusing their negativity.
2. Encourage Constructivity: Instead of allowing complaints to linger in the air, encourage them to provide constructive feedback. Ask them what solutions they might propose for the issues they’re raising.
3. Set Boundaries: While it’s important to listen, you also need to set boundaries. If their complaints become excessive or disruptive, gently remind them of the need for positivity and collaboration in the workplace.
4. Promote a Positive Culture: Encourage other team members to share successes and celebrate achievements, no matter how small. This can help shift the focus away from negativity.
5. Provide Support: If you notice that chronic complaining stems from feeling overwhelmed or unsupported, consider providing additional resources or guidance. Sometimes, employees just need a little extra help to feel more confident in their roles.

The Know-It-All

This person seems to have an opinion on everything, whether it’s related to work or not. They often dominate conversations, offer unsolicited advice, and can make collaboration feel more like a battle of wits than a team effort.

But what makes a know-it-all tick? Believe it or not, most of these guys are driven by insecurity. They feel that they need to prove their worth by showcasing their knowledge, even if it comes off as overbearing. Besides that, these individuals often have a deep-seated fear of being wrong or looking foolish. To combat this anxiety, they overcompensate by asserting their opinions loudly and frequently, hoping to establish themselves as the “expert” in any situation.

Dealing with Know-It-Alls:

1. Validate: When the Know-It-All starts sharing their thoughts, try to listen actively. Acknowledge their input with phrases like, “That’s an interesting point,” or “I appreciate your perspective.” Sometimes, all they need is to feel heard.
2. Encourage Collaboration: Foster an environment where teamwork is prioritized over individual opinions. Encourage group discussions where everyone can contribute, making it clear that collaboration leads to better outcomes than one person dominating the conversation.
3. Ask Open-Ended Questions: Instead of shutting down their ideas outright, ask open-ended questions that encourage deeper thinking. For example, “What do you think about this approach?” or “How do you see this affecting the team?” This can help them reflect on their ideas and consider other viewpoints.
4. Provide Feedback: If their behavior is affecting team dynamics, consider having a private conversation with them. Discuss specific instances where their know-it-all attitude has been counterproductive and offer suggestions for improvement.
5. Celebrate Team Successes: Highlighting team achievements will help them switch from individual contributions and reinforce the idea that collaboration is key to success. Recognizing collective efforts can help diminish the need for any one person to take center stage.

 The Procrastinator

You know the type—the employee who’s constantly racing against deadlines, leaving tasks until the last minute, and often delivering work that feels a bit rushed or incomplete, which leads to frustration for teammates who rely on them.

However, procrastination isn’t just about poor time management. Procrastinators are either paralyzed by the fear of not meeting expectations or producing subpar work or simply lack motivation to tackle the tasks they are given. This, in turn, results in avoidance behavior as they try to escape the stress.

Coping with Procrastinators:

1. Open Up the Conversation: Ask them about their challenges and listen without judgment.
2. Set Clear Expectations: Outline deadlines and milestones for projects.
3. Break Tasks into Smaller Steps: Encourage procrastinators to break larger tasks into smaller, more manageable steps to make projects feel less overwhelming and help them build momentum as they complete each step.
4. Use Time Management Techniques: Introduce techniques like the Pomodoro Technique (working for 25 minutes followed by a 5-minute break) or time-blocking to help employees manage their time more effectively.
5. Offer Flexibility: Sometimes, procrastination stems from rigid schedules or environments. Offering flexible working hours or remote work options can empower employees to find their most productive times and spaces.

The Office Gossip

Now, it’s time to analyze the teammates who have the latest scoop on everyone’s business. While it may seem harmless or even entertaining at times, gossip can have detrimental effects on team dynamics, morale, and productivity.

Gossip is a complex social behavior that stems from various psychological factors, such as lack of connection or the need to establish social hierarchies within a workplace. Employees may also spread rumors or share confidential information to gain favor or assert dominance over others.

Eliminating the Office Gossip:

1. Address the Issue Head-On: If you notice gossip spreading, bring the issue to light in team meetings or one-on-one discussions, highlighting how gossip can harm relationships and undermine trust.
2. Model Positive Behavior: Demonstrate positive communication by avoiding gossip yourself and addressing issues directly with those involved. Show your team how to engage in constructive conversations.
3. Invest in Team-Building Activities:  Look for new ways to foster trust and collaboration among employees. When team members build strong relationships, they’re less likely to engage in gossip and more likely to support one another.
4. Offer Training Sessions on Effective Communication and Conflict Resolution:E quipping employees with these tools will help them navigate difficult conversations without resorting to gossip.
5. Create Relevant Feedback Channels: Allow your employees to voice concerns or share information without fear of judgment. Thus, you will reduce the need for gossip as a means of communication.

The Lone Wolf

These individuals often prefer to work independently, shying away from teamwork and collaboration. While their self-sufficiency and focus can be assets, they can also present challenges for managers and teams.

The main problem of these guys is the fear of being vulnerable in front of others. They may worry that collaborating will expose their weaknesses or lead to judgment from peers. These fears usually stem from previous negative experiences in team settings—such as conflicts, lack of recognition, or feeling marginalized.

Bringing Lone Wolves Back to the Team:

1. Foster Open Communication: Ensure your employees feel comfortable expressing their thoughts and concerns. Encourage lone wolves to share their ideas in one-on-one settings where they may feel more at ease.
2. Define Roles: Help lone wolves understand how their contributions fit into the larger picture and encourage them to engage with the team.
3. Support Gradual Integration: Invite lone wolves to participate in smaller group activities or collaborative projects gradually. Start with low-stakes tasks that allow them to build relationships without feeling overwhelmed.
4. Acknowledge Unique Skills and Contributions: Emphasize how their expertise benefits the team.
5. Provide Autonomy with Accountability: Offer opportunities for independent work while ensuring that lone wolves remain accountable for their contributions to team objectives.

Fix a Difficult Employee or Let Them Go?

When you’re managing a challenging individual, you can stuck in this dilemma too easily. You want to support your stuff and help everyone thrive, but there are times when you have to face the hard truth: sometimes it’s just not working out. And now you are already going back and forth, weighing the pros and cons for hours on end.  But instead of getting lost in that cycle, let’s cut to the chase with one important question: “What’s best for the team?”

To help you figure this out, here are three things to consider.

The Impact

The first point to consider is the impact of the employee’s behavior on the team and overall performance. For instance, if an employee consistently misses deadlines or produces subpar work, it can disrupt team productivity and morale.

Imagine Sarah, for example. She was part of a marketing team but started missing deadlines and appearing disengaged. After investigating, it became clear that she felt unchallenged in her role. While initially concerning, this situation highlighted that her lack of performance stemmed from a mismatch between her skills and her responsibilities.

As a manager, ask yourself:

• How is this employee’s performance affecting team dynamics?
•  Are their actions leading to decreased morale or productivity among colleagues?

If the negative impact persists despite efforts to address it, it may be time to consider whether they can continue contributing positively to the team.

Utilization of Resources

Next, evaluate how effectively resources are being utilized. This includes not only financial resources but also time and energy spent on managing the employee’s issues. If an employee is consistently underperforming or exhibiting a negative attitude, it can drain resources that could be better spent elsewhere.

For example, Mike was a solid performer who developed a cynical outlook that affected his colleagues. His negativity required additional management time and emotional labor from the team, diverting focus from productive work.

Consider these questions:

• Are we investing too much time and energy in trying to support this employee?
• Is their performance justifying the resources allocated to their development?

If you find that an employee is consuming more resources than they contribute, it may indicate that their presence is no longer beneficial for the organization.

Growth Potential

Finally, assess the growth potential of the employee in question. A challenging employee may sometimes simply need guidance and support to thrive. However, if repeated attempts to foster their development yield little improvement, it may signal that they are not aligned with the company’s goals.

Take Jenna, who often questioned management decisions in meetings. While her passion for improvement was commendable, her approach undermined authority and created uncertainty within the team. After providing feedback and support, if Jenna continues to resist growth or adapt her behavior, it might be a sign that she is not a good fit for the organization.

Reflect on these points:

• Does this employee show a willingness to learn and adapt?
• Are there opportunities for them to grow within the organization?

If their growth potential appears limited despite your best efforts, it may be time to consider parting ways for both their benefit and that of the team.

Statistics show that up to 73% of employees are quitting due to a difficult boss or coworker.  So, each time you give yourself permission to let someone stay or go, remember, you’re not alone. Think of this as your permission slip—whether you need to make one last effort to turn things around or recognize that it’s time to part ways. Just know that grappling with these decisions doesn’t make you weak; it shows you care about your team and want what’s best for everyone.

Your team is looking to you for guidance. They might not know all the details, but they can sense when something isn’t working. Taking decisive action—whether that means making one final push for improvement or choosing to let someone go—demonstrates your commitment to a healthy and high-performing team culture.

So, what’s your next move? The path forward starts with that decision.