Every workplace has challenges, but few are as tricky—and important to tackle—as dealing with a difficult employee. Whether it's the team member who constantly resists feedback or the one whose negative attitude drags everyone down, managing these people and situations is a skill every manager needs.
Unresolved issues with difficult employees can ripple through the entire team, affecting morale, productivity, and even your company’s culture. But addressing these challenges head-on not only strengthens your leadership but also fosters a healthier, more collaborative workplace.
In this article, you will learn how to identify the signs of a difficult employee and get insights into what works (and what doesn’t) when you're having a difficult conversation with an employee.
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What defines a difficult employee?
A “difficult employee” is someone whose behaviors consistently disrupt team dynamics, hinder productivity, or create tension in the workplace. However, it’s worth noting that labeling someone as difficult isn’t always fair. “Often people are labeled as difficult when they just need advice, mentorship, training, or clarity with communication,” says Wendy Sellers, an HR consultant with over 25 years of experience.
Signs of a difficult employee
So, how can you identify a truly difficult employee? Here are some key signs:
- Disruptive behavior: This could include frequent interruptions in meetings, talking over others, or making inappropriate comments.
- Lack of accountability: This involves avoiding responsibilities, making excuses, or deflecting blame onto others.
- Negative attitudes: For example, chronic complaining, resistance to change, or a pessimistic outlook that dampens team morale.
- Disorganization or procrastination: This can include missing deadlines, being unprepared, or repeatedly failing to deliver on commitments.
- Overly sensitive or overly confident behavior: For example, disproportionate reactions to feedback or underestimating challenges and overpromising results.
While these behaviors can make workplace interactions challenging, they’re typically symptoms of deeper issues. “[They] often stem from personal dissatisfaction, lack of motivation, or poor interpersonal skills,” Sellers says. “For instance, employees might complain frequently, seeking validation or avoiding responsibility, or they might procrastinate due to fear of failure or a lack of motivation.”
How to know if it’s a pattern or a one-time issue?
Sometimes, a “difficult” employee is actually someone grappling with personal struggles.
“Personal issues often manifest in an employee’s behavior in subtle but telling ways,” Sellers says. “Signs include noticeable mood changes, unexplained emotional reactions, or a drop in performance that is inconsistent with their typical behavior.”
For example, an employee who’s usually reliable might suddenly be disorganized or start missing deadlines. The change in behavior could be due to stress, health problems, or family challenges—so approach with empathy while maintaining accountability.
“Managers should be aware of company benefits, including therapy, so they can provide that information to the employee and allow time off to get help, while also holding the employee accountable for their behavior and performance,” she says.
How to deal with a difficult employee as a manager
Managing a difficult employee requires patience, empathy, and clear communication. It’s crucial to address these challenges early. “Many managers avoid tough conversations or let small issues snowball into larger problems, creating an environment where difficult behaviors can thrive unchecked,” Sellers says.
Another common pitfall? Focusing on the person rather than the behavior. “Labeling an employee as 'difficult' without addressing specific actions can alienate them and make the situation worse,” she says. Instead, managers should provide concrete examples and actionable feedback to drive change.
Here’s how to manage different types of difficult employees.
The underperformer
Underperformers may miss deadlines, fail to meet expectations or produce inconsistent work. They often lack clarity about their role or feel they don’t have the skills needed to succeed.
How to handle:
- Clarify roles and expectations. Role ambiguity may lead to underperformance. Ensure the employee understands their responsibilities and what success looks like in their role.
- Set SMART goals. Break tasks into Specific, Measurable, Achievable, Relevant, and Time-bound objectives to help them focus on achievable targets.
- Offer support for skill development. Assess whether the employee has the tools and training they need to perform well. Providing learning opportunities can boost both competence and confidence.
- Provide frequent feedback. Regular one-on-one check-ins create opportunities to address progress, obstacles, and adjustments promptly. (Here’s how to give good feedback.)
The negative attitude
Negative employees frequently complain, resist change, or undermine team morale. Their negativity may stem from personal dissatisfaction, workplace stress, or feeling undervalued.
How to handle:
- Address behavior privately. Start with a calm, one-on-one discussion to avoid public embarrassment. Focus on specific incidents that illustrate their attitude's impact.
- Focus on facts, not emotions. Instead of saying, “You have a bad attitude,” mention specific examples, like interrupting in meetings or speaking negatively about a project.
- Explore underlying causes. Use open-ended questions like, “What’s been challenging for you at work lately?” to uncover any personal or professional frustrations.
- Recognize positive behaviors. Reinforce moments when the employee shows a constructive attitude. Small acknowledgments can encourage more of the same.
The authority challenger
These employees frequently question decisions, dismiss policies, or push back against leadership. While they can appear defiant, their behavior can stem from frustration or a need to feel heard.
How to handle:
- Encourage open communication. Invite constructive feedback during team meetings or in one-on-one settings. This can help channel their challenging nature into productive conversations.
- Reinforce team values. Remind the employee of the shared goals and the importance of respect within the team.
- Address behavior directly. If their challenges cross the line into disrespect, provide specific examples and explain the impact on the team.
The workplace disruptor
Disruptors create chaos by gossiping, instigating conflicts, or disregarding workplace norms. They often thrive on attention or struggle with collaboration.
How to handle:
- Set clear rules for conduct. Create and enforce guidelines for professional behavior to reduce opportunities for disruption.
- Mediate conflicts quickly. If their actions spark disputes, act swiftly to mediate and resolve the issues fairly.
- Promote collaboration. Engage them in team-building activities or collaborative projects where they can focus on contributing rather than disrupting.
The resistant-to-feedback employee
These employees may reject constructive criticism, deflect responsibility, or react defensively. Their resistance usually originates from fear of failure or feeling undervalued.
How to handle:
- Be specific and objective. When providing feedback, avoid vague statements and use concrete examples instead.
- Frame feedback positively. Highlight areas for improvement as opportunities for growth. For instance, say, “This skill could help you advance in your role,” instead of, “You need to fix this.”
- Encourage a dialogue. Ask questions to understand why they resist feedback. This two-way conversation can uncover concerns and make feedback feel less like a judgment.
Whether dealing with underperformance or negativity, maintaining consistent communication, follow-up conversations, and accountability is essential for long-term success. “Even if a conversation addresses a behavioral issue, continuous support and check-ins are vital for sustainable improvement, and to let that difficult person know that you—as their manager—are not going to let their behavior slide,” Sellers says.
How to have a difficult conversation with an employee
From time to time, every manager will need to have conversations with difficult employees—whether it’s a routine meeting or one to address a complicated situation. These talks, while uncomfortable, provide an opportunity to talk about important issues and find solutions.
Below is a practical six-step guide to handling these conversations.
1. Identify the problem and gather information
Before having a difficult conversation with an employee, take the time to clearly identify the issue and gather all relevant information. Whether it's a performance problem or a behavioral concern, preparation is key.
For example, instead of giving vague feedback like “You seem distracted,” be specific: Point to missed deadlines or a decline in quality. Concrete evidence makes the conversation more focused and opens up the chance to explore underlying causes, like burnout or lack of clarity in role expectations.
2. Set clear objectives
Think about the outcome you want from the conversation. Are you aiming to correct behavior, explain a new company policy, or address performance issues? Having a clear goal will guide the discussion and help you measure its success later.
If you want to improve performance, make sure you know exactly what behaviors need to change and what success looks like. This clarity will keep both you and your employee focused during the conversation.
3. Understand the employee’s personality
The way you approach a difficult conversation depends on who you're speaking to. Whether it's a one-on-one discussion with an individual or a group conversation with the team, understanding the recipient's perspective is crucial. Tailor your message and tone based on the employee’s personality and your relationship with them. Timing also matters—choose a time and setting that minimizes distractions and ensures your message is received well.
4. Plan your approach
Prepare a structured message or outline for the conversation. It’s helpful to have a script or key points that clearly communicate your goals for the discussion. Start on a positive note to set a constructive tone, even if the topic is difficult. This can ease tension and make the employee more receptive. Outline the key points, provide specific examples, and prepare for possible reactions by thinking ahead about how you will respond.
5. Conduct the conversation
Choose a private and comfortable setting where the employee can feel safe to open up. Start the conversation with facts rather than emotions, and stick to specific examples to avoid sounding accusatory. For instance, instead of saying, “I’m disappointed in your work,” you can say, “I noticed that you missed the deadline on X project.”
Asking open-ended questions like, “What do you think caused the delay?” will encourage dialogue and allow the employee to express their side of the story, keeping the conversation solution-focused rather than becoming a blame game.
6. Follow up
Sometimes, one conversation might not be enough to resolve the issue fully. Plan to check in regularly and follow up to assess progress and adjust the plan if necessary. Follow-ups help guarantee the issues are being addressed and allow employees to demonstrate improvement. It also signals that you, as a manager, are invested in their development and care about their success.
General strategies for handling difficult employees
Successfully managing difficult employees requires a mix of emotional intelligence and practical strategies—which you likely already possess as an effective manager. Rely on the following general tips to guide you.
- Stay calm and professional. Approach every situation with composure, ensuring your emotions don’t cloud your judgment or actions. Reacting emotionally can escalate the issue, making it harder to fix. Remaining professional sets a positive example and helps you control the situation.
- Practice active listening. Take the time to hear the employee’s perspective without interruption, showing you respect them and understand their concerns. This not only fosters better communication but also shows the employee that their viewpoint matters, potentially leading to a more productive resolution.
- Prioritize fairness and consistency. Treat all employees equitably and address similar behaviors with consistent approaches to maintain trust and avoid perceptions of bias. Inconsistent responses to issues can lead to resentment and undermine your credibility as a leader.
- Document everything. Keep a clear record of incidents, interactions, and steps taken to address the issues. This ensures accountability and provides a reference point if escalation is needed. Written documentation serves as evidence in case the situation requires HR intervention or further action down the line.
If an employee’s behavior persists despite your best efforts and starts to affect team morale or productivity—or violates company policies—it’s time to involve HR or higher leadership.
“For example, if an employee is exhibiting bullying behavior, as seen with employees who intimidate or mistreat colleagues, or if there are legal implications such as discrimination or harassment, HR should be consulted immediately,” Sellers says. “HR involvement is also important for ensuring that any disciplinary actions are compliant with company policies and labor law, including (Americans with Disabilities Act) ADA and (Family and Medical Leave Act) FMLA.”
Getting the most out of employees
Addressing difficult employees proactively is essential for a healthy and productive workplace. By confronting challenges early and with empathy, managers can prevent issues from escalating and foster a supportive environment where everyone can thrive. It’s important to view these situations not as obstacles, but as opportunities to grow as leaders and strengthen your team.
Remember, every difficult situation is a chance to improve team dynamics and create a stronger organization, building trust and loyalty within your team.