How to Deal with Difficult Employees

Knowing how to deal with difficult employees is an essential skill for managers and business leaders. While performance or behavior challenges are common in any workplace, failing to address them appropriately can create serious risk and compliance concerns. From inconsistent discipline to potential legal exposure, unresolved employee issues can quickly escalate. Here, we'll go over some essential tips to help deal with challenging employees and de-escalate problematic situations. 

Quick Overview: How to Deal with Difficult Employees

• Difficult employees are defined by patterns of disruptive behavior, not personality traits, and managers must separate conduct issues from protected or situational circumstances to reduce legal risk.
• Common challenges include toxic attitudes, poor performance, insubordination, communication conflicts and attendance issues, all of which can impact morale, productivity and compliance.
• Address issues early and privately, focusing on observable behaviors, setting clear expectations, listening actively and delivering consistent, constructive feedback.
• Proper documentation and progressive discipline are essential to ensure fair, defensible decisions and reduce legal exposure.
• Proactive management like clear policies, regular feedback and HR or PEO support helps prevent issues from escalating and protects workplace culture long term.

What Is Considered a Difficult Employee?

A difficult employee is someone whose behavior, performance or attitude consistently disrupts productivity, teamwork or workplace culture, despite clear expectations and reasonable management efforts. It's important to understand that difficult behavior in a team member is not considered a personality trait or label. Instead, it's a pattern of conduct that can create risk for the employer and may negatively impact an organization's overall success over time.

To maintain fairness and reduce legal risk, it’s critical to separate difficult behavior from protected or situational issues. A difficult employee is not:

• Someone asking questions or offering respectful disagreement
• An employee experiencing a short-term personal or medical issue
• A new hire still in training
• An employee exercising legally protected rights

This distinction helps prevent misclassification, bias or retaliation claims.

Common Types of Difficult Employee Behavior

Oftentimes, you can tell that you're dealing with a difficult employee when they possess one or more of the following characteristics. 

Negative or Toxic Attitudes

Certain behavioral issues are unacceptable within the workplace and can severely impact employee morale and overall team dynamics. If an employee's behavior encompasses any of the following, you may need to schedule a potentially difficult conversation:

• Complains frequently or undermines morale
• Resists feedback or becomes defensive
• Displays cynicism toward leadership or coworkers

Poor Performance or Lack of Accountability

Occasional mistakes are normal in any role. However, patterns of underperformance are not. If the employee in question does any of the following, it's important to communicate that something needs to change.

• Misses deadlines or fails to meet job expectations
• Produces low-quality or incomplete work
• Requires excessive supervision or correction

Insubordination or Resistance to Authority

Challenging employees can create difficult situations for everyone at work, especially when they resist organizational policies or act like the rules don't apply to them. Difficult people at work may: 

• Refuses to follow reasonable instructions
• Challenge authority inappropriately
• Ignore company policies or procedures

This can create serious disciplinary and compliance risks if left unaddressed, so it's recommended that leaders take action sooner rather than later. 

Poor Communication or Conflict With Coworkers

Disengaged employees can affect overall team performance and can create a ripple effect among their peers. Over time, problems within the team can create tension or escalate conflict instead of resolving it. However, interpersonal issues are one of the most common reasons managers seek support from the HR department. Ongoing check-ins and active listening regarding concerns can go a long way, but ultimately, it's necessary for an employee to improve their behavior. Otherwise, the whole team can suffer.

Attendance or Reliability Problems

Additional problematic behavior with a difficult employee is the lack of regard for punctuality or showing up altogether. If an employee showcases the following, it may ultimately require you to terminate their contract. 

• Frequent lateness or unplanned absences
• Failure to follow scheduling expectations
• Pattern of unreliability affecting team coverage

Why Difficult Employees Should Be Addressed Early

Addressing difficult employee behavior early is a critical part of effective employee behavior management. When issues are ignored or delayed, they tend to escalate, creating avoidable legal risks, damaging workplace culture and increasing long-term costs for the organization.

Early intervention allows managers to correct problems while they are still manageable, protecting both the business and the employee.

How to Deal With Difficult Employees Professionally

Effectively handling difficult employees requires consistency and a structured approach. Managers who address issues early, communicate clearly and follow employee discipline best practices are more likely to resolve problems before they escalate. The goal is not to “win” a confrontation, but to correct behavior and support a productive workplace.

Address Issues Privately and Promptly

Difficult conversations should take place in a private setting and as close to the incident as possible. Delaying feedback can allow problematic behavior to continue and may signal that the issue is not serious.

Approach the discussion calmly and professionally. Focus on observable actions rather than assumptions, and clearly explain why the behavior is a concern. Timely, respectful conversations often prevent misunderstandings from becoming larger performance or morale problems.

Focus on Behavior, Not Personality

When managing challenging employees, it is essential to concentrate on specific behaviors, not personal traits. Statements such as “You missed the deadline on three projects this month” are more effective and defensible than labeling someone as “unreliable” or “difficult.”

Using objective language helps maintain professionalism and supports proper documentation. This approach also reduces the risk of bias or claims of unfair treatment.

Set Clear Expectations and Consequences

Employees should leave a performance discussion with a clear understanding of what needs to change. Outline:

• The specific behavior that must improve
• The expected standard moving forward
• A reasonable timeline for improvement
• Potential consequences if improvement does not occur

Consistency is key. Expectations should align with company policies and be applied uniformly across employees. Clear communication reinforces accountability and strengthens employee discipline practices.

Listen Actively and Ask Questions

In many cases, problematic behavior may stem from underlying issues such as unclear expectations, workload challenges, lack of training or personal stressors. Providing employees with an opportunity to share their perspective can uncover root causes that are correctable.

Active listening demonstrates fairness and professionalism. Even when disciplinary action is necessary, allowing employees to respond supports transparency and strengthens trust in the process.

Deliver Constructive Feedback

Performance management should not be limited to corrective conversations. Regular feedback, coaching and check-ins help reinforce expectations and prevent recurring issues.

Managers who consistently communicate performance standards and provide constructive feedback in a supportive manner create an environment where improvement is possible. When employees understand what success looks like and receive timely guidance, they're more likely to adjust their behavior before formal discipline becomes necessary.

How to Document Employee Performance and Behavior Issues

Properly documenting employee performance issues is essential for maintaining HR compliance and ensuring fair, defensible management decisions. Some things that you should document include the following:

• Dates and times of incidents or performance issues
• Specific facts about what occurred (what was said or done)
• Impact on the business or team, such as missed deadlines or disrupted workflow
• Actions taken by management and employee responses
• Next steps or expectations moving forward

Some things you should avoid when documenting disruptive behavior and making your evaluation include:

• Personal opinions or assumptions about intent
• Emotional or subjective language
• Inconsistent or informal notes
• References to protected characteristics or medical information

Using Progressive Discipline to Manage Difficult Employees

A structured progressive discipline process provides employers with a fair and consistent framework for addressing ongoing performance or behavior concerns. When applied correctly, it reinforces accountability while supporting compliance with applicable employee discipline laws.

While the exact steps may vary by organization, progressive discipline typically includes:

• Verbal warning: A private conversation outlining the specific issue, expectations for improvement and the potential consequences if behavior does not change. Even verbal warnings should be documented internally for recordkeeping purposes.
• Written warning: A formal notice detailing the performance or behavioral issue, prior discussions, required corrective action and a timeline for improvement. This step creates a clear written record that expectations were communicated.
• Performance Improvement Plan (PIP): A structured plan that defines measurable goals, support resources and review timelines. A PIP is designed to give the employee a meaningful opportunity to correct behavior or improve performance within a defined period.
• Final warning or termination: If improvement does not occur, employers may issue a final written warning or proceed with termination in accordance with company policy and legal requirements.

Preventing Difficult Employee Situations in the Future

Preventing difficult employee situations starts with proactive management and clear expectations. While not every issue can be avoided, consistent practices help reduce misunderstandings and support a positive workplace culture.

Some best practices to prevent difficult employee situations include:

• Setting clear job expectations and performance standards from day one
• Communicating workplace policies consistently and enforcing them fairly
• Providing regular feedback instead of waiting for annual reviews
• Coaching managers on effective communication and conflict resolution
• Documenting performance conversations and corrective actions consistently
• Addressing small issues early before they escalate
• Encouraging open communication and employee feedback
• Partnering with HR or a PEO for guidance on employee behavior management and compliance

How a Professional Employer Organization Can Help

Managing difficult employees requires a strong understanding of employment laws, alongside consistency and proper documentation. This can be a lot for SMBs to handle, which is why a professional employer organization (PEO) can be a great solution for leaders. By working with a PEO like TriNet, employers can approach difficult employee situations with confidence. TriNet helps businesses stay compliant, support managers with expert HR insights and create healthier workplace cultures through proactive employee relations support. Book a demo with us today to learn more.