Managing a Difficult Coworker—When You’ve Tried Everything Else

An unavoidable, and often uncomfortable, reality of corporate life is conflict resolution at work.

Every leader will inevitably encounter a difficult employee at some point in their career. It may be a high performer who behaves like the rules don't apply to them, a long-tenured employee who refuses to evolve, or someone who constantly deflects accountability and shifts blame.

Leaders may face an uphill battle when dealing with difficult people at work. This pressure may cause undue stress, hurt their productivity, and sometimes bleed into their personal lives.

However, there are ways to transform difficult employees’ behavior into positive behavior without affecting one's well-being.

This article discusses specific conflict resolution strategies, which involve positively coaching difficult employees and setting them up for success.

How to Deal with Difficult People at Work?

Managing a difficult employee who behaves unprofessionally and erratically and is unresponsive to feedback or coaching can be challenging.

The following are helpful strategies for addressing challenging behavior at work.

1. Identify what makes the employee “difficult” 

A difficult employee is typically seen as someone whose behavior does not conform to what is considered professional in the workplace. It's important to determine the challenging behavior one is dealing with and approach the situation accordingly.

Typically, three main reasons contribute to perceived challenging behavior in employees:

• 1) Self-awareness gap: Employees may often not realize they’re being difficult. They may be unaware that a certain behavior is perceived as undesirable or unprofessional. 

In such situations, managers must support and guide them towards correct behaviors. For instance, if they dismiss a specific rule or process, the manager should clearly convey how this hampers team productivity. More importantly, the manager should explain to them why the protocol exists in the first place and how they might benefit from adhering to it. 

• 2) Performance gap: Sometimes, the perceived difficult behavior is subpar performance. The employee may consistently miss deadlines or inconsistently deliver on expectations. 

Underperformance could typically be due to a lack of ability, motivation, or both. However, it might also be caused by poor communication, ineffective management, restrictive policies, limited resources, or other underlying factors.

As managers, it’s essential to keep things in perspective. Seek to uncover the root cause for their defaulting behavior and offer support to reverse it: “Let’s talk about the challenges you are facing with the deliverables. How can I help to overcome them?”

• 3) Accountability gap: As leaders, you may have encountered employees who constantly dodge accountability using justifications and deflections. Each missed deadline comes with a detailed explanation. Every bit of feedback sets off a cascade of excuses pointing fingers at other team members.

To bring about behavioral change in such cases, managers need to establish clear consequences: “If we keep missing these deadlines, it will affect your performance review and limit our ability to involve you in important projects.”

In most cases, individuals are more likely to take the issue seriously if they have a clear course of action and understand the consequences of inaction.

Work with the employee to develop a plan establishing clear expectations and a timeframe to improve their behavior. “Over the next two weeks, I’d like to see progress in these three specific areas.”

Regardless of the challenge, regular progress evaluations are helpful to track behavioral changes when managing difficult employees. The following considerations can pave the way for further action:

• After introducing structure and support, has there been a noticeable performance improvement?

• Have they demonstrated genuine intent to remedy their behavior, beyond surface-level compliance?

2. Limit exposure to the difficult employee

Managers can consider limiting exposure to them, provided the difficult employees are good at their jobs. They can figure out the least stressful mode of communication (e.g., asynchronous communication modes) and set clear expectations regarding their role, such as their responsibilities towards the team, projects, and the organization.

Doing so can help reduce negative interactions and prevent the depletion of one's emotional reserve.

3. Provide feedback and a course of action

A leader’s objective should be to find a way to end the difficult employee's unacceptable behavior. 

It's essential to convey clear and detailed feedback—pinpoint how the employee's actions affect their performance and team members with concrete examples. 

Create objective benchmarks: “Here are the measurable standards for this role,” and provide a clear course of action: “Here are the specific actions I want you to take.”

4. Document the employees' transgressions 

It helps track the employee's transgressions, whether big or small, to determine whether (and how) their behavior hurts organizational performance. If there is a pattern of consistent, difficult, and ongoing behavior on the employee's part, it may be time to acknowledge that disciplinary action is warranted. 

Managers can either reconcile the situation themselves—provide that person feedback directly, reprimand them—or bring the issue to leadership for further review.

5. Decide to part ways

Every manager has limited time and emotional bandwidth to manage a difficult employee. 

Managers shouldn't hesitate to make necessary personnel changes if the challenging employee refuses to recognize the issue or show resolve and willingness to remedy their actions. Conflict resolution at work in such situations must favor the team's best interest. 

The following key considerations can help managers make an appropriate decision:

• How much time and energy do you and your team invest in handling the difficult employee?

• Is it diverting focus from other team members who might benefit from a bit more support?

• Have they begun to take ownership of their actions, even partially?

• Are you noticing actual progress, or just temporary adjustments followed by regression?

Before escalating the situation, however, ensure you've taken all reasonable steps to be fair and have documented the problematic behaviors and their impact. This can minimize resistance from leadership or the challenging employee and may also reduce legal risks or potential damage to the organization's internal reputation or public image. It may help to seek counsel from a senior leader or the HR department. 

6. Demonstrate empathy and humility

Leaders must be responsible for how they approach conflict resolution at work. 

An employee may seem complicated, but there could be a rational explanation for their behavior. Personal issues may distract them, they may be new to the organization, or they may be under pressure from higher-ups to deliver results. 

This certainly doesn’t excuse their actions, which may even damage productivity. However, understanding that there could be underlying factors outside their control can ensure managers deal with the situation more calmly and healthily and productively.

7. Seek feedback

Often, leaders’ actions unconsciously trigger anxiety or worry in employees. It could be harsh criticism, dismissive behavior, or disregard for employees’ problems. These actions inevitably lead to employee performance, productivity, and cooperation deficits.

Common examples of unfavorable leadership behaviors include: 

• Use of negative language.

• Behaving in inconsistent or unpredictable ways.

• Exhibiting emotional volatility or pessimism during crisis periods. 

• Micromanaging tendencies.

It can help if managers look inwards and analyze how their actions or management styles might unintentionally be contributing to perceived challenging behavior in employees. They need to hold more one-on-one check-ins with team members, ask open-ended questions encouraging employees to engage, and demonstrate empathy whenever possible. Seeking feedback and adjusting one's management techniques to be more effective are necessary.

Conclusion

Dealing with difficult employees—those who are dismissive of rules, show passive-aggressive behavior, or deliver inconsistently on expectations—can be challenging. However, conflict resolution at work is crucial and should be carried out in a way that doesn't create hostility or harm professional relationships.