Dealing With Difficult Employees As the CEO

Difficult Employee in the Workplace Graphic

Dealing with difficult employees is a challenging task for any CEO. Navigating the obstacles associated with managing diverse personalities in the workplace can be daunting, yet this is what separates an average leader from a great one. 

Here are some strategies for dealing with difficult employees and transforming problems into opportunities for growth and productivity within your team.

Table of Contents:

  • Signs of a Difficult Employee
    • The Underperformer
    • The Negative Nelly
    • THe Know-it-All
  • Managing Troublesome Employees
    • Identify the Problem
    • Establish Boundaries
    • Communicate Effectively
    • Listen Carefully
    • The Art of Active Listening
    • Offer Support
    • Be Flexible
  • Take Action
  • What to Do if The Difficult Employee Has Created a Toxic Work Environment
  • FAQs in Relation to Dealing With Difficult Employees
    • What is the best way to deal with difficult employees?
    • What are 8 types of difficult employees?
    • How do you deal with a disruptive employee?
    • How do you deal with an aggressive employee?
  • Conclusion

Signs of a Difficult Employee

A difficult employee is a significant challenge for any CEO or business owner. Their behavior often disrupts employee morale and affects overall performance in the workplace. But how do you identify these problematic employees?

Type #1: The Underperformer

This worker fails to carry out their duties satisfactorily, not living up to their abilities despite having them.

Type #2: The Negative Nelly 

They’re always complaining, spreading negativity which ultimately undermines leaders and team members alike. Their bad attitude directly impacts productivity levels and creates a toxic work environment that could lead to higher staff turnover rates if not addressed quickly.

Type #3: The Know-It-All

This individual believes they are superior in knowledge or skill set than others around them. They disregard input from colleagues leading to demoralized team members.

Managing Troublesome Employees

One obvious solution to dealing with your most challenging employees is to terminate them. But let’s assume that you have a good reason not to terminate them just yet. It could be because you think they can be coached to turn things around or you need them to be part of the team until you can find their replacement. 

Assuming you are going to manage them, here are steps you can take.

Identify the Problem

The first step in managing difficult employees is for you to identify the problem. It’s important to understand that bad attitudes and poor performance are often symptoms of underlying issues.

A problematic employee might be struggling with personal challenges, lack specific skills required for their role, or feel overwhelmed by responsibilities. In some cases, your employee won’t fulfill their duties due to a misunderstanding about expectations or poor communication from leaders.

To identify these root causes, you need to observe your team members closely and engage them in open conversations. Open communication (done well) allows employees who exhibit difficult behavior to express concerns without fear of retribution.

This process can help reveal whether there’s an issue with management styles within your organization that may affect employee performance negatively.

Establish Boundaries

Dealing with difficult employees includes setting clear expectations. This is a crucial step in managing problematic behavior and ensuring that your hard-working employee understands their role within the team. To ensure an employee’s success, it is important to establish and communicate expectations for acceptable behavior.

If your employee fails to meet their obligations or exhibits inadequate performance, you need to establish consequences.

  • Create a Code of Conduct: This document outlines expected behaviors and potential repercussions if those standards aren’t met.
  • Promote Open Communication: Encourage direct reports to express concerns without fear of retribution, fostering trust between leaders and team members.
  • Maintain Consistency: Apply rules uniformly across all levels of staff; this prevents feelings of favoritism which can lead to higher staff turnover rates.

Remember, boundaries are not about control but creating an environment where everyone feels respected and valued.

Communicate Effectively

Effective communication is critical. This involves more than just delivering clear instructions or setting expectations, you need to foster an environment where open and respectful dialogue can take place.

Research shows poor communication often leads to misunderstandings that exacerbate issues such as bad attitudes, difficult employee behavior, and even disrupts employee morale.

  • Create Clear Expectations: Make sure each team member knows their responsibilities; this reduces chances of poor performance due to confusion.
  • Provide Honest Feedback: Constructive criticism helps the hard-working employee improve while addressing problematic behaviors directly. Remember: It’s not a personal attack but a means for growth.
  • Establish Frequent Check-ins: Avoid waiting until annual reviews to discuss any underlying issues affecting an employee’s disruptive behavior.

The key here is consistency in your messaging – be direct yet empathetic towards your direct reports’ concerns. This approach not only aids in managing difficult employees but also fosters better relations within the entire team.

Listen Carefully

You need to develop skills for listening carefully. This doesn’t just mean hearing their words, but truly understanding the underlying issues that may be causing them to exhibit difficult behavior. Oftentimes a bad attitude or poor performance can stem from feeling unheard or unappreciated at work.

Leaders who actively listen are better able to build strong teams and foster positive environments.

The Art of Active Listening

To effectively manage problematic employees, you need specific skills required for active listening:

  • Show empathy: Let your direct reports know that you understand their feelings and concerns.
  • Maintain eye contact: This non-verbal cue indicates respect and attentiveness toward the speaker’s thoughts.
  • Nod occasionally: This simple gesture demonstrates agreement or comprehension of what’s being said without interrupting the flow of conversation.

Remember, effective communication isn’t solely about conveying your own ideas; it also involves comprehending others’ perspectives.

Be Flexible

Navigating the terrain of managing difficult employees requires a blend of firmness and flexibility.

The key is in discerning how to be flexible to benefit not just the problematic employee but also your team as a whole. For instance, if you have an incredibly hard-working employee who exhibits difficult behavior due to stress or burnout, implementing flexible work hours or remote working options might help alleviate their pressure while maintaining their valuable contributions.

This approach can often turn around a bad attitude and transform them into more cooperative direct reports. It demonstrates that as leaders we’re willing to meet them halfway – acknowledging underlying issues affecting their performance rather than merely focusing on punitive measures for poor performance.

Bear in mind though; being flexible doesn’t mean tolerating negative behaviors that disrupt team harmony indefinitely. There should still be clear boundaries set out from the onset about what constitutes acceptable conduct within your organization – thus preventing any single individual from creating a toxic work environment leading to higher turnover rates.

Take Action

If an employee’s disruptive behavior continues to affect the performance of others and disrupts employee morale, it might be time for more serious steps such as written warnings or even termination..

You should always consult with HR professionals before taking any drastic measures against a problematic employee to ensure you’re following company policy and legal guidelines correctly.

This process isn’t easy but remember that one person’s negative behavior shouldn’t undermine leaders or create a toxic work environment leading to higher staff turnover or poor customer relations.

What to Do if The Difficult Employee Has Created a Toxic Work Environment

If you’re stuck with a challenging employee who has created an unhealthy work atmosphere, it’s imperative to take action promptly and firmly. As we have discussed, a negative culture can lead to higher staff turnover, poor customer relations, and disrupts employee morale.

The first step is acknowledging the issue. Ignoring an employee’s disruptive behavior only exacerbates the problem.

Open Communication:

  • Talk openly with your team members about what they are experiencing. This will help identify underlying issues that may be contributing to this negative atmosphere.
  • Poor communication often fuels problematic behaviors so ensure everyone feels heard.
  • Lay out specific rules of conduct for all employees which includes consequences for bad attitude or any other form of misconduct.
  • To manage such situations better in the future, invest time into teaching managers specific skills required when dealing with difficult employees.

FAQs in Relation to Dealing With Difficult Employees

What is the best way to deal with difficult employees?

The best approach involves identifying the problem, establishing clear boundaries, maintaining open communication, listening carefully to concerns, offering support and resources, being flexible when necessary, and taking decisive action if needed.

What are 8 types of difficult employees?

The eight types include: The Know-It-Alls, The Slackers, The Drama Queens/Kings, The Loners, The Gossip or Rumor Spreaders, The Negativity Spreader, The Overly Ambitious, and finally those who Resist Change.

How do you deal with a disruptive employee?

Addressing disruption requires direct communication about the problematic behavior. Set clear expectations for improvement while providing supportive resources. If the issues persist, consider disciplinary actions.

How do you deal with an aggressive employee?

Dealing with aggression entails an assertive but respectful confrontation about their behavior. Establish firm boundaries and encourage them to consider professional development programs that promote emotional intelligence in workplace interactions.


Dealing with difficult employees doesn’t have to be a CEO’s nightmare, but by using the proper techniques, you may be able to turn them around.

Contact an Experienced CEO Coach

My name is Glenn Gow, CEO Coach. I love coaching CEOs and want to help make you an even better CEO. Let’s decide if we are a fit for each other. Schedule a time to talk with me at I look forward to speaking with you soon.

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