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Where to start when managing challenging employees

By September 28, 2021November 2nd, 2021No Comments

If you’re in a management position, there will come a time where you must supervise a “difficult” employee. Sometimes these colleagues are simply irritating, or unproductive — like employees who are distracting during meetings or have a snide attitude about work. Other times, things are more serious, and an employee’s behavior can create a hostile or unsafe work environment.

It’s no secret that hard-to-manage employees create less-than-ideal work environments, and managers must be prepared to deal with these employees effectively, but compassionately. While job termination may be your first instinct when you’re fed up with problematic behavior, there’s a larger toolbox of strategies available.

(NOTE: For more on this topic, watch our complete webinar.)

What does a difficult employee look like?

 Difficult employees come in many forms, including but not limited to:

  • Employees who fail to fulfill work responsibilities
  • Employees who are uncooperative
  • Employees who undermine authority
  • Employees who display anger

These employees may negatively impact the productivity of others, interfere with team objectives, and make it difficult for managers to do their jobs. Notably, employees who bring a bad attitude to work are oftentimes facing problems in their home or personal lives that affect their demeanor and behavior at the office.

“Employees may be difficult at work if they’re dealing with a situation at home,” says Maureen Marfell, HR Director for 501(c) Services, “This is especially true today as we’re going through the COVID-19 crisis. People are facing challenges with their health and are worried about childcare.”

Rehabilitation, not termination

Terminating an employee may seem like the path of least resistance, but that doesn’t mean it should be Plan A. “Even the most difficult of employees can be turned around,” Marfell says. And in terms of your bottom line, “it’s usually more cost-effective to do so than to try to fire and replace them.”

Why not fire difficult employees?

  • Replacement costs are high
  • Recruiting new employees takes time
  • You avoid the cost of fighting potential discrimination or wrongful termination lawsuits
  • High turnover rates can impact employee morale

Of course, there may be times when firing is your only option —like if “annoying” behavior becomes threatening, discriminatory, or affects the safety of others. Other times, reassigning the employee to another team may be a viable option.

“Sometimes employees may have a personality conflict with their supervisor or someone in their environment,” Marfell says. “In these cases, simply reassigning them to a new team might work.”

Make time for a self-talk

When dealing with a difficult employee, it’s important to examine and manage your own feelings and emotions regarding their behavior.

“Ask yourself, are you discouraged by the situation? Are you feeling resentful towards the employee? It’s important to understand your real feelings toward the employee so that you can control them, and not let them sneak out,” Marfell says.

Moreover, managers must assess if they may have played a role in creating the situation. Perhaps you’ve let the employee get away with unacceptable behavior or failed to explicate your expectations.

Above all else, remember to always respond positively. If you’re able to keep your own emotions in check, you’ll find yourself in a better position to effectively deal with the problematic employee.

Always evaluate and document behavior

Objectively documenting problematic behavior is a crucial step when dealing with difficult employees. When doing so, you should identify specific behaviors and incidents that are troublesome, as well as explanations for why those behaviors are problematic.

“Don’t let your judgments of the employee get in the way — you have to be objective in your documentation,” Marfell says. “Think solely in terms of the job and try not to get hung up on personality traits.”

Writing yourself a report on the employee’s behavior can help you to identify specific problems that can then be discussed with the employee, and recording specific incidents and dates can also help you avoid liability in the future. “Stick to the facts, not feelings or opinions,” Marfell says. “Seeing everything on paper can help you identify and objectify key problems, and then you can start dealing with them one by one.”

When documenting, be sure to include:

  • What happened
  • Where it happened
  • When it happened
  • Examples of the problem

Once problems have been documented, you can then identify the specific behaviors to the employee as they come up.

Example: If an employee is frequently late for work, start documenting their arrival times on a daily basis.

Next, make a plan to meet with the employee and provide them with a written copy of your organization’s attendance policy and your arrival time document. Ask them to read the policy while in your presence, and then open up the discussion by asking why they are frequently late.

Give the employee the opportunity to explain their lateness or absence, and try to find something in your policy that can help. Be sure to explain the consequences of late attendance, and document future occurrences.

If they continue to be late, you can coordinate with HR and apply “progressive discipline” to show them that violation of company policies is not tolerated.

Responding positively

If you want to correct an employee’s behavior, you need to approach them with compassion and positivity. Begin by clearly explaining your concerns and giving specific examples of times when they have displayed problematic behavior. Be sure to avoid criticizing or placing blame on them, and provide them with suggestions on how they can meet expectations. Stay focused on the issues, and be firm by using statements instead of questions.

Most importantly, let the employee know that you want to help them and are there to support them in the workplace. Then, agree on a plan of action and set a date for a follow-up meeting to reevaluate.

If an employee’s problems are performance-based, consider if their poor performance is rooted in unclear expectations, inadequate training, or conflict with a coworker. If poor performance is rooted in health problems, see if they can take leave under the Family and Medical Leave Act or the Americans with Disabilities Act.

501(c) Services customers have unlimited access to HR Services. 501(c) Agencies Trust members or HR subscribers can contact us anytime regarding this subject or any other HR situations.

Need HR help for a low monthly fee? Contact us today. The information contained in this article is not a substitute for legal advice or counsel and has been pulled from multiple sources.


Lia Tabackman is a freelance journalist, copywriter, and social media strategist based in Richmond, Virginia. Her writing has appeared in the Washington Post, CBS 6 News, the Los Angeles Times, and Arlington Magazine, among others. She writes weekly nonprofit-specific content for

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