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The Strategic Guide to Managing Difficult Employees


Congratulations!  You have a new employee on your team. That’s the good news. The bad news is… this particular employee is someone who had made your life (and others’ lives) miserable for the past several years.

Unless this employee has done something illegal or unethical (and someone has documented his actions), you will have to find a way to live with them. Not only that, but you’ll have to coach, advise, advocate for, and support this new member of your team.

Impossible? Of course not. You’re by no means the first manager to cope with a team member you don't like. As a result, there are some excellent resources available for handling what may seem like an impossible situation.

Before implementing any particular strategy, it’s important to analyze the situation. What exactly is this employee doing, and how serious are the behavior issues you’re facing?  Does the employee’s bad behavior rise to the level of being harassment? Is the employee malicious, or simply clueless? Does the employee’s behavior jeopardize his own or anyone else’s safety? Work performance? Ability to function well in the workplace? Once you’ve determined the level of problem you’re facing, you can begin to structure a strategy to manage it.

In the Worst Case: Is Your Employee Engaging in Illegal or Unethical Behavior?

Illegal Behavior

If you have an employee on your team who is engaging in illegal or unethical behaviors, and you can document their actions, it may be appropriate to consider firing them. But what constitutes such behavior? Illegal behavior, of course, is against the law, and may include:

  • Using or selling illegal substances such as drugs.
  • Stealing money or valuable goods.
  • Taking or offering bribes.
  • Undertaking or commissioning illegal trades or payments.
  • Serious and documented sexual harassment.

While this type of behavior is reprehensible, it does take the burden off you, the manager. Illegal behavior, once it’s documented, is out of your hands and into the hands of human resources and, ultimately, the police.

Unethical Behavior

Unethical Behavior may or may not be illegal, but it does involve actions which are prohibited by corporate policy and common ethical standards. It may be too minor to prosecute under the law, or it may be a breach of custom rather than rules. Unethical behavior, like illegal behavior, should be documented and handed over to human resources, as it is not appropriately handled by a team manager. Unethical behavior may include:

  • Pilfering of office supplies or food in the workplace.
  • Borrowing” of office equipment or supplies for personal use.
  • Misuse of business-only resources such as use of company car, club memberships, etc.
  • Submission of questionable reimbursable expenses.
  • Accepting “gifts” from clients beyond what is allowed under company policy.


Harassment in the workplace is illegal. But one person’s harassment is another person’s bad joke—and it isn’t always obvious when a behavior represents more than poor judgment. Here’s how the US Government’s Equal Opportunity Commission defines harassment:

Harassment is unwelcome conduct that is based on race, color, religion, sex (including pregnancy), national origin, age (40 or older), disability or genetic information. Harassment becomes unlawful where 1) enduring the offensive conduct becomes a condition of continued employment, or 2) the conduct is severe or pervasive enough to create a work environment that a reasonable person would consider intimidating, hostile, or abusive. … Petty slights, annoyances, and isolated incidents (unless extremely serious) will not rise to the level of illegality. To be unlawful, the conduct must create a work environment that would be intimidating, hostile, or offensive to reasonable people. Offensive conduct may include, but is not limited to, offensive jokes, slurs, epithets or name calling, physical assaults or threats, intimidation, ridicule or mockery, insults or put-downs, offensive objects or pictures, and interference with work performance.

Imagine you have an employee named Bob who has been accused of making unacceptable comments on more than one occasion. If has made occasional comments which might or might not be considered offensive, his behavior may not be considered harassment. If, however, Bob shows a pattern of behavior that includes offensive jokes and slurs, it may well fall under the category of harassment.

If Bob is truly a harasser, you have legal recourse, and, in many situations, the help and support of human resources and upper management. If Bob is simply annoying, you may need to take a more active role in helping Bob to mitigate his behavior—and helping his co-workers to grow a slightly thicker skin. The reality is that very few employees are actually breaking any serious laws or corporate policies, so the likelihood is that you’ll be coping, not with criminals, but with plain old difficult employees.

In the Majority of Cases: Coping With Plain Old Difficult Employees

Few difficult employees break the law. Much more often, they skirt the edges of unethical behavior—driving the family around in the corporate car, for example. They are probably not harassers under the definition provided by law, though they may make an occasional off-color joke or racial comment.

In fact, most of the time, you will be coping with difficult employees who, while they may drive you and others crazy, are not likely to be arrested, fired, or otherwise taken out of the business picture. It will, therefore, be your job to figure out how to manage employees like Bob so that they are as positive, productive, and as motivated as possible.

What do difficult employees do? Here are just a few of the difficult and/or hostile behaviors you may need to manage:

  • Gossiping about other employees and/or spreading negative rumors.
  • Taking credit for or undermining others’ achievements.
  • Constantly pointing out the negative in any situation or change.
  • Dragging their heels or sabotaging new initiatives or projects.
  • Showing up late or leaving early for work or meetings.
  • Disrespecting managers and colleagues through comments or actions.
  • Doing a poor job on their assigned projects (and, often, blaming others).
  • Picking fights with co-workers.
  • Disregarding feedback, evaluations, or requests from managers and co-workers.

Strategies for Managing Difficult Employees

According to an article on the Small Business Administration website there is no way to dodge the need to manage bad behavior: “Difficult behavior rarely goes unnoticed by other employees and, if not addressed quickly, can prickle one too many feathers and lead to potentially explosive situations.” Yet, if you’re like most people, you dread confrontations and the possibility of living with a resentful, angry team member.

What should you do?

Keep an Open Door and an Open Ear

First, as a manager, you want to be sure that you know what’s going on among your employees. Often, difficult behavior doesn’t crop up in staff meetings, but instead rears its head in the lunchroom, at client meetings, or in other settings where you are not present. Employees need to feel free to report problems so that you’re not the last to know. That means your employees must see you as receptive to their input and unbiased in your judgment. An open-door policy, a willingness to listen, and a reputation for fairness will all work in your favor.

Keep an Open Mind

Once you start to hear about negative behavior, however, you need to ensure that what you’re hearing is accurate. Is Bob really being consistently offensive, or is the person reporting Bob’s behavior hyper-sensitive or even mean-spirited? To find out, you’ll need to document accusations and actual events, do your own observing, and also have a frank conversation with Bob.

Take the Bull by the Horns

There’s no point in beating around the bush. If a particular employee is causing problems, and you’ve ensured that the employee really is the source of those problems, you need to talk with that employee face to face, and as soon as possible. Of course, you’ll want a private setting, and you’ll want to choose the right time to talk—when no deadlines or meetings stand in the way.

Keep Your Emotions in Check

You may be furious about a team member’s behavior, but, as you probably know, the person who loses his cool loses the battle. You’ll need to put your feelings aside, stay calm, and focus on a successful, positive outcome.

Be Specific About the Issue

If Sam has come in late and left early every day for a week, say exactly that. If you suggest that he’s “unpunctual,” you may wind up in an argument about how often he’s turned up on time for staff meetings or handed in reports on time.

Discuss the Problem, Not the Person

Julia may be a pompous, close minded person—but for the purposes of your meeting, that’s not relevant. What may be more relevant is her penchant for undercutting every idea put forth at team meetings. Let Julia know what behaviors you want changed, but refrain from describing her personal qualities.

Provide Clear, Actionable Direction

In Sam’s case, you’re asking that he arrive no later than 9 and leave no earlier than 5. In Julia’s case, you’re asking that she hold her remarks until ideas have been fully described and explained, and that she frame her thoughts as open-ended questions rather than as negative comments. These are concrete goals that can be implemented, documented, and evaluated.

Ask Questions

Once you’ve had your say, let your employee have his or hers. In some cases, you may learn a great deal about your employee or about their situation. In other cases, your employee may have good ideas for improving their own behavior or the situation. For example, you may discover that a negative vibe between two employees has its roots in a high school rivalry that you knew nothing about. This information may not change the problem, but it does provide you with context.

Follow Up

Once you and your employee have had your conversation, follow up with a memo (copied, if appropriate, to human resources and/or your manager). Describe the conversation, the issues discussed, and the remedies agreed upon. Include a date for a follow-up discussion. This is the start of a documentation trail: if your employee continues to create problems, you have the ability to point to concrete evidence of a discussion about the issues.

Give Credit When It's Due

If your employee does as they are asked, and the situation improves, be sure to praise their efforts and their outcomes. The more positive feedback they receive, the more likely they are to continue doing good work.

Follow all of these strategies, and you may or may not reform your difficult employee. Whatever the outcome, however, you have used the right skills and followed the right path to improve the situation. At the very least, you and the other members of your team will have gathered the evidence and followed the right steps to address problem behaviors. If worse comes to worst, you’ll have the documentation to address the issue with your human resources department.

Managing for the Best Outcomes

It’s important to remember that every business has its share of difficult employees. Even the world’s greatest managers are sometimes saddled with employees they don’t like. In some cases, nipping problems in the bud and providing problem employees with clear cut direction really can have a tremendous positive impact. Some individuals simply need more clarity and specific instruction to manage their behavior. Whether an individual turns themselves around or not, though, you’ll have gained many of the skills you need to become a truly top-notch manager.

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