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Illustration by Ralph Butler

An Invitation to Change

Problem employees. Difficult staffers. Workers in need of behavioral modification and attitude adjustment. However they are described, problem employees are the dread of every manager, and they require special skill and attention. As the experts attest, there’s no silver bullet solution, no ready-to-use spiel or psychological exercise that can suddenly make a difficult employee easy to work with.

“When you are talking about dealing with well-entrenched personal qualities, you need to be a bit of a black belt in your personal skills and in your management,” says Marie G. McIntyre, a workplace issues expert who writes a weekly syndicated career advice column, “Your Office Coach.” She is also the author of The Management Team Handbook and Secrets to Winning at Office Politics.

When it comes to best-practice advice for working with problem employees, experts offer numerous approaches, covering various parts of the process. The first piece of guidance is simple–don’t let staffers become problem employees in the first place. While that may sound like short and snappy advice, following it through actually entails sustained effort on the manager’s part. And the effort starts during the hiring process, says Michael Timmes, senior human resource specialist at Insperity, a national human resources provider with 60 offices across the United States. 

Timmes, who has nearly 30 years of experience in HR, sees a clear trend in the field. There are more resources available in the “emotional intelligence space” that emphasize the importance of relationship management skills, self-awareness, and social awareness, he says. As a result, more managers are deploying their knowledge of these concepts in the employee selection process. A candidate’s qualifications are still important, but managers are also looking beyond the résumé. 

“They’re hiring for the right attitude as much as for the right skill set,” Timmes says. Making an effort to ensure from the start that new employees have the right attitude for the position reduces the chances that they will become problem employees later, he adds.  

Veteran security manager Sam Curry, who is now chief technology and security officer for Arbor Networks, agrees with this emphasis on positive attitude and high emotional intelligence. “It’s easier to correct skill deficiencies than it is to fix attitude. Attitudinal issues will soak up the most time and will most often end in heartbreak,” Curry says. “You can teach someone a new skill, but you can’t give them empathy, self-awareness, altruism, or an amenable personality.” ​


But hiring is only the beginning of the process of ensuring that a staffer stays well-adjusted and engaged, Timmes says. During the onboarding process, a manager should initiate conversations with the new employee on expectations, responsibilities, and other topics that will make the employee’s role clear. In these discussions, the employee should be encouraged to ask questions to help build their understanding of their own position. 

Once onboarding is finished, these regular conversations should continue. They do not need to be time-consuming; a 10-minute informal chat every few weeks or so should suffice, Timmes explains. These short conversations serve several functions. For one, they allow the manager to emphasize how the employee’s role is tied to the success of the organization, which goes a long way toward maintaining the employee’s sense of mission. 

They also allow each party to provide feedback. If the manager periodically provides feedback on the employee’s performance, “it eliminates some surprises when it comes time for the annual performance review,” Timmes says. If signs of difficult behavior in the workplace are starting to crop up, they can be discussed before they have time to solidify. And employees can let the manager know how they feel about their role, “so there’s a finger on the pulse there,” Timmes adds. 

But these periodic conversations also afford an opportunity for the manager to gauge an employee’s alignment with the organization. Through active listening, the manager can learn about employees on a deeper level: their sense of mission, values, life goals, and involvement in the community. In these types of discussions, the following message from the manager, even if it is not actually articulated, often shines through: “I’m having this discussion because I care about you as an individual and as a team member,” Timmes says. From the employee’s perspective, this helps build trust. “People understand that there is someone in leadership who cares about them,” he explains.

When the manager gains this deeper knowledge, he or she can better understand how the values of the employee align with the company’s mission, and the ways in which the worker feels most connected with the organization. When trust, connection, and value alignment are established, both parties benefit. The employee is more likely to be engaged and professionally fulfilled, and a lot less likely to become a difficult or problem employee, Timmes explains.  ​


Of course, some managers do not have the opportunity to work with employees from day one. A new security manager may take over a department staffed with longstanding workers—a few of whom could be considered problem employees. Similarly, a merger or acquisition could result in new staff in the department that the manager didn’t hire. Whatever the reason, some managers do find themselves face-to-face with difficult employees—and working with them on a regular basis.

In these cases, experts advise that the manager strive to be as self-aware as possible when approaching the problem. McIntyre says that, in these situations, self-awareness means that managers should be honest enough with themselves to ask the following question—are my behaviors or actions making this problem worse?

In more than 20 years of career coaching, McIntyre has seen a few recurring ways in which managers do make the problem worse. Some managers, she says, practice what she calls “psychic management”—they see problems with a staffer’s behavior or attitude, get frustrated, but never take concrete actions to address it, and the problem becomes worse. In other cases, she has seen managers give a tremendous amount of special attention and time to problem employees, which she says merely rewards the bad behavior. That, too, can make things worse. 

Another common error, McIntyre says, is when a manager assumes that the employee knows there is a problem. In this case, a manager who mistakenly assumes em­­ployee knowledge of the issue can become more and more frustrated, because they feel that the staffer is knowingly con­tinuing to transgress. Finally, the man­ager will approach the employee in a very annoyed and frustrated manner—an approach that is neither professional nor managerially sound.

Besides self-awareness, managers should also strive for fairness in their approach. “It’s important to not leap to conclusions early and to be as open to input as possible,” Curry says. “The first thing to do is make sure that there’s no witch hunt, that facts truly are facts—and they can change, so be careful here—and to have an approach similar to a jurist in a court case.”

Maintaining professional respect is also key, says Maxine Attong, an organizational development expert and author of Lead Your Team to Win: Achieve Optimal Performance by Providing A Safe Space For Employees. Even though the worker may be considered a problem employee, a manager-staffer meeting should never have the tone of a parent-child scold session, but rather an adult-to-adult conversation between two intelligent professionals. The manager would be well-served to take a positive and optimistic stance, with the focus on future improvement, Attong says. “Declare this to the employee, for example, ‘My intention is for us to find a way forward on your job,’” she says.  

It is also a good practice for the manager to strive for agreement and feedback from the employee, she adds. If certain procedures or policies were breached, a manager should state these and check for understanding. The employee’s ideas on how to move forward should also be solicited.  ​


In all the cases above, documentation is an important part of the process, experts say. This is especially true if a disgruntled employee seeks legal action. 

“Any action that can be interpreted as discriminatory or harassment can lead to a civil action by employees. Hence the reason for proper documentation,” Attong says. “The manager must build a consistent trail that shows that this employee was not singled out for special treatment.” 

Curry agrees with the importance of documentation. However, he also cautions against over-documentation. Over-documentation adds “gravitas” to issues and can cause them to get too much “play time,” under the philosophy of: if there’s all this paperwork, the problem must be enormously significant.

“We tend to think of things being as serious as the mindshare they gain, and nothing drives mindshare like conscious recording and creation of material on a subject,” Curry says. “So document, sure.  But be leery of over-documentation, and the effect the documentation has.”

Attong suggests cooperation in documentation when discussing issues with problem employees. “If the manager documents the meeting, ask the employee to agree with the documentation.”  ​


In some cases, an employee’s problem­atic behavior and attitude—be they un­co­operative, overly negative, or excessively distracted—is a manifestation of a deeper underlying issue: lack of engagement with the job, Timmes says. 

A manager can discuss this possibility with the employee. And, sometimes, an honest and supportive conversation will reveal a truth—the staffer is simply not in the right job. That’s an unpleasant thought for some.

“Sometimes people will be denial,” Timmes says. “They have the attitude of, ‘I’ve been here for so long, I just don’t know where I would go or what I would do.’” Still, if that is the situation, it is best that it is acknowledged, experts say, and then the manager can work with the employee on an exit strategy that would benefit them both.

“The manager can help the employee frame a vision for his life. This may give him the impetus to resign and find a job that he may be more aligned to, or see the value in his current position as a stepping stone to where he wants to be,” Attong says. 

But in many cases, the lack of engagement is not because the job and the employee are inherently a poor match. The deeper reasons that drove the staffer to enter the profession are likely still valid. But somewhere along the way, the connection was lost. Often, that’s because the employee is not seeing clear evidence of why his or her work is crucial to the organization, how it helps the company fulfill its mission, and how that mission is important to the larger world. 

This evidence of importance and value can be obscured in different ways. Day-to-day repetition can make work seem rote; overworked staffers are focused, above anything else, on keeping their heads above water; and concepts like mission and purpose are given lip service, but never explicitly expressed or explored. Once the connection is lost, it’s a rare staffer that will flat-out ask management—can you show me why my work matters? 

But a manager can take the initiative and, through exploratory discussion, help the employee regain perspective on their contributions and value, to the organization and beyond, Timmes says. 

“You can show them where the connection is,” he says. “Hopefully, that can reignite them, and they will recommit to their mission.”


Every employee is a unique and distinctive individual, but there are certain types of difficult behaviors and attitudes that occur in many workplaces. Below are descriptions of several problem employee archetypes, based on conversations with workplace issue experts as well as a review of published HR literature. Each thumbnail sketch is followed by some best-practice advice on how managers should deal with each one.  

Negative Nancy. Naysays projects and assignments. Shoots down the new ideas of others. Often predicts doom. Frequently makes comments such as, “We tried that before, and it never works.” “This project is turning into a complete disaster.” “There’s just no way we can meet a deadline like that.” 

Sometimes, negativity is used by an employee as a badge of intelligence, Curry explains. Critics often seem like authorities, and so naysaying a project can be an attempt for an employee to try and highlight their expertise and their range of professional experience. The manager, then, should strive to redirect that expertise in a more positive direction. 

If the pattern of negativity becomes disruptive, a manager may want to have a conversation about this pattern, while “issuing an invitation to change” to the employee, McIntyre says. “You can’t make someone change, but you can invite them to change,” she says.

In doing this, the manager should use a factual approach, noting behavior patterns such as the employee’s tendency to criticize when new ideas are proposed at staff meetings. The manager can also explain how a past failure may be the result of a timing issue, not problems inherent to the idea. Finally, the manager can encourage and coach the employee on changing focus toward making the project better, not obliterating it. 

“Ask this employee what success looks like to him. Have him paint the picture for success and ask what he would do differently to remove the incidents of the past,” Attong says. 

Egotistical Eddie. Acts condescendingly. Dominates discussion at staff meetings. Resents being asked to do mundane but necessary tasks. His immense self-regard alienates coworkers. 

While prima donna behavior can be frustrating for other staffers to deal with, the manager should be careful to keep the focus on business factors, and not on irritating personal characteristics, when discussing the problem with the employee. “To say something like: ‘You apparently think you’re all that, and a bag of chips, and this is very annoying to people,’ that’s not a conversation you want to have,” McIntyre says. 

Instead, focus on how specific actions may hurt staff productivity. For example, a manager might discuss how the employee’s domination of staff meeting discussions hinders others from contributing ideas­—and that makes for a diminished output from the team on the whole.  

However, some employees “are prima donnas who really can dance,” and they possess top-flight skill sets that are a tremendous asset to teams, Curry says. Here the manager should adopt a dual strategy: communicate to the employees that their work is highly valued, but also that it does not entitle them to a pass on actions that hinder other team members. 

“When they are really good at what they do, you must both create the right workplace and make it visible that the wrong behaviors won’t be tolerated,” Curry says. 

In addition, Attong recommends that the manager consider giving the employee additional projects appropriate to their skill level. “Since this is in her self-interest, she will be happy to do other work to strengthen her résumé,” she says. If the employee still feels underutilized and desires to leave the organization, a strengthened résumé could help her do so, and leaving would be in the best interests of the staffer and the organization. 

Crisis Charlie. Life problems frequently interrupt his work life: long personal phone conversations in the office, mood swings, and oversharing about relationship issues to other employees. Life events, like weddings and divorces, can affect performance for weeks.

Tread carefully here, with sensitivity, say the experts. 

“Crises can come in blocks, especially with children and elderly parents, divorces, et cetera,” Curry says.  “People melt down all at once, and how you help someone through a cluster of crises is important. It is not just the right thing to do—it can create incredible loyalty with employees.”  

It’s also possible that mood swings and oversharing may reflect medical issues, which is all the more reason for a manager to be careful. Considerate and candid conversation is appropriate, but discussions should be nonthreatening when it comes to employment issues. “Make sure to avoid harassment and miscommunication, and involve HR, and keep them apprised,” Curry adds. 

In one-on-one conversations with the employee, the manager can begin to gauge the level of the problem, and also explain how a staffer’s demeanor can affect others on the staff. “This employee may be unaware of the impact of his behavior,” Attong says. “Human resources can also get involved, since this may be a reflection of deeper psychological problems that the employee is facing.” A 360-degree performance review can be helpful in providing feedback from peers, she added. 

In addition, the one-one-one conversations afford an opportunity for the manager to gain a deeper understanding of an employee’s life context—the challenges they face outside of the workplace that may affect their performance at work, Timmes says. It may also be an opportunity for the manager to highlight the organization’s employee assistance program or other resources the company may have to help, he added.  

Challenging Cathy. Thrives on taking on authority. Will often challenge a manager’s directives and be privately critical of decisions by upper management. Derisive of “company men.” 

Thoughtful criticism of operations can lead to greater innovation and efficiency. Attong recommends that a manager coach this type of employee to help make her presentation and style more palatable, but still offer constructive suggestions that lead to improvements.  

“I want this employee to keep challenging and will work with her, so that she can ask better questions, be less attacking, and have some compassion for others,” Attong says. If the employee’s manner of speaking is too cutting or derisive, “I would ask her to reframe her questions to ‘what’ or ‘how’ questions, since these help people to think and be less defensive.”

Ghostly Gerty. With frequent sick days, medical appointments, and lunchtime errands that last all afternoon, she is absent as often as present. Some coworkers even wonder if she is still on staff. 

In a clear-cut case, Curry says, involve HR, document the absences, provide feedback to the employee if absences seem excessive, and “find out what’s going on, and why.” 

Attong also says that company attendance rules are important to emphasize. “Point out the number of days and the policies around this, and ask the employee how he will remedy the situation,” she says. “Enforce the company remedies for absenteeism.”