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Crucial Conversations for Accountability

Working with a Difficult Employee

Dear Crucial Skills,
When I recently assumed my current job, I “inherited” an employee who has a long history of bad behavior such as being rude, stirring up trouble, and refusing to work with coworkers as a team player. How do I confront this person when the whole department has played into his behavior for years?

Inherited Employee

Dear Inherited,

“Inheriting” an employee with a history of bad behavior is a concern for any leader. I strongly recommend your first conversation with this employee not be a “shake-down” or a “you’d better be careful cuz I’m watching you!” speech. Rather, you ought to extend a sincere handshake followed by friendly introductions.

The next step is orienting your employees to your leadership style and expectations. Even before exploring specific duties or concerns, explain the operating values and principles of your team and your expectations of team members. It’s best if this is a collaborative process involving the entire team, but at a minimum, everyone needs to be clear about the team values and operating principles. Explain that employees are not only responsible to produce results but are also responsible to produce results in a way that strengthens the team in the process. Give specific examples of what is acceptable behavior and what is out of bounds. This kind of orientation with your team sets clear expectations and gives everyone a chance for a new start—independent from past patterns and personality conflicts.

Your next leader-role with the team is teacher and coach. This requires gathering data through contact and observation, especially with the employee you have concerns about. Over the next few days, catch the employee, in the moment, doing things right. Acknowledge when his behavior approximates an important team value or principle and thank him. For example, you might say:

“Hey, Brent, I noticed in the team meeting when Alice asked for ideas about her project, you gave several helpful suggestions. That is a great example of our team value of collaboration. Your input helped Alice and helped to build a stronger team. Thank you.”

Similarly, when you see behavior that violates the team’s values, confront it as soon as is reasonably possible. Do this by first describing the gap by factually detailing what happened compared with what is expected. Next, ask why it happened this way. You could say:

“Brent, I noticed that when Jerry presented his proposal, you said his plan was ‘idiotic’ and asked him if he had ever heard of ‘professional standards’ before. One of our team principles is to treat each other with respect. Your comment was clearly disrespectful. Why did you say that?”

If he responds that he didn’t realize his comment was disrespectful, take the opportunity to define more precisely what is meant by the value of respect.

If he replies that it’s no big deal, then you have the opportunity to teach consequences and make the invisible visible. It could be that one reason for his past friction with employees is that no one helped him understand the negative, natural consequences his behavior had on others.

If he replies that he knows he shouldn’t do that, but can’t help himself, it becomes an opportunity to teach him the skills to start with heart or master his stories.

After each conversation, move to action. Get a clear and specific commitment from him about who will do what by when, and then follow-up on that commitment.

Clear expectations, as well as frequent and immediate praise and confrontation, are your best chance to help someone work well with others in a new setting.

Of course, this approach requires patience and persistence, and you must always give people the opportunity and the help they may need to improve. However, if over time, he does not comply and his poor behavior continues, make sure he understands that following the team principles and values is not a suggestion, it’s a requirement of his job.

At this point, it’s time to move from helping him understand the natural consequences of bad behavior to the consequences you will impose on him if he doesn’t comply. Clarify that the consequences of not working within the team standards are the steps of discipline identified by the organization, even including termination. Make sure he understands that failure to comply with your requirements around teamwork will result in you applying the steps of discipline. Moving this far is very serious and will most likely damage your working relationship with him, but at some point, his failure to abide by the team’s standards is a detriment both to the results you’re after as a leader and your other team members’ quality of life. Choosing what’s best for the team is more important than trying to preserve a troubled relationship.

My experience has been that this approach helps most employees—even those with a history of bad behavior—to improve their behavior and relationships with others. It also improves the team’s results. Please keep in mind this approach does not guarantee the changes in others you desire; it’s not a way of controlling others; it’s not a trick for manipulating others. This is a way to respectfully help individuals choose to be successful. Ultimately, it’s the individual’s choice whether or not to be a part of the enterprise you lead, and that’s as it should be.

All the Best,

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9 thoughts on “Working with a Difficult Employee”

  1. Rachel Peterson

    Hi Ron,

    I could be one of those “Difficult Employees” I work in a medical clinic, I am the only person on the administrative side, every one else here are nurses or physicians. I am the front desk person, the phone operator, medical records, and many other duties that in other clinics are handled by many others. In my office, I do not feel respected as a person or the job I do because of the way I am treated mainly by the Nurses. They do not greet me, ask me how my weekend was, my husband has been out of work for almost 2 years and deals with depression, no one asks me “How are you?” This has lead me to shut down and just do my job. I can take responsibility for my actions, I can see where I have contributed to this situation, but please don’t assume that just one employee is behaving badly. I learned early on as a Sunday School teacher never to take to heart when someone tells you, “Better watch out for that one, he’s a trouble maker.” I would have missed out on some real joys and blessings in keeping a child in my own mind labled “Trouble maker.” Perhaps your “Difficult” employee has been left out, or gossiped about, I think your whole group needs to work on the team spirit thing and value each other.

    1. stop whining

      Stop playing the victim.

  2. Samantha Olson

    I am not a supervisor or mangager/no one of real authority at my job. I started working in my office over 2 yrs. ago and I “inherited” an employee who has a long histroy of bad behavior such as being rude, stirring up trouble, and refusing to work with me as a team player. She has been with this company for over 30 years and knows through her past experiences that she can get away with mistreating certain staff. I’m the only one in the office with her most of the time so I’m the lucky one who gets mistreated. I’ve gone to my supervisor, Director and Boss. They all tell me the same… she’s been here too long to fire, she isn’t going to change, you are just going to have to figure out how to deal with her. We have went through counseling and while that taught me a lot and I put it in practice all the time with her, I don’t see anything we were taught put into practice by her with me. It was a VERY hard few months of work, sitting with this lady who in front of people acted like my friend but when it is just her and I she acts like I’m her worst enemy. Since she has been with this company for so long she has a lot of vacation time stored up, so she goes on 2 week vacations a couple times a year. My supervisor has even told me “just look forward to those 2 weeks here and there when she is on vacation, maybe that’ll help you get through how she treats you.” I’m now 7 months pregnant, I refuse to let her continue to mistreat me and especially don’t need it while pregnant so I continue to let my supervisor know whats going on. My supervisor is finally fed up with me coming to her and she has now turned on me, making up lies and saying I’m the one the problem lies with. I’ve called the previous gal who worked with this “inherited” employee and she told me she was mean back to her and was never in the office in order to get through working there with her. I’ve let my supervisor know that but it doesn’t make a difference to my supervisor. I’ve asked to be transferred and I’m told I can’t. When asked if I could be moved to a different office I’m told no. Other people in the company have volunterely come to me asking how it is working with her and telling me stories of when they’ve had to work with her and how mean and rude she was to them. They all say they can’t imagine how my work days are with her. Got any help or advise since I’m not a person in authority?



  3. Stephen Ruten

    Sometimes, these articles happen just as I need them and today’s lesson is a perfect example.

    Thank you,

  4. Kimberlee

    Years ago I worked for a Government agency that was experiencing a major growth spurt, due to newly mandated programs. The Program Manager was thrilled to have me on his team. However, there were several individuals assigned to his team that had been labeled “difficult”. The Program Manager took; what I thought at the time, a very novel approach to the situation. He not only treated everyone as if he thought they were the cream of the crop, he did little things that made it clear to his colleagues that he was extremely fortunate to have this. Being treated this way, most of my co-workers strived to be as good as they were told they were. There were a couple who really were not capable of it. This was also easily handled. We had a meeting where we listed all the duties we would have to have accomplished with our new unit. Management assigned each of us a couple of major tasks that best suited each employee. After that, one by one the employees picked the remaining tasks. First we went through and picked the ones that matched as closely as possible with what we were already doing. After that we each picked a task we really wanted. But in order to do this, we had to accept a task that was less desirable as well.

    This worked so well, I noticed it being used in a couple of other newly formed units as well. It was amazing seeming people who were considered “damaged goods” being an asset to their department.

  5. Barbara Blakely

    Being a parent of a teen that shares many of the characteristics as your difficult employee I found a lot of great tips in the article that I plan to use. It outlines real strategies we can use to “turn around” our teens bad behavior. Unfortunately we bred the bad behavior by tolerating it for so long. Of course we can’t fire our teen, but hopefully he will come around!
    Any tips on how to start the conversation for our “renewed” expectations for behavior in the family would be appreciated.

  6. Celine

    Hi Ron,

    Reading your response makes it sound so easy to help this employee improve the behavior and working relationship with others. How would this approach be applicable to a soulmate who is acting rude and seems not to understand how it is affecting the other partner even when it is expressed?

  7. Josie

    Hi Ron
    While my issue is similar, it is not exactly the same. I have an employee who I used to think was a “cup is half full” person. We had a conversation about that almost 3 years ago and she underwent a “remarkable transformation”,.. until marital and home issues have unveiled the truth – she is a “cup is empty” person.
    She is productive, reliable, honest, and good at her job BUT her negativity has poisoned the office moral. Another “conversation” about her “negativity” will not work, as she is extremely sensitive about this.
    All suggestions are welcome!

  8. Jane

    I, too, have worked with employees that have 20-30 years with the company and have been allowed to be ugly and rude. The same excuse is “They have been here for so long we can’t fire them”. It is unfortunate that this is the excuse a small or large company would use, because, eventually you will lose the good employees because they are sick and tired of working with these ugly and rude behaving employees. I was able to transfer to a completely different department within the company, just to get away from this person. They eventually retired and what does the company do…name an area after her! WHAT?

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