Stay Cool with a Challenging Employee

Aug. 1, 2007
Certain situations call for having a difficult conversation

Dave Schmidt’s dad owned a tire company and a retread plant in Missouri. One day when it was 100 degrees outside and 130 degrees inside, his father walked into the plant and chewed out a supervisor in front of several other employees. The man was humiliated, and even though the elder Schmidt apologized within the hour, the supervisor — one of the best the plant had ever had — quit within six months.

The younger Schmidt learned a powerful lesson in that experience, one he’ll remember as a prime example of what can happen when people let things build up instead of tackling them as they come. A leadership consultant and professional speaker from Kansas City, Mo., Schmidt acknowledges that as hard as it is to have a delicate conversation with an employee about his or her performance, it is crucial to the continuous improvement and success of any business.


Moving away from pain is instinctive in human nature — so strong that our feet might flee from danger, even as our brains freeze. The instinct is so pervasive it sometimes dictates how we communicate with other people, particularly when communication with a problematic employee is likely to turn into a confrontation.

“The number one reason that managers don’t confront a difficult employee is because they do something else well,” says Schmidt. “Of course, most people don’t like confrontation at all, but a boss must be committed to changing the problem behavior.”

Schmidt prefaces his views on dealing with difficult employees by stating “we’re not talking about the employees you want to get rid of,” but about the fact that the employees you do keep must be held accountable. And sometimes when a worker doesn’t do things in the way the boss wants it done, we tend to take it personally. “But you can’t take it personally; keep the focus on work,” Schmidt says.

But that’s hard to do, and when it’s just not possible, the result is often going to look like the retread-plant scenario. When other employees witness the boss’s explosion, they tend to take sides, Schmidt says, and invariably they will side with their fellow employee. Now there’s an “us versus them” climate instead of one where a private, albeit uncomfortable, conversation can let employees feel respected and safe from public embarrassment.

“It’s very hard to have these conversations,” Schmidt says. “No one heads toward pain, and it is painful to correct people and do it intelligently.”

He adds: “That’s the hardest thing to do when there’s a problem employee: Overcome your reluctance to talk.”


When it comes to working with a difficult employee, keeping things on a professional level is crucial. One of the most effective ways to help an employee change problem behavior is to show them, literally, the effect or the impact of his or her misstep or poor performance. For example, “Because you didn’t get this car finished yesterday, it’s going to cost us $55 for this customer’s rental vehicle for one more day.”

“Be very specific about what it cost and the impact of their mistake,” Schmidt says. “Give him a chance to explain things, because you might not know everything.”

Maybe there’s a good reason why this employee “screwed up” and no further action is needed. But maybe it’s another excuse in a long line of reasons why he couldn’t stay to get the job done, or why he was late again. The owner or manager’s role now becomes that of coach, not counselor, on how to improve performance.

Counseling is when you get the other person to tell you what they’re going to do to fix a problem: In essence, they come up with the solution, Schmidt says. “Coaching is when you have to prescribe, like a doctor prescribes for a patient; you have to prescribe exactly what is going to change and when. Then you have to add an element — whether they come up with the answer or you come up with it, you have to become a partner in the correction.”

One way to do this is to strike a deal with the difficult employee and offer firm consequences for acceptable behavior and non-compliance. For example, “If you do this for me, I can continue to trust and count on you,” or, “If you don’t do it this way, you won’t be the guy I go to for overtime” or any other outcome undesirable for the worker. Says Schmidt, “There has to be something at stake.”


An additional point to consider when figuring out a plan for dealing with a difficult employee, Schmidt says, is to determine whether your focus is on the short-term or the long-term.

“Is your long-term goal to hang onto this person? Or is it to chew them out?” Schmidt says. “If you’re focused on long-term goals, it’s amazing how different we talk. You make different choices based on the long term.”
We all have tempers and we all need to be right, sometimes, Schmidt says. But fixing attitudes is harder than fixing behaviors or the personalities of a bunch of men who grew up competitively pushing one another around on the playground. Plus, when one party insists on “winning” a conflict or a difference of opinion, the other party must be the loser. This can be avoided in an atmosphere guided by emotional intelligence, not emotions.

“A leadership model is to always show respect for others, which is a hard thing to do in a competitive work setting,” Schmidt says.

Showing respect means that when it comes time to have a difficult talk, it’s time to find a place where other employees won’t overhear the conversation. It’s also time to put hard feelings about past mistakes aside and to focus on one thing at a time — even it means repeated conversations.

“It’s just not worth it to blow your stack,” Schmidt says. “In today’s employment world, I don’t know how you can afford to lose somebody because you had a bad temper.”

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