5 Things I’ve Learned About Dealing With Difficult Employees

Gene Marks

Every small business has its challenging personalities: The “yeller” is someone in your office who talks loudly and tends to distract and annoy others. The “loafer” is the person who’s known for goofing off. The “meddler” is the nosy gossiper who sticks their nose into people’s personal lives and asks rude questions. These, and a few others, are typical types of difficult employees you’ll have in your office. How can you prevent these problem employees from hurting your small business?As a business owner with 10 employees, I know these people. Really know them. And a few things about how to deal with them—the hard way, unfortunately. But let me share with you five things I’ve learned.

1. Accept that every employee is a problem employee.

For a while I would get annoyed when people didn’t behave the way I would behave in a professional environment. I would get frustrated when someone didn’t demonstrate the same work ethic or just said things I wouldn’t say. But after a while—and a lot of employees—I came to this realization: No one’s perfect. Least of all, me. You are employing humans, and humans have their quirks. You’re never going to find that perfect person. Some will work harder than others. There will be people who like to gossip. You will have introverts and extroverts, narcissists and charity-minded. There will be grumps, complainers, and whiners. You will employ people who are overly enthusiastic, highly energetic, and super-active. Sometimes people will come in late, miss work, blame others, hide their mistakes, and make excuses. These are humans, so, by definition, you should be setting your standards low and give your people every opportunity to exceed your expectations.

2. Don’t be afraid to get rid of someone.

Of course, when you’re running a small business, even just the loss of one employee can have a very disruptive effect. But sometimes I’ve used that as an excuse to hold onto people. I’ve been lazy or I hope against hope that a problem behavior will just magically go away. It never does. So instead, I hang onto an employee because I don’t want to endure the inconvenience of losing that person and then having to go through the time and cost to find someone else.

At some point, I began to realize that this thinking is wrong, because in the instances where I did let someone go—for whatever reason—I looked back months later and kicked myself that I hadn’t made the move a long time before I did. By not doing so, I not only caused more problems in the office, but also I wasn’t showing my existing employees the respect they deserve. Because no one deserves to come to work and be uncomfortable or be around people they don’t like, especially when it distracts them from doing the job they were hired to do.

The lesson: Don’t punt the problem away. Deal with it. The odds are in your favor that it will be the right move.

3. Evaluate the person as an asset.

Sometimes we forget that, as much as we love our people, it’s unlikely that we would have much—if any—of a relationship with them if they weren’t working for us. In the end, your relationship with your employee is a professional one. It’s employer-employee. It’s an implied contract. It’s subject to laws and rules. I know it sounds a little cold, but when a company says its greatest asset is its employees, then we must all accept the fact that yes, our employees are just that: assets.

The most effective way to avoid getting hurt from your problem employees is to evaluate that person quantitatively, based on metrics that can be benchmarked and compared to goals. When the numbers aren’t matching up, it’s easier to show that person the door.

Where things get complicated is when that “problem” employee—the grump, the narcissist, the meddler—is also a very profitable one. That’s when subjectivity has to take precedence. But are the additional profits generated from that person really worth the aggro caused in the office? Couldn’t a replacement contribute at least as much? Which brings me to the next thing I’ve learned about problem employees….

4. Hire/fire with the goal of minimizing people in your life that you don’t enjoy being around.

Right? Life is just too short, and we are all spending too much time in the office, to be around people that we don’t like being around. I’m not saying you have to be best friends with every employee, but you—and your employees—should enjoy coming to work and being with the others there. If there’s an employee who’s creating disruptions, upsetting others, taking advantage, or just being a jerk, then that’s not someone nice to have around.

Easier said than done? I’ve found that not to be the case. If you’re willing to offer a good wage and decent benefits, you’ll find plenty of people looking to change jobs and come to your business, regardless of how low the unemployment rate is or how strong the economy’s going.

Don’t short-sell happiness. Be with people that make you happy, if you can possibly manage that. Wait…you can. You’re the boss!

5. If possible, let the employee be the one who decides to leave.

My dad taught me this—only it was about customers. “Son,” he used to say, “Never fire a difficult customer. Just price them accordingly and let them decide to leave.” I think the same goes for problem employees. You can do a lot of things to encourage an employee out the door. You can, for example, not give a raise, forgo bonuses, make more demands, or—like the movie Office Space—move that employee down to the basement with nothing but a bare desk and his stapler. At some point, that employee may realize the writing’s on the wall.

If you do it the right way and keep it amicable, then you can avoid fights, lawsuits, and other nastiness that sometimes comes with an employee departure. And besides—who knows when you may bump into that person again? The world is not as big as you think.


When I started my business and it was just me and my dad, we eked out a living. A lot of businesses are run that way. But I really started to make a decent living once I started hiring people. Now, with 10 people in my company, I can delegate work and keep most of them working at clients, doing things I could never do. That’s a great thing. But there’s also a downside: All 10 of them—and I love them—have their problems. And I wouldn’t have it any other way.

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5 Responses to "5 Things I’ve Learned About Dealing With Difficult Employees"

    • Eunice freeman | June 5, 2019 at 9:05 am

      This was very helpful. I have an employee that I am going through…..I know that I should have terminated her but I chose to rebuild her. So far so good.

    • Cassie | June 11, 2019 at 10:14 pm

      Great list but I disagree with number 5. By keeping a difficult employee around, you send a message to your team that you will tolerate a poor employee. This lowers morale. It can boost morale by letting a difficult employee go because the rest of the team sees you standing up for the company culture. Gary Vaynerchuk does an excellent job explaining this.

    • Vanessa | June 12, 2019 at 10:57 am

      Great read! Thank you.

    • Michelle | July 24, 2019 at 1:12 pm

      Helpful insights. Thank you.

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