Firing people isn’t ever a pleasant experience—unless, of course, you’re Donald Trump starring in your own reality television show on NBC. He seems to relish the job, shouting, “You’re fired!” as he points his finger at the next unlucky apprentice candidate.

In my career, I’ve had to fire many people, and let me tell you, it’s not as easy or fun as “The Donald” makes it look. The reality is that it’s a gut-wrenching, lump-in-the-throat, guilt-laden job. In bookstores and on the Internet, advice abounds on the proper way to fire employees in order to minimize emotional pain and legal risks. So I’m not going to write about that stuff. Instead, I’d like to discuss what underlies the decision-making process in one of the most difficult decisions leaders have to make.



When It’s Black and White

Of course, sometimes there are clear reasons to fire an employee: fraud, theft, harassment of fellow employees. Situations where there is proof of unethical or illegal behavior are no-brainers that simply have to be taken care of immediately to protect your organization.

But what if you only have anecdotal evidence that an employee is dishonest or lacks integrity? You still can’t ignore it. Follow your intuition and try to catch him or her in the act. Once you’ve caught someone in a few lies or instances of abusive behavior with co-workers, can you really believe it stops there? Is that person lying to customers and shareholders, too? Cussing out vendors? It’s a risk you can’t afford to have around.



Then It Gets Gray

Unfortunately, the list of easy decisions about firing an employee is short. Decisions in the gray, fuzzy area are more numerous. That’s why firing someone is so difficult, and why most leaders avoid it for as long as possible.

Maybe you’ve simply lost confidence in the person’s ability to do the job. It’s probably someone who’s very nice, who you especially don’t want to hurt. It may be the salesperson who always promises results but never delivers. Or the engineer who has great designs that are not practical to manufacture. Or the middle manager who’s been promoted to his or her best level of incompetence. Eventually, you have to realize that no amount of training or patience will change that person’s performance.

Another fuzzy situation is when someone is not effective, but as this person’s manager, you realize that you’ve done a poor job of defining expectations. You feel guilty for not doing regular performance reviews with this employee, and spend time blaming yourself for the problems instead of dealing with them.

Or perhaps the person has the right skills, but has a personality that’s disruptive or destructive to your organization. Some personalities, even with a lot of coaching and mentoring on your part, will never change—short of a lobotomy. Leopards don’t change their spots.

An interesting phenomenon is when we hesitate to fire someone because that person has been such a problem child that we’ve spent a lot of time together in remedial training and have come to know each other well. Sometimes, we even promote these people because we’ve created them in our own image. But that never works out well.