Managing Employees

How to Fire Your Best Friend

Be direct. Be quick. And if they are still talking to you, help them find a new job.
How to Fire Your Best Friend
Image credit: Westend61 | Getty Images
Guest Writer
CEO and Co-founder of Nav
5 min read
Opinions expressed by Entrepreneur contributors are their own.

Ever been fired from your job? I have, and it sucks. There’s nothing quite like the feelings of despair, humiliation, discouragement and setback that results from losing gainful employment -- expected or otherwise.

Ever fired someone from their job? I have, and it’s every bit as sucky. There’s nothing quite like the feeling of being directly responsible for all the negative emotions listed above.

There are exceptions to the rule, of course. Sometimes the employee in question is rude, arrogant and downright bad at their job. They poison your company culture and continually underperform. Both of you see a parting of ways long before the day actually arrives.

Related: Should You Hire Your Friends?

But then there are those others. The decent ones who show up early and try hard but just can’t quite seem to cut it. These make for painful interviews. But worst of all, by far, are those times when you have to fire a friend. It might be someone who’s been with you from the beginning, but your company has simply outgrown them. It might be someone who finds themselves in over their heads, and though given every chance to swim to shore, succumbs to the waves again and again.

I can promise you that these separations will be among the most heart-rending of your career. But as with everything else, there are right and wrong methods of handling them. Here’s how to do it right.

Set definite expectations long before the dreaded day arrives.

When you’re close to someone, it’s tempting to set lower standards for their performance. Your affection will bathe their behavior in a rosier light than enjoyed by their lesser-esteemed colleagues. That’s a psychological fact. Don’t be naive about it, and don’t lie to yourself about it. View your friend with the same clear, objective eye that you would anyone else on your payroll, and set clear performance goals.

If those goals aren’t met, your duty becomes 100 percent easier. You both agreed beforehand that X, Y and Z were the necessary standards for their continued employment. Those standards weren’t met, and only one course of action remains.

Be as direct and natural with them as you’d hope they’d be with you.

This isn’t a time for funeral airs and solemnity. Nor is it time for false cheeriness and a this-isn’t-as-bad-as-it-seems vibe. You’re not the principal of a high school calling the class clown into your office to suspend them. Nor are you a buddy merely passing on a bit of negative news. You’re their boss. They’re your employee. And you’re letting them go. I speak from experience. I can promise you that no matter how much you prepare internally, nothing will completely fortify you for the actual exchange.

Related: How These 6 Entrepreneurs Dealt With Difficult Employee Issues

So be yourself, and let them be themselves. Let them respond. Let them get angry. Let them get sad. Hell, if you need to cry together, cry together. But be firm, calm and unambiguous.

For both your friend’s good and the good of the company, don’t delay.

I’m an optimist, and I like to err on the side of people. Needless to say, this optimism leaps into overdrive if those people happen to be bosom buddies. I’ve delayed firing individuals for a year longer than I should have because of this.

In other words, I took my whole company to the edge of catastrophe because I convinced myself that what was really happening wasn’t really happening. I didn’t want it to be so; therefore, it wasn’t.

It is much better to err on the side of caution and fire a floundering friend a few months early than a few months late. This sounds draconian and cold-hearted, but it’s absolutely true. You owe it to your investors, customers and other employees.

Steel yourself for the possibility of hurting a relationship temporarily or even permanently.

The more personal the relationship, the more personal the firing will feel. An emotional confrontation, a stormy scene, accusations of betrayal -- don’t be so naive as to think that either of you will walk out of the meeting unscathed.

Be prepared to be called a Judas. Be prepared to be castigated on social media, to be contacted by mutual friends who just can’t believe what you did, to be defined as cold, heartless and worse.

There’s a chance that things will blow over. Even if it takes years, reconciliations do occur. For now, you’re making the best decision -- for you, for your friend, for your company. Hold on to that truth tight and weather the storm.

Related: Why You Shouldn't Hire Your Friends

If it’s warranted, help your friend find new employment.

As already mentioned, there are plenty of occasions where a firing is called for because your company outgrows an employee. They just can’t keep up with the demands that a quickly expanding tech startup calls for, for example.

That doesn’t mean that they aren’t skilled, hard working or incredibly good at what they do. It only means that they need a different environment in which to shine as brightly as they did when you were beginning together.

In this case, move heaven and earth to assist them in finding solid employment elsewhere. Use all your contacts, all your connections, all your pull. In this case, you owe them a debt of gratitude, and you can repay that debt by making sure that wherever they land, they land on their feet.

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