This isn’t personal: How to diplomatically fire your friend

Nothing feels better than onboarding a friend — someone you know, trust, and can speak bluntly to, right? Nobody imagines that when they hire or partner with a friend, they may one day need to fire them, but that’s often the case.

Hiring friends can lead to the very best, and the very worst outcomes. If you have the fortitude to weather the latter, then it might be well worth the risk. For instance, my fellow co-founder, David Mainiero, has been my best friend since freshman year of college, and I can’t imagine running my business without him.

Still, having fired friends a few times before, I thought I would pass along a step-by-step guide on how to confront what may be every entrepreneur’s worst nightmare.

1. Realize that, either way, your friendship is over

Most individuals I’ve spoken to tell me their biggest concern is that firing their friend will jeopardize their relationship. “She won’t forgive me!” Indeed, she may not forgive you. But one thing is certain: if you don’t call it quits when the business relationship clearly isn’t working out, it will be you who does not forgive them.

If you are debating whether to fire a friend, chances are that your friendship is already over – you just don’t know it yet. Hopefully, your friend will handle their termination with grace and forgiveness, but that’s the exception, not the rule.

2. Focus on the legal situation at hand

Now that you’ve lost your friend, things could get ugly, and it’s time to get your legal approach in order. Oftentimes, when people feel personally invested, they tend to overlook those pesky legal details. But it’s precisely during that time that you should pay particular attention. You’d be surprised by the number of legal issues that arise due to personal, rather than business-related, issues.

Read your friend’s employment agreement, and if necessary, the operating agreement for your company. If your friend is just an employee, consult an employment lawyer in your state, or if they’re a partner, consult an attorney. Be sure to ask what your rights are, what his/her rights are, and how you can make termination legal and incontestable.

Before your friend has even an inkling that you intend to fire them, you should essentially have your entire approach planned out.

3. Set up an in-person meeting

Much like breaking up with a significant other, firing a friend should be done face to face. Once you’ve gathered yourself and your legal strategy, it’s time to send them an email setting up a place and time to chat.

It will behoove you not to betray your intentions at this meeting. You’ve made up your mind, and this is what’s best for your business. If you make it clear that you’re coming in guns blazing, you’ll only give them more of an opportunity to prepare.

Remember that self-preservation is human instinct, and if you were in their position, you would also leverage feelings of personal attachment and guilt to keep your job. They will likely do the same, and providing advance warning will only make it worse.

4. Be honest and transparent

This is where things get really difficult, because you don’t want to hurt your friend’s feelings. As well, your friend (hopefully) doesn’t want to let you down or lose their job. If you aren’t extremely direct, open and firm, you’re going to find yourself in an argument about how you can make things work. But this isn’t the time for an argument; this is the time for separation.

So, muster up all the courage you have, look directly at your friend and say, “I’m going to be completely honest. This isn’t working out, and I don’t believe we can work together. I’m very sorry, and it hurts me to do this.”

Afterward, you may choose to provide examples and justifications. Give your friend the opportunity to vent, ask questions, and generally be angry. If possible, explain how your own shortcomings have contributed to the situation. But don’t lie or sugarcoat your comments. The correct answer to, “I wasn’t that bad” is not, “I know, I’m just looking for something else.” It’s, “Yes, you were that bad.”

This may seem unduly harsh, but there are only two options from your friend’s perspective. Either a) They couldn’t meet your expectations, or b) You’re a horrible friend who couldn’t give your best friend a break. Trust me, you do not want the latter.

5. Remind your friend that this wasn’t personal

This entire affair means that you must remain dispassionate. It’s a difficult thing to do, but it’s necessary. Once it’s clear that the business relationship has ended, remind your friend that this has nothing to do with your friendship, that you hope you can remain friends, and that you will help them however you can.

Joel Butterly is the co-founder of InGenius Prep, an admissions consulting company.

This article first appeared at BusinessCollective.