How to Fire Someone

Andrea Sharfin Friedenson
5 min readMay 26, 2015

It’s the sh*ttiest part of any job, but it has to happen. Here’s how to do it well.

I’ve been watching Sam Altman’s class on How to Start a Startup. In it, one of the teachers says that you’re not really a founder until you’ve had to fire someone.

That’s because firing people is one of the hardest things you’ll have to do in any managerial role. It’s especially so for founders because they often don’t have the same resources to which managers at larger companies have access. Regardless, firing someone is emotionally draining for you and the other person.

I’ve unfortunately had to fire several people. Here’s what I’ve learned:

Take Ownership and Forgive Yourself

Face it: you are partly responsible for your employee’s non-performance. You picked the wrong person, or you didn’t provide enough guidance to help them be successful. Their failure is your failure.

Accept it, learn from it so it won’t happen again, and move on. You’re going to need to be mentally strong for this process; and that requires forgiving yourself for this mistake.

Do It With Respect

You have limited bandwidth, so you may consider taking shortcuts when it comes to firing someone. After all, you should spend the majority of your time focused on your star performers, not those who are struggling.

However, very few things show character like treating people with respect when they have limited social status. Someone who’s getting fired is as low on the totem pole as you can go.

Do it the right way, if only because the rest of the organization will be watching as you handle it.

Take Action Early

People generally know when you’re not happy with them, whether or not you’ve had direct conversations about it.

They’ve noticed that you seem unhappy around them. They’ve noticed that you’re spending less time with them than you used to. They’ve noticed that you’re no longer taking an interest in their work.

Don’t leave them in limbo. Have a direct conversation about performance so they know where they stand. If you need to take immediate action from that conversation, do so.

Communicate

The startup mantra is “hire fast, fire fast.” I have fired people on the spot before, when their performance was so poor or behavior so egregious that it would have damaged the productivity of the rest of the team to let them stay on.

However, in other situations, coaching someone has proven to be the best course. Have an initial conversation about their behavior. If the problem is performance, talk to them about their OKRs. Are they living up to them? If the problem is attitude, talk to them about the company’s values. Does the employee feel that they’re living those?

Once you get them talking and agreeing with you that their performance or attitude is not meeting their own standards, schedule a follow-up conversation in a few weeks’ time to give them time to change.

Some people will adjust; in those people you have a valuable employee who has proved they can learn.

Some people won’t, and of those, a majority will agree with you that it’s just not working out, and will quietly move on. A minority will take the negative feedback poorly, and those you can quickly let go.

Decide on an Appropriate Timeline

Firing someone is emotional, but it doesn’t have to be traumatizing. One of the major factors that can make firing someone go more smoothly is to figure out the right timeline for helping the employee move on.

I’ve seen everything from the 1-second-wait-here-while-I-get-security-to-escort-you-out timeline resulting from legal transgressions; to a protracted exit over years for a founder who just wasn’t a fit for the next stage of the company.

So how do you make the decision regarding what’s right for your organization?

Here are some criteria that I’ve found helpful:

  • Seriousness of the Problem: How bad is their behavior? If this person has committed some serious HR violations (harassment, etc.), has stolen from the company, or done anything illegal, they have to go as soon as you find out. If they are merely under-performing, consider the following.
  • Money: How early stage are you? If you’re pre-Series-B or unprofitable, you’re probably still early enough that every second of salary counts, so let people go as soon as possible. If you’re later stage, let the person leave with their dignity. Tell them you’ll keep them on payroll for a month or two, but they should take time away from the office and use it to focus on finding something new.
  • Maturity: Can you count on this person not to engage in behaviors that will undermine the company — i.e., stealing company IP, making threats, gossiping to coworkers, making a scene? If they have a history of acting out, then it’s best to have them leave immediately to avoid disrupting the rest of the team. If you can trust them to act with the company’s best interests in mind, then you should reciprocate that level of maturity by letting them help you shape their exit.
  • Personal Relationship: Is this someone you’ve known for a long time? A friend, a family member, or a former coworker you brought in personally? Your first responsibility is to do the right thing for the company, and your second responsibility is to preserve the relationship. Talk to them openly and honestly about the issue and allow them some time to make a clean break.
  • Seniority: How well-connected is this person? The more influential they are, the more important it is to part amicably. Negotiate a mutually beneficial schedule for them and the company so you part ways saying nice things about each other.

Do It In Person

Always fire people face-to-face, with a third party present. I’ve been pressured to fire remote employees over the phone, or on Skype, and I’ve refused. This is about to be one of the worst days of this person’s life. The least you can do is to address them in person.

The third party is there for your protection. It’s an emotional time for the person being fired, and regrettably, some people lie about what happens behind closed doors.

The third-party should be someone from HR, but if you’re part of a smaller startup or a satellite office without an HR department deputize someone on your team who is known to be mature enough and senior enough within the organization to sit with you and the other employee while you go through the firing process.

Make sure that the fired employee knows that the third party will preserve their privacy and not discuss their firing with coworkers.

The fact is that we live and work in a litigious society. You should always have a witness.

Be Your Best Self

You may be tempted to show your anger or disappointment with this person. They haven’t performed; maybe you feel they’ve held the team back, or damaged the company in some way.

Do not show it. Now is the time for professionalism, not emotion. Treat them with kindness and empathy. They will be judging you, and word will spread.

Firing people is hard, but it’s sometimes necessary. The better you get at it, the more people will see you as a worthy leader, and the stronger your company will be.

Click Recommend if you liked this article. Questions, comments? Let’s talk. Tweet me: @asharfin.

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Andrea Sharfin Friedenson

Formerly marketing @ MSFT, Facebook, Disney. Cornell AB, MIT MBA. Occasional stand-up comedienne. Into mentorship, leadership, and writing.