I had to fire multiple people when I took over the CEO role at Scribe.

This really upset the co-founders a lot. Even though they eventually realized that these people had to go, they were still pretty emotionally shaken. After all, these were all good people, they were just bad fits with our company. Firing a terrible person is easy, but how do you fire a good person in a way that doesn’t hurt them?

There is a way to do this. Unfortunately I’ve been in management positions long enough that I’ve had to fire so many people, I’ve gotten good at it (if there is such a thing). Over time, I’ve developed a way to fire people that works best for both parties.

And in fact, in this case, it worked very well—four of the five people I fired wrote me emails thanking me afterwards.

Here’s exactly what I did:

  1. Transition from coaching them up, to coaching them out

Before you fire someone you should identify where they’re not performing, show them, set clear objectives, and give them the coaching they need to achieve them.

If you’ve done this, and they nail it, great—you won’t have to fire them.

But, as you’re working through this process, you generally know if they are going to make it or not. If they don’t look like they’re going to make it, then the process to fire them starts then, not later. You start to move from from coaching them up, to coaching them out.

But done right, the processes naturally flow into each other, because they’re both about empathy.

Once you shift to coaching them out, it’s a very delicate series of conversations to get this person to see that they’re not a fit, see why they don’t fit, and where they can’t grow with the company, and maybe see a path for them towards something else.

The first coaching out conversation is diagnosing whether they’re not performing because they’re in the wrong chair.

Ask them, ‘If you could do any job in the company, what would it be?’

If you get a decisive answer, then it’s about understanding if they have the skills for that role, and maybe even testing them in it.

If you get an answer like, ‘I’m not sure’, then go one step further and ask, “If I could create any role you want, what would it be? Describe to me the perfect job for you.”

If they can’t tell you that, then it’s obvious, and not just to you. They’ll start to see this isn’t the place for them.

The best result here is that they describe a job that does fit them really well, but does not exist in your company. Then they not only see that the company isn’t the right place for them, but that a place DOES exist for them somewhere else.

So the real thing you’re trying to understand yourself, and help them to see, is not only are they not performing, but they’re probably not performing for a reason, and so the best thing possible for THEM is to move roles.

  1. Make the dismissal about their dignity and humanity, not corporate HR rules

Once the decision has been made to exit them, it’s time to stop coaching them out, and exit them.

Now you make it completely about them. During the exit conversation, don’t focus on why you’re exiting them; that groundwork has been laid already. Now it’s time to help them.

In the exiting conversation, I don’t focus on the negatives of what they’ve done. We’ve already talked about this over the past few weeks, so why do that? I’ll go over it quickly, and then move on.

I want to focus on the best plan of action for the exit so this person can move on with their life. I want to do right by them.

This also means not talking to them in a dry, corporate, distant style. It means talking to them and like a human, and treating them like someone I know and value and care about.

Big corporations have turned firing conversations into these HR nightmares where they’re afraid to say or do anything. The conversations are so cold and cutthroat, they really dehumanize people. To hell with that. You know this person, they are a good person, treat them like it.

But this also means not pretending everything is fine. It’s not. They’re being exited.

On the startup side, the problem I see is that entrepreneurs let their feelings get in the way of saying what needs to be said. You have to be able to have a straight conversation with someone regarding the stark truth of what’s happening. Candor is a way of being kind, because it’s showing them that you respect them enough to tell them the truth.

And sometimes, this means letting them say goodbye. For many people, if they aren’t a complete ass, you let them say goodbye, especially to the people they were friends with. Especially in startups where some of these folks were key in helping the growth of the company. You let that person save face and exit gracefully. You don’t escort them out with security, like they’re some animal. You treat them with respect by showing them you care about them.

  1. Let them know you will support them, and then actually do it

That final conversation also needs to let them know, very clearly and specifically, what you are going to do to help them now. Remember: for you, this is the end of their tenure at your company. But they’re not dying. For them, this is their life.

First off, I always give the best severance we can. If possible, we like to pay 4 weeks severance. To have a month safety net to find their next opportunity really makes them feel safe and cared for, and they can relax.

Second, I not only tell them I’ll write them a recommendation, I tell them what I’ll say in it. I give them suggestions about what roles to go after, based on our earlier conversations about what they want. I even offer to refer them to places I believe they will be a good fit with.

And most importantly, I tell them that this doesn’t have to be the end of our relationship. I’ll answer any questions, and I’ll give them any advice or help I can. Email me. Call me. Text me. I’m here for you if you need me. And I mean it.

Most don’t take me up on this, but they still appreciate it, because they know it’s real. And they feel valued and cared for, even while being fired.

And this works.

Done correctly, they will learn a lot about themselves, and they will eventually end up in a better place in their life from what they learned from the process, and they will email you and thank you afterwards.

The co-founders never would have believed this was possible until they saw it happen. Five different people sent me thank-you emails after they left. My coaching had helped them see things about themselves, and his candor and kindness had been a real benefit to them.

I am not trying to brag about this. I think for them, they were just happy to be let go with dignity and respect—which is NOT how most places work.

Firing people is never fun, but it can leave everyone better off if it’s done right.


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