When you should fire someone
If you are a manager of people, there comes a time when you will have to fire somebody. Firing a person sucks. It’s obviously very impactful to the individual that gets fired. It’s painful. It feels like a breach of trust. And really, we should all work really hard to prevent these things from happening.
There is a time and place to discuss how we can prevent having to get to the point, but for the sake of this article, let’s talk about what is the moment that you should part ways.
You’re never too early
A mentor once told me that no founder has ever said, “Oh, I fired that person too early.” And I have to say that I agree with this. This may sound harsh, but if you’re trying to build a fast-growing company, there’s a point at which you’ll start to feel like a particular person is not well matched to the job that they are doing at that moment.
Whenever that happens, you -as the manager of that person- should be in action mode. You should immediately give the person feedback and help them become better at the job that they have at that very moment.
Be very direct with your feedback. Be very direct with what your expectations are and how they are not aligned with what you’re getting. And work with the person to create a plan to improve this.
If at the earliest hint of underperformance you don’t act on this, you are failing to do an important part of your job. And in retrospect, you will learn that months later after you fired this person or simply feel frustrated with them, that it was not them but you who really failed.
Now if you do this well, then one of two things are going to happen. Either the person is going to improve, do better, and you don’t have to fire them. This should be obvious pretty quickly because if your feedback is direct, clear, and actionable, then that person should be able to meet your expectations in a short period of time.
Now the other outcome is that this person does not improve, and this is where I find that most mistakes are made. If you don’t see clear improvements from somebody that you’ve given very direct feedback, and assuming that you give them feedback about this fact, the path from there to parting ways should be very, very short.
The longer a person who is underperforming at a company, even after feedback, stays at that company, the more damage they do. Their damage might not be actual direct damage, but there’s always a cost to having somebody underperform in a position where you could have somebody who’s performing highly. Let’s call it opportunity cost.
For the individual who is underperforming and has gotten feedback, which can be hard to hear, and still feels like they’re not living up to the job and they continue to get negative feedback about their work performance, this can also be a very frustrating and difficult position. It doesn’t feel good to feel like you’re not living up to expectations.
It’s good to be optimistic and to have confidence and to think that you are doing your best and therefore you have a right to stay. Managers are responsible for ending and employment rather than expecting employees to leave after they’ve gotten some negative feedback.
And so as a manager, this is when you should fire somebody. After clear feedback, multiple times, without seeing sufficient improvement.
This whole process should generally take a number of weeks. Not quarters.
When early is still too late
The above all assume that we are talking about underperformance, which is somebody just not being able to meet the expectations of the job consistently. However, there are moments when you have to fire somebody essentially on the spot (aside from criminal behavior).
When there is a cultural misalignment between somebody and the rest of the organization, this is extremely hard to fix. I would argue you should still give feedback about this, but especially if it’s about interpersonal behavior, it’s very unlikely to shift meaningfully.
And to be very blunt, what I find is that if somebody is an asshole, you should not work with them because they do active damage to your whole organization for every day that they are there.
Unfortunately, you often hear stories about companies or managers using the words cultural misfit or cultural misalignment to fire somebody when really they haven’t done a good job of giving that person feedback. That’s a shame, let’s all try to do better.

