When to let somebody from your team go is always going to be a key issue for any leader. It's always going to be a sensitive issue for any manager. There will always be the two questions that every boss has regarding this dicey issue: "Do I give them some more rope and latitude to see if they can improve? Or am I at the point where I realize that their performance is not going to be able to get up to an acceptable measure, and I need to let them go?"

I have wrestled with this many times over the last several years, even decades, and it is one of the hardest things to ascertain. Let me put it this way: It is an absolute tightrope that you are walking trying to find the perfect balance when to make this decision…Do they stay, or do I liberate them and let them move on to something else that's better for them?  

It's crazy hard to figure this out, and it's crazy important. Lives are being impacted. The person in question – their life will be heavily impacted. And not just the direct report in question but an entire team will also be impacted. Because it only takes one person to change a team dynamic when they join the group, and it only takes the removal of one person to change the dynamic of a group. That's the impact that one person has. Said more bluntly, if you remove somebody too early, it can really do a number on everybody else on the team, knowing that they now have to pick up the slack for the open gap with one less teammate. Conversely, if you keep the sub-performer around too long, it can be toxic to the team.

It's a balancing act. And guess what? You're never going to get it perfect. You're never going to walk that tightrope perfectly. Ever. It's impossible. I've yet to do this perfectly. I have yet to see it executed perfectly by somebody else.  

I have often made the mistake of letting somebody go too early. When I was a dominating leader, I would discard people when I felt like they were given at least a couple of chances, but the truth is that I fired them too quickly. I look back on that with regret. I've reached out to people and apologized for how fast I was to move them off the team. If I could have a do-over, I would.

I've also made the other mistake of letting people go too late. They've stayed on the team way longer than they should have. They create toxicity on the team because everybody else is wondering, "When's Doug going to let him go? This person is sabotaging the team; he's cancerous to this culture; it's way overdue to let him go." But I kept them on way longer than I should have. This is when I was in the overprotecting mode (where I overly supported people but didn't really challenge them). Here, as well, I owed some apologies. This time, however, the apologies were to the team for not acting with courage and decisiveness sooner. I had to go and say, "I'm sorry, I didn't get that right. I waited too long."

Again, I come back to the point that you're always going to err on one side or the other. It's a tightrope that you are going to fall off of, either to let someone go too early, or too late. No one is ever going to get it perfect.

So, which side should you err on?

Consider all of the books or movies where you are rooting against the boss, or coach, or leader who's making everything about dollars, touchdowns, and outcomes – don't you love rooting against that person? You end up cheering on the underdog, who is more human, personable, and kind. Right? Every time.

Those books, movies, and documentaries have such a big following because it resonates that there's something bigger and better than all of those data points I just mentioned. People are more important than things. People are more important than dollars, touchdowns, and outcomes.

Consider yourself as a leader. Do a self-audit and look at yourself in the mirror. Any time you have discarded somebody or turned somebody into a pawn, you deeply regret it. There's probably some residual guilt that you have. That's because it's just not right.

People are more important than data points, profit, KPIs, touchdowns, and outcomes.  

All this to say, you're not going to walk the tightrope perfectly. So if you're not going to walk it perfectly, lean (slightly) on the side of holding onto somebody too long, and don't be somebody who discards people too early. I've done it. I regretted it. Yes, I regret holding onto somebody too long, as well. However, if my hypothesis is correct that you will never get this just right, fall to the side of keeping somebody too long.

What's the value of this? The value is giving yourself grace. Yes, give yourself grace. You need to give yourself a little bit of latitude to mess this up, but you are going to mess it up and keep someone maybe just a bit too long on your team. There's another value point in this formula. Another point around grace. And that is, you want to extend some extra grace to the person that works for you. You want to be the leader who gives grace to the person who's tripped over themself at least a couple of times, maybe giving them one or two more chances to trip over themselves again. You've coached them, poured into them, and given them more latitude than they deserve. You should. That's being a liberating leader fighting for your people's highest possible good.

And then, it becomes clear that you need to let them go. Yes, you probably should have let them go a week earlier, or a month earlier, or a quarter earlier; but if you're not going to get this perfect, lean on the side of the person, lean on grace.

So here's the question when you look at your leadership and how you manage challenging direct reports: Do you tend to let them go too early, or do you tend to let them go too late?