Keeping Only the Best Athletes on Our Team
I remember the first time I realized that someone I had thought of as a “franchise player” had become a bad fit for the team.
Not a low performer who was screwing up and entitled. Not someone who had taken more than they had contributed. Not someone who was dragging everyone down.
This was someone I genuinely liked. Someone I trusted. Someone who had done the kind of work that ends up woven into the origin story of the company. The kind of teammate you thank in the victory speech.
And then one day, in a meeting that wasn’t supposed to be dramatic at all, it hit me: the role had changed so much that we were basically asking this person to play a different sport.
It wasn’t that they’d gotten worse.
The league had gotten harder.
You can define what it takes to be a major league baseball player, or a NFL quarterback, or a NBA point guard, and that definition might change a little bit but it will stay relatively stable.
High-growth companies, on the other hand, are rapidly changing the game they are playing every quarter. Over the course of a year or two, that person who was truly an elite business athlete can turn into someone who is severely underperforming in their role — a person who simply doesn’t have the right fit between their talents / skills / aspirations, and what the company needs next.
If you lead long enough in a growing organization, you will face this. And if you care about your people and your mission, you cannot outsource the decision to time, hope, or “maybe it’ll sort itself out.”
It won’t.
“We’re a family” breaks right here
I’ve heard people apply the “family” analogy to businesses a thousand times. Heaven knows, I’ve probably done it too.
I get what people mean. The best workplaces create deep relationships. You’re there when they meet spouses, or welcome a new child, or go through losing a loved one.
But businesses aren’t families in one critical way — you don’t fire your little brother when he screws up for the tenth time.
Ultimately, any growth business has to behave a lot more like a professional sports team. Baseball is still my favorite model for this, because baseball forces you to respect specialization, performance, and the brutal reality that the team needs every position to produce.
A winning team needs contributions from every spot on the roster. Unlike baseball, the “game” of a growth company is changing so rapidly, it’s as if the caliber of player you need in order to compete for a championship is rising every single month.
In the early days of that business, you need utility players — people who can do a little of everything, sprint all day, and tolerate chaos.
Later, you need specialists.
Later still, you need leaders who can build machines: process, systems, coaching, recruiting pipelines, decision frameworks, accountability rhythms.
Many of your people will make that transition. But many of them can’t, or simply don’t want to.
They helped you win a lot of games. But what you need in the future is very different from what you needed in the past.
Loyalty is powerful — but it can kill both of you
This is where leadership gets emotional, and hard. We all feel a sense of loyalty to teammates who worked hard, stayed late, sacrificed, and gave it their all.
Sometimes they were there before the product worked. Before the fundraising was easy. Before the world believed.
So when you feel the fit slipping, your brain starts doing somersaults to avoid the pain:
- You tell yourself they just need a little more time.
- You tell yourself the role can be reshaped.
- You tell yourself you can “coach them up” if you just invest a few more months.
But deep in your heart of hearts, you know those ideas are just a band-aid that is covering up the real problem.
Here’s the uncomfortable truth: when you keep someone in a role that no longer fits them, you don’t just harm the business. You don’t just harm the rest of the team. You also harm that person.
They’re spending valuable career time building a record of mediocre performance or failure, when they could be in a role where they can thrive and succeed.
If you have any kind of performance bonuses or sales commissions, that person is chewing up a finite amount of “prime earning years” with underperformance that could have a long-term effect on their ability to retire, or help their kids succeed.
Great coaches see the truth through the emotion, and ask the question: “how can I help this person get into the right role that supports their career, while ensuring that I get an elite business athlete into that position on my roster?”
Pitchers never take themselves off the mound
The other trap is thinking the employee will “figure it out.”
They won’t.
It is extremely rare for someone to volunteer that the fit has passed them by. Pitchers almost never take themselves off the mound. That’s not how competitors are wired.
And they won’t take hints either.
A lot of leaders think they are being kind when they try to send indirect messages. They stop inviting the person to meetings. They slowly reduce their responsibilities. They give vague feedback. They hope the person will get uncomfortable enough to quit.
This is like the high school coach who can’t bear to cut someone from the team, so they move their locker next to the bathroom so they will “get the message.”
That’s not kindness — it’s avoidance.
If you’ve ever been cut from a team, you know the best coach isn’t the one who creates maximum discomfort in the hope that you’ll solve their problem for them.
The best coach is the one who walks out to the mound, looks you in the eye, and tells you the truth — calmly, directly, and with respect.
“Thank you for what you did to get us to the seventh inning. I’m pulling you from this game.”
The most helpful thing you can say
When you’re dealing with someone who has been successful at your company in the past, the most helpful thing you can do is communicate the core truth in plain language.
Not legalese. Not the fog of “maybe you’d be happier somewhere else” or “I’ve been thinking maybe we should consider a change.”
Something very concrete, decisive, and clear — like this.
“You have been a great contributor to this team. This is not about your past performance or contributions. What the business needs in the future is simply different than what it has needed in the past. There is a better fit out there for your skills and talents, and that’s why I have to make this change today.”
Don’t negotiate with yourself. Don’t meander. Don’t add disclaimers. Don’t hedge your thinking, or create false hope of changing your mind.
Decisiveness is part of compassion.
Generous severance is the right way to reward great past performance
The other side of the coin is that you should absolutely reward great past performance with generous severance.
The right way is not: “Good luck out there.”
The right way is not: “Here’s two weeks, because that’s what the handbook says.”
The right way is generosity, layered with gratitude for all that person has contributed to your success.
Every company’s finances and budget are different, but here’s my rule of thumb as a baseline — and if you are a strong cash generator, I’d double or triple these numbers in a heartbeat.
- One month of severance is automatic if you’re not fired for cause
- Two months for employees with more than a year of tenure
- Three months for people with exceptional “franchise player” contributions
Again, if you’re generating a lot of cash, I wouldn’t hesitate to make this three, six and nine months. You’ve got the money in the budget, and it’s going to take you some time to replace the position anyway.
This does a few important things.
First, it gives you the courage to act quickly when it’s time to upgrade the person playing that position on your roster. Making this decision six months earlier than you would otherwise saves you six months of wasted salary. Why not invest it in helping that great player land on their feet, and getting your upgrade in place earlier?
Second, it sends a message to the rest of your team. That player did nothing wrong; they contributed well, but the team needed something different from that position in the future. We may be playing to win, but we don’t treat people like disposable parts.
I always offer this kind of severance subject to a standard separation agreement with non-disclosure, non-disparagement, and non-solicitation clauses. If I’m going to spend a bunch of salary to show loyalty to you, I’m asking for you to agree to show loyalty back.
And I always offer the opportunity for positive references and referrals, which in this type of circumstance, I can always do with honesty. It means a lot to tell someone “you’re part of my posse, even if we won’t be on the same roster together.”
That last part really matters. I will go a long way to help people who have made great contributions on my team. Introductions. References. Nudges to a recruiter you know. A thoughtful email to a hiring manager.
These things cost you very little, and it’s a powerful way to show loyalty to people who played hard for your team.
The roster is the job
Here’s what I wish every leader would internalize: your team roster is upstream of almost everything.
Your strategy, your culture, your speed, your innovation, your customer experience — all of it is downstream from who you keep on the field.
So when you avoid making a hard call because you don’t want to feel like the bad guy, you’re not being kind. You’re being selfish. You’re protecting your comfort at the expense of:
- the team that needs elite performance to win,
- the customer who deserves excellence,
- and the person who deserves a role where they can be elite again.
The paradox is that the “nice” leaders are often the ones who create the most pain, because they stretch the inevitable outcome into a long, confusing, and dignity-eroding soap opera.
The best leaders are decisive and clear.
The bottom line?
If you want to build a great company, you have to think like a GM and act like a coach.
Be grateful for franchise players. Celebrate their historic contributions. Tell the stories. Mean it.
And when the chapter changes — when the fit is gone — don’t move their locker next to the bathroom.
Walk out to the mound.
Pull the pitcher.
Tell the truth.
Then do everything you reasonably can to help them find a new team where their talents fit the game they’re being asked to play.
That’s leadership at its best.
