Hey, it’s Aaron. I’m super excited this month, because on Wednesday the 28th, I’ll be stepping onto the stage for the unveiling of MeetingOS, the AI platform I’ve been building to transform every meeting into a decisive moment.

Watching this product come together in these last couple of weeks has been thrilling — it has truly become my brilliant meeting strategist, superhuman memory, and hyper-intelligent Chief of Staff. I rely on it for every meeting I walk into, and it dramatically increases the chance we understand exactly what decision we need to make, and helps me turn that decision into action afterward.

We are in a mad-dash sprint for these last 16 days, working to smooth out the final features, tune the AI models, sand off the edges, and be ready for the big day.

I’d LOVE for every one of my friends on this email to join us for the livestream event. (Or if you’re local to Boise, come join us in person!) It’ll be Wednesday, January 28 at 9am Pacific / 12pm Eastern, and you can grab your seat here.

This month, I’ve got an essay for you on the challenging subject of only keeping the best business athletes on your team. What happens when that person who used to be a strong player for your company just isn’t able to fulfill their role on the team any longer? It happens, and we’ll talk about how to manage it.

Welcome again to all the new folks! I love hearing from you, so send back questions, thoughts, ideas, or just a hello any time by hitting reply.

Remember, great leadership is contagious. Thanks for being here.

Talent on the Prowl

Before we get to this month’s essay, I love helping connect great people with great opportunities. If you’re looking for talent, here’s a few people to keep in mind.

• A friend who is a fintech founder / operator is exploring his next role. He spent 25+ years scaling profitable, regulated fintech and SaaS companies with two successful exits. I think he’d be a super valuable accelerator to a growing company who needs to bring in that senior leader to help with business development, operations, and contribute to strategy as a plus.

• Another friend would bring energy and dynamism to your team and her expertise spans from executive assistant to people operations to running events. I’d love to hire her myself, but don’t have a seat at the moment. Snag her before she’s taken!

• And one more friend has years of experience in both sales and revenue operations, building out CRM implementations, connecting quote-to-cash systems, building out data analytics, and supporting sales teams and sales leaders.

• And then a reverse talent search — I have a friend who is a wealthtech CEO on the prowl for product marketing and/or content writing talent. That’s right, in the age of AI, this CEO is smart enough to know you need a great person to be empowered by the AI, you can’t just be a slop machine on your own. 😂 

If you want an intro to any of these folks, hit reply and tell me “intro to fintech founder,” “intro to EA/ops,” “intro to revenue ops”, or “product marketing opportunity” and I’ll make it happen!

Okay…on to this month’s essay!

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.

Great Reads / Listens of the Month

A few of the great articles or podcasts I’ve read this month…

• A16Z: The Power Brokers. Packy McCormick writes a deeply researched profile of Andreessen Horowitz, the powerhouse venture capital firm that has raised 18% of recent venture capital dollars.

• Nvidia vs. Google, Scaling Laws, and the Economics of AI. One of the smartest investors in AI is Gavin Baker, and this podcast is an entertaining listen. Colossus also posts highly-readable transcripts, so it’s worth the read if you’re not a podcast person.

If you have a suggestion for a great read or listen of the month, hit reply and let me know — if I love it, I’ll give you credit in next month’s email!

If I can help, let me know.

That’s it for this month! As a reminder, I am coaching five CEOs or leadership teams. That’s all I have time for, but I’m having fun doing it, and it’s allowing me not to pay myself a lot from the new company while we are in the build phase. 😉 

I don’t think I could have been nearly as effective for my team without the help of a CEO coach. There’s just something about having someone who has walked that journey before as a “safe” sounding board who you can speak freely to.

At the moment, I have one coaching slot open, and given how busy January was going to be, I decided not to fill it immediately. I will start chatting with potential candidates in early February. If you want to discuss, click here to learn more about my approach, and hit reply if you’d like to talk about it.