There is a moment in nearly every growing company when loyalty becomes a problem.
It does not arrive dramatically. It arrives quietly, in the form of a leadership team that was perfect for the company two years ago and is now subtly holding it back. The founders see it. The investors see it. The high performers on the team see it. And almost everyone hesitates to name it — because the people in question were there. They were there for the late nights, the near-death moments, the wins that almost did not happen. How do you have an honest conversation about fit with the people who helped you build the thing in the first place?
In Episode 11 of Call to the Bullpen, Clint Overton and Ted Stann took on this exact tension head-on. Their framing is one every founder and CEO should internalize: loyalty is a beautiful instinct, but when it goes unexamined, it becomes a liability.
Where Loyalty in Leadership Comes From
Most early leadership teams form in one of two ways. Either the founders knew each other before starting the business — friends, former colleagues, family members — or they hired their first executives during the survival phase, when speed and trust mattered more than scalability. In both cases, the team is bonded by what Clint called “battle scars and challenges that they’ve kind of merged in together.”
That shared history is genuinely valuable. It produces speed, candor, and a kind of trust that takes years to build from scratch. It is also one of the most common sources of leadership blind spots in growing companies.
As Clint put it, “loyalty creates blindness to a certain degree.” When you like someone, when they have been with you since the beginning, when they had a real hand in getting you from where you were to where you are — it becomes very difficult to evaluate them with the same rigor you would apply to a candidate you were considering today.
The Question Loyalty Quietly Prevents
The healthiest leadership teams ask themselves a recurring question: Are these the right people for where we are going?
Loyalty makes that question almost impossible to ask honestly. The default question becomes a much softer one: Are these the people who got us here? And of course they are. That is precisely why the question is so misleading.
Clint framed the harder version of the question with surgical clarity on the episode: “They were the right people a year ago. Are they still the right people today, a year from now? Are they going to be the right people? Do we have the right positions in the organization to be successful?”
Notice the structure. Three time horizons. Three different answers possible. A leader who only asks the first question — were they the right people? — will always answer yes. A leader who asks all three is doing their actual job.
Loyalty Does Not Have to Mean Termination
One of the most important points Clint made on the episode is also one of the most overlooked: re-evaluating an early team member does not automatically mean letting them go.
In his words, “the question about loyalty doesn’t necessarily mean that you have to eliminate someone from your business, but it may mean they just need to move into a different role.”
This is the move many leaders miss. They treat the situation as binary — keep someone in their current seat or remove them entirely — when the reality is usually more nuanced. The person who was your first VP of Sales when revenue was $2 million may be a phenomenal Director of Strategic Accounts at $20 million. The COO who built your operations from scratch may thrive as the head of a specific function rather than the leader of all of them.
Ted echoed this point later in the episode. When a leader keeps coming back to the CEO for every decision and cannot be coached out of that pattern, they may have hit their personal ceiling in their current role. But, as Ted put it, “that doesn’t mean that we’re going to push them to the side and let them go. It’s they fill a productive role for you and they found the right role.”
The right role. That is the framing that protects both the business and the person.
The Five Signs Loyalty Has Become a Liability
How do you know when loyalty has crossed from asset to liability? A few patterns to watch for:
Decisions stall on a particular leader’s desk. Initiatives slow predictably whenever a specific function gets involved, and the team has quietly learned to route around it.
Strong new hires keep leaving. Talent brought in to elevate the team finds itself blocked by founding-era leaders who are unwilling to evolve.
Feedback about that leader is muted. People who would happily give you direct feedback about anything else go silent when the topic turns to a specific founding executive.
They keep showing up at the same level. A year ago they were operating as a senior individual contributor. Today, despite a bigger title, they are still operating as a senior individual contributor.
You catch yourself defending them more than developing them. When most of your management energy goes into protecting someone’s seat rather than growing their impact, the relationship has shifted from leadership to advocacy.
None of these on their own is a verdict. Together, they are a signal worth paying attention to.
The Founder’s Real Responsibility
The deepest point Clint made in the episode might also be the most uncomfortable. As a leader, your responsibility is not only to the people who helped you build the company. It is, as he listed it, to “the team in its entirety,” to your clients, and “potentially to investors who have invested in your business.”
Loyalty to one early hire is not the same as loyalty to the whole team. Keeping someone in a seat they have outgrown, in fact, is a quiet act of disloyalty to everyone around them — the people whose work is dragged down, the customers who feel the friction, the investors whose returns depend on the company actually scaling, and ultimately the early hire themselves, who is being kept in a role where they will eventually be set up to fail.
The loyal thing — the genuinely loyal thing — is to make sure every person on the team is in a position where they can win.
Doing It With Grace
Handling loyalty transitions well requires a few things most leaders underestimate:
Honest conversations early, not crisis conversations late. The kindest version of this conversation happens when there is still time to find a great-fit role together. The cruelest version happens after a year of avoidance, when both parties are already frustrated.
Clear language about fit, not failure. “This role has outgrown what we both signed up for” is a different conversation than “you are not good enough.” The first is almost always closer to the truth.
Real options, not performative ones. If you are offering an alternative role, it should be a real role with real scope, not a parking-lot title designed to protect feelings while the person edges toward the door.
Outside perspective when you cannot see it clearly. This is one of the most useful applications of an outside advisor or board: someone who can ask the harder questions you cannot ask yourself about people you care about.
The Bottom Line
Loyalty built your team. Loyalty cannot scale your team.
The founders who navigate this well are not the ones who become ruthless. They are the ones who become honest — with themselves first, and then with the people who helped them get here. They recognize that loving the people who built the company with you and ensuring those people are in roles where they can keep winning are two different commitments. The first is automatic. The second takes courage.
If you are sitting with a quiet feeling that one of your early leaders has outgrown — or been outgrown by — their current seat, that feeling is information. It is not disloyalty. It is leadership.
Inspired by Episode 11 of Call to the Bullpen with Clint Overton and Ted Stann. Visit boardroombullpen.com and themercurycollective.com for more.