The Leadership Shift: When the People Who Got You Here Can’t Get You There
This is the blog post I almost didn’t write.
Not because the topic isn’t important — it’s one of the most important leadership lessons I’ve learned. But because it’s personal. It involves real decisions about real people who gave you everything they had during the hardest chapter of your company. And now you’re sitting across from them realizing…they’re not the right person for where the company needs to go next.
That moment is brutal. And if you haven’t faced it yet, you will.
The Moment You Know
It doesn’t hit you all at once. It’s gradual. You start noticing that the person who was incredible at getting the first 50 clients is struggling to manage a team of 20. The scrappy operator who could do everything themselves can’t build systems for others to follow. The loyal early employee who “figured it out as they went” is now a bottleneck because the company needs someone who’s done this at scale before.
I went through this at Outsource Access. Multiple times. We grew from a handful of people to 500+ team members. We hit Inc. 5000 at #326. And along the way, some of the people who were absolutely essential to our early success reached a ceiling — not because they weren’t talented, but because the job changed underneath them.
The company they joined wasn’t the company we became. And the role they were hired for no longer existed.
Why Founders Avoid This
Most founders delay this decision far too long. I know I did.
You feel loyalty. You should — those people bet on you when your company was nothing but a pitch deck and a prayer. They worked weekends. They covered gaps. They believed in you before there was any reason to.
So you make excuses. “They’ll grow into it.” “I just need to give them more time.” “Maybe if I send them to a training…” And six months later, the problem is worse, the team around them is frustrated, and you’ve lost time you can’t get back.
Here’s the hard truth: loyalty is a reason to handle this with integrity. It is not a reason to avoid handling it at all. In fact, keeping someone in a role they can’t succeed in isn’t loyalty…it’s cruelty dressed up as kindness.
The Jim Collins Framework
Jim Collins talks about getting the right people on the bus, in the right seats. That concept changed how I think about team building.
The mistake most founders make is assuming “right person” is a permanent label. It’s not. Someone can be absolutely the right person for stage one of your company and the wrong person for stage three. That doesn’t make them a bad employee. It makes them a stage-one superstar who needs a stage-one company.
The bus metaphor is useful because it separates the person from the seat. Maybe they’re still on the bus…just in a different seat. Maybe the seat they were in needs someone with a different skill set. The question isn’t “is this person good?” The question is “does this person have the specific capabilities this seat requires at this stage of our growth?”
When you frame it that way, it stops being personal. It’s not about the person failing. It’s about the role evolving beyond what any single person should be expected to adapt to without support.
How to Handle It with Integrity
There are three paths, and I’ve walked all of them.
Path 1: Invest in upskilling. Before you move anyone out of a role, ask yourself honestly — did you give them the tools to succeed at the next level? Did you provide training? Mentorship? Clear expectations for what “good” looks like at this stage? If you threw someone into a scaled-up role without support and they struggled…that’s on you, not them. Invest first. Always.
Path 2: Create a new role. Sometimes the person is incredible at a specific thing but the role has expanded beyond that thing. The solution isn’t to lose them — it’s to carve out a role that leverages their superpower. The scrappy operator who can’t manage 20 people? Maybe they become your special projects lead. The relationship builder who isn’t detail-oriented enough for operations? Maybe they move to business development. Don’t force a square peg into a round hole when you could just build a square hole.
Path 3: Have the honest conversation. Sometimes paths 1 and 2 don’t work. The person genuinely doesn’t have the capability for what the company needs, and there isn’t a role that fits. That’s when you sit down and have the hardest conversation in leadership.
Here’s how I approach it: with honesty, gratitude, and a commitment to their landing. You tell them what they meant to the company during the stage they were part of. You’re specific about it — not platitudes. You explain that the role has evolved and what it now requires. You give them time, support, and a genuine reference. And you help them find their next thing if you can.
What you don’t do is blindside them. If this is truly the first time they’re hearing there’s an issue, you failed as a leader long before this conversation.
The Conversations No One Talks About
The leadership books make this sound clean. It’s not.
I’ve had these conversations with people I genuinely cared about. People who came to my wedding. People who helped build something from nothing. And telling them that the something we built together now needs something different…that’s a kind of pain that doesn’t show up on an org chart.
But here’s what I’ve learned: the people who are genuinely good — the ones you’re most worried about having this conversation with — usually already know. They feel it. They know they’re struggling. They’re staying late trying to keep up and wondering why it’s not working anymore. And more often than not, the honest conversation is a relief for both of you.
The ones who don’t see it coming? That’s usually a sign that the feedback loop was broken long before the conversation happened.
Building for the Next Stage
After you navigate the shift, the next question is: who do you need now?
At OA, I learned to hire for the stage we were entering, not the stage we were in. That means bringing in people who have already operated at the scale you’re heading toward. People who’ve managed 200 when you have 100. People who’ve built the systems you need before you realize you need them.
This is uncomfortable for founders because those people are expensive. They push back on your ideas. They tell you things you don’t want to hear. And they don’t have the emotional attachment to “how we’ve always done it” that makes early team members so loyal and so limited at the same time.
But that discomfort is the price of growth. And it’s worth paying.
The Lesson I Keep Learning
I wish I could tell you I got this right every time. I didn’t. I held on too long in some cases and moved too fast in others. But the principle I keep coming back to is this: the best thing you can do for someone is put them in a position where they can succeed.
If that position is at your company in a new role…great. If it’s at another company where their skills are exactly what’s needed…that’s great too. What’s not great is leaving them in a role where they’re drowning while you pretend not to notice because the alternative is a hard conversation.
Leadership isn’t about avoiding hard conversations. It’s about having them with enough care that the person on the other side walks out with their dignity intact and a clear path forward.
Want the Full Framework?
My book “Automate and Delegate” goes deep on building teams that scale — including how to know when you’ve outgrown your current structure, how to design roles for the next stage, and how to have the conversations that make or break your culture. It launches May 30, 2026. Pre-order here.
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