You’re Not Loyal — You’re Stuck
Here’s the Problem:
We all have those people on our team we never really think about.
They’ve been around. They don’t stir the pot. They know the systems (because they built the systems). You tell yourself they’re doing fine—and it feels “loyal” to keep them.
I did this for way too long. I had guys in IT who’d been around forever. I knew them. They knew the ropes. But here’s what I didn’t realize until much later:
I had no idea how far behind we were—because I’d never seen what “better” looked like.
The Fix? Hire Someone Who Knows More Than You.
Eventually, I brought in a new IT leader. Different level. This person had worked at scale. Knew how to ask the right questions. Within two weeks, they started pointing out things we were doing that made no sense.
Things that had been running for years.
They weren’t trying to stir things up—they just genuinely didn’t understand why we were doing stuff the way we were doing it. And once they started showing us a more efficient path? Game over. I couldn’t go back.
Here’s What I Learned:
1. Loyalty Can Be a Crutch
I wasn’t being loyal—I was being passive.
I kept people around because it was easier than having hard conversations. I didn’t want to rock the boat.
But keeping someone in a role they’ve outgrown doesn’t help them or the business. Loyalty should never mean settling.
2. New Blood Exposes Old Problems
When someone new joins the team and starts asking, “Why do we do it like this?”—pay attention. That question is a gift.
In my case, it revealed a bunch of legacy processes that were wildly inefficient. Stuff that took hours could’ve taken minutes. We had entire workflows built around limitations that no longer existed.
We’d just accepted the inefficiency as normal.
3. Tools Don’t Scale Your Company—People Do
Founders love upgrading tools. New CRM. Better dashboard. AI this, AI that.
Cool. But when’s the last time you upgraded your people?
Seriously ask yourself:
Who’s still here because it’s easy?
Who challenges how we work?
If I started from scratch, would I rehire everyone on this team?
Those questions suck—but they matter.
The Bottom Line:
I wasn’t being loyal. I was avoiding change.
And once I saw what a higher-skill person could bring to the table, I felt like an idiot for not doing it sooner.
Don’t wait as long as I did.