From Owner-Led to Manager-Led: Navigating One of the Hardest Shifts in Small Business
From Owner-Led to Manager-Led: Navigating One of the Hardest Shifts in Small Business
It starts out with good intentions.
You’re growing. You’re tired. You want your life back. So, you hire a manager. Finally. Someone to help you carry the load, wrangle the chaos, and bring some structure to your business.
But then things get... weird.
Suddenly, the team that used to look to you for everything is nervous. They’re unsure how to act. Do they go to the manager or to you? The new manager starts making changes. The staff, used to autonomy, start resisting. Tension brews. Your inbox fills up again—not with tasks this time, but complaints.
This is what I call “the awkward middle.”
And it’s completely normal.
The “Manager Wedge” Isn’t a Sign of Failure—It’s a Rite of Passage
A friend of mine (a smart, scrappy business owner with a rock-solid admin team) just went through this. She hired her first manager and was surprised by how rocky the transition felt.
Here’s what was happening:
The team was used to her. Her rhythms, her feedback, her quirks. The new manager—though competent—was different. And different, especially when it comes with change, can feel like a threat.
The employees weren’t being difficult. They were just trying to figure out:
“Where do I fit now?”
“Am I still trusted?”
“Do I have to run everything through this new person?”
And the manager? She was moving fast—probably too fast. But that’s common, too. New managers often feel a lot of pressure to prove themselves. Their instinct is to show results. And fast.
The Owner’s Role in This Moment is Crucial—But Not What You Might Think
Here’s the hard truth I shared with my friend:
If you want your manager to lead, you’ve got to let them.
That doesn’t mean you ghost your team or pretend you don’t care. It means you step back with intention.
If you jump in to mediate every conflict or override every decision, you’re unintentionally training your staff to never go to the manager. And the more that happens, the less credibility your manager has.
It’s like trying to teach your kid to trust a babysitter... while constantly correcting the sitter in front of them.
Eventually, the sitter feels powerless, the kid ignores them, and you’re still the one wiping up spilled juice.
So What Should You Do? Coach Privately, Support Publicly
If your team flags something that concerns you, don’t dismiss it. But don’t immediately call a meeting to hash it all out in front of everyone either.
Instead:
Talk to your manager privately.
Ask her to slow down. Encourage her to take time to observe, to understand how things work today before trying to fix them.Changes that come with the team—through collaboration and listening—will always stick better than changes imposed on them.
Coach the manager on building trust first.
A team is far more likely to follow someone who’s shown they care, who asks good questions, and who respects what’s already working.Reinforce your trust in the manager—publicly.
Your words and actions should consistently point people toward the manager, not back to you. This is how you protect her authority and empower her to lead.
This is the Price of Freedom—and It’s Worth Paying
Hiring a manager is one of the most powerful decisions you can make as a business owner. It’s a step toward getting your time, your creativity, and your sanity back. But it comes with a cost: letting go.
And letting go doesn’t mean abandoning.
It means leading at a different level.
Sometimes that means biting your tongue. Sometimes it means coaching someone behind the scenes. Sometimes it means watching a manager try something you’d do differently—and resisting the urge to fix it.
But over time? It’s how you scale. It’s how you move from doer to builder. From business operator to business owner.
And yes, sometimes that means replacing a manager if they’re not a fit. But don’t pull the plug just because it’s awkward.
Transitions are supposed to be messy. Growth usually is.
