When’s the Right Time to Hire an Operator for Your Business?

Let’s just say it upfront — hiring your first GM or senior operator isn’t something you do just because “you’re supposed to.” It’s a big move. And like any big move in business, timing matters.

If you're running a small to mid-sized business — especially in the trades — and you're thinking about hiring an operator, these are the three questions I walk through with every founder or owner I work with:

1. Can your company afford the role?

This isn’t just a budget question — it’s about capacity.

The real tell? You’re stretched. You’re missing calls, forgetting tasks, losing sleep. You’re the decision-maker, firefighter, and part-time HR manager — and the weight of that is starting to show.

You might not have a clean P&L line that says “Operator Budget,” but your gut’s telling you something’s got to give. You’ve become the bottleneck, and it’s holding your business back.

Hiring an operator isn’t about adding cost — it’s about buying back your time and unblocking your business.

2. Are you ready to spend the money?

This one’s more personal.

You might technically have the funds… but when the offer letter hits your inbox and it’s time to write the check, something tightens up. That’s normal.

I've seen plenty of excited searches hit pause halfway through. Not because the business couldn’t swing it — but because the owner realized they weren’t quite ready. Whether it's timing, headspace, or something deeper, that's an important signal.

And honestly? That’s part of the value I try to bring. Helping you slow down, gut-check the decision, and figure out whether this is a step forward — or a step too soon.

3. Are you ready to let go of control?

This is the hardest question of all — for owners and for me.

Control is what built your business. It’s what got you through tough seasons. And letting go of it — even in small ways — can feel like you’re risking everything you’ve worked for.

But here’s the truth: the same control that helped you grow is the same thing that will eventually cap your growth.

Hiring a true operator means trusting someone else to lead. It means stepping back in certain areas so someone else can step up. That doesn’t mean walking away — it means evolving as a leader.

It’s uncomfortable. It’s vulnerable. And it’s usually the unlock for your next level.

So… when’s the right time?

There’s no perfect answer. But if you’re feeling the stretch, overwhelmed by the day-to-day, and starting to see growth stall out — it’s probably time to start having the conversation.

At Smooth Operators Search, we help owners find operators who get it — folks who can bring order to the chaos without wrecking the culture. And we especially love placing veterans who’ve been there, led teams, and know how to build trust fast.

Thinking about hiring your first GM or ops leader?
Start with these questions.
And if you’re still not sure, I’d be glad to talk it through with you — no pitch, no pressure. Just real talk.