Is Your Team Push You?

His insight hit deep: owners need a team that pushes them not a team they are pushing.

One of the ways this happens is by promoting too many leaders from within into roles neither the owner nor the employee know how to do. For example, you’re a sales-driven owner who moved your loyal operations person into HR.

How do you coach someone in areas you've never mastered?

You can't. And that's killing your growth.

We love the people who built this thing with us. Believe me, I’ve been there. They took the early risk. Worked the long hours. Believed when nobody else did.

So when we need a VP of Sales or Head of Operations, we promote from within. Loyalty over competence. Heart over capability.

Big mistake.

Those foxhole mates who were perfect for a $500K business often become blockers at $2M+. The skills that got you here won't get you there.

Here's how you know you have the wrong person in a leadership role:

You're constantly driving strategy for their department.

Good leaders drive YOU. They come to you with solutions, not problems. They present options, not questions. They own their domain so completely that you learn from them.

If you find yourself coaching instead of being coached, micromanaging instead of being updated, explaining instead of being educated—you need a better person.

I see owners try to solve this by reassigning struggling leaders to "find their right fit."

This almost never works longterm.

You're just moving someone who knows they failed into a new position. Now you have a disgruntled employee who's defensive, unmotivated, and probably sharing their frustrations with other team members.

The kind thing—for them and for you—is to help them move on. Give them a great reference for a role that fits their experience level somewhere else.

Keeping them is damaging: to them, to your team, and to your business.

You need experienced leaders for roles outside your expertise. People who've run sales teams before. Built operations systems before. Managed HR challenges before.

Yes, they cost more upfront. Yes, they don't have the emotional connection to your early journey.

But they'll drive results instead of requiring constant management. They'll teach you instead of needing constant teaching.

As you grow your business, you need to add these leaders one at time. Your business will tell you where to invest. There’ll be chaos there and no one will know exactly what to do.

Don’t fall for the trap of trying to bring a bunch of leaders at once either. That causes its own chaos.

Look at your leadership team right now. Who are you constantly coaching instead of learning from?

That's your answer.

The loyalty you feel toward your early team is admirable. The growth you're sacrificing to maintain it isn't sustainable.

Schedule that conversation this week. Your business—and honestly, they—deserve better than a role that's too big for their current capabilities.

Alan

The hardest thing about hard things isn't the business challenges. It's making tough people decisions with people you care about. But that's what separates owners who grow from owners who stay stuck.