When your team drops the ball (and why it’s not always a bad thing): lessons from a $5000 mistake

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A few years ago, I found a mistake in a client’s business: a coaching client of hers hadn’t been invoiced in four months.

Four. Months.

She’d been receiving ongoing support—without paying a single invoice. Thousands of dollars in revenue, just… missed.

I still remember the exact moment I realized it. The pit in my stomach. That internal scramble of how did this happen? and what do I do next?

Here’s the thing: technically, I could have just started invoicing her again and moved on. My client might never have noticed.

But I brought it up. Not because it was easy, but because we had built a solid foundation of trust. I knew she valued transparency. I also knew that owning the mistake was the only way to actually prevent it from happening again.

And here’s what happened next:

She didn’t lash out. She didn’t make me feel guilty. In fact, she didn’t make it about me at all.

Yes, she was frustrated (who wouldn’t be?!). But she chose in that moment to stay grounded and made it clear that her frustration was with the situation, not with me personally.

She reminded me that while I was in charge of invoicing, she also could’ve caught it earlier if she’d been reviewing her numbers more closely. She didn’t treat me like someone who had failed her—she treated me like a partner in the business, someone she trusted to work with her to solve the problem.

That moment—and her response—only strengthened our working relationship, and I am so grateful to her for how she handled the situation.

Because when mistakes happen (and they will happen), how you move through them together shapes the kind of team culture you’re building.

For me, it deepened my investment in the business. It built more trust—on both sides. And it led us to streamline our systems even further, clean up client management workflows, and make the business more efficient overall.

Here’s why I’m telling you this:

When your team drops the ball, I promise you—they feel it. (I felt awful when this happened.) The real opportunity is in how you respond. By choosing to separate the mistake from the person and reacting calmly rather than out of frustration, you create an environment where mistakes become a catalyst for building something better.

So the next time your team member makes a mistake (because they’re human and they will), consider how that moment might actually be an opportunity.

To build more trust.
To open up better communication.
To tighten your systems.
To make the business stronger in the long run.

Because empowered teams aren’t perfect—they’re practiced. And how you handle those imperfect moments? That’s what turns them into real partners in your business.