Leadership Insight

The Question That Changed the Conversation

May 1, 2025

Brandon had a problem.

He owned a small HVAC business. The work was there and the invoices had gone out, but too many were still unpaid.

So the question seemed obvious:

How do I get people to pay me?

It was a reasonable question.

It was also keeping us focused on the wrong problem.

A few days earlier, Brandon had repaired our air conditioner. My husband and I were ready to pay him. We were trying to pay him.

But he couldn't take our credit card from his phone.

That small detail changed the conversation.

What if the problem wasn't simply that people weren't paying?

What if some of them were ready to pay, but something was getting in the way?

The question became:

How could you make it easier for people to pay you?

Suddenly, different possibilities appeared.

Payment links. Mobile credit card processing. Automatic reminders. Even tools he might already have but wasn't using.

Nothing about the underlying situation had changed.

The question had.

Good collections aren't really about collecting money. They're about removing whatever is preventing payment.

And that's when this stopped being just a conversation about collections.

It became a leadership lesson.

We often begin solving a problem the way it was first presented to us. Then we work harder at finding an answer without stopping to ask whether we're solving the right problem.

Sometimes the most useful thing a leader can do isn't provide another answer.

It's notice something that doesn't quite fit.
Listen a little longer.
And ask the question that helps people see the situation differently.

The answer may have been there all along.

We just needed a better question to see it.

SOMETHING TO NOTICE

Think about a problem you're working hard to solve. What might become possible if you changed the question?

Every good insight deserves a conversation.
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