A client once said something to me that I hear in different forms all the time.
“I know.”
She knew the price needed to change. She knew the client was getting far more than they were paying for. She knew she couldn’t keep delivering the work the way she had been.
She didn’t need me to tell her any of that. So I didn’t. Instead, I asked her a different question.
“Then what’s making it hard to change?”
And that’s where the real conversation began. Because knowing what makes sense for the business and being willing to act on it are two very different things.
We Don’t Start With the Answer
When someone comes to me with a business problem, it’s tempting to jump straight to the solution.
Raise the price. Change the package. Hire someone. Stop doing the work. Let the client go.
On paper, the answer can look incredibly obvious. But I’m rarely interested in giving someone an answer they already know. I’m interested in understanding why the obvious answer hasn’t happened yet. Because that’s usually where something much more useful is hiding.
Maybe raising the price means having a conversation with a longtime client. Maybe changing the package means taking something away that you’ve always included. Maybe delegating means letting someone else do something differently than you would. Maybe changing a team member’s role means acknowledging that nothing is wrong—and making the change anyway.
Those aren’t information problems. They’re Money Conversations – and more information won’t resolve them.
So Let’s Have the Actual Conversation
This is where working with me can feel a little different. I’m going to ask questions. Not because I’m trying to lead you toward the answer I want. I’m listening for the place where what you know and what you’re doing stop matching.
You might tell me: “I can’t charge that. It only takes me three hours.” And I might ask: What does the amount of time it takes you have to do with the value of what you’ve created?
You might say: “I know this isn’t included, but they’ll be disappointed if I stop doing it.” And I’ll probably want to know: What have you taught the client to expect from you?
Or: “She’s really good at what she does. I can’t justify changing the role.” And I might ask: Why does she have to be bad at the role before you’re allowed to decide the role isn’t what your business needs anymore?
That’s usually the moment the conversation changes. Because we’re no longer talking about the price. Or the package. Or the employee. We’re talking about what the decision means to you.
That’s the Conversation Underneath the Business Problem
There are three Money Conversations happening in every business. One of them is the conversation you have with yourself. And it shows up everywhere.
In the price you can’t quite bring yourself to charge. The boundary you keep moving. The client you continue accommodating. The work you keep doing because you’re faster at it. The role you know needs to change. The investment you keep postponing. The opportunity you aren’t quite ready to say yes to.
Sometimes the decision you’re avoiding is a bad decision. That’s important too. I’m not here to convince you to do something simply because you’re afraid to do it.
But sometimes we’ve looked at the business. We’ve looked at the numbers. We’ve tested the assumptions. And the answer is clear. The business needs something different. Now we have to understand what’s keeping you from giving it what it needs.
I Don’t Want You to Borrow My Confidence
This matters to me. I could tell you what I think you should do. I’ve been looking at businesses and their numbers for a long time. I can usually see patterns quickly. But if you make a difficult decision because I told you to make it, what happens the first time someone pushes back?
What happens when the longtime client says, But you’ve always done that for me? What happens when someone questions the new price? What happens when the employee is disappointed? What happens when the decision gets uncomfortable?
You need more than the right answer. You need to understand why it’s the right answer for your business—and be able to hold it when the decision is tested. That’s the work.
The Goal Isn’t to Make the Discomfort Go Away
I recently had to remind myself of this. Two roles on my own team needed to change. I knew it. The business supported it. And I still didn’t want to do it. There was nothing I could discover in another spreadsheet that was going to make the human part of that decision disappear. I had to have my own Money Conversation.
Could these people be talented and the roles still need to change? Could I value what they had contributed and decide the business needed something different now? Could I allow someone to be disappointed without making their disappointment evidence that I’d made the wrong decision?
Eventually, the answer was yes. Not because the decision became comfortable. Because I became clear about what the discomfort meant—and what it didn’t. That’s an important distinction.
You Don’t Leave the Money Conversation Behind
This is why the Money Conversation isn’t something we solve once and move on from. The business keeps changing.
You raise the price. A client pushes back. You create a new offer. You hire. You reach capacity. You make more money. A bigger opportunity arrives.
And every new level gives you another opportunity to meet the conversation you’re having with money. The goal isn’t to eliminate those conversations. It’s to recognize them. To understand what’s actually happening. And to stop letting an unexamined conversation make business decisions for you.
Because sometimes you really do need more information. Sometimes you need a better strategy. Sometimes the numbers are telling you not to make the move you’re considering. And sometimes you already know.
When that’s true, the work isn’t finding another answer. It’s becoming willing to act on the one you already have.
