michael
THE 5 MINUTE FRACTIONAL CFO

160. You Trained Them!

Aug 29, 2026

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160. You Trained Them!

Aug 29, 2026

It's 9:47 on a Tuesday night. Your phone buzzes.

"Hey! Quick question about the AP aging report..."

You look at it. You know the answer. It'll take you 90 seconds. And honestly, it feels kinda cool to be the person who knows, so you type it out and hit send.

He replies with a πŸ‘

That's it. That's the whole story. 90 seconds, one thumbs up emoji, everybody's happy.

Except you just taught him something and he was paying VERY close attention.

Last week we talked about scope of work, which is what you agreed to deliver. This week is about what happens after the agreement, which is a completely different animal and, if I'm being honest, the one that got me worse.

Why you ask?
Because, yes, I had a decent scope on paper. What I didn't have was the discipline to hold the line on the scope when actual clients started pushing boundaries.

Let's dive in.

The One Tip: You Are Setting Boundaries Right Now, Whether You Meant To or Not

Here's the brutal thing about boundaries.

You don't set them in the kickoff call. You don't set them in the engagement letter. You set them at 9:47pm on that Tuesday, in the 90 seconds it takes you to decide whether to answer.

Every single one of your boundaries got established that way. By accident. On some random weeknight, in that split second where answering the text felt easier and kinder (and frankly more fun!) than holding off until working hours.

And then it became the expectation.

Dang it, precedents

Here are the three parts of this that took me way too long to understand.

1. Every Exception Becomes the Baseline

Say yes once and it's a favor. Say yes twice and it's a pattern. Say yes three times and it isn't a favor anymore, it's the new standard.

Your client experiences this differently than you do. To you, that AP question was a one off. To him, it was a data point about how this relationship works.

You are available at night. Sweet!

He isn't scheming. That's the part firm owners get wrong when they start resenting clients. He's not sitting there plotting to extract free labor. He just learned a fact about you and people act on facts.

Two months later he texts you at 10:10am on a Saturday about something that takes 40 minutes, and you feel that flash of irritation, and the irritation is aimed at the wrong person.

YOU published your updated working hours a couple weeks ago. He's just following your lead.

2. You Trained Every One of Them

Every boundary problem I've ever had with a client, I built myself. Every. Single. One. The client who called instead of emailing, the one who added a project mid-month and assumed it was included, the one who treated our monthly call as the place to hand me a to-do list.

I taught all of them. And I taught them while feeling great about it, because in the moment it looked a lot like excellent customer service.

That's what makes this so hard to catch. Bad habits usually feel bad. This one feels like being helpful, which is the exact quality that made you good enough at this whole Fractional CFO thing to have clients in the first place!

Being helpful is not the problem. Being helpful with no boundaries is the problem, because a service with no boundaries isn't great service. It's an open bar tab, and eventually somebody has to pay it, and it's going to be you at night and on the weekends for the rest of your relationship with the client.

No thank you.

 

3. Resetting Costs More Than Setting

So why don't you fix it?

Because setting a boundary on day one is free but resetting one 18 months in feels like you're taking something away.

That's not just a feeling, either. It genuinely IS taking something away. He's had night access for a year and a half. Now he doesn't. From where he's sitting, things got worse.

Which is why most firm owners just don't. They eat it. They keep sucking it up until they're so fried that they blow the whole thing up (this is a bad thing) usually over something small, and now there's a huge problem where there used to be a fixable one.

Here's the reframe that finally got me to do it.

You are not taking something away from him. You are correcting something you gave him by accident, that he never asked for, that isn't in what he's paying for, and that is making you worse at the job he hired you to do.

And, if I'm being honest, the conversation is probably not as big of a deal as you think it is.

You are dreading a fight that legit never happens. In my experience the client says some version of "OMGosh, I'm so sorry! I didn't realize I was doing that. No problem. Won't happen again." and adjusts.

The dread is doing far more damage than the conversation ever will.

Pro tip: reset it with a reason attached to their outcome and not your inconvenience. "Hey. Great questions. I'm going to handle them (insert how you're supposed to answer client questions here) so you get a proper answer instead of a text message answer" lands about a thousand times better than "Knock it off! I need my evenings back!" even though both are completely legit.

Your Challenge This Week

Write down the last 5 things you did for a client that weren't in your scope of work.

If you did the exercise from last week, you have the page to check against. If you didn't, do that one first, because this exercise doesn't work without it.

Now for the harder part.

Put a name next to each of those 5. Then put a date on your calendar (this week!), for a conversation with each of those people.

That's the assignment.

You already know how the conversations go. You're going to dread all 5 and then discover somewhere around the second one that nobody is actually upset about it.

PS - if the idea of having those conversations makes you want to close this email and go do something else, pay attention to that! 

That reaction is the reason there's a problem in the first place and it's a heck of a lot cheaper to deal with it this week than it is 18 months from now when you're fried and the conversation becomes a reason for churn instead of a reset.

You trained them.

Which is the good news, because it means you're the one that can REtrain them.

Your coach,
Michael

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