How to Turn Client Check-Ins into Money Conversations

Your clients are already planning next year's budget. Here are six questions that put you in that conversation, without feeling pushy.

You're sitting in your client's office for a project check-in. Halfway through, they mention they're starting next year's budget. You nod, finish the project update, shake hands, and leave.

That meeting stayed as a client check-in, instead of turning into a money conversation.

This month, Jim wrote about our color-coded calendar: blue for a client meeting, green for a money conversation with an opportunity in it, yellow for caution or confusion, and red for warnings about losing deals or accounts in jeopardy.

I wanted to talk about one of our most common questions. "How do I turn a blue meeting into a green one?"

Why smart people skip the money question

Most of the professionals I work with know they should ask about the next opportunity, but they skip it anyway. The reasons typically sound the same:

• "I don't want to seem pushy. We have a good relationship."
• "I'm here as the engineer, not the business developer."
• "If they wanted more help, they'd tell me."
• "What if they say no, and it gets awkward?"

Each of those is a confidence problem, and it's common among otherwise smart professionals. The good news is that confidence follows preparation. When you know what you're going to ask and how you'll say it, the question stops feeling like a risk and more like an opportunity to help both parties.

Pick your punch-list item

Every meeting on your calendar should have one thing you're there to get done. Before a blue check-in meeting, decide which type of money conversation you want to have.

Are you there to collect a check, review the project, or talk about next year?

Pick one, and write it in the calendar invite notes so you and your client know that it is coming up on the agenda.

That one line in the invite does most of the preparation. We've written before about why preparation matters when the meeting matters. Clients notice in the best way possible.

Six ways to turn a blue meeting green

You don't need all six. Pick the question that best fits the meeting and the relationship.

1. Set it up at the start. Ask permission early, so the question at the end isn't a surprise. "I want to make sure we cover the project update. If we have a few minutes at the end, I'd like to ask about your plans for next year. Does that work?" Clients almost always say yes, and now you've both agreed it's part of the meeting.
    
2. Ask about next year. If you know they're budgeting, say so. "You mentioned you're starting the 2027 budget. What's on the list for next year that we haven't talked about yet?" You're asking about their priorities, and the opportunity usually shows up in the answer.
    
3. Ask the last question. Jim's favorite. Right before you wrap up: "Before we go, can I ask about something we've never talked about?" Then ask about a service you provide that they don't use or a part of their business you haven't worked with.
    
4. Ask who else is dealing with it. "Is anyone else in your organization working through something like this?" Many of the best opportunities sit one department over from the work you're already doing.
    
5. Ask for the introduction. If they're happy with the work, they'll often help. "Who else do you know who's facing the same problem we just solved?" Ask for a name, a company, or an industry, whatever makes sense, and then ask whether they'd be comfortable making an introduction.
    
6. Leave with a second date. A meeting that ends with "Let's talk soon" stays blue next time. Before you leave, put the next conversation on both calendars while you're still in the room, and discuss an agenda that would make it most impactful for both of you.

One green question per meeting is plenty. A check-in that turns into an interrogation about future deals won't get you where you want to go. If you need a refresher on the difference, here's our earlier post on moving past "just checking in".

Change the color

When you're back at your desk, open the calendar and update the meeting. If it turned into an opportunity, make it green. If something worried you, say a new decision-maker or a hesitation you didn't expect, make it yellow so you remember to follow up.

It gets easier with repetition. Pick one blue meeting on next week's calendar. Decide your green before you walk in, and choose one of the six questions.

More of our clients are asking us for one-on-one coaching and accountability, often with this exact moment. They're in the room with the client, and the question won't come out. If you need help prepping for these money conversations or driving behavioral change across the team, I can help. Let's talk. 

What question will you ask at your next client check-in that you skipped last time?