Three Questions to Turn a Tax Client Into a Planning Client

From Compliance to Connection: How CPAs Can Expand Their Impact 

You already meet with your clients regularly — reviewing their numbers, preparing returns, filing on time. You know their businesses, their income, and their families often better than anyone else. But when it comes to deeper, forward-looking planning, many CPAs get stuck in the cycle of compliance.  

Many clients don’t realize the kind of guidance they could be getting — and most CPAs don’t realize how naturally positioned they are to offer it. You don’t need to overhaul your services or add hours to your week. Often, the most powerful shift starts with a single, thoughtful question — one that moves the conversation from what’s happened to what’s possible. 

Why This Matters: Most Clients Don’t Know What to Ask For 

Business owners, especially high-net-worth clients, aren’t often explicitly saying “I’d like integrated planning support.” But they are feeling uncertain about the future. They’re wondering how to transition the business, protect their wealth, and plan for their family — and they’re looking for someone they already trust to lead the way. 

That someone can be you. 

These three questions help you break out of the compliance-only mold and open the door to holistic, proactive planning. Try asking: 

“What are you building this all for?” 

The goal: Connect to their bigger ‘why’. 

This is a great question to ask during any check-in — financial review, year-end wrap-up, or business milestone: 

“You’ve done a great job building this business. I’m curious — what’s the vision behind it? What’s all this for?” 

This moves the conversation from spreadsheets to significance. It helps clients articulate what truly matters — retiring early, supporting their kids, giving back, or building something that lasts. 

From there, you might say: 

“That’s really helpful context. Let’s make sure your planning is aligned with that bigger picture.” 

You’re not pitching. You’re inviting. And that builds long-term trust. 

“Have you had a conversation with any key stakeholders about succession or exit?” 

The goal: Surface a common pain point. 

This one is especially powerful with business owners approaching the later stages: 

“A lot of clients in your position are starting to think about succession — or at least what an eventual exit might look like. Have you had any conversations about that yet?” 

If the answer is no: 

“Totally understandable. It’s one of those things that sneaks up on people. I can help you start thinking through it before it becomes urgent.” 

If the answer is yes: 

“That’s great. If you’d like, I can help make sure the financial, tax, and estate pieces are aligned with your goals.” 

Either way, you’ve opened the door to deeper planning. Now you’re shaping to become a strategic partner. 

“Do you know how much is enough to retire comfortably?” 

The goal: Invite them into bigger-picture planning. 

This question works especially well with clients nearing retirement or transition: 

“Out of curiosity — do you have a sense of how much is enough for you to feel comfortable stepping back or slowing down?” 

Most will say no — or give an uncertain answer. That’s your cue: 

“Let’s put some time on the calendar to figure that out. It’s one of the most valuable things we can do together.” 

This isn’t just a financial conversation. It’s a life conversation — and most CPAs are in the perfect position to lead it. 

Next Step: Don’t Pitch. Invite. 

You Already Have the Relationship. Now You Have the Questions. 

When a client opens up in response to one of these questions, there’s no need to immediately launch into a product or proposal. Instead, extend a simple invitation: 

“This isn’t something we have to tackle today, but I’d love to have a follow-up conversation about planning — big picture. It could make a huge difference in how you move forward.” 

That small step changes the trajectory of the relationship. 

Compliance may bring clients in the door. But planning is what keeps them for life. 

Start with these three questions — and watch how quickly your role expands from trusted tax preparer to most valued advisor.