The Conversation 95% of CPAs Aren’t Having — And What It’s Costing Their Clients

If you’re a CPA working with business owners, I want you to think about your clients who are over 50 years old. Now ask yourself: how many of them have a clearly stated, delineated transition plan?

If you’re like most practitioners, the answer is uncomfortable. And if you’re being honest, you probably haven t initiated that conversation with most of them.

You’re not alone. In my experience, across 150 deals, only 3 to 5% of CPAs are proactively having this discussion. But that means 95 to 97% are watching the clock tick on their clients’ most valuable asset while saying nothing.

This isn’t a technical skills gap. This is a systemic avoidance pattern, and it’s costing clients losses that are both tangible and incalculable.

Why Business Owners Avoid Transition Planning

Business owners avoid transition planning the same way they avoid estate planning because it forces them to face their own mortality. It requires admitting they won’t be here forever, that their business will outlive their involvement, that the thing they built will eventually belong to someone else or cease to exist.

That discomfort is deeply human. The problem is when CPAs become complicit in that avoidance by staying silent.

When you don’t bring it up, you’re giving your client permission to delay. Another year. Another quarter. Another tax season. And every year that passes without a plan makes the eventual transi-tion more chaotic, more costly and more likely to fail entirely.

The Incalculable Cost

I’ve seen first-hand what happens when transition planning starts too late or doesn’t happen at all.

The tangible losses are measurable after the fact. The tax bill that could have been cut in half with proper planning. The deal that fell apart because financials weren’t clean or the owner was still the only person who understood operations. The valuation that dropped 30% because no one had built transferable systems.

But the intangible losses? Those are incalculable. The legacy that never materialized. The employees who got blindsided. The family relationships that fractured over a chaotic succession. The owner who worked 40 years building something meaningful and then just faded out   no plan, no ceremony, no intentional passing of what they built.

You can’t put a number on that. But every CPA reading this has seen it happen.

The Strategic Advisor’s Role

Here’s the reframe: your role as a strategic advisor isn’t just about maximizing dollars on exit. It’s about preventing the incalculable loss that happens when avoidance becomes the default plan.

Think of transition planning like fixing up a house before you sell it. You don t wait until you ve already listed the property to discover the roof leaks and the foundation is cracked. You address those issues early, when you still have time and options.

The same principle applies to businesses. Transition planning should start years before any actual transition occurs. It’s about building transferable value, cleaning up operations, developing leadership and creating optionality for the owner.

And, critically, it’s about managing the emotional interference that derails good deals. I’ve watched sellers lose their minds during transactions — getting off the ledge becomes as important as structuring the deal itself. When you’re the trusted advisor who’s been having these conversations for years, you’re the one who can provide that stabilization.

The Line in the Sand

So here’s my challenge to you: every one of your clients over 50 without a clearly stated, delineated transition plan needs to hear this question from you.

Not when they bring it up. Not when it feels comfortable. Not if they seem open to it.

Every client over 50 gets the conversation. Make it a standard of care, like aski8ng about dependents during tax prep.

This removes your discomfort from the equation. You’re not singling anyone out or making it personal. You’re simply saying, “This is what we do for every client at this stage.”

What Happens Next

Will some clients resist? Absolutely. Will some tell you they’re not ready? Of course. But you’ve planted the seed. You’ve created awareness. And when they’re ready — or when circumstances force the issue — you’ll be the advisor they turn to.

The 3 to 5% of CPAs who are already having this conversation aren’t just better advisors. They’re building different practices entirely. They’re the ones getting pulled into deals, becoming trusted strategic partners and creating value that goes far beyond compliance work.

The revenue will follow. But, more importantly, you’ll be preventing incalculable losses for the clients who trust you most.

The question is: will you join the 3 to 5% or stay with the 95%?

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Jay L. Levine Jay Levine, CPA, CGMA, is a partner at Prager Metis and can be reached at jlevine@pragermetis.com.