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Exit Planning for Baby Boomer Clients: CPA Guide

Exit Planning for Baby Boomer Clients: CPA Guide

Aug 13, 2025

Exit Planning for Baby Boomer Clients
Exit Planning for Baby Boomer Clients

If you’ve been running a CPA firm for a while, you can see what’s happening — the Baby Boomer retirement wave isn’t on the horizon anymore… it’s at our doorstep.

For many small and mid-sized firms, this is more than a demographic trend. It’s a career-defining opportunity to position your practice as the go-to advisor for business exits.

And let’s be clear — exit planning isn’t “selling a business and handing over the keys.” It’s navigating a highly emotional, high-stakes process that shapes your client’s legacy, financial security, and post-ownership life.

1. Start Early, Dig Deep

The best exits don’t start with a valuation — they start with a conversation.

Ask:

  • What does success look like? (Highest price, family continuity, employee buyout… or something else entirely?)

  • What’s the “after” picture? Travel? Mentoring? Consulting?

  • Who’s next? Is there a successor in place — and are they truly ready?

Action item: Have these talks years ahead of time, not months. The earlier the roadmap, the more options and leverage you have.

2. Kill the Data Bottlenecks

Messy data is the silent deal killer.

Most delays in exit planning aren’t strategic — they’re operational:

  • Missing or late documents

  • Inconsistent formats

  • Endless manual entry (and the inevitable errors)

Action item:

  • Use a standardized intake checklist

  • Require secure uploads to a single portal

  • Deploy tools that automatically extract and organize data

It’s not just about speed — a clean, complete data package boosts client confidence and makes you look buttoned-up to buyers and attorneys.

3. Handle 1099s & K-1s Like a Pro

Ownership changes trigger reporting headaches. Late or inaccurate filings can kill goodwill fast.

Your playbook:

  • Identify reporting requirements at the start

  • Automate form generation through your tax software

  • Educate clients on what you need and when you need it

  • Keep them informed if IRS rules change mid-process

A smooth compliance handoff is one of the easiest ways to protect trust.

4. Automate What You Can — Keep the Human Where It Matters

Automation isn’t about replacing relationships; it’s about protecting them from missed deadlines and confusion.

  • Send automatic email reminders for document uploads

  • Give clients a secure dashboard to track progress

  • Book recurring check-ins automatically so they always feel guided

Clients don’t care if the reminder came from you or an app — they care that you never forget them.

5. Make the Numbers Visual

When emotions are running high, dense spreadsheets aren’t your friend.

Better:

  • Use valuation and modeling tools to show “what if” scenarios live

  • Turn key projections into charts and graphics

  • Share live models in collaborative platforms so everyone sees the same truth

The clearer the numbers, the faster — and more confident — the decisions.

6. Make Compliance Your Quiet Differentiator

Nobody brags about compliance… until the other firm drops the ball.

Watch for:

  • Accurate income reporting on business sales

  • Capital gains exposure

  • Opportunities for tax deferral (Like-Kind Exchanges, Deferred Sales Trusts, etc.)

Action item: Keep your team trained and plugged into AICPA and IRS updates — and bring tax-saving ideas into the conversation before clients ask.

7. Treat Documentation Like a Product

Every client exit should feel like a consistent, professional machine powers it.

  • Kick off with a standard onboarding checklist

  • Require secure uploads — no emailed tax returns floating around

  • Schedule periodic document reviews so nothing gets left behind

A predictable process means fewer surprises and better decision-making.

8. Educate Your Clients Into Loyalty

The more your clients know, the smoother the process — and the stronger their loyalty.

Run:

  • Short workshops or webinars on succession, valuation, and tax impacts

  • Customized guides for their specific business

  • Ongoing “what’s changing” updates, even post-sale

When you’re both executing and educating, you’re not just their CPA — you’re their exit strategist for life.

Bottom Line
The Boomer exit wave is here. Firms that start early, run a tight process, and guide clients with both data and empathy will thrive.

Next Step: Identify one bottleneck in your current exit planning process — whether it’s document intake, client communication, or compliance — and fix it this quarter. Small wins stack fast in this space.

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Get hands-on with AI-powered tax automation today.

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Get hands-on with AI-powered tax automation today.

Start Free. No Credit Card Required.

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