One of the most uncomfortable conversations business owners face is evaluating whether the advisor who helped build the business is still the right advisor for the next stage of growth.
This is especially true when that advisor is a sole practitioner approaching retirement.
Let me be clear: this is not necessarily a criticism of the accountant.
Many sole practitioners are highly experienced, deeply trusted, and technically excellent. In fact, they may have played a significant role in your success.
But as businesses move into the emerging middle market, owners need to ask a different question:
Can the firm support where we’re going, not just where we’ve been?
Concern #1: What Happens if Your Accountant Retires Tomorrow?
Many businesses discover that their CPA has become one of the most critical people in the company.
They know:
- Your tax history
- Your entity structure
- Your financing arrangements
- Your ownership agreements
- Your compensation plans
- Your key contacts
The problem is that all of that knowledge may reside with one person.
If that individual retires unexpectedly, experiences health issues, or decides to sell their practice, your business could face significant disruption.
The larger your company becomes, the greater this risk becomes.
Concern #2: Is There a Succession Plan?
Business owners spend considerable time developing succession plans for their own companies.
Yet many never ask their accounting firm the same question:
“Who will be serving us in three years?”
That question is entirely reasonable.
A growing company should understand:
- Whether a successor has been identified
- Whether introductions have occurred
- Whether internal transition plans exist
- Whether service continuity has been addressed
If the answer is vague, that’s a warning sign.
Concern #3: Does One Person Have All the Expertise You Need?
Middle-market businesses encounter increasingly sophisticated issues:
- Multi-state taxation
- Acquisitions
- Employee ownership programs
- Sales tax exposure
- International vendors
- Retirement planning strategies
- Succession planning
- Exit readiness
No matter how talented an individual advisor may be, today’s business environment has become increasingly specialized.
Many growing companies benefit from access to multiple specialists instead of relying on a single generalist.
Concern #4: Can the Firm Scale With You?
A company that grows from $5 million to $20 million in revenue often requires much more support than it did a few years earlier.
Questions become more frequent.
Planning becomes more complex.
Decision-making becomes more strategic.
Business owners should ask:
- How quickly can the firm respond?
- What happens during busy season?
- Is there backup coverage?
- Who else understands our business?
If the answer is nobody, the relationship may be vulnerable.
Concern #5: Are You Receiving Strategic Advice or Compliance Services?
Many sole practitioners built successful practices around tax compliance.
There’s absolutely nothing wrong with that.
However, many emerging middle-market companies begin looking for:
- CFO-level insights
- KPI analysis
- Cash flow forecasting
- Growth planning
- Acquisition support
- Succession planning
- Advanced tax strategies
The question becomes whether the current relationship was designed to provide those services.
Sometimes the issue is not capability.
Sometimes it’s simply a mismatch between what the client now wants and what the engagement was originally built to deliver.
Concern #6: Technology and Process Risk
Growing companies increasingly expect:
- Secure client portals
- Workflow management
- Digital document systems
- Collaborative planning tools
- Business intelligence reporting
- Real-time financial visibility
A practice built around one person can sometimes struggle to make the investments necessary to stay current.
That doesn’t make the advisor ineffective.
It does create operational risk for larger businesses.
The Most Important Question
I believe every business owner should periodically ask:
“If we were selecting an accounting firm today, knowing what our business looks like now and where we want to be five years from now, would we make the same choice?”
If the answer is yes, stay the course.
If the answer is no, don’t wait until your advisor announces retirement to begin evaluating alternatives.
The best transitions happen years before they become necessary.
Final Thoughts
Loyalty matters.
Many business owners feel a tremendous amount of gratitude toward the accountant who helped them get started.
But your responsibility is ultimately to the future of your business.
The goal isn’t finding a bigger accounting firm.
The goal is finding a firm with the depth, continuity, expertise, and resources to support your next stage of growth.
When you’re building a middle-market company, you shouldn’t be asking whether your accountant can handle this year’s tax return.
You should be asking whether their team can help you navigate the next decade of growth.
That is a very different question.
Michael Jamison, CPA, CGMA
President, OnTarget CPA
