Most business owners have a CPA. Far fewer are getting as much value from that relationship as they could be.

The dynamic is understandable: CPAs are busy, particularly during tax season. Clients often do not know what questions to ask. And the annual or semi-annual meeting can feel more like a transaction than a strategic conversation. You hand over documents, you get back a tax return, and you go back to running your business.

But the relationship can be significantly more valuable than that — if you approach it the right way.

Come Prepared With More Than Just Documents

The standard approach is to send over your financial records and let the CPA do their work. That is the minimum. If you want more value, come to your meetings with questions and context.

What is happening in your business this year that is different from last year? Are you planning to hire, make a significant purchase, take on a partner, or change your business structure? Are you considering a major contract that would significantly change your revenue profile?

Your CPA can only advise you on what they know. When you share more context, you create the conditions for more useful guidance. Tax planning works best when it is proactive, not reactive — and proactive requires conversation throughout the year, not just at filing time.

Ask Specifically About Tax Planning Opportunities

There is a difference between tax preparation and tax planning. Preparation is documenting what happened. Planning is structuring what will happen in a way that minimizes your liability.

Ask your CPA directly: Are there strategies I should be considering given my current situation? Are there deductions I am likely missing? Is my business structured optimally from a tax perspective? Should I be making retirement contributions, accelerating or deferring income, or timing capital expenditures in a particular way?

These conversations are most valuable when they happen mid-year, when you still have time to act. An October strategy conversation can meaningfully affect your tax bill. A February conversation cannot.

Make Sure They Have Clean Data to Work From

One of the most common complaints I hear from CPAs about small business clients is that they receive disorganized, incomplete, or inaccurate financial records at tax time. This creates extra work for the CPA — which you are paying for — and increases the risk of errors on your return.

When your books are clean, current, and well-reconciled throughout the year, your CPA can spend their time with you doing higher-value work rather than cleaning up records. You also give them the confidence that the numbers they are working from are accurate.

Treat It as an Ongoing Relationship, Not a Transaction

The business owners I see getting the most from their CPA relationships are the ones who reach out periodically throughout the year — not just when documents are due. A quick call or email when you are facing a significant financial decision can be worth far more than any single tax return.

Your CPA has a full picture of your financial history and a deep understanding of the tax implications of various choices. That knowledge is available to you year-round, not just in March. Use it.

The Broader Point

A great CPA relationship — like any great professional relationship — is collaborative and ongoing. You bring the context of your business. They bring the expertise. When those two things meet consistently and proactively, the results are almost always better than what a once-a-year transaction can produce.

If your current CPA relationship does not feel that way, it is worth having a direct conversation about what you need and whether they are set up to provide it. You deserve advisors who are genuinely invested in your success — not just your compliance.

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About the Author:

Joe Herskowitz, EA, is the President and CEO of Lionstone Bookkeeping+, where he helps small and medium-sized businesses take control of their finances with expert bookkeeping and financial insights. With years of experience in business finance, Joe is passionate about making numbers work for business owners—not against them.

Have a bookkeeping or business finance question?

Reach out to Joe at [email protected] or call/text 732-803-7793 (no WhatsApp).