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Most accounting relationships fail long before there's a tax mistake.
The return gets filed, the numbers are technically correct, the client receives a PDF with maybe a quick explanation, and everyone moves on.
Then six months later the attorney learns they should have adjusted payroll, started a retirement plan, changed their estimated tax payments, or made a different year-end purchase. The advice itself is fine; it just arrives too late to use.
One of the first questions I encourage attorneys to ask any accounting firm is simple: how often are we expected to talk?
Some firms are built around annual compliance. They keep the books up to date, prepare the tax returns, answer questions as they come up, and that's the engagement. That's OK. It keeps you in compliance, and it's kind of boring. The downside is that most of the conversations are about what already happened rather than what should happen next.
Other firms position themselves as advisors, and the difference usually comes down to the cadence of the relationship rather than technical ability. A firm that schedules quarterly meetings, runs projections during the year, reviews compensation, discusses entity structure, and reaches out when something changes is providing a completely different service. That service costs more, and in many cases the additional planning more than pays for itself. A financial advisor friend of mine likes to say, "Do you want to buy a Toyota or a Lexus?"
The problem is that many attorneys don't figure out which model they're in until a planning opportunity has already passed.
The Cost of Delayed Conversations
Attorneys understand timing better than most. You wouldn't want a client showing up after a filing deadline or after the statute has run asking what options remain. The best strategy often depends on having enough time to act.
Tax planning works the same way. Changing reasonable compensation before year-end can help, and changing it after December 31 generally can't. Establishing a retirement plan before the deadline can create meaningful tax savings, while thinking about it as you're signing the return usually leads somewhere else.
The same goes for estimated tax payments, partner distributions, major purchases, hiring decisions, and entity elections. Most planning opportunities have an expiration date, and the firms that create the most value are the ones having those conversations before decisions become permanent.
What You Should Expect to Understand
Most attorneys didn't go to law school because they wanted to learn payroll taxes, shareholder basis, depreciation schedules, or partner capital accounts. You should still understand what's happening inside your own firm.
I've seen attorneys receive a completed return showing a six-figure tax bill with almost no explanation of how the number was calculated. The return may be technically correct, and technical accuracy on its own doesn't give anyone confidence.
A good advisor translates: what changed this year, why taxable income and cash in the bank aren't the same thing, why the estimates moved, and what decisions are worth making before the next one.
Ask Better Questions Before You Hire
When evaluating an accountant, the fee is only part of what you're deciding. Ask questions like:
- How often do we meet during the year?
- Will I receive proactive tax projections?
- What is your typical response time?
- Do you explain recommendations or simply provide deliverables?
- How do you communicate complex issues?
- How do you identify planning opportunities before year-end?
The answers will tell you far more about the relationship than the engagement letter will.
Finding the Right Fit
There are excellent compliance-focused firms and excellent advisory firms, and there are also firms that market themselves as proactive but rarely initiate contact. What you're looking for is a communication style and a planning cadence that match how your practice runs.
Tax advice has a shelf life, which is why the cadence question is worth asking before you sign anything.
If this series has you looking at your own setup and you'd rather not guess, book a time with me . Happy to walk through what I'd review.
About Dark Horse CPAs
Dark Horse CPAs provides an integrated suite of services including tax , accounting , fractional CFO , and wealth management to small businesses and individuals across the U.S. The firm was established to transform the client experience by offering personalized, high-quality services that small businesses and individuals deserve. As Dark Horses in their industries, these businesses benefit from advanced tax strategies and accounting insights typically reserved for larger companies. With a nationwide presence and a team of dedicated professionals, Dark Horse CPAs is committed to your success. Get a quote today.
