If your only conversation with your accountant happens in the spring, it is a conversation about a year that has already finished. By then the only decisions left are how to report what happened. Planning happens before the year closes, and it is a different conversation with a different posture on both sides.

If your accountant contacts you only at filing time, you are buying compliance. That is a legitimate service worth paying for. It is not planning, and you should know which one you have.

Which conversations belong on the calendar?

Each item below is a question to bring, not a position to take. Your CPA is the one who applies the rules to your situation.

Entity structure. How the practice is organized affects how income is taxed and how much of it is exposed to payroll taxes. Ask whether your current structure still fits the size and shape of the practice, and what would change under an alternative. This deserves periodic review rather than one decision made when you incorporated.

Owner compensation. Ask how the split between wages and other distributions is determined in your structure, how that determination is judged, and what documentation supports the figure you are using.

Retirement plan design. Contributions are one of the larger levers available to a profitable practice, and some plans must exist before certain dates to count for a given year. Ask which deadlines apply to the plan you are considering, and ask well before the year ends.

Timing of equipment purchases. Depreciation choices affect which year a deduction lands in. The question is not only whether to buy but when, and whether the deduction is worth more to you this year or next given where income is heading.

Deductions sensitive to income level. Some deductions change or disappear as taxable income moves, and service businesses can face particular treatment. Ask which of these apply to a dental practice in your situation and how close you are to the edges.

Real estate. If you own the building or are considering it, the interaction between the practice entity, the property entity, the lease between them, and depreciation is worth a dedicated meeting rather than a footnote.

Family employment. Employing family can be legitimate when the work is real and the pay is reasonable. Ask what documentation is expected before any examination.

What questions should you bring?

Better questions produce better planning. These consistently open something useful:

• What is my effective tax rate, and which direction has it moved?
• What are my estimated payments based on, and are they still accurate given this year’s collections?
• What did we do last year that we should repeat, and what did not work?
• What am I paying tax on now that could reasonably be deferred, and what does deferring cost?
• What would change if income rose sharply? What if it fell sharply?

Then one more: what should I be asking that I am not?

How do you tell a planner from a preparer?

A planner asks about things that have not happened yet. They want to know whether you are hiring, buying, expanding, adding an associate, or thinking about a transition, because each changes the analysis.

A preparer asks for your books in February.

Signs of planning: contact during the year, a mid-year and a fourth-quarter check-in, willingness to speak with your other advisors, explanations of why rather than only what, and a fee arrangement you understand.

Stay equally alert to the opposite failure. Aggressive positions promising outsized savings, built on structures nobody will explain plainly, deserve real scrutiny. Ask what the position is, whether it has been tested, what happens under examination, and who bears the cost if it does not hold. Anything that only works while nobody looks closely is not a strategy.

What does doing this well cost?

More than the cheapest preparation available, and usually less than the value of one decision made with better information. If you are paying for planning, ask what it includes and how often you will meet. An accountant who has never asked about your plans cannot plan around them.

This is general context for a conversation with your own CPA, not guidance to act on.

FAQ

How often should I meet with my accountant?
Owners doing real planning tend to meet at least twice: a mid-year look at how the year is tracking, and a fourth-quarter meeting while decisions can still affect it. Filing season then confirms rather than discovers. Transitions and large purchases justify more contact.

Should my CPA and my financial advisor talk?
Ideally, with your permission. Plan design, entity structure, and investment decisions interact, and advisors working in isolation sometimes optimize against each other. One short annual call with all three of you surfaces conflicts neither professional would catch alone.