Most business owners view their CPA as someone who “keeps them compliant” — filing returns, reviewing financials, preparing statements. But in today’s fast-moving world, that reactive approach isn’t enough. Your CPA should be helping you think beyond the numbers and proactively plan for the future. The good news? Many CPAs are ready for that conversation — they just need the green light from you. Whether you’re planning growth, considering an exit, or just trying to protect what you’ve built, here are the top questions you should be asking your CPA this year.
1. Am I Paying Myself the Right Way — Salary, Dividends, or Both? The structure of how you pay yourself as an owner has tax, retirement, and cash flow implications. The “right” mix can change as your business matures or tax rules evolve. Your CPA can help you align this with both your personal financial goals and long-term planning.
2. How Can I Start Preparing My Business for an Eventual Exit? Even if you’re not planning to sell anytime soon, your CPA should help you think like a buyer. That means assessing your financials, operational dependencies, and shareholder agreements. The earlier you start, the more leverage you’ll have when the time comes.
3. Are There Tax Opportunities I’m Missing as a Business Owner?
Beyond annual filings, ask your CPA to walk through:
- Optimizing your corporate structure
- Leveraging capital dividend accounts
- Using holding companies strategically
- Year-end tax planning moves Many of these are proactive, not reactive — and they can have a lasting impact on your net worth.
4. Should We Be Revisiting My Shareholder or Buy-Sell Agreements? If it’s been more than a few years — or there have been changes in ownership, valuation, or succession plans — it’s time for a review. These documents tie directly into insurance, tax planning, and business continuity. They need to reflect your current intentions and risk exposure.
5. Is My Current Structure Still Serving My Goals?
Your original corporate setup may have made sense when you started. But what about now? Have you grown? Added partners? Bought assets? Your CPA can help evaluate whether a reorganization, trust, or holdco structure could better support your business and personal wealth goals.
6. Do I Have the Right Insurance in Place — and Is It Held by the Right Entity?
This isn’t about selling insurance. It’s about how policies interact with your corporate structure and planning. Life insurance, critical illness, and disability coverage can all be structured for tax efficiency and strategic funding (e.g., for buyouts or estate needs).
7. What Should I Be Doing Now to Protect My Family and Estate?
If most of your wealth is tied up in the business, estate planning can’t wait until retirement. Your CPA can help model scenarios, identify liquidity gaps, and work with legal and financial advisors to create a coordinated estate strategy — especially important for family-owned businesses.
The Bottom Line: Don’t Just File — Plan
Your CPA isn’t just a compliance partner — they’re one of your most important strategic advisors. But you only get the full value of that relationship when you use it.
This year, make it a priority to go beyond the financials. Start a conversation about where your business is headed, what your goals are, and how your financial structure can support those goals.
You don’t need all the answers — just the right questions.
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