When Do I Need a Tax Lawyer?
Florida business owners regularly juggle multiple tax obligations—corporate, payroll, sales, and more. While most rely on accountants or CPAs for compliance and reporting, certain situations require legal representation. A Tax Attorney at Cobb Cole brings legal analysis, strategic planning, and privilege protections that CPAs can’t offer.
Below are key scenarios when a business should consider legal tax counsel.
Audits, Notices, and Disputes
If the IRS or Florida Department of Revenue audits your business or challenges your filings, it’s time to involve a tax attorney. These situations may involve:
- Complex document requests.
- Disputes over the classification of assets or deductions.
- Potential penalties or litigation.
Unlike accountants, attorneys can represent you in court and offer attorney-client privilege—meaning your communications and documents are protected from disclosure, which is stronger than the accountant-client privilege afforded in federal tax matters. This is especially critical if a dispute escalates into a criminal investigation or civil enforcement action.
Strategic Structuring and Growth
Choosing the right legal structure for your business—LLC, S-Corp, C-Corp—has tax implications. A tax attorney can help evaluate the long-term consequences of these choices, particularly when paired with:
- Bringing on new partners
- Opening new locations
- Acquiring real estate or other assets
- Merging with or purchasing another business
Structuring done without legal input often misses how tax interacts with liability, governance, and business continuity. The attorneys at Cobb Cole bring cross-disciplinary knowledge from corporate law, real estate, and litigation to help navigate this complexity.
Minimizing Tax Liability Without Increasing Risk
Florida business owners often pursue aggressive tax savings strategies. But some approaches—such as independent contractor classification, depreciation tactics, or fringe benefit deductions—straddle a fine line.
A tax attorney provides legal interpretation of ambiguous rules and evaluates litigation risk before positions are taken. This allows businesses to reduce their tax burden without increasing exposure.
Sales, Transfers, and Asset Deals
When buying or selling assets, tax treatment can significantly affect net proceeds and liability:
- Should the sale be structured as an asset or stock deal?
- Does depreciation recapture apply?
- Are you triggering the Florida documentary stamp tax?
Asset transfers are not just accounting events—they are legal transactions with complex implications.
CPAs and Tax Attorneys: Not Either/Or
Many Florida businesses already retain skilled CPAs. However, accountants and attorneys play distinct roles. CPAs handle day-to-day compliance, while attorneys interpret law, draft legally binding documents, and defend positions in dispute or litigation.
More importantly, conversations with your accountant are not protected by privilege except as provided in federal tax laws —those with your attorney are. This becomes especially important in any setting involving regulatory risk, business litigation, or disputes among partners or shareholders.
Cobb Cole’s tax attorneys often collaborate directly with a client’s CPA to ensure a full picture of both legal and financial risk. As a trusted full-service Law Firm, we can also coordinate seamlessly across construction, real estate, employment, and other practice areas as needed.
Planning for the Future
Tax issues are also deeply connected to succession and estate planning. Many Florida business owners want to pass down their companies or assets without triggering unnecessary tax. A tax lawyer can:
- Draft trusts or ownership vehicles for tax-advantaged succession.
- Address estate and gift tax liability.
- Structure buy-sell agreements to avoid valuation disputes.
- Integrate corporate and family planning into one coordinated structure.
Even a basic change in ownership can trigger capital gains, loss of step-up in basis, or unintended tax on retained earnings—issues that should be addressed proactively.
A tax lawyer isn’t necessary for every filing or deduction, but when decisions affect structure, litigation, growth, or legacy, legal guidance matters. The Tax Lawyers at Cobb Cole can provide that guidance with the backing of a coordinated legal team across multiple business-related fields.
