By: Jordan Gerheim, CEO – Outside Chief Legal LLC
Tax filing season hits growing businesses hard. It is not only about getting numbers into your CPA’s software. It is also about the legal fine print behind those numbers: contracts, payroll, ownership changes, and state-specific rules that can quietly create risk if they are not in the file your CPA sees.
From where we sit as outside general counsel and fractional chief legal officers for a growing list of companies and their owners, we see the same pattern every year: strong, growing companies walk into filing season underprepared on the legal side, and it costs them money, leverage, and focus they should be putting into growth. Having the right documents organized in advance allows your CPA to focus on the tax analysis while your legal team focuses on the business, contract, employment, and structure issues that sit underneath those figures.
Outside Chief Legal does not provide tax advice or prepare tax returns. Your CPA or tax advisor should lead on all tax questions. What my team and I do is help make sure that the documents and legal positions behind your numbers are clear, consistent, and as protective as they can be before your CPA files anything.
This is not about being perfect. It is about being intentional. If you are going to hand your business over to your CPA and your attorney once a year, you might as well get strategic benefit from both, inside their respective lanes.
Why Prep Matters for Your Business
Filing season is not only about taxes. It is one of the few times each year that your financial and legal worlds are on the table at the same time. Done well, this can function as a built-in annual strategy checkup. Done poorly, it becomes a rushed scramble that builds risk into the year ahead.
When you do not have key documents ready, your CPA may miss important context about income streams, expenses, or elections, and your attorney may never see the contracts or employment records that control your rights and liabilities. That can contribute to audits or penalties by tax authorities, or leave you exposed in a dispute you could have prevented with better documentation and clearer agreements.
What I see most often is not bad intent. It is fragmentation. The owner has some items in email, some in a prior lawyer’s portal, some in a payroll system, and some in a banker’s inbox. When you pull it together in one place, your CPA can do better tax work, and your outside counsel can do better legal work. You put yourself in control.
Do This Next: Your Prep Checklist (8 items)
Use this eight-item checklist to gather everything now, before your CPA starts asking and before your legal team is trying to catch up midstream. Aim to compile everything digitally in clearly labeled folders so you can share one organized package instead of a series of follow-up messages.
1. Business Basics
Employer Identification Number confirmation, formation documents (Articles of Organization or Incorporation, bylaws, and current operating agreement), and current business license. If there has been an ownership change or structure change during the past year, include those documents in the same folder so your CPA and your attorney are all working from the same picture of your entity.
2. Prior Year Returns and Notices
Last year’s federal and state business tax returns (for example, Form 1065 for partnerships or Form 1120S for S corporations), plus any notices you received from the Internal Revenue Service or state agencies. Your CPA or tax advisor should interpret the tax impact. Your legal team’s role is to help you understand what those notices may signal about underlying compliance, documentation, or entity structure issues.
3. Income Records
All Forms 1099, sales reports from point of sale or electronic commerce platforms, invoices and payments, and bank statements that show deposits. Your CPA will determine what is taxable and how to report it. What I care about as your outside general counsel is whether the documentation of those deals aligns with your contracts and policies, and whether any large or unusual items reflect disputes, refunds, or settlements that deserve legal attention.
4. Expense Receipts
Categorized documentation for deductions such as office expenses, travel with mileage logs when applicable, and marketing, along with totals from your accounting software. Your CPA will advise you on what is deductible. Your attorney can help ensure that your expense patterns do not conflict with your contracts, internal policies, or regulatory obligations, and that the underlying agreements are strong if any of those expenses ever become part of a dispute.
5. Payroll Documents
Forms W 2 and W 3, Forms 1099 issued to contractors, payroll summaries, and state withholding reports. Your CPA or payroll provider is responsible for how these are reported for tax purposes. My focus as your legal advisor is on the classification and documentation behind them: whether workers are properly classified, whether offer letters and bonus plans match what is being paid, and whether your handbook and practices support the way your team is compensated.
6. Contracts and Agreements
Active vendor and client contracts, loan documents with interest statements, and leases, with any disputes or changes clearly flagged. These documents drive much of what shows up in your revenue, expense, and liability lines. Your CPA will interpret the numbers; your attorney should evaluate the terms, risks, and enforceability of these contracts, and help you understand whether any disputes, indemnities, or default risks need to be addressed now rather than after you file.
7. Asset Details
Depreciation schedules, fixed asset purchases, year-end inventory counts, and home office measurements when applicable. Your CPA will determine how to treat these assets for tax purposes. Your legal team can help you confirm that ownership, titles, security interests, and key purchase or sale agreements are in good order, especially if you have recently bought or sold a business line, a building, or major equipment.
8. State Specific Items
Alabama Business Privilege Tax records, apportionment schedules when you sell into multiple states, and your state tax account numbers. Your CPA or state and local tax advisor should guide how these are filed and calculated. Outside Chief Legal can help with the business and regulatory side of operating in and into Alabama, such as registrations, licenses, and compliance obligations that sit next to, but are separate from, the tax computations.
If you pull this information together now, your CPA can move efficiently in their lane, and your legal team can actually advise in its lane, rather than merely react to problems later.
A Common Mistake and a Better Way
Consider this example. Alex, who owns a growing service firm, walks into filing season with a stack of unorganized bank statements and a rough export from his bookkeeping software. He forgets to include his vendor contracts and the documents about a disputed invoice from last summer. The CPA does the best work possible with what is provided, files on time, and no one evaluates the legal implications of that unresolved dispute or the missing documents.
Months later, that vendor dispute turns into a lawsuit. In the meantime, Alex overpays or underpays taxes because the contested amount was never fully documented or communicated, and now he has potential tax exposure and active litigation. He pays twice: once in avoidable tax related cost and again in legal fees to clean up the dispute.
Get Proactive Legal Support, Not Tax Advice
At Outside Chief Legal, we work as subscription-based fractional general counsel for growing businesses that want ongoing, proactive guidance, not one time fire drills. We do not provide tax advice or prepare tax returns. Your CPA or tax advisor is, and should remain, the leader on what your business owes, how your returns are prepared, and how transactions are treated for tax purposes.
Where we add value is in the legal architecture that surrounds that work. Filing season is one of the natural leverage points in that relationship, because the documents you gather for your CPA often reveal contract, employment, ownership, and compliance issues that we can help you address before they become claims or operational headaches.
During the filing season, consider a structured business checkup with us. This is a focused legal review where we identify common blind spots such as outdated agreements, missing signatures, misaligned compensation terms, or state-specific gaps, and then prioritize the changes that most affect your risk and leverage. You are not simply getting through tax season. You are using a moment when everything is already on the table to make your business cleaner, more resilient, and more attractive to lenders, buyers, and key hires.
If you are a growing business and you are not confident that you could locate everything in this checklist today, that is a strong signal to obtain help. Schedule a conversation with Outside Chief Legal. We will partner alongside your CPA or tax advisor and help turn this filing season into a planning moment, not only a deadline.
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Outside Chief Legal LLC is a modern, forward-thinking law firm serving as fractional chief legal officers and outside general counsel for businesses and their owners. With over 200 years of combined litigation, in-house, general counsel, and administrative legal experience, the firm delivers approachable, comprehensive counsel that blends legal expertise with practical business insight to help clients navigate ownership complexities with confidence. OCL is a trusted partner for founders, business owners, and leadership teams nationwide. Learn more about our firm, meet our team, or schedule a Risk-Free Strategy Session to talk with an attorney about how we can help your company.
