Session Prep
Accounting sessions produce the best outcomes when you arrive with your financial situation organized, your specific questions written down, and a clear picture of the decision or problem at the center of your conversation. Vague questions produce vague answers; specific, well-framed questions produce specific, actionable guidance that you can use immediately. Before your session, gather the relevant documents: recent financial statements or reports, your most recent tax return, any outstanding IRS or state tax notices, and a summary of the specific issue or decision you're trying to address. If you're asking about business accounting, understand your current accounting method (cash vs. accrual), your software setup, and the approximate volume and complexity of your transactions. If you're asking about tax strategy, know your entity type, approximate annual revenue, and the major financial events expected in the coming year. This guide covers four areas: understanding your financial position and where the gaps are, tax planning and compliance questions, systems and process improvements, and forward-looking strategy. Not every question applies to every situation — use this as a starting framework and adapt it to your specific needs.
1.Based on what I've shared, what's the most important financial issue you'd want to address first — and why?
Forces prioritization from an expert perspective rather than leaving you with a long undifferentiated list. A strong accounting advisor will be direct about what matters most given your specific situation — not what matters most in general. If they can't prioritize without extensive additional information, push for a conditional answer: 'If X is the case, then Y is most urgent.'
2.Are there any obvious problems, anomalies, or risks in my current financial setup that I might not be aware of?
A quick diagnostic that often surfaces things you've normalized but shouldn't have — a contractor classification that looks like misclassification, a revenue recognition treatment that doesn't match your contracts, or a deduction pattern that would draw scrutiny. Advisors with broad exposure to similar businesses spot these quickly.
3.Am I on the right accounting method (cash vs. accrual) for my business size and situation, and is this the right time to switch?
Most small businesses start on cash-basis accounting and need to switch to accrual as they grow — but the timing matters for tax implications and for the quality of your financial reporting. An accountant who has helped similar businesses make this transition will give you a clear recommendation and walk you through what changes.
4.What financial metrics should I be tracking that I'm probably not tracking yet — and why do they matter?
Reveals the gap between your current financial visibility and what a sophisticated advisor needs to do their best work. Better inputs produce better advice. This question also tells you what your accountant considers the leading indicators for a business like yours — which is valuable even if you don't immediately implement everything they suggest.
What are the two or three most impactful tax planning strategies for a business at my stage and in my situation?
Separates proactive advisors from compliance processors. A strong tax-aware accountant will name specific strategies — entity structure optimization, retirement contributions, timing of deductions, R&D credits, QSBS eligibility — not give generic answers. Ask them to explain which would have the biggest impact for your specific situation and why.
6.Is my current entity structure still optimal given where my business is headed, or should I be thinking about changing it?
Entity choice has major tax and liability implications that evolve as a business grows. The right structure for a solo consultant is different from the right structure for a 10-person company planning to raise venture capital. An accountant who proactively thinks about this for their clients will have a concrete view.
7.Are there any compliance risks in my current setup — deductions I'm taking that might not hold up, contractor classifications that look questionable, or filings I might be missing?
A candid compliance diagnostic. Advisors who are willing to point out where your current practices create risk are more valuable than those who validate everything you're doing. Identifying and correcting compliance issues proactively is far less expensive than addressing them after an audit or notice.
8.What should I be doing before December 31 that I'm probably not doing — and when do we need to start to make it happen?
Most tax planning strategies have to be implemented before year-end to be effective. This question surfaces time-sensitive opportunities and forces a concrete calendar — not just a list of strategies, but a timeline for implementing them. Asking this in Q3 gives you the most flexibility; asking it in December limits your options significantly.
9.What's the biggest gap in how I'm currently managing my books, and what's the most important thing to fix first?
Gets you a prioritized diagnosis of your accounting infrastructure, not a comprehensive list of everything that could be better. The most important thing to fix first is usually what's creating the most risk or consuming the most unnecessary time. A good accountant will have a clear answer based on what you've described.
10.Is my current accounting software setup appropriate for where my business is now and where it's headed?
Accounting software that was appropriate at an earlier stage can become a significant bottleneck. An accountant who knows your software and your stage will tell you whether you're approaching the limits of your current setup and what the right next step would be — whether that's a configuration change, additional integrations, or a platform migration.
11.What information should I be giving you regularly — and in what format — to make our work together as efficient and accurate as possible?
Establishes clear expectations for your working relationship and ensures you're providing inputs in the format that minimizes correction and rework. Accounting errors often originate in messy or incomplete inputs, not in the accountant's work. Understanding exactly what they need from you is the most direct path to higher quality output.
12.How do you handle it when I have an urgent question or something time-sensitive comes up between scheduled sessions?
Sets expectations about responsiveness and process. Knowing whether your accountant responds to messages within hours or days, whether they have a dedicated process for urgent questions, and what constitutes 'urgent' to them prevents frustration when a deadline or opportunity arises unexpectedly.
13.Given where my business is headed, what accounting and financial infrastructure should I be building now to avoid problems at the next stage?
Gets you ahead of problems rather than waiting for them to surface. The accounting infrastructure appropriate for a $500K revenue business is different from what you need at $5M — and building the right foundations early costs far less than retrofitting them under pressure. A forward-thinking accountant will have a clear view of what you'll need and when.
14.If I'm planning to raise capital, sell the business, or bring on investors, what do I need to have in order financially before that process starts?
Due diligence scrutinizes your financials carefully, and problems discovered during a fundraise or sale are expensive to fix under deadline pressure. Understanding what investors or acquirers will want to see — clean books, multi-year financials, audited statements, a clear cap table — and how long it takes to get there informs your timeline for the transaction.
15.What would you want to review or discuss mid-year — outside of tax season — to make sure I'm on track and haven't missed any planning opportunities?
Surfaces whether your accountant thinks proactively throughout the year or only engages at filing time. A mid-year review is where most strategic tax planning actually happens — by December, most decisions are already made. Advisors who schedule proactive check-ins are worth significantly more than those who only respond to your calls.
16.If you were running a business like mine, what financial decisions would you make differently from what I'm doing now?
The direct recommendation question — asking the advisor to apply their expertise to your specific situation as if it were their own decision. Experienced accountants with genuine depth will give you a specific, concrete answer rather than a diplomatic non-answer. This surfaces their real opinion, which is what you're actually paying for.