Session Prep
The best tax sessions happen when you come in with specific questions tied to real decisions you're facing. These questions help you get strategic advice, not just compliance answers — and they signal to the advisor that you're serious about planning, not just filing. This guide covers three areas: your current tax exposure, planning around upcoming events, and building an ongoing advisory relationship. Review all three before your session and identify which questions apply to your situation. The most valuable tax advice almost always comes from the planning section — because those are where action is still possible. Come prepared with your entity type, rough income estimate for the year, and any major events you're anticipating. That context turns a general consultation into a specific, actionable session.
1.Based on my situation, what's the single biggest tax risk or missed opportunity you see?
The first-pass diagnosis. A good tax advisor will have a clear answer within minutes.
2.Is my current business structure (LLC, S-Corp, C-Corp) still the most tax-efficient for where I am now?
Entity type has major tax implications that often go unreviewed as businesses grow.
3.Am I on track with estimated taxes, or am I likely to face a penalty at year-end?
Simple but often skipped — underpayment penalties are avoidable with basic forecasting.
4.Are there deductions or credits I'm probably leaving on the table?
Gets specific recommendations, not just general categories like 'home office' or 'business meals.'
5.I'm planning to [sell equity / hire employees / buy property / expand internationally] — what are the tax implications I should know before I do it?
The most valuable use of a tax advisor: getting advice before the event, not after.
6.How should I be timing income and expenses to manage my tax obligations efficiently this year?
Year-end planning is critical — this surfaces strategies while there's still time to act.
7.What's the most tax-efficient way to take money out of my business?
Salary vs. distributions vs. dividends has big implications depending on entity type and income level.
8.How often should we be meeting, and what should trigger an unscheduled conversation?
Sets expectations for a proactive relationship, not a year-end scramble.
9.What records and documentation should I be keeping that I might not be?
Audit-proofing your position before you need to — not after.
10.What's one thing you've seen businesses like mine do that cost them significantly in taxes?
The cautionary tale question — often reveals the most actionable insight.
Written by James Chae — Co-Founder, Expert Sapiens
Platform expertise: Tax advisory & enrolled agent services · Reviewed March 2026