Hiring Guide
Most businesses overpay taxes simply because they don't have proactive tax guidance. A good tax advisor doesn't just file returns — they help you make decisions throughout the year that minimize your liability legally.
Use these in an intro call or first session to quickly assess fit and expertise.
1.What proactive tax planning strategies do you typically recommend for someone in my situation?
Why it matters: If they can't immediately name 2–3 strategies, they're probably reactive, not proactive. Good tax advisors always have a mental checklist for common situations.
2.How do you handle entity structure decisions — and do you think my current structure is optimal?
Why it matters: Entity choice has massive tax implications. An advisor who engages seriously with this question understands strategy, not just compliance.
3.When during the year do you typically engage with clients, and how?
Why it matters: The best tax advisors check in quarterly, not just at filing time. Annual-only engagement limits the strategies available to you.
4.Have you dealt with my specific situation — equity, crypto, international income?
Why it matters: Specialized situations require specialized experience. Don't assume a general CPA knows the nuances of QSBS, FBAR, or stock option taxation.
5.What's one thing most clients in my situation miss that costs them money?
Why it matters: A great tax advisor will have a thoughtful, specific answer. A weak one will give a vague or generic response.
A tax advisory session focuses on strategy, not just compliance. Your expert will review your current tax situation, identify opportunities to reduce your liability, and explain the implications of upcoming financial decisions. You'll leave with a clear action plan — not just answers, but next steps.