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Questions to Ask Before Hiring a Tax Strategist

Use a structured interview to learn how a firm will handle your business.

Ask about your facts

Begin with a concise description of your business and the decisions ahead. Ask what else the adviser needs to know before recommending an engagement. The quality of the follow-up questions can tell you more than a prepared presentation. Look for questions about ownership, records, jurisdictions, prior filings, and implementation capacity.

Then ask for an example of a similar type of engagement without requesting confidential client information. Focus on the process: what the team reviewed, where it encountered uncertainty, and how it coordinated with other professionals. A useful answer need not disclose a client name or a dramatic savings number.

Ask about the people and workflow

Who is your day-to-day contact? Who reviews technical work? What happens if that person is unavailable? Ask whether you will work with the person conducting the sales call or a different delivery team. Clarify how you will meet the assigned team before major work begins.

Request an explanation of the first ninety days. The answer should include document collection, review, a decision meeting, and next steps appropriate to the scope. Ask which dates depend on your team and which are controlled by the firm.

  • What does completed work look like?
  • How are outstanding actions tracked?
  • How are urgent questions escalated?

Ask about disagreement

What happens if your current preparer disagrees with a recommendation? Ask how the firm documents its reasoning, revisits assumptions, and coordinates a resolution. You want a process for differences of judgment rather than an assurance that disagreement never happens.

Ask what the firm does when the facts do not support the outcome originally discussed. A strong engagement permits the conclusion that a proposed approach is unsuitable. That is more useful than pressure to implement an idea simply because it appeared in an initial pitch.

Ask about money and exit

Ask for the fee schedule, likely extra work, renewal terms, and transition assistance if you leave. Determine whether documents and work products will be available through a portal after the engagement ends. Ask who answers questions from a replacement preparer.

End the interview by restating the scope in your own words. If the provider corrects you, write down the correction and request a matching agreement. This final step often reveals misunderstandings that a longer list of questions leaves unresolved.

  • Next step: send the same written interview questions to each shortlisted firm.

Sources & further reading

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