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Working with a Tax Pro: Questions to Ask to Get Real Strategic Advice, Not Just Filings



By: Jack Nicholaisen author image
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Most tax pros just file returns. They don’t provide strategy. They don’t give advice.

Most owners accept this. They get filings. They miss opportunities. They pay more than necessary.

Right questions get strategic advice. They unlock value. They save money.

This guide shows questions to ask to get real strategic advice, not just filings.

article summaryKey Takeaways

  • Ask right questions—get strategic advice
  • Understand value—know what to expect
  • Build relationships—work with professionals
  • Get strategy—not just filings
  • Save money—optimize taxes
tax professional tax accountant tax advice tax strategy tax planning

Working with Pros

Tax pros provide different services. Some just file. Others provide strategy.

Filing-only pros: They prepare returns. They file forms. They don’t provide strategy.

Strategic pros: They provide advice. They plan taxes. They optimize strategy.

Why this matters: Pro understanding enables value. If you understand pros, value improves.

Questions to Ask

Right questions unlock strategic advice. Ask about strategy. Ask about planning.

Questions About Strategy

Ask strategic questions:

  • What tax strategies apply to my situation?
  • How can I reduce my tax burden?
  • What deductions am I missing?
  • How should I structure my business?

Why this matters: Strategic questions get strategic answers. If you ask strategic questions, answers improve.

Questions About Planning

Ask planning questions:

  • What should I do this year to reduce next year’s taxes?
  • How should I time income and expenses?
  • What estimated payments should I make?
  • How can I plan for growth?

Why this matters: Planning questions get planning advice. If you ask planning questions, advice improves.

Questions About Structure

Ask structure questions:

  • Is my entity structure optimal?
  • Should I consider changing structure?
  • How does structure affect taxes?
  • What are the tradeoffs?

Why this matters: Structure questions get structure advice. If you ask structure questions, advice improves.

Pro tip: Use our TAM Calculator to evaluate market opportunity and inform business planning. Calculate market size to understand growth potential.

questions to ask questions about strategy questions about planning questions about structure

Getting Strategy

Strategy requires engagement. Ask questions. Get advice. Apply strategies.

Engage Proactively

Be proactive:

  • Ask questions regularly
  • Seek advice before decisions
  • Discuss strategy quarterly
  • Engage year-round

Why this matters: Proactive engagement gets strategy. If you engage proactively, strategy improves.

Evaluate Advice

Assess advice:

  • Understand recommendations
  • Ask for explanations
  • Consider alternatives
  • Make informed decisions

Why this matters: Advice evaluation enables decisions. If you evaluate advice, decisions improve.

Apply Strategies

Implement advice:

  • Follow recommendations
  • Track results
  • Adjust as needed
  • Optimize continuously

Why this matters: Strategy application improves results. If you apply strategies, results improve.

Building Relationships

Good relationships get better service. Build trust. Communicate clearly. Work together.

Find Right Pro

Choose wisely:

  • Look for strategic focus
  • Check experience
  • Ask for references
  • Evaluate fit

Why this matters: Right pro provides strategy. If you find right pro, strategy improves.

Communicate Clearly

Communicate effectively:

  • Explain your situation
  • Ask clear questions
  • Provide information
  • Follow up regularly

Why this matters: Clear communication enables service. If you communicate clearly, service improves.

Work Together

Collaborate:

  • Share information
  • Discuss strategy
  • Make decisions together
  • Build partnership

Why this matters: Collaboration improves results. If you work together, results improve.

Pro tip: Use our TAM Calculator to evaluate market opportunity and inform business planning. Calculate market size to understand growth potential.

Your Next Steps

Working with tax pros gets strategic advice. Ask right questions, understand value, build relationships, get strategy, then save money to optimize taxes.

This Week:

  1. Begin identifying tax pro questions using our TAM Calculator
  2. Start finding right tax pro
  3. Begin asking strategic questions
  4. Start building relationships

This Month:

  1. Complete finding tax pro
  2. Set up regular communication
  3. Begin getting strategic advice
  4. Start applying strategies

Going Forward:

  1. Continuously ask questions
  2. Get strategic advice regularly
  3. Apply strategies
  4. Optimize taxes

Need help? Check out our TAM Calculator for market evaluation, our tax basics guide for fundamentals, our entity tax strategy guide for structure, and our tax strategy hub for tactics.


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Sources & Additional Information

This guide provides general information about working with tax professionals. Your specific situation may require different considerations.

For market size analysis, see our TAM Calculator.

Consult with professionals for advice specific to your situation.

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About the Author

jack nicholaisen
Jack Nicholaisen

Jack Nicholaisen is the founder of Businessinitiative.org. After acheiving the rank of Eagle Scout and studying Civil Engineering at Milwaukee School of Engineering (MSOE), he has spent the last 5 years dissecting the mess of informaiton online about LLCs in order to help aspiring entrepreneurs and established business owners better understand everything there is to know about starting, running, and growing Limited Liability Companies and other business entities.