20 Questions

CPA Questions to Ask

Essential questions to ask a CPA to maximize your tax strategy, financial planning, and ensure you're getting the most value from your accounting relationship.

1

What tax strategies can I implement now to reduce my tax burden for next year?

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Why this works

Proactive planning helps you take advantage of opportunities before year-end and ensures you're not missing any tax-saving strategies.

2

How should I organize my financial documents throughout the year to make tax preparation easier?

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Why this works

Proper organization saves time and money during tax season while ensuring you don't miss any deductions or credits.

3

What business expenses can I deduct, and how do I properly document them?

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Why this works

Maximizes your deductions while ensuring you have proper documentation to support your claims in case of an audit.

4

Should I be making estimated tax payments, and if so, how much and when?

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Why this works

Prevents underpayment penalties and helps you manage cash flow by spreading tax payments throughout the year.

5

What retirement account options would benefit me most given my current situation?

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Why this works

Retirement planning is crucial for long-term financial health and often provides immediate tax benefits.

6

How can I optimize my business structure for tax purposes?

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Why this works

The right business structure can significantly impact your tax liability and provide other financial benefits.

7

What records should I keep and for how long?

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Why this works

Proper record retention protects you legally and ensures you have documentation for future tax planning or audits.

8

Are there any tax credits I might be eligible for that I'm not currently claiming?

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Why this works

Tax credits provide dollar-for-dollar savings and many people miss out on credits they're entitled to receive.

9

How should I handle income from side hustles or freelance work?

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Why this works

Gig economy income has specific tax implications and proper handling prevents costly mistakes and penalties.

10

What's the best way to handle major life changes like marriage, divorce, or having children from a tax perspective?

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Why this works

Life changes significantly impact your tax situation and early planning can save money and prevent problems.

11

How can I prepare for a potential IRS audit, and what should I do if I get audited?

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Why this works

Audit preparation reduces stress and increases your chances of a favorable outcome if you're selected for examination.

12

What investment strategies can help reduce my tax liability?

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Why this works

Tax-efficient investing can significantly improve your after-tax returns and long-term wealth building.

13

How do I handle taxes if I work remotely for a company in another state?

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Why this works

Remote work creates complex multi-state tax issues that require careful planning to avoid penalties and double taxation.

14

What's the difference between tax avoidance and tax evasion, and how do I stay on the right side?

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Why this works

Understanding the legal boundaries helps you maximize legitimate tax savings while avoiding serious legal consequences.

15

How can I use my home office deduction effectively while staying compliant?

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Why this works

Home office deductions can provide significant tax savings but require strict compliance with IRS rules to avoid problems.

16

What should I know about quarterly tax planning and year-end tax moves?

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Why this works

Timing is crucial in tax planning - knowing when to make moves can significantly impact your tax liability.

17

How do I handle cryptocurrency transactions for tax purposes?

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Why this works

Crypto taxes are complex and rapidly evolving - proper handling prevents costly mistakes and ensures compliance.

18

What's the best way to handle student loan interest and education-related tax benefits?

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Why this works

Education tax benefits can provide significant savings but have specific rules and limitations that must be followed.

19

How can I use charitable giving to reduce my tax burden while supporting causes I care about?

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Why this works

Strategic charitable giving can provide tax benefits while allowing you to support meaningful causes.

20

What should I do if I discover I made an error on a previous tax return?

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Why this works

Addressing past errors proactively is usually better than waiting for the IRS to discover them, and can often reduce penalties.

Maximizing Your CPA Relationship

Expert tips and techniques for getting the most out of these questions.

Best Practices for Working with Your CPA

Communicate Year-Round

Don't wait until tax season to talk to your CPA. Regular communication helps them provide better advice and catch opportunities you might miss.

Keep Detailed Records

Maintain organized records throughout the year. This saves time and money during tax preparation and provides protection in case of an audit.

Ask Questions Early

If you're unsure about a financial decision, ask your CPA before acting. It's much easier to plan correctly than to fix mistakes later.

Question Sequences

The Tax Planning Sequence

1
What strategies can I implement now?
2
How will these affect my current year taxes?
3
What should I do differently next year?
4
How do I track the effectiveness of these strategies?

The Business Structure Review

1
Is my current business structure optimal?
2
What are the tax implications of changing?
3
What other factors should I consider?
4
When would be the best time to make changes?

Common Pitfalls

Don't Wait Until April

Tax planning is most effective when done throughout the year, not just during tax season when it's often too late to make changes.

Don't Make Assumptions About Deductions

Tax rules are complex and change frequently. Always verify with your CPA before assuming something is deductible.

Don't Ignore Estimated Tax Requirements

Underpayment penalties can be significant. Work with your CPA to determine if and when you need to make estimated payments.

Conversation Templates

The Proactive Planner

1
Step 1: Start with: 'I'm planning to [specific financial decision] and I want to understand the tax implications.'
2
Step 2: Ask: 'What should I consider before moving forward?'
3
Step 3: Follow with: 'How can I structure this to be most tax-efficient?'

The Problem Solver

1
Step 1: Begin with: 'I think I may have made a mistake on my taxes when...'
2
Step 2: Ask: 'What are my options for fixing this?'
3
Step 3: Request: 'What's the best way to handle this situation?'

Further Reading

IRS Publication 17: Your Federal Income Tax
"Tax Planning for the Small Business Owner" by Keith Hall
Your state's tax authority website for local tax information

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