375 Questions to Ask an Accountant When Starting a Business

Starting a business? Exciting times, right? But let’s face it, the numbers game can be a real head-scratcher. But don’t worry! Your accountant is like a GPS for all those financial twists and turns. You have to ask the right questions to make sure you’re on the path to success.

So, whether it’s about taxes, loans, or how to make your business bigger and better, we’ve got a list of questions to get you sorted. Let’s dive in!

Questions About Startup Costs

  1. What counts as a startup cost?
  2. Can I deduct startup costs from my taxes?
  3. How do I categorize different startup expenses?
  4. How much should I budget for startup costs?
  5. Are there any grants or funding to help with startup costs?
  6. Can I use personal funds for startup costs?
  7. How should I record costs for initial inventory?
  8. What’s the best way to manage initial marketing costs?
  9. How do utility deposits and initial rent factor into startup costs?
  10. Should I account for employee training as a startup cost?
  11. How do I handle costs for business licenses and permits?
  12. What costs should I anticipate for initial legal advice?
  13. What’s the best way to finance my startup costs?
  14. Should I take out a loan for startup costs?
  15. How soon should I expect to recover my startup costs?
  16. Are there industry-specific costs I should be aware of?
  17. Do I need to separate startup costs from operating expenses?
  18. How do I allocate shared costs between startup and operational expenses?
  19. How much should I set aside for unexpected startup costs?
  20. How does initial product development costs factor in?
  21. Should I include technology setup costs as a startup expense?
  22. How do I treat the cost of buying business equipment?
  23. Do initial travel costs count as startup expenses?
  24. Should I include the cost of market research?
  25. How do I handle the costs of setting up a website?
  26. What are some commonly overlooked startup costs?
  27. How do I calculate the cost of time invested?
  28. How do interest rates affect my startup costs if I take a loan?
  29. Can I use crowdfunding to cover startup costs?
  30. Should I include the cost of insurance premiums as a startup cost?

Questions About Taxes

  1. What are the tax benefits and drawbacks of each business structure?
  2. How often do I need to file taxes?
  3. What tax forms do I need to fill out?
  4. What tax credits can my business qualify for?
  5. What are the tax deadlines I should be aware of?
  6. Do I need to collect sales tax?
  7. What’s the best way to handle payroll taxes?
  8. How do I pay myself, and how is it taxed?
  9. Can I write off business expenses?
  10. Do I have to pay quarterly taxes?
  11. What happens if I miss a tax deadline?
  12. How does having employees affect my taxes?
  13. How do I handle taxes for business vehicles?
  14. How are international sales taxed?
  15. What’s the deal with Value Added Tax (VAT)?
  16. Do I need an Employer Identification Number (EIN) for taxes?
  17. How are online sales taxed?
  18. What should I do if I get audited?
  19. How can I lower my business taxes?
  20. Do I need to pay local and state taxes, too?
  21. How does working from home affect my taxes?
  22. Are there any special tax rules for my industry?
  23. What records do I need to keep for tax purposes?
  24. Can I carry forward losses to the next tax year?
  25. How are donations and sponsorships taxed?
  26. What happens if I use personal funds for the business?
  27. Can I get a tax extension?
  28. What are capital gains, and how are they taxed?
  29. How does depreciation work for taxes?
  30. What’s the tax impact of selling my business?
  31. How do state taxes differ from federal taxes for my business?
  32. Are there tax benefits for hiring veterans or other specific groups?
  33. How does leasing or buying equipment affect my taxes?
  34. What kind of documentation do I need for tax-deductible expenses?
  35. Are there any special tax considerations for freelancers or gig workers?
  36. How do tax laws change if my business becomes a franchise?
  37. Is it better to use a standard deduction or itemize expenses?
  38. Do I need to pay taxes on bartered services?
  39. What are the tax implications of business partnerships and joint ventures?
  40. What are the tax rules for business mergers or acquisitions?
  41. What are the tax considerations for having remote or out-of-state employees?
  42. What is the Alternative Minimum Tax (AMT), and could it affect my business?
  43. What kinds of taxes will I face if I sell products or services overseas?
  44. Are employee benefits like health care or retirement plans tax-deductible?
  45. What are estimated taxes? Do I need to pay them?
  46. How do I account for tips if my business is in the service industry?
  47. Are there special tax considerations for seasonal businesses?
  48. What are “pass-through” taxes?
  49. How do they apply to my business?
  50. How do I handle taxes if I want to run my business as a non-profit?

Questions About Business Structure

  1. What’s the best type of business structure for me?
  2. What are the costs of setting up each type of structure?
  3. How will the structure affect my ability to get loans?
  4. What paperwork do I need to set up a business structure?
  5. Do I need a lawyer to help with forming a business structure?
  6. What are the risks of each structure type?
  7. How easy is it to change my business structure later?
  8. Can I switch from a sole proprietor to an LLC or corporation?
  9. How does each structure affect my personal assets?
  10. Can I have partners with this type of structure?
  11. What happens if my business partner leaves?
  12. How does the structure impact how I pay myself?
  13. What’s the best way to bring in investors?
  14. How many owners can each structure have?
  15. How does business structure affect my relationship with employees?
  16. Do I need to have board meetings and keep minutes?
  17. How does each structure affect my business credit?
  18. Do I need to make public disclosures with certain structures?
  19. How does a business structure affect selling my business later on?
  20. What are the yearly fees for each type of structure?
  21. Can I operate in multiple states with my chosen structure?
  22. How are decision-making powers divided in different structures?
  23. Do I need to register my business structure with the state?
  24. How does a business structure affect my ability to get government grants?
  25. How does each structure affect profit sharing?
  26. Can I own multiple businesses with my chosen structure?
  27. What happens if my business gets sued?
  28. How easy is it to dissolve the business with each structure?
  29. Are there any special licenses or permits needed for different structures?

Questions About Cash Flow

  1. How do I create a cash flow statement?
  2. What’s the best way to monitor cash flow?
  3. How can I improve negative cash flow?
  4. How often should I check my cash flow?
  5. How do I handle cash flow from different revenue streams?
  6. What are the key indicators of good cash flow?
  7. How do seasonal fluctuations affect cash flow?
  8. How do I forecast future cash flow?
  9. What should I do if I run into cash flow problems?
  10. What is a healthy cash reserve for my type of business?
  11. How can invoice timing affect my cash flow?
  12. Do late payments from clients impact cash flow?
  13. How can discounts or incentives affect cash flow?
  14. Should I get a line of credit to help with cash flow?
  15. How do different payment terms impact cash flow?
  16. What is the cash conversion cycle, and why is it important?
  17. How does inventory management affect cash flow?
  18. What is operating cash flow, and how do I improve it?
  19. How do I handle unexpected expenses and their impact on cash flow?
  20. How do business loans affect cash flow?
  21. How can I speed up accounts receivable to improve cash flow?
  22. Should I be concerned about a sudden increase in cash flow?
  23. How do taxes impact my cash flow?
  24. What’s the difference between cash flow and profit?
  25. Can I use cash flow to pay off debt?
  26. Should I reinvest positive cash flow back into the business?
  27. How do dividends or owner withdrawals affect cash flow?
  28. What are the cash flow implications of expanding my business?
  29. How do economic downturns affect cash flow?
  30. What are some cash flow red flags to look out for?
  31. What are some quick ways to boost my cash flow?
  32. How do supplier payment terms affect my cash flow?
  33. How do membership or subscription models affect cash flow?
  34. What impact does offering refunds have on cash flow?
  35. How do I handle cash flow if my business is project-based with irregular income?
  36. Is it a good idea to take a short-term loan for immediate cash flow needs?
  37. How do I handle a cash surplus effectively?
  38. How can changes in tax rates or regulations impact my cash flow?
  39. What role do deposits and down payments play in cash flow?
  40. Should I use accounting software to help manage my cash flow?
  41. How can I set up an emergency fund without hurting my cash flow?
  42. How do penalties for late payments from clients or suppliers affect cash flow?
  43. What are some common cash flow mistakes to avoid?
  44. Can I use cash flow to evaluate the performance of different business units or locations?
  45. How do I adjust my cash flow strategy as my business grows?

Questions About Business Loans And Funding

  1. What are the types of business loans available?
  2. How do I qualify for a small business loan?
  3. What are the pros and cons of taking out a business loan?
  4. How do interest rates affect loan repayments?
  5. What is the process for applying for a loan?
  6. What documentation do I need for a loan application?
  7. Can I get a business loan with bad personal credit?
  8. What are the tax implications of taking out a loan?
  9. Are there grants available for my type of business?
  10. How do crowdfunding and peer-to-peer lending work?
  11. What’s the difference between secured and unsecured loans?
  12. How do SBA loans work?
  13. How much of a loan can I afford?
  14. Can I use a personal loan for business purposes?
  15. What are the costs involved in getting a loan, like application fees?
  16. What is loan amortization, and how does it work?
  17. What is a line of credit, and how does it differ from a loan?
  18. What happens if I default on a loan?
  19. Can I pay off a loan early, and are there penalties for that?
  20. How do I build business credit?
  21. Are there industry-specific loans I should consider?
  22. How do I compare loan offers from different lenders?
  23. What is a co-signer, and do I need one for a business loan?
  24. What are convertible loans, and are they suitable for startups?
  25. Can I renegotiate a loan if my financial situation changes?
  26. What are microloans, and are they a good option for small businesses?
  27. How do I handle multiple loans or debts?
  28. What is equity financing, and how does it differ from a loan?

Questions About Financial Planning

  1. How do I create a realistic business budget?
  2. What’s the best way to set financial goals for my business?
  3. How should I prioritize my business expenses?
  4. How do I create a profit and loss statement?
  5. What financial ratios should I keep an eye on?
  6. How much should I pay myself as the business owner?
  7. What’s the ideal profit margin for my type of business?
  8. How much should I reinvest into the business?
  9. How do I plan for business growth financially?
  10. What are some key performance indicators (KPIs) for financial health?
  11. How do I manage business debt effectively?
  12. How can I improve my business’s profitability?
  13. How should I price my products or services for the best financial results?
  14. How can I financially prepare for economic downturns or slow seasons?
  15. How much working capital does my business need?
  16. What kind of reserve fund should I have?
  17. Should I hire a full-time financial planner or CFO?
  18. How do interest rates affect my business planning?
  19. Should I consider diversifying my product or service line?
  20. How do I measure the financial success of a marketing campaign?
  21. What’s the best way to manage vendor and supplier costs?
  22. How do I plan for unexpected expenses?
  23. When should I consider merging with or acquiring another business?
  24. How do I evaluate the ROI of new projects or investments?
  25. What should I include in a 5-year financial plan?
  26. What’s the financial impact of hiring more staff?
  27. How do I calculate my break-even point?
  28. What steps can I take to increase business value if I plan to sell?
  29. How do I assess the financial health of potential partners or investors?
  30. How often should I review and adjust my business budget?
  31. Should I buy or lease equipment, and how does each option affect my finances?
  32. What strategies can I use to improve accounts receivable turnover?
  33. How do different types of debt financing impact my financial planning?
  34. How do I calculate customer lifetime value, and why is it important?
  35. How do I forecast revenue and expenses accurately?
  36. What financial metrics should be in my monthly report?
  37. What should I include in an exit strategy from a financial perspective?
  38. How do currency exchange rates affect my financial planning for international business?
  39. What steps should I take to prepare for a financial audit?
  40. How do I decide if a new project or product line is financially viable?
  41. Should I focus on gross margin or net margin?
  42. How can I create a financial contingency plan for emergencies?

Questions About Growth Strategies

  1. What key financial indicators show my business is ready for growth?
  2. How much capital will I need to expand my business?
  3. What are the risks and rewards of expanding to new locations?
  4. How can I expand my business without over-leveraging?
  5. What type of funding is best for business growth?
  6. How do I budget for marketing and advertising to fuel growth?
  7. Should I focus on customer retention or acquiring new customers for growth?
  8. What are the tax implications of business growth?
  9. How do I evaluate the ROI of growth strategies?
  10. What are the operational challenges I might face with rapid growth?
  11. When is the right time to hire more employees to support growth?
  12. How can I scale my supply chain effectively?
  13. What financial metrics should I monitor to measure growth success?
  14. Should I consider international markets for growth?
  15. What are the financial benefits and drawbacks of franchising?
  16. How do I adjust my pricing strategy for growth?
  17. How do growth strategies differ for service-based vs. product-based businesses?
  18. What steps should I take to prepare for a capital campaign?
  19. How do I create a 5-year growth plan?
  20. How can I leverage customer data for growth?
  21. What role do partnerships and collaborations play in growth?
  22. How can I use technology to improve business scalability?
  23. Should I invest in research and development for future growth?
  24. How can I ensure quality is maintained during rapid growth?
  25. How do I manage increased overhead costs?
  26. Should I focus on organic growth or look for external opportunities?
  27. How do I manage debt and equity when scaling?
  28. What’s the best way to manage inventory for a growing business?
  29. How do changes in market conditions affect my growth plans?
  30. How do I prepare my business for due diligence if I am looking for investors or selling?
  31. How do I manage cash reserves effectively during rapid expansion?

Questions About Record-Keeping

  1. What records do I absolutely have to keep?
  2. What’s the best software for keeping records?
  3. How long do I need to keep tax records?
  4. Do I need separate bank accounts for my business?
  5. How should I track my expenses?
  6. How do I keep track of sales and revenue?
  7. Do I need to keep paper receipts?
  8. How do I record online transactions?
  9. What records do I need for employees?
  10. What’s the best way to manage invoices?
  11. Do I need an audit trail for my financial transactions?
  12. How should I manage petty cash?
  13. What’s the best way to track inventory?
  14. How should I record business travel expenses?
  15. What records do I need for subcontractors?
  16. Do I need to record board meeting minutes?
  17. What documents are needed for investments in the business?
  18. How do I keep track of loans and interest?
  19. What financial reports should I be generating?
  20. How do I record grants or funding?
  21. Do I need to keep records of customer information?
  22. How do I record asset purchases like equipment?
  23. What’s the best way to manage digital records?
  24. Do I need to keep records of business licenses and permits?
  25. How do I record refunds and exchanges?
  26. What should I do if documents are lost or damaged?
  27. How should I record equity and shares?
  28. How do I track tax-deductible donations?
  29. How should I record business gifts and freebies?
  30. What records should I keep if I close or sell my business?
  31. How do I set up a chart of accounts for my business?
  32. What records do I need to keep for virtual or digital currencies?
  33. How do I handle record-keeping for business-related meals and entertainment?
  34. How should I record my start-up costs?
  35. Do I need to record every single sale, or can I summarize daily sales?
  36. How do I keep track of recurring subscription revenue?
  37. What records should I keep for promotional offers and discounts?
  38. How should I document any loans I give to the business?
  39. Do I need to keep copies of contracts and agreements?
  40. How should I record advances to suppliers or employees?
  41. What records do I need to keep for outsourcing or subcontracting work?
  42. How do I record adjustments for things like returned goods?
  43. What’s the best way to record crowdfunding income?
  44. Do I need to keep track of digital downloads or online content sales?
  45. How should I document business losses, like theft or damage?
  46. How do I keep track of warranty and guarantee claims?
  47. Should I be keeping records of customer complaints or feedback?
  48. What’s the best way to manage and record gift cards and vouchers?
  49. How do I document changes in ownership or business structure?

Questions About Deductions And Credits

  1. What are the most common tax deductions for small businesses?
  2. What kinds of business expenses are not deductible?
  3. How do vehicle expenses work for deductions?
  4. Can I deduct the cost of business meals?
  5. How do I claim deductions for business travel?
  6. What’s the deal with the Research & Development tax credit?
  7. Can I get a tax credit for hiring employees?
  8. Are advertising and marketing costs deductible?
  9. Can I deduct utility bills for my business?
  10. How do educational expenses for training factor into deductions?
  11. Can I deduct business-related software subscriptions?
  12. Are there any deductions for businesses that are eco-friendly?
  13. Can I get a tax credit for providing healthcare benefits?
  14. How do I handle deductions for freelance or contract workers?
  15. What are the limits on charitable contribution deductions?
  16. How do state-specific deductions and credits work?
  17. Can I claim a credit for business property taxes?
  18. Are there special deductions for businesses hit by natural disasters?
  19. How do retirement contributions affect deductions and credits?
  20. Can I deduct legal and professional fees?
  21. What are the rules around the Work Opportunity Tax Credit?
  22. Are there any deductions for exporting goods?
  23. Can I claim deductions for business insurance premiums?
  24. What is Section 179, and how can it help with deductions?
  25. Can I get credit for making my business more accessible?
  26. How do I claim a credit for paid family and medical leave?
  27. What deductions can I claim for repairs and maintenance?
  28. Are there any age or revenue restrictions for certain deductions and credits?

Questions About Payroll

  1. How do I set up a payroll system for my business?
  2. What are the important deadlines related to payroll taxes?
  3. How do I classify employees vs. contractors for payroll?
  4. Do I need workers’ compensation insurance?
  5. What’s the best payroll software for my business size and type?
  6. What are the rules for overtime pay?
  7. How do I handle employee benefits in payroll?
  8. What payroll records are required by law?
  9. How do I handle tips in the payroll system?
  10. What’s the best way to distribute paychecks: direct deposit, checks, or pay cards?
  11. How do I calculate payroll deductions?
  12. What are my responsibilities for matching Social Security and Medicare taxes?
  13. How do local and state taxes affect payroll?
  14. How do I account for sick leave and vacation time?
  15. Can I handle payroll myself, or should I outsource it?
  16. How do I set up and manage retirement plans like a 401(k) through payroll?
  17. What are the penalties for payroll tax mistakes?
  18. How do employee bonuses impact payroll taxes?
  19. How often should I run payroll?
  20. What are the rules for paying minors or interns?
  21. What is garnishment, and how is it handled in payroll?
  22. How do I report and pay payroll taxes?
  23. What forms do employees need to fill out for payroll?
  24. Are there tax credits related to payroll that I should know about?
  25. How do I handle raises and promotions in the payroll system?
  26. How does telecommuting or remote work affect payroll?
  27. Can I set up automatic payroll?
  28. What are the steps for terminating an employee in the payroll system?
  29. How does payroll work if I have employees in multiple states?
  30. What happens to payroll if I decide to sell the business?
  31. What is the Fair Labor Standards Act (FLSA), and how does it affect my payroll?
  32. How do commissions and bonuses work in payroll?
  33. Can I offer non-cash benefits, like stock options, through payroll?
  34. How does payroll work for temporary or seasonal workers?
  35. How do I adjust payroll for salary advances or loans to employees?
  36. What is the Employee Retention Credit, and how does it affect payroll?
  37. What are my obligations for public holiday pay?
  38. Do I need to set up a separate payroll for international employees?
  39. How can I protect my payroll data from fraud or theft?
  40. How often do I need to update payroll software or systems?
  41. How does maternity or paternity leave affect payroll?
  42. What’s the process for an internal payroll audit?
  43. How do I reconcile payroll at the end of the year?

Frequently Asked Questions

How do you assess an accountant?

To assess if an accountant is right for you, look at a few key things:

  1. Credentials: Make sure they’re certified and have the right training.
  2. Experience: Ask if they’ve worked with businesses like yours before.
  3. Communication: They should explain things in a way you understand. You should feel comfortable asking questions.
  4. Timeliness: They should get work done on time, especially important things like tax filings.
  5. Cost: Know what they charge and make sure it fits your budget.
  6. References: It’s a good sign if other people recommend them.
  7. Gut feeling: Sometimes, it’s about how comfortable you feel with them. You will share a lot of important information, so trust is key.

Remember, it’s okay to talk to a few different accountants before you make your choice.

How often should I meet with my accountant?

The frequency of meetings with your accountant can depend on your specific financial situation and needs. However, some businesses may find it adequate to meet with their accountant annually for tax purposes, while others might benefit from quarterly or even monthly meetings.

What tasks are accountants expected to perform?

Accountants can do a lot of different tasks to help your business. Here’s a quick rundown:

  1. Bookkeeping: This basically keeps track of all the money that comes in and goes out.
  2. Tax prep: They help you prepare for tax season, making sure you pay what you owe and find any tax breaks.
  3. Financial reports: They make reports that show how your business is doing. This is really helpful for planning.
  4. Budgeting: They can help you make a budget so you know what you can spend and where you can save.
  5. Payroll: If you have employees, an accountant can manage their paychecks and benefits.
  6. Legal stuff: They ensure you follow all the money and tax laws.
  7. Advice: They can give you tips on leasing or buying equipment, growing your business, and other big decisions.
  8. Audit support: If the tax folks want to check your records, an accountant can help you through that process.

Each accountant might offer different services, so it’s a good idea to ask what they can do for you.


Remember, asking the right questions can make all the difference in steering your business to success. Think of your accountant as your co-pilot in this adventure—there to help navigate the financial clouds and keep you soaring. So take this list with you, and make that meeting count.

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Robby Salveron

Robby is a multimedia editor at UpJourney with a journalism and communications background.

When she's not working, Robby transforms into an introverted art lover who indulges in her love for sports, learning new things, and sipping her favorite soda. She also enjoys unwinding with feel-good movies, books, and video games. She's also a proud pet parent to her beloved dog, Dustin.