Training Your Clients: How CPAs Can Get Customers Prepped for Tax Season


If the plethora of emails containing links to documents and ads for tax filing software are anything to go by, it’s tax season again. For CPAs this is an understandably busy time of year. For CPAs with disorganized and unprepared clients, this is a time of year that may produce a lot of headaches.

Solo Hustle is the kind of software that, in retrospect, would be great for your clients to start using last January. Without a time machine, we can’t solve that problem for you. But we can give you the talking points to get your clients on track for next year.

Let’s get started making 2024 your easiest tax season. We’ll cover:

  • Pointing out possible deductions to track.
  • Communicating strategies to minimize liability.
  • What documentation they need to have ready for their tax appointment.
  • Which tax laws and regulations they need to stay on top of all year.
  • Checklists to share to make it easier to stick to your advice.

Evaluating and communicating deductions to track

Deductions are probably the biggest question clients will have for a CPA, and also the place where clients bear most of the responsibility for proper documentation.

Make clear to your tax clients from the start which deductions they qualify for and how to document them. Provide a helpful checklist so they can prep for this evaluation before your first meeting:

  • Highlight any regular charitable donations, business expenses, etc. in financial records.
  • Bring copies of previous tax returns and any supporting documentation for previous deductions taken.
  • Be prepared to discuss the business in detail so research can be conducted on applicable deductions and other tax considerations.
  • Provide access if possible to Quickbooks, Solo Hustle, or other software used to track finances and invoices.

Having clients pre-prep before first meetings achieves several goals:

  1. Clients start as you mean them to go on—taking personal responsibility for their finances, tax obligations, and related paperwork.
  2. Quick discovery speeds up your on-boarding process and allows you to quickly pinpoint issues with organization, legal pitfalls, and financial concerns.
  3. Answers that are lacking or unanswerable give you the foundation to broach recommendations for investing in management systems to help them better organize and manage their business.

Focus on organization

Tax time with any particular client can be made or broken on organization. If the pre-prep and introductory meeting reveals they have no current system for organizing and tracking finances, recommend your favorite systems and offer to train and help them set it up in the most efficient way. If they already have a system, review their setup to ensure that they are using it in a way that will streamline financial planning and taxes.

Keep in mind that client expenses may preclude some of the pricier options. Getting them started on free systems like Solo Hustle can be a way to train them in organization practices without adding to their monthly bills. Any recommendations should include the ability for you to access their record keeping, making it easy to file their taxes, plan their financial management, keep them on budget, and any other services you are providing.

In addition, provide tips and tricks that will make your job easier while protecting their financial responsibilities and growth plans:

  • Help them set a regular practice of reconciling bank and credit card accounts.
  • Provide a list of receipt types and other documents that will be required to qualify for certain deductions.
  • Work with them to properly organize their current or new systems so they have both good habits moving forward and you can quickly access needed documentation.
  • Create an easy to follow budget overview, including due dates and amounts, for monthly and quarterly expenses, so clients know what to reserve and can make better decisions about new expenses or expansions.
  • Schedule regular check-ins to keep everyone accountable and make sure organization is not lapsing, especially approaching key tax periods.

Pay special attention to tax documentation requirements

Provide an easy checklist clients can consult on a daily and weekly basis as they process bills and invoices. If possible, set up their current or new financial and project planning tools to easily keep things organized.

  • Invoices and receipts for all business expenses, such as office supplies, equipment, and services.
  • Bank and credit card statements, as well as other financial records that show income and expenses.
  • Records of any sales tax collected from customers and paid to the government.
  • Payroll records, including employee W-2 forms and 1099 forms for independent contractors.
  • Records of any business use of a personal vehicle, including the vehicle’s make, model, and license plate number, as well as the business mileage driven.
  • Records of any depreciation taken on business assets, such as equipment or vehicles.
  • Records of any home office expenses, if the business owner is claiming a home office deduction.
  • Records of any charitable contributions made by the business.
  • Any other documents required by the government, such as licenses and permits.

As your clients are likely to come from a variety of businesses, have a checklist template on hand and save different versions for different businesses you encounter so it’s easy to put together an on-boarding package.

Laws and pay periods for small businesses and side hustles

Let’s focus for a moment on clients who are running side hustles and small businesses (self-employed, solo entrepreneurs, etc.). These clients are likely to have limited experience with business taxes and other legal obligations. Keep a generic but customizable calendar that can match their budget cheat sheet so they are not surprised by sudden periods. Items to include:

  • Self-Employment Tax: Explain that if a side hustle is a sole proprietorship or a partnership, the client will be responsible for paying self-employment tax on earnings, including the employee and employer portions of Social Security and Medicare taxes.
  • Income Tax: Obviously side hustle income must be reported on personal income tax returns. Depending on income level and type of business, clients may be required to make estimated tax payments throughout the year to avoid underpayment penalties.
  • Sales Tax: If a side hustle involves selling goods or services, clients may be required to collect and remit sales tax to their state’s tax department.
  • Payroll Tax: If your client has any employees in their business, they could be responsible for withholding and remitting payroll taxes, including federal and state income taxes, Social Security and Medicare taxes, and unemployment taxes. Side note: At initial meetings, walk them through employees vs. subcontractors.
  • Pay period: Depending on the nature of a side hustle, clients may need to pay themselves a salary or wages and file form W-2 and/or 1099-MISC for independent contractors. The pay period and frequency of pay will affect the pay period and frequency of payroll tax deposits.

Keeping clients on track

Conveying disappointment to a client can be a delicate matter, as it involves potentially negative information and may also affect the client-professional relationship. Here are a few tips on how to handle this situation:

  1. Be tactful and professional. Avoid using accusatory or blameable language, and instead focus on the facts and what needs to be done to resolve the situation.
  2. Be clear and specific about the issues. Clearly explain the problems and the reasons why they occurred. Provide supporting documentation or evidence if necessary.
  3. Provide possible solutions and alternatives. Instead of just pointing out the problems, also offer suggestions on how to fix them. Go over the calendars and checklists you’ve shared, review their software systems, and frankly discuss what has been working and what they struggle with to find better solutions.
  4. Be empathetic. Understand and acknowledge the client’s feelings and concerns, and assure them that you are working on finding a solution.
  5. Communicate openly and honestly. Be transparent and honest with your client, and keep them informed of any progress or changes.
  6. Be ready to take responsibility. If the problem is caused by your mistake or negligence, take responsibility and apologize for it.
  7. Follow up and review. Follow up with the client to ensure that the issues have been resolved and to review the situation to prevent similar issues from happening again in the future. Consider regular automated emails to gently remind them of upcoming tasks and due dates and to stay on task.

It is important to remember that effective communication is key to maintaining a positive relationship with your client and to address any issues in a professional and timely manner.

Solo Hustle is a powerful resource

Even if you can’t get clients to try Solo Hustle for free to start developing good habits, use your relationship with them to share Solo Hustle’s other resources, including valuable blog content that will give them advice on growing their business, setting goals, dealing with subcontractors, and more.


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