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Completing your Tax Questionnaire

Updated: Jan 16

As tax season approaches, I thought it might be helpful to provide some guidance on how to successfully proceed in collecting and organizing your information.

Tax Questionnaire

The first step is to download this year’s tax questionnaire. The questionnaire is our basis in understanding your unique tax situation and provides the opportunity for you to assist us in the preparation of your taxes.  The tax questionnaire covers all tax situations. Since your situation is unique, not all sections in the questionnaire will apply to you, so please feel free to skip over those sections. However, for those sections that do apply to you – please fill them out completely and to the best of your ability.  Should you have any confusion over a section please don’t hesitate to contact me.

Wage, financial, and mortgage statements are a few of the documents you will receive that need to be included with your questionnaire. In some sections, we have asked if you have included a receipt. The receipts will help us ensure we have properly classified the item. Below, I’ve outlined a few of the mentioned documents and provided a little background on what information each provides and when you should expect to receive them.

Background Information

The first two pages give us a sense of your current situation. Please include yours (and your spouse’s) information. Along with your information, please upload yours (and your spouse's) current driver's license and social security card. If they are unchanged from last year, we already have them on file. Additionally, you (and your spouse) may receive a letter from the IRS providing you with an IP PIN. Please upload a copy of that letter as we will be unable to electronically file your taxes without the provided number. Not everyone will receive an IP PIN from the IRS. You will either have had to request it or you (or your spouse) would have had to be victims of identity fraud.

For the mailing address, please provide one we can add to our records where we could reliably forward any tax refunds and/or correspondences we may receive on your behalf.

To help facilitate the tax preparation process, we are also asking for contact information for your agent and financial advisor (if applicable). This will help us track down missing information or receive clarification as questions arise without asking you to take time out of your busy schedule.

We would strongly advise utilizing direct deposit for any refunds or balances due. If you are due a refund, you receive the money much faster. If you have a balance due, we will contact you prior to filing. Please provide your bank information to do so. If we did your taxes last year, we have the information on file.

Finally, please provide any information on your dependents that may be missing from our records. If you incurred any childcare expenses, college tuition, or student loan payments for you or a child, please include that information and any tax documents you received.

Tax Documents

Wage Slips

Employee wage statements (W-2’s in the U.S. or T-4s in Canada) need to be provided to you by January 31st (February 28th in Canada) – therefore you should receive your statements prior to this date. 

Statements from endorsement or contracted income will be reported on a 1099-MISC or 1099-NEC and they too are required to be provided to you by January 31st.  If you received income during 2023 but do not have a W-2’s or 1099-MISC/NEC from the payer, it’s extremely important to note the amount and who it was received from on your questionnaire in order for us to help you track them down and properly report your income.

For anyone who worked or played for a team based outside of the U.S. or Canada, please forward any documents you have that detail your earnings throughout the year. Ideally, a year end wage statement will be issued to you by your team. However, we recognize it is sometimes difficult to get that document from some foreign teams. If that is the case, please forward any paystubs or other documents showing your earnings you may have received through the year. One of the most common errors is neglecting to report this income and being audited later. Our goal is to make sure this doesn’t happen.

Itineraries & Missing Games

Team itineraries provide us beneficial information to assist us in preparing your taxes.  Please include your team’s monthly itinerary with your tax questionnaire. Not traveling to a road game will reduce your income earned in the state and could lower your tax liability. If you did not travel to a game, please include the dates/games you missed.

Financial statements

This information is reported on three separate documents that indicate interest (1099-INT), dividends (1099-DIV), and capital gains (1099-B) earned. If you work with a financial advisor, you will receive these statements in a combined report that will be provided to you by February 15th, however, in the past, the U.S. government has allowed an extension to March 1st due to the statement’s complexity. If you work with a financial advisor, please include their contact information with the questionnaire so we can touch base with them if we have questions or to assist you in tracking down missing documents. Since this income is reported to the Internal Revenue Service (IRS), should you fail to report it on your tax return – it sets off a red flag and you will be audited.

Please include whether or not you held, bought, and/or sold Cryptocurrency through the year. Buying or holding Cryptocurrency will have no impact on your tax liability but does need to be reported. If you sold any, please include any summaries you receive.

Foreign Bank Information

Having money in a bank based outside the United States must be reported if you file a resident tax return in the United States. Reporting these accounts have no impact on tax liability. It is strictly a reporting concern. Please do your best to include the maximum amount held in each account you may hold.

Retirement Contributions

There are multiple options available to individuals who wish to contribute to a retirement account. You are able to contribute to both a 401(k) through your employer and a IRA through a financial advisor. Both provide retirement savings and tax savings in different manners. A 401(k) contribution through your employer lowers your taxable income in the year the contribution is made. In 2023, you could have contributed up to $22,500 and for 2024 you are able to contribute up to $23,000. If you are interested, you should request information from your employer.

Additionally, you may make a combined $6,500 contribution for your 2023 taxes (up to $7,000 for 2024) to a Traditional IRA or ROTH IRA account prior to the April 15th filing deadline. Traditional IRAs provide immediate tax savings, while ROTH contributions provide no immediate tax savings but allow your investments to grow and be withdrawn later tax free. There are income limits on a direct ROTH IRA contribution, but a legal backdoor way exists to contribute if you fall above the income limit. If you would like to discuss further, please let us know. Anyone 50 years of age or older may contribute an additional $1,000.

There are additional retirement contributions available to self-employed individuals and Canadian tax residents. For self-employed individuals, you are eligible to contribute to a simplified employee pension plan (SEP). This must be done prior to filing your tax return, including an extension. The amount you are eligible for will be based on your self-employed income. Therefore, if you are interested please let us know and we will provide you further information after calculating your tax return. If you will file a Canadian resident return, you may make a registered retirement savings plan (RRSP) contribution prior to February 28th. Please let us know if you intend to do so.

Business Deductions

The changes in tax law have greatly reduced the ability to deduct businesses expenses not related to self-employment. To help simplify what may be beneficial to you, we would recommend only spending time on including agent fees, union dues, and conditioning expenses.

Mortgage Statements

If you financed your home, you are able to deduct your mortgage interest and property taxes.  If your taxes are escrowed through your mortgage, both the taxes and mortgage interest paid will be reported on a 1098 mortgage statement.  Mortgage interest statements are provided to you by January 31st and in general are included with your January mortgage statement or can be downloaded from your mortgage providers web site.  If you don’t have a mortgage, or pay your property taxes separate from a mortgage, you need to obtain a receipt showing that these taxes were paid.

Green Energy

The government provides tax credits for individuals who investment in plug-in hybrid/electric vehicles, home improvements related to those vehicles as well as other substantial home improvements aimed at reducing your heating/cooling/electric consumption/carbon footprint.

Medical Expenses

Although medical expenses can be used as a tax deduction, you will need to have had little income or a large amount of expenses for them to provide any savings. Unless that applies to you, you should skip this section.

Income from Self-Employment and Rental Properties

If you earn income from running your own business and/or a rental property it is important to keep good records and provide the most accurate information to us. You should total all of the income you earned throughout the calendar year for each business and/or rental property you own. You are allowed to take any expenses that are related to earning that income. Those expenses should be substantiated by a receipt. If you own or operate more than one business or rental property, please do your best to keep your income and expenses separate.


The tax deadline this year to file your 2023 return or to request an extension is April 15th in the U.S. and May 1st in Canada. In order for us to have ample amount of time to complete your tax return please do your best to provide your documents to us between March 1st to March 15th.


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