Questionnaire to determine the potential to save taxes

My business adviser, a data scientist, asked me to compile a list of questions necessary to determine the tax saving potential of an individual person. The intent is to keep the list as short as possible but allow us to calculate an estimate of the amount of tax savings that are possible through comprehensive financial and tax planning. To me, this assignment is as complex as making a list of questions for a mechanic to know if an engine can be rebuilt or to tell a surgeon to know what operation should be performed. Yet I understand from readings on artificial intelligence that any human thinking process can be broken down into components and digitized with simply logical tests. This blog post is the beginning of that thinking. So far, I think it might be possible in less than a dozen questions.


  1. What is your W2 (salary) income?
  2. What is your 1099 (contractor) income?
  3. What is your taxable investment income (rental, securities, interest, etc.)?
  4. Are you the owner (5 percent of more) of a business? Does this generate income or loss? If so how much?
  5. Is your spouse an employee of the business where you are an owner?
  6. If so, what is the legal form of the business(es)? (sole proprietorship, partnership, LLC, S corporation, C corporation).
  7. Which of these expenses do you incur, and how much, as out-of-pocket expenses: heath care costs, medical or dental insurance cost, long-term care cost, life insurance cost, business-related travel or housing expenses, commuting expenses, business-related auto expenses, home office, tax preparation fees, retirement planning fees,
  8. Do you expect to pay educational expenses? If so, for who (yourself spouse,  child, grandchild, employee, other)?
  9. Do you have any strong community or charitable interests (that you may wish to fund)? Describe that plan.
  10. Do you anticipate selling any large assets (home, vacation house, business, etc) that will generate a gain? If so, describe this expectation in terms of timing and amount.
  11. Do you expect to have assets at the end of your life? If so, what is the approximate value of your assets and what do you intend to have happen with them?

These questions presume a small business environment where the respondent has access to influence employer compensation and benefits policies.

These questions are intended to address income taxes only and ignore the possible limiting effect of the alternate minimum tax and are no mean to delve into the possibility of estate taxes.


Leave a Reply

Your email address will not be published. Required fields are marked *