Engaging an advisor, whether for financial, tax, or legal advice, is a significant decision in your financial life. Advisors are able to add value in numerous ways as you identify new goals, seek to address financial concerns, and approach significant life events. Moreover, an advisor decision is a long-term one, intended to last years or even decades. As such, ensuring you find the right advisor is essential.

Finding the right advisors for you consists of both finding an advisor with the right skillset for your unique needs as well as ensuring they service you in the way that you would like. There is no substitute for speaking directly with advisors to understand how they talk through issues, identify actions to take, and address your overall concerns.

In order to get the most out of your initial meeting(s), knowing which questions to ask can ensure you are able to obtain all the necessary information before making a final decision. We outlined some guidelines for you to consider here, based on the type of firm and also on your own needs.

Questions for Financial Advisory Firms
Questions for Tax Firms
Questions for Estate Planning Firms
If you’re a startup founder or early employee
If you’re an experienced investor
If you work in venture capital
Miscellaneous questions based on your specific situation


Questions for Financial Advisory Firms

When exploring a new financial advisory relationship, the following questions will help you understand the advisor’s view on what improvements you can make to your current portfolio, how you can better make future financial decisions, and also how the advisor reacts to market downturns and focuses on client-centric portfolio creation. These questions include:

Investment Approach:

  1. What are the biggest opportunities you see based on the way I am currently managing my capital?
  2. Which of my current investments (if any) would you definitely keep?
  3. Which asset classes/types of investments don’t I have that you would recommend?
  4. What types of insurance do you think I should have for risk protection or, if applicable, investment purposes?

Financial Planning Approach:

  1. For the major purchases/expenditures that I have planned or wish to make in the future, how would you help me think through the decision?
  2. Do you have current clients in my industry and at a similar phase of financial journey?
  3. Tell me about some of the client relationships where you have had the biggest positive impact?
  4. What are the most important information/research resources you use to determine your approach?
  5. How did you manage your clients during the 2008 recession?

Client Service Approach:

  1. Who would take over my account if you were to become sick or need to leave your practice?
  2. How often do you like to communicate with your clients? What would you expect me to proactively reach out about
  3. Why did you choose to work at (or start) this firm? What do you think makes it unique?


Questions for Tax Firms

When looking to engage a tax advisor, whether simply for yearly tax compliance or for more complex, ongoing tax planning, it is important to understand what role the firm and its team members will play in assisting you, how the firm has made an impact for previous clients, and other important details. Questions to explore include:

Tax Management Approach:

  1. Are you willing to review my prior year 1040 filing?
  2. Do you have current clients in my industry and at a similar phase of financial journey?
  3. Tell me about some of the client relationships where you have had the biggest positive impact?
  4. How many of your clients were audited last year? How did you help them through the process?
  5. When would you advise a client to think about putting an investment(s) in a LLC or other entity structure?
  6. I had a [recent personal example tax scenario/decision]. How would you have recommended I handle this?

Client Service Approach:

  1. How many clients do you work with where you prepare their individual taxes and not one for a related business?
  2. How will the team that works with me be structured? What role do you play and what do more junior people do?
  3. Who would take over my account if you were to become sick or need to leave your practice?
  4. Why did you choose to work at (or start) this firm? What do you think makes it unique?

 

Questions for Estate Planning Firms

When exploring a trust and estate lawyer, learning about how the team around you is structured, what the firm has done to have the greatest impact for previous clients in a similar position, and what structures the firm most often creates for clients, among other details, is essential to fully understanding how the lawyer will engage with you based on your personal situation. Areas to probe on include:

Trust & Estate Management Approach:

  1. Do you have current clients in my industry and at a similar phase of financial journey?
  2. Tell me about some of the client relationships where you have had the biggest positive impact?
  3. What are the most important information/ research resources you use to stay on top of changes in tax laws?
  4. How many of your clients were audited last year? How did you help them through the process?

Client Service Approach:

  1. How will the team that works with me be structured? What role do you play and what do more junior people do?
  2. Who would take over my account if you were to become sick or need to leave your practice?
  3. Why did you choose to work at (or start) this firm? What do you think makes it unique?
  4. What type of trusts/legal documents do you create most often?


If you’re a startup founder or early employee

These questions are best suited for your potential financial advisory and tax firms:

  1. For individuals with multiple tranches of equity, tell me about the criteria you use in advising clients on which specific options or shares to sell at a liquidity opportunity?
  2. What are some of the strategies that you recommend to clients that have short-term stock sales (e.g. they are selling options immediately after exercise) to optimize taxes in that year?
  3. How do your investment strategies differ when working with a client with a very large concentrated position in their portfolio?
  4. What are some of the estate planning strategies that you recommend clients think about before liquidity events?
  5. What is your familiarity level with QSBS eligibility and rules around rolling proceeds into other eligible investments without triggering tax obligations?


If you’re an experienced investor

These questions are best suited for your potential financial advisory and tax firms:

  1. Tell me about clients you work with that have previously self-managed and like to be actively involved. Are you comfortable factoring in fund managers I select with your overall portfolio and planning strategies?
  2. What role have you played in helping clients think about large purchases and potential financing, e.g. primary and secondary residences, etc.


If you work in venture capital

These questions are best suited for your potential financial advisory, tax, and estate planning firms:

  1. Tell me about how you work with clients that have unpredictable cash needs to fund co-investments or tax obligations related to carried interest?
  2. For clients where a majority of their capital is invested in funds at a firm where they work, what adjustments do you make to your investment management approach?
  3. For venture capital clients, what retirement strategies do you recommend to maximize tax deferrals?
  4. Do you provide assistance with helping to track clients private holdings and their tax treatment, e.g. QSBS?
  5. What are some of the estate planning strategies that you recommend to venture capital clients?


Miscellaneous questions based on your specific situation

These questions are best suited for your potential financial advisory firm:

  1. Tell me about how you have worked with couples where one partner has/controls the majority of assets.
  2. For younger clients with high starting asset levels, tell me about your approach to maximizing retirement accounts/ strategies to generate the highest long-term value.
  3. Do you have clients that have navigated a change in their state or country of residence?

Working with an advisor to manage the financial, tax and legal complexities you face provides a lot of value, but specifically finding the right advisor tailored to your personal goals, needs, and concerns can make all the difference as you strive to plan for the future and ultimately achieve the impact you desire.

To learn more about the firms who work with us, visit Our Firms and learn more about our Our Firm Evaluation Process.