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Ten Questions Advisors Should Ask You

By Tim Scannell on February 27, 2024

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If you’re like most business owners, your desire for freedom is hardwired into your psyche.

But you know that being the boss doesn’t mean you’re free of demanding customers and employees.

For that level of independence, you may need to sell your business to fund the lifestyle you really want.

If you’re considering doing that – here are 10 key questions your advisor team should be asking you.

  1. How do you see your involvement in your business changing in the future?
  2. What is your plan for your ownership interest?
  3. If not you, have you thought about who the best leader might be?
  4. What obstacles could derail your business?
  5. If something happened to you, what would happen to your customers, vendors, and employees?
  6. How have you assessed the value of your business, and how confident are you in that assessment?
  7. What suggestions have your other business advisors given you to prepare for the future ownership of your business?
  8. What do you see as your greatest challenge when planning for the future?
  9. What’s your next great adventure after you leave?
  10. And what role does your business need to play in helping you achieve that financial freedom?

One of the most common questions I get is, “Tim, can you help me step away from my business with a plan to be financially secure?” And the answer is Yes.

I help business owners like you everyday step back from their business and plan for a future where work is optional – where family and passions are a priority again.

The next step is to call or e-mail me to schedule a free 1 hour “Exit Plan” meeting to get

  1. A clear picture of what your Work Optional life could look like..
  2. A clear picture of any gaps between that, and where you are now…
  3. And At least 3 strategies to help you get there faster and pay less in taxes.

You’re just 90 days from having a plan to make that a reality

Whether you have never thought about how to step away from your business on your terms,

Whether you have worked on exiting your business but did not get the results you wanted, or

If you are far into your exit planning process and want to make sure you’re doing it right – because you only get one shot at it.

I can help you.

Click here to set up a meeting with me.


Hightower Great Lakes is a group of investment professionals registered with Hightower Securities, LLC, member FINRA and SIPC, and with Hightower Advisors, LLC, a registered investment advisor with the SEC. Securities are offered through Hightower Securities, LLC; advisory services are offered through Hightower Advisors, LLC.

This document was created for informational purposes only; the opinions expressed herein are solely those of the author(s) and do not represent those of Hightower Advisors, LLC, or any of its affiliates.

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Hightower Great Lakes is a group comprised of investment professionals registered with Hightower Advisors, LLC, an SEC registered investment adviser. Some investment professionals may also be registered with Hightower Securities, LLC (member FINRA and SIPC). Advisory services are offered through Hightower Advisors, LLC. Securities are offered through Hightower Securities, LLC.

This is not an offer to buy or sell securities, nor should anything contained herein be construed as a recommendation or advice of any kind. Consult with an appropriately credentialed professional before making any financial, investment, tax or legal decision. No investment process is free of risk, and there is no guarantee that any investment process or investment opportunities will be profitable or suitable for all investors. Past performance is neither indicative nor a guarantee of future results. You cannot invest directly in an index.

These materials were created for informational purposes only; the opinions and positions stated are those of the author(s) and are not necessarily the official opinion or position of Hightower Advisors, LLC or its affiliates (“Hightower”). Any examples used are for illustrative purposes only and based on generic assumptions. All data or other information referenced is from sources believed to be reliable but not independently verified. Information provided is as of the date referenced and is subject to change without notice. Hightower assumes no liability for any action made or taken in reliance on or relating in any way to this information. Hightower makes no representations or warranties, express or implied, as to the accuracy or completeness of the information, for statements or errors or omissions, or results obtained from the use of this information. References to any person, organization, or the inclusion of external hyperlinks does not constitute endorsement (or guarantee of accuracy or safety) by Hightower of any such person, organization or linked website or the information, products or services contained therein.

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