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Value Acceleration & Exit Planning

Questions an Exit Planning Advisor Should Ask for Better Results

At a Glance

Main Takeaway

A competent exit planning strategy is critical to your company’s future if you own a business. Exit planning allows you to transfer knowledge, identify employee needs and skill gaps, and bring in new and diverse top talent. With a solid exit plan, you can ensure that your business continues to thrive once you leave.

To facilitate a smooth transition of ownership, business owners should plan to meet with an exit planning advisor long before exiting. An exit planning advisor will look at your company’s organizational structure and scope of your plan and formulate a strategy that places your unique personal and business goals at the forefront.

Next Step

The initial session between the client and the exit planning advisor is an opportunity for the advisor to glean critical information about you and your business. Learn the questions exit planning advisors should ask to yield the most constructive and beneficial results.


Avoid Unproductive Questions

An exit planning advisor is a relationship-builder and a problem-solver. In your initial conversation with an advisor, they will aim to gather valuable information and establish meaningful rapport and a positive relationship with you.

Their questions can influence the success or failure of your first discussion. For the most productive first meeting, they should avoid generic planning questions that do not yield specific, actionable goals for your company.

At first, you may feel like your advisor is giving you a sales pitch and feel guarded about what information they are asking for, making you hesitant to share valuable information.

Understand that opening up to your advisor’s questions can help you prepare an exit strategy to ensure a smoother and more profitable transition when you decide to leave your business. Without an honest and in-depth question and answer session to provide a sound succession planning strategy, you may fail to meet your financial goals and put your business at risk.

7 Topics to Cover in Exit Planning Conversations

If your advisor asks the right questions in your initial exit planning conversation, you will be more likely to open up and share valuable information. The most beneficial initial discussions touch on the following seven topics:

1.  Client Current Involvement

They should ask you about your current involvement in the business and if you plan to stay involved in any capacity after the transition. These questions prompt discussions about recruiting and maintaining key talent, incentive plans, and the upcoming management transition.

2.  Client Desired Post-Exit Future

To gain insight into your preferred exit timeline, your advisor should ask what you plan to do after exiting the business. They may ask how soon you intend to leave so they can help determine the best strategies to move people into new roles in the time needed.

Also, they may want to know your retirement plans post-exit; for example, do you want to start another business, buy a vacation home, or invest in real estate? The answer to these questions can help your advisor find solutions that work for the transition.

3.  Client Financial Needs

Your advisor must learn about your finances to develop a strategic exit planning solution. To gauge your financial status, they may ask questions such as:

  • Do you know what your business is worth? Do you currently have a value acceleration strategy in place?
  • What will your financial needs be post-transition? Will you have a source of income?
  • Is your retirement plan contingent on proceeds from the sale of your business?
  • How detailed is your estate planning?
  • What strategies have you put in place to maximize your current business value?

4.  Client Challenges and Obstacles

Your advisor should ask what worries you the most about exiting your business. Learning about your fears helps your advisor to identify gaps in your exit planning strategy and what business areas to prioritize.

Open and honest conversations with your advisor builds trust. Increasing your willingness to share critical business and financial details of your company’s operations enables your advisor to help ensure all your financial and emotional expectations and needs are met.

5.  Client Current Transition Plan

Some clients come into their first exit planning conversation with an exit plan already decided, while others have not thought about the transition. Wherever you fall along this spectrum, it is crucial for your advisor to ask who you envision leading or owning your business in the future.

Depending on who you plan to pass the business to (outside buyer, employee, family member), your advisor may need to create a management development plan or outline instructions for business continuity.

6.  Client Contingency Plans

An effective exit strategy plan should allow your business to remain financially buoyant despite a temporary or permanent absence. It is crucial to have contingency plans that consider possible future circumstances, such as illness or divorce.

Your advisor may ask questions to determine how much your business might suffer if it lost a key client or high-performing employee – strategizing the “what ifs” in advance allows the advisor to develop solutions for problems before they arise.

7.  Client Progress on Current Exit Plan

Many business owners miss out on the benefits of exit planning by waiting to start the process until they are ready to retire. Succession planning financial advisors should remind clients that effective exit planning is a multi-step process that they should begin years before they plan to leave their business.

Exit planning should begin 5-10 years in advance to provide adequate time for education about different exit paths, coordinate with internal advisory teams, and problem-solve when unforeseen issues arise.

Furthermore, your advisor may remind you that exit plans are personalized strategies unique to each client and business, not a “one-size-fits-all” solution. They may encourage you to embrace unique goals and strategies to find the right exit planning strategy for you.

Continue the Conversation

The initial meeting with your advisor should clarify your goals; however, thorough exit planning requires more than one interaction. Maintaining a mutually beneficial relationship with your advisor throughout the exit planning process is critical.

Your advisor should use the following practices to ensure continuing productive conversations with you as you transition out of your business:

  1. Clarification questions: After you respond to a question, your advisor should repeat your answer to confirm that they understood you correctly.
  2. Practice diligent note-taking: Your advisor should take detailed, readable notes at each meeting.
  3. Choose open-ended questions: Advisors should ask questions that warrant more than a “yes” or “no” response and invite you to elaborate on key points.
  4. Team collaboration: If your advisor works with a team of exit planning advisors, they should provide each member with a list of action items and set deadlines to hold them accountable.

Exit Planning with Windes

If you own a business, creating a competent succession plan is crucial to the future success of your business and your financial situation.

Windes’ exit planning advisors can help facilitate a smooth transition when it comes time for you to transition out of your business. Windes offers exit planning and value acceleration services that align your personal and business goals and secure your financial future.

Connect with us today to get started protecting yourself and your business.


Rob Henderson
Robert B. Henderson, CPA, MST, CEPA, CM&AA

Practice Leader, Value Acceleration and Exit Planning
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