Are You Ready for the Largest Financial Transaction of Your Life? Answer These 10 Questions to Find Out!

September 12, 2022 by Interchange Capital Partners

Are You Ready for the Largest Financial Transaction of your life_ Answer these 10 Questions to Find Out

By Ahmie Baum, CFP® CFBA

Choosing to run a business is not for the faint of heart. And it’s not only work—it’s personal. Your business represents your hopes, dreams, and, yes, your finances. That’s why it’s crucial to plan for when and how you’ll transition out of your role as a business owner in a way that maximizes your financial independence.

While 70% of business owners report having a succession plan in place, of those, nearly 50%-60% report having concerns about the long-term success of their current plan. (1)

So, why not rely on the experience and expertise of professionals who can guide you through the process? At Interchange Capital Partners, we have over 40 years of experience creating and implementing succession/transition plans for business owners.

If you’re concerned about your current plan, here are 10 questions we use to help our clients assess their readiness for the largest financial transaction of their lives.

1. When Do You Want to Exit Your Business?

Deciding when to leave your business is the foundation of a transition plan. It will determine your time frame and help to assess the speed and intensity with which the plan should be implemented. Transitioning in two years is a much different picture than transitioning in ten. Have you decided when your exit will be?

2. How Much Cash Will You Need for Your Lifestyle When You Leave?

This is a key component in determining your lifestyle after your transition. If you plan to continue working, your annual cash flow needs from the transition plan will probably be less than if you plan to retire completely. Have you calculated how much cash flow you will need once you exit?

3. What Is Your Business Worth Today?

This question is important in understanding how much you could realistically receive if you were to sell the business, as well as what kind of cash flow your business would generate if you plan to take disbursements after you step away. Do you know what your business is worth?

4. Is Your Business Maximizing Its Value to a Buyer?

Just because you see endless potential and value in your business doesn’t mean others will. Sometimes the value you see doesn’t translate well when trying to market the business. Understanding where your business stands is a key step in marketing it for sale.

5. Whom Do You Want to Transfer Your Business to?

Do you want to transfer your business to someone in the family? To a key employee? Or sell it to a third party? Knowing who will be taking over is a critical aspect of both the business transition plan and the long-term success of the company. Do you have a plan for whom you will sell or transfer the business to?

6. Are You Maximizing Your Income Before and After the Transition of Your Business?

There’s a lot that goes into maximizing income. Are you aware of the tax consequences? Do you plan to invest the funds? This is an area of planning where a financial planner can be particularly valuable. Have you spoken with a planner regarding how your finances will change once you sell your business?

7. How Do You Sell Your Business to a Third Party and Mitigate Your Taxes?

Between understanding your cost basis and knowing the true value of your business, it can be challenging for business owners to navigate the tax implications of a sale. Don’t lose out on profits because you’re not an expert in taxes. Have you spoken with a CPA about the tax implications of selling your business?

8. Do You Know How to Transfer Your Business While Reducing Taxes and Enjoying Financial Sturdiness?

There are many tax-efficient ways to transfer a business that don’t involve selling to a third party. If you plan to keep the business in the family, or transfer it to employees, ensure your plan is as tax-efficient as possible.

9. Do You Have a Plan in Place if the Unexpected Happens to You?

A business transition plan is not the same thing as a succession plan. Having both is a crucial component in the long-term viability of your business. Something could happen unexpectedly years before you had planned to step away. Who would take over and how would the business run if that were to happen? Do you have a plan in place if you could no longer run the company?

10. Have You Taken Steps to Preserve Your Family’s Wealth?

It’s very common for business owners to have large amounts of personal wealth tied up in the business. That’s why it’s so important to consider what would happen to your family’s wealth if something happens to you unexpectedly. 

How Did You Score?

Now that you’ve had a chance to read through the questions, how did you score? If you could answer “Yes” to:

  • Fewer than 3 questions: It’s time to start planning, you are leaving a lot on the table.
  • 3-6 questions: You have a good start, but some critical pieces are missing.
  • 7+ questions: Congratulations! You are well on your way to a successful transition. You may want a second opinion to make sure the I’s are dotted and the T’s are crossed.

No matter where you fall on this scale, working with a Certified Exit Planner is never a bad idea when it comes to building a solid business transition plan. To learn more about how Interchange Capital Partners can provide a collaborative, comprehensive, and disciplined transition plan, email us at or call our office at 412-307-4230 to schedule your very own Q&A call today!

About Ahmie

Ahmie E. Baum is the CEO and Founder of Interchange Capital Partners. Using a collaborative and comprehensive process developed over 43 years of working with wall street banks and financial services firms on behalf of families.
Interchange Capital Partners provides family office and transition strategy services for family businesses, helping families protect and grow their family capital with clarity, understanding, and action by being relevant and resourceful around their unique circumstances.
As a graduate of the University of Pittsburgh, Ahmie began his career with EF Hutton in 1979 and transitioned to UBS in 1993. Ahmie is a CERTIFIED FINANCIAL PLANNER™ (CFP®), received the Executive Certificate in Financial Planning from Duquesne University School of Leadership and Professional Advancement and has a Certificate in Family Business Advising (CFBA) from the Family Firm Institute. He also has Certificates from The Growth Institute around Growing and Scaling Business and Cash Management. For the past 20 years, he has been involved with Strategic Coach, an international entrepreneurial training program
When he’s not working, Ahmie enjoys spending time with his wife, Sara, their three children, and their granddaughters. He recognizes that health is wealth so he has committed to daily yoga, meditation, and plant-based eating. His other hobbies include woodturning, golf, reading, listening to music, and biking. He is active in his community and served as the Foundation Chair of the Jewish Federation Community Foundation of Greater Pittsburgh and supports the Big Brothers Big Sisters of America (BBBS). To learn more about Ahmie, connect with him on LinkedIn.

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