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Ten questions to ask small business owners


Innovators by nature, small business owners are the backbone of the U.S. economy and have been from the very beginning. According to the U.S. Small Business Administration, there are almost 30 million small businesses in the U.S., more than 47% of the working population works in a small business, and small businesses created 1.9 million net new jobs in 2015.

As a financial advisor, you have a tremendous opportunity to help this growing wealth segment plan for and achieve their goals. Think about what small business owners want. Many of them want to sell a business, or pay less in taxes, or need help managing personal and business finances. Some of them are looking for ways to spend more time with family and loved ones.

As you advise your small business clients, and prospect for additional business owners, here are 10 questions I’ve compiled over the years from advisors that may help you have better conversations—and help you uncover a small business owner’s true financial needs.

In your next meeting with a small business owner client, consider asking a few of these to see how the conversation shifts, in a good way:

  1. You had the vision to start (or buy) this business. What three things define your vision for tomorrow?
  2. As a business owner, think about your own unique value proposition. What are three things you’re doing to stay true to that mission statement?
  3. It can be difficult—financially and/or emotionally—to completely retire from the business. Who can do what you do and run the business? Can he or she do it as passionately and efficiently as you?
  4. Name three ways your family is impacted by your business decisions. 
  5. Some small business owners put themselves last, choosing instead to focus on their customers and employees. When is the last time you took a paycheck for yourself?
  6. Describe three things you do to relieve the stress of being your own CEO?
  7. You’re great at what you do and you know how to build a successful business. List three ways you manage your personal and business finances. 
  8. Often, small business owners rely on their business to create the wealth they want. What happens if you cannot go to work tomorrow? What happens if you cannot return to work for six months? How would that impact your household income?
  9. Did you pay too much in taxes last year?
  10. What is your plan to shield your business and assets from the transfer tax system?