The odds of successfully transitioning a business from one generation to the next are extremely low. In fact, as each generation grows to the point of needing a successor, it is even less likely that a transition to the next generation can be successfully accomplished.

Succession is something that should always be on the minds of business owners. While good health and age are factors that may lead you to a high level of confidence that you’ll be able to show up for work tomorrow – there are no guarantees. But more than the issue of succession is how do you solve your potential problem today without compromising your long-term objective to keep the business in the family.

If you know down deep that your next generation of family is not quite ready to take over the reins, you need to have a stop gap plan. For this, you may need to work with a key non-family employee or perhaps even another unrelated firm like yours. Hopefully you have one or more long-standing employees that are significant to the day-to-day operations of the business. These key employees also wonder what would happen if you didn’t wake up for breakfast. Are they out of work? Is the business getting sold? Will they be working for a 25-year-old who knows nothing about the business?

These thoughts are common amongst long-standing loyal employees. Your best bet is to be completely up front with these folks. They need to know that your plan is to keep the business as family owned. But you also need to create a plan that keeps them engaged and motivated to assist with that noble objective. This plan can come in many forms.

The best way to start the conversation is to role-play your disappearance tomorrow. Now re-create job descriptions, lines of hierarchy and communication for each key person. Some will want and possibly deserve a pay increase to expand their role. But for the most part, loyal employees will be appreciative for the fact that you’ve recognized their significant role and would like them to be a part of your company’s long-term plan.

Even if your children are mature and experienced with respect to your business – you still need a plan. That plan also needs to include job descriptions and who is reporting to whom. It can be dysfunctional when there are three family owners tripping over themselves all trying to do the same thing. This issue gets even muddier when one or more of your children may have nothing to do with the day to day of the business, yet be an equal owner with those who run the day to day. For this, you may consider equalizing your children’s inheritance and exclude business ownership from those who don’t work in the business. If that doesn’t work, lay out clear guidelines now about who makes the decisions – including the important decisions about compensation, mergers, buying or selling.

John P. Napolitano CFP®, CPA, PFS, MST is Founder and Chairman of Napier Financial in Braintree, MA.  Visit for more information. The opinions voiced in this material are for general information only and are not intended to provide specific advice or recommendations for any individual. Investment and financial planning advice offered through US Financial Advisors and Great Valley Advisor Group, Registered Investment Advisors.

By John P. Napolitano CFP®, CPA, PFS, MST Founder & Chairman Read More