When I was 16 years old, I didn’t learn to drive stick shift from my father. Although I knew my father could drive a manual transmission, it was one of my friends whom I asked to teach me, whom I knew wouldn’t get upset with me for grinding the gears at first or increase the pressure with what is already a stressful experience and can be a difficult skill to learn. When I consider the many family businesses I have supported as an executive coach and family advisor over the years, it’s no different!

Successful Baby Boomer business owners don’t achieve their success simply by teaching others what to do. They achieve that success by being driven, results-oriented leaders striving to accomplish more than those before them. This strong character trait, however, often presents itself through a more dominant and autocratic leadership style – one that may work for the chief executive of a family business or the principal of a family office, but likely doesn’t work as well when you want to groom your next generation child to assume huge responsibilities as your successor. This is very likely why I’m regularly hired by NextGen children to facilitate their transitions rather than the Baby Boomers themselves.

One of the other key challenges with the father/son relationship is the long history these individuals have together. While I may have learned to drive stick shift from my friend, that doesn’t mean I was a responsible teenage driver. I earned at least a couple speeding tickets in my first year of driving, and even got into a couple minor fender benders. Now imagine if my father ran a multi-generation family business and allowed me to work for him. How do you think he would feel about his somewhat irresponsible and overly adventurous son taking the reins? My guess is he wouldn’t have given me the keys to the kingdom before I could demonstrate I had matured – and rightfully so!

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