This book presents outcomes of a unique research project in which family managers of eleven of the oldest and largest German family businesses, at least the fourth generation, met for more than three years on a regular basis and presented the essence of their family governance structures to each other and to the authors. It was a joint “learning journey” that admits identifying twelve core questions that these families had been answering to keep up the relationship between family and business successfully over generations. Obviously, there is no “right” answer to these questions. The key to success is rather engaging the families in a process to find out their own answers and make them aware of the “two sides”: being a family is different from being a business family.