The Cards

How do you recognize that the best possible successor in the business is not anyone from the family, but a professional external manager?

Have you created protected positions in the company for long-serving employees or family members, and what consequences does that have?

When was the last time you let a successor or management make a painful mistake, and how did you process the urge to help fix it?

Under what circumstances would selling the company be a better way to preserve the family legacy and harmony than keeping it in the family?

In which areas does family tradition serve as an anchor that stabilizes you, and where does it instead become a weight that pulls you down?

How does your family define fairness when dividing assets?

How do you handle the conflict between viewing family wealth as your own property for free use, and the role of steward of entrusted value for future generations?

What mechanisms do you have prepared for the moment when shared wealth becomes a 'bag of fleas' and even a single passive family member starts blocking rational management?

Do you pledge healthy assets, such as real estate, as security for the operating business? What would you have to do to stop this practice?

What criteria must the next generation meet to receive an ownership stake, and what role does active work for the company play in that process?

By what measures do you choose the future leader of the family business?

How would you explain to your child and the rest of the family the need to place that child's inheritance into a trust fund without voting rights in order to protect the company from the child's incompetence?

What impact does the fact that you, as owners, have long refrained from paying yourselves full market compensation — out of love for the company or for tax reasons — have on financing a future CEO?

Do you keep operations alive that have been loss-making for years? If so, what would an ideal scenario for putting them to sleep look like?

In what specific ways does your company behave like an investment, a positive-sum game, and in what respects does it instead resemble a gamble with your own health and money?

How do you process your feelings when the new generation takes over leadership and begins radically changing what exists?

What specific business mistakes or failures do you hide from others? Is it hard for you to share your defeats with your family as well?

Where is your inner boundary beyond which you would rather let the company fall than risk losing your home or savings?

How can you ensure that dismissing an incapable relative does not cause a lifelong family war?

Will your business generate positive cash flow if you leave for a year and do not personally intervene in day-to-day operations?

What is your favorite excuse for avoiding discussions about succession or other uncomfortable topics?

You die suddenly. Do company processes collapse? Do your relatives gain access to sufficient liquidity? Do they know what to do?

How would the conversation unfold if, while still alive, you had to look your child in the eyes and tell them that you are disinheriting them or cutting them off from influence over the company?

How do you ensure business continuity beyond merely writing a will, given that the transfer of a company is a multi-year process?

What legal mechanisms do you have prepared for a situation in which family wealth becomes a battlefield where some heirs join forces against the rest?

Does the concept of a 'family bank' operate in your family? How do you handle a situation in which a child spends entrusted funds without being able to return them?

Do you feel personally responsible for the livelihoods of your long-term employees? Do you protect them from potential family disputes?

What exactly constitutes the ultimate 'Why' and purpose of your family if we completely remove the company and jointly managed wealth from its identity?

When you are on your deathbed looking back, by what criteria will you evaluate relationships in the family and the business?