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10 Questions to Ask Before Joining the Family Business

In the midst of uncertain economic realities for many, I am hearing more and more young professionals seriously considering the transition into their family’s business. For some, working for their parents wasn’t something they had considered before. For others, it has simply been expedited by a changing job market and shifting values.


If you are considering going to work with a parent, I encourage you to think about these 10 questions as a starting point to those discussions.


1. Are they interested in growing?: Is your parent interested in growing, or more interested in maximizing dividend? Do they fall somewhere in between? Getting on the same page about growth, investment, and risk is essential to minimize miscommunication and maximize your mutual understanding of where you are heading, both for your own professional life as well as for the future of the business.


2. How do they perceive your skills?: Where does your parent see your strengths, and where do they see you needing to develop? This is a question about both the here and now and about the future.


Two primary questions can operate as a starting point: “What capabilities and talents do you feel you bring to the company today and how does that compare with what your parent(s) think?” and “What skills do I need to develop to be a leader (or THE leader) in the future? While this conversation can be difficult, it is an important one. You need to be aligned about perceptions of your skills and capabilities, as this alignment allows you to constructively address the next consideration (#3).


3. What role do they see you taking? Where would your parent(s) put you in the business? Is that what you are interested in doing? Does it offer you a starting-place for the direction you want to go in on the short and long term?


4. How do they measure success? How is your parent assessing and considering your success and progression as you transition and develop in the business. How would you determine success for yourself in this role? Are they aligned? Working through this question also entails considering concrete ways to measure success, including quantitative and qualitative assessments and determining your KPI’s.


5. How will they support your success?: Will the company offer ongoing training and development? Will there be both formal and informal opportunities for you to develop your skills and evolve your practice in the business?


6. Who would be your direct supervisor?: Is this a person you respect and/or admire, and you could see acting as a mentor for you in the company?


7. Do they see you as their successor? This is a big question, but an important one to discuss before you begin rather than confront it later. Do you want to eventually take over the business? If so, how soon do you think you would be ready? Does your father/mother agree? Does that align with her/her timeline for stepping down? What would that succession process look like?


8. Are you aligned around money? What do you think is a reasonable pay for your role? What does your parent see as a reasonable salary? How would you structure your bonus? What is the room for growth, and how will that be measured?


9. Have you talked about equity? Have you and your parent(s) discussed what they intend to do with their stock? If it is intended to be passed on to you, will it be sold, given, or put in a trust? If there is a Trust, who are the trustees? What about your siblings?


10. Is there a Board of Directors? If your mother/father does not already have a Board of Advisors / Directors, would they consider creating one? Creating an independent Board would help you in the future, and can streamline future transition planning.


These can be difficult conversations, and they require a commitment to honest and respectful communication. The skills required for such conversations may or may not be part of your family’s skill set, but a good starting point is for you to be willing to listen to the feedback without getting upset or angry. These discussions are absolutely critical to your success in the future, and an unwillingness on the part of a parent (and future boss) to have these kinds of discussions is a warning sign. Most importantly, don’t wait until your first day on the job to have these conversations.


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