Consider each of the following three aspects of fit and try to get as specific and quantifiable as you can in your assessment.

1) Professional Fit – Consider the two questions below and assess each using a 1 to 5 scale.

        a. Is this a good career for me? How well does the trajectory of the company and the career opportunities available to me as a family employee match my professional goals, priorities, interests, and capabilities?

        (1) No match
        (2) Weak match
        (3)  Adequate match
        (4) Good match
        (5) Excellent match

        b. Is this a company where I want to work? How compatible are the company values, culture, and organization with my desired work environment and priorities?

        (1) No match
        (2) Weak match
        (3)  Adequate match
        (4) Good match
        (5) Excellent match

2) Relationship Fit – If you were to join the family business or family office, who are the 3 or 4 family members that you would interact with most regularly regarding the family business, or whose support you will be in most need of to be successful? These individuals might be your manager, direct report, colleague, a board member, or a significant owner to whom you would be accountable.

For each person, assess the likely quality of your working relationship on a 1 to 5 scale using the four factors listed below.

        a. How easy would it be to work together?

        (1) Very difficult
        (2) Difficult
        (3)  Moderate
        (4) Easy
        (5) Very Easy

        b. How enjoyable would it be to work together?

        (1) Not enjoyable at all
        (2) Not enjoyable most of the time
        (3) Somewhat enjoyable
        (4) Most enjoyable
        (5) Always enjoyable

        c. How productive would you be working together?

        (1) Difficult to get things done
        (2) Moderate
        (3) Easy to get things done

        d. How much would you each learn and grow by working together?

        (1) Learn a little
        (2) Moderate
        (3) Learn a lot

3) Life Fit – Imagine you are 80 years old, looking back contentedly on your meaningful, fulfilling life. What do you see? What dreams and goals did you achieve? What key relationships supported you? What resources (financial assets, health, time, etc.) propelled your life forward? What activities left you energized and inspired?

        a. How likely is it that a career path within the family business would help you realize your vision of a quality life?

        (1) Not likely at all
        (2) Somewhat likely
        (3) Very likely

If you’ve rated a 4 or above in response to most of the questions above, it is likely that joining the family business would be a good fit. Particularly if you have a sense of excitement about the prospect, you should feel confident about taking the next steps to explore joining your family business.

If you’ve rated a 3 or below in response to any particular question, you have some further considerations to think about, and would likely benefit from delaying a final decision, at least for now:

1. How willing are you to accommodate this reduced level of compatibility in your career, relationships, or life? We make tradeoffs all the time in our lives. Would this tradeoff be worth it to you?
2. What would need to change to improve the degree of fit in this area? What specific actions could you take to improve the situation?
3. How much time and energy are you interested in devoting to those efforts? How much power do you have to effect change in these areas?

If you’ve rated a 2 or below in response to most of the questions above, this is a good time to pause. Consider what specifically would need to change to improve the compatibility. Alternatively, it might mean that deciding not to enter the family business and instead pursuing your career elsewhere would be the most appropriate decision for you. Particularly, if you have a sense of relief about the prospect of not joining, you should feel confident about taking the next steps to communicate your decision thoughtfully and respectfully to others.

This is a deeply personal and highly contextual decision. Only you can determine what is the right path forward for you. Will you join? Not join? Or keep the door open for now?