How do you encourage someone to step down and nominate a successor to help out with the organization?
It is always difficult to convince a reluctant owner to plan a succession, largely because there are so many emotions connected to a business that has been founded or managed for some time by that owner. The business owner is in an emotional position similar to empty-nest syndrome, the feelings that parents experience when their children leave home.
Also, most business leaders are "warrior" leaders. They have placed their personal capital and families' financial future at risk to achieve success based on individual initiative and merit, and often feel that the business cannot survive without them. As with all kinds of planning, individual emotions, fears and day-to-day worries also complicate the picture.
Usually the best way to "encourage" someone to begin succession planning is by simply asking the owner about his or her own mortality: "No one is immune from tragedy, death or retirement, so what happens if you are not here to lead the business?" These are immediate concerns, but they often lead to thinking about larger issues such as who will succeed the chief executive officer.
These questions should be asked at an appropriate time, perhaps in general management discussions, when business planning or when conducting visioning exercises. These are times when big-picture thinking is encouraged. These are not issues to be discussed when the leader is routinely putting out fires and dealing with details.
Also, find the appropriate person to raise these questions. Most owners don't listen to just anyone, so the questions should be asked by someone the owner trusts and respects. If this is not a trusted lieutenant, employee or family member, then it should be an outside advisor such as an accountant or other financial advisor, lawyer, consultant or board member.
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