In the nonprofit sector we face this challenge all the time, especially with founders who have more of a psychic than a financial investment, and whose organizations often lack a deep bench due to financial constraints. I say this as one who founded and has led Share Our Strength for 25 years and now find myself asking if an organization is better off if its founder stays 20 or 30 years. In general the answer is probably closer to 20, but every situation is different and must be taken case by case.
Bring purposeful about succession planning -- not when you are forced to confront it but when you have the luxury of not being forced to -- is essential, as is building a deep bench of talent so that there is an option to handle on succession from within, or to at least have stability during a transition that looks externally for new leadership.
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