Perhaps that should read “when and how” because so often the problem is one filled with emotion and a reluctance to lose what has been a major part of a life.
Worst of all is the leader who will be damned if he/she is going to move over to satisfy the jumped up ambitions of a young Turk with a jumped up idea of his/her abilities.
By the way, the age of the leader may be a factor but it is not necessarily so. The emotional ties to a business stem from so many psychological factors and are often difficult to pin down.
I have experienced the father who will not give up to a son who he considers to be wayward and shallow, a leader who thinks that without him the business will go into terminal decline, another whose life revolved absolutely around the business and who could not even contemplate being parted from it, and perhaps the worst of all, a leader at the age of 70+ who even refused to consider how succession could have a positive effect on the business.
Over the years I have seen so many instances which seemed insoluble but which, in time, were resolved satisfactorily with perhaps only a few bruised egos and several sighs of relief.
The problem is usually the stickability of the in-post leader and their insistence on persuading themselves that only they can run the business as it needs to be run.
It all comes down to a feeling of rejection and even a loss of power even though the pill can be sugared to some extent by, for example, the leader moving up to Chairman (non-Executive) or by taking on pro-bono positions outside the business. In the end it is all about feeling wanted and needed and to lose that can be very painful.
There are, of course, some leaders who really can’t wait for the next generation to take over so that they can reap the rewards of a lifetime of work. Sensibly that would demand good planning of the eventual wind-down, handover and retirement.
I have something of a vested interest in the subject and I often refer to my wonderful colleague in Vistage USA, Pat Hyndman, who at the age of 90+ still runs a Vistage CEO group and says that he intends to go on until they have to carry him out on his own flip-chart. I know just how he feels.