ARE YOU PREPARING THE SUCCESSOR, OR PREPARING YOURSELF?
- Trevor Dickinson

- Jul 6
- 8 min read
The half of succession every family plans for, and the half that determines whether it holds.
Who is preparing you?
The half nobody plans
Ask any family business what it is doing about succession, and you will hear about the successor. The development plan. The outside experience. The governance induction, the shareholding schedule, the staged transfer of responsibility. The advisory industry has built an entire discipline around the preparation of the next generation, and the earlier articles in this series have contributed to it: the criterion of return, the distinction between choosing and being absorbed, the question of whether the enterprise should continue in the family at all.
Ask the same family what it is doing to prepare the incumbent, and the question is usually met with silence. Not evasion. Genuine incomprehension. The incumbent does not need preparing. The incumbent is the one doing the preparing.
This final article in the series is addressed to that silence, because in my experience the unprepared incumbent is the point at which more successions fail than at any other. The documents can be perfect. The successor can be ready in every sense the previous article described. And the handover can still fail, quietly, across the years that follow it, because the person releasing the enterprise was never prepared for what the release would take from them.
What an unprepared release looks like
I watched what an unprepared release looks like from close range, in my own family, across nearly 2 decades. A leader who had resisted succession for years, who could not separate his identity from the enterprise, finally released his grip on the business. What followed was not freedom. It was a vacuum that never filled. No second chapter. No creative pursuit. No framework capable of holding the diminishments of ageing. The business had been the citadel, and when it was handed over, the man was exposed.
I do not offer this as criticism. I offer it as evidence, because the pattern is structural rather than personal, and I have since observed it in other families more times than I can comfortably count. The leader spends 30 years preparing the enterprise for their departure and no time at all preparing themselves for it. Then the departure arrives, on schedule, exactly as planned, and takes with it the identity, the purpose, the daily structure and the standing that the enterprise had quietly provided for decades. The succession documents record a transfer of shares. What has actually occurred is the demolition of a life's architecture, with nothing built behind it.
The developmental task of the outgoing generation
The developmental literature is precise about what is being asked of the incumbent, and it is worth stating plainly because almost no succession plan does. Erik Erikson named the central task of this season of life generativity: the concern with establishing and guiding the next generation, whose virtue, when the task is met, is care. In the family business, the distortion of that task is specific. The generative instinct, the desire to invest in what comes next, is entangled with the ownership instinct, the desire to control what one has built. Succession, at its deepest level, is the discipline of separating the 2: learning to care for the enterprise and its people without needing to possess them.
Kenneth Kaye carried the point to its conclusion. The developmental task of the outgoing generation is not the handover of operational control. It is the release of the identity investment that made the enterprise possible in the first place. The distinction matters because control can be transferred by document and identity cannot. The incumbent who has built no identity independent of the role cannot open the hand, whatever the shareholders' agreement says. They will transfer the title and retain the authority. They will vacate the office and occupy the decisions. Every family business professional has watched this: the retired chairman who attends the operations meeting, the founder who signs nothing and approves everything.
The preparation of the self, then, is not a soft supplement to succession planning. It is succession planning. It consists of building, during the incumbent's tenure rather than at its end, an identity, a purpose and a daily structure that do not depend on the enterprise. The incumbent who has somewhere to stand after the handover releases cleanly. The incumbent who does not, holds on. And the holding on is experienced by the successor as mistrust, by the business as paralysis, and by the family as the very entrapment this series began by naming.
Have you built, during your tenure rather than at its end, a version of yourself the enterprise did not make?
What the steward actually hands over
An earlier article in this series distinguished a dynasty from dynastic architecture. The handover is where that distinction is executed rather than merely understood. The steward hands over 3 things, and only one of them is managed by professionals.
The first is equity. The solicitor drafts, the accountant structures, the transaction closes. This is the transfer the advisory industry serves well, and it is the least consequential of the 3.
The second is authority, and only the incumbent can transfer it. Authority does not move with the share certificates. It moves in a hundred small moments after the handover: the client who telephones the old chairman and is redirected to the new one, the executive who tests where the real decision now sits and finds it has genuinely moved, the board meeting at which the outgoing leader holds their tongue and lets a decision they would not have made stand. Authority is transferred by the discipline of role boundaries. Chairman rather than operator. Counsel when asked rather than instruction unrequested. Presence without interference. Hovering does not protect the enterprise. It teaches everyone in it that the succession is nominal.
There is a structural component here as well, and it settles a promise made in the previous article. The structure the successor returns into matters as much as their readiness to return. A successor who receives shares in an enterprise still framed as one person's possession has received possession by another name; where equity is given without an articulated principle of stewardship behind it, the gift arrives as obligation. The steward's task is to hand over an architecture rather than a possession: an enterprise held in trust for the family, governed by frameworks that do not require the successor to become the next version of the incumbent to lead it.
The third is the written legacy. The instruments were named earlier in the series: the ethical will, the letter of wishes, the family constitution, the record of values and of what was learned and at what cost. This article assigns them as the incumbent's final piece of work. Not the lawyer's work. The incumbent's. The written legacy is the only transfer that carries judgement rather than assets, and it is the one inheritance the next generation cannot obtain anywhere else. It also does something for the incumbent that no transaction can. It converts decades of accumulated experience from a private possession into a permanent contribution, which is precisely the movement, from acquisition to contribution, that this season of a leader's life demands.
And there is a fourth transfer that cannot be made, and honesty requires naming it. The relational capital, the web of clients, colleagues, industry peers and allies built across a working lifetime, is held in the person rather than the institution. It cannot be bequeathed in a trust deed. What can be done, and what almost no incumbent does deliberately, is to sponsor access: to walk the successor into those relationships during the incumbent's tenure, one introduction at a time, so that when the role transfers, the successor inherits standing rather than a contact list. This work takes years. It cannot begin at the exit.
Of the 4, which have you actually planned, and which have you simply assumed will happen on their own?
The exchange itself
The mechanics of the exchange deserve the same discipline as its psychology, and here the framework Glenn Ayres proposed, introduced earlier in this series, returns with practical force. Ayres argued that succession must be structured around 2 balancing measures: what the outgoing generation actually needs, and what the business can honestly afford to provide. From those 2 measures flow 4 questions, and they must be answered before any transaction is structured. What does the outgoing generation require, in income, lifestyle and legacy provision, to leave confidently? What can the business afford to provide while still growing, modernising and attracting talent? What does the successor need in capitalisation, authority and developmental support? And what does the family intend to be beyond this enterprise?
The transition I received did not apply this framework. The capital base was materially diluted at the point of transfer. I sold my industrial property portfolio to fund the acquisition, and the 17 years that followed were, in significant measure, a recapitalisation exercise conducted under continuous pressure. Every investment in modernisation, talent or development competed against the obligations inherited from the previous transition. Ayres compared the business to a forest: selective cutting preserves and renews, indiscriminate harvesting destroys the very thing being used. I inherited a harvested forest. I am determined not to hand one over.
In the absence of a structured process, these 4 questions are still answered. Implicitly, by default, by personality, and by the gravitational pull of precedent. The only choice available to the incumbent is whether they are answered deliberately.
The baton
The image I have settled on for what a good handover asks of both parties comes from the relay. The baton is not exchanged between a stationary runner and a moving one. It is exchanged at speed, inside a marked zone, with both runners in motion. The outgoing runner does not stop before the exchange and does not hold on after it. And the race is judged by the team's time, not by the split of any single leg.
Succession is that exchange zone. A period rather than an event, entered with both generations in motion, in which letting go and carrying forward happen concurrently rather than in sequence. The successor must be running before the baton arrives, which is what the previous article asked of them. The incumbent must keep running after it leaves, which is what this one asks. And the incumbent's leg is measured by one thing only, and it is not what they carried. It is what happens after they release.
Where the series ends
Across 7 articles, this series has moved from the hidden costs of the family enterprise, to the structural mechanism of the inheritance paradox, through the question of what is being transmitted to your children, to whether the enterprise should continue at all, to the distinction between dynasty and dynastic architecture, to the criterion by which a successor is truly ready to return, and finally to the preparation of the person who must let go. It ends where succession itself ends: with the open hand.
The interior architecture that makes the open hand possible, what sustains a leader when the business no longer can, is the territory of the series that follows this one, The Practised Life. Its opening article, What Were You Actually Looking For?, begins where this one ends: with the person rather than the enterprise. It is the other half of everything written here.
To the incumbent: if the handover completed tomorrow, what in your life would still require you?
To the successor: what is your predecessor building beside the business, and what does that tell you about how they will let go?
When the baton leaves your hand, will the team be faster or slower because of how you carried your leg?





