The CEO Who Leaves
When successfully delivering the deal also means leaving the company
A CEO can successfully deliver the biggest deal of his career and, in doing so, bring his own tenure at the company to an end.
He may have spent months carrying two enormous responsibilities at once: continuing to lead the business, maintain performance and hold the confidence of his senior team, while simultaneously navigating a transaction involving shareholders, board members, corporate finance advisers, lawyers, potential buyers and a level of confidential information he cannot freely share with many of the people who rely upon him every day.
For a considerable period, he is living in two worlds.
There is the visible world of the company, where people continue to look to him for certainty, direction and reassurance, and there is the much smaller private world of the transaction, where decisions are being made that could fundamentally change the future of almost everyone around him.
Then, eventually, the deal completes.
The shareholders have achieved the outcome they wanted, the buyer has acquired the company, the transaction has been successfully delivered and the CEO has done exactly what was asked of him.
And his own role may now be over.
This is one of the things that fascinates me about the personal impact of selling a company, because an extraordinary amount of expertise surrounds the transaction itself. There are people thinking about valuation, due diligence, financing, tax, legal structure, integration, communication and what the acquisition means for employees, shareholders and the new owners.
Far fewer people are asking what all of this means for the man who has carried much of the responsibility for getting everyone safely across the line.
There may, of course, be perfectly sound commercial reasons for his departure. The acquiring company may already have its own leadership team, roles may overlap, a new structure may require something different, or his departure may have been agreed many months earlier and understood by everyone involved.
He may agree completely with the decision.
And still, when the final meeting is over, the announcements have been made and the company begins its next chapter without him, there is a personal reality to contend with that no amount of intellectual understanding can entirely prepare him for.
For years, people have wanted to know what he thinks the company should do next.
Suddenly, that question disappears.
And somewhere underneath the relief, the achievement, the congratulations and perhaps the exhaustion, a very different question begins to emerge.
What do I want from my own life now?
When success ends the role
There is something particularly interesting about leaving in this way because the departure may arrive at one of the most successful moments of his career.
The company may have grown considerably under his leadership. He may have created enormous value for shareholders, built a formidable senior team, strengthened the culture, transformed the organisation and successfully led it through one of the most complex periods in its history.
His reputation may never have been stronger.
And yet, on Monday morning, nobody needs him to run the company.
The diary that once dictated the shape of his life has emptied. The meetings disappear. The decisions belong to somebody else. The conversations he once sat at the centre of continue without him.
There may be a long holiday booked, some overdue time with family, perhaps the welcome prospect of waking without an alarm and discovering what a weekday feels like when nobody is waiting for an answer from him.
At first, that freedom may feel glorious.
Then something quieter can begin to happen.
Being a CEO creates a very particular relationship with the world. Your judgement carries weight. People want your time. Your presence changes a meeting. Decisions involving hundreds or thousands of people eventually arrive at your desk because, somewhere in the structure of the organisation, responsibility stops with you.
Over many years, all of that becomes woven into the fabric of everyday life.
Then the role goes.
The man who walks away remains every bit as intelligent, capable and experienced as the man who walked into the boardroom the previous week, yet many of the things that have spent years reflecting his significance back to him are suddenly gone.
That raises a question I find endlessly interesting.
How much of the man he sees in the mirror belongs to him, and how much has gradually become entangled with the position he occupies?
That question rarely arrives neatly labelled as an identity issue. It may show itself as restlessness, an urge to become busy again, frustration with having too little structure, impatience with family life, anxiety about the future or a surprisingly powerful desire to find the next significant role as quickly as possible.
There is often something deeper underneath it.
For a man who has spent decades being needed, what happens when nobody needs him to be CEO anymore?
And what about everyone he leaves behind?
Leaving a company after many years is rarely an entirely individual experience.
A CEO will often have built deep relationships throughout the organisation, particularly with his C-suite and senior leadership team. He may have recruited these people, promoted them, challenged them, backed them when things went badly, celebrated extraordinary moments with them and spent thousands of hours alongside them building something that mattered.
During an acquisition, he may also have known things about their future that he could not tell them.
That can be an extraordinarily lonely position.
He may sit across the table from somebody whose role he knows is likely to disappear, reassure a team while knowing that the culture around them is about to change, or continue asking people to deliver against a strategy that will soon belong to somebody else.
Then the acquisition completes and, very quickly, the relationships change.
He is no longer the person they report to. A new CEO may arrive. New priorities begin to take shape. People he cares deeply about may flourish, leave, lose their positions or struggle under a culture he no longer has any influence over.
For a man accustomed to carrying responsibility for an organisation, relinquishing the role also asks him to relinquish responsibility for what happens to it.
That can be far harder than it sounds.
Because care does not disappear when authority does.
He may still care enormously about the business, the customers, the brand and the people whose careers he helped shape, while having to accept that the decisions now belong to someone else.
This is one of the realities at the heart of The Private Side of Exit.
The transaction ends. The transition continues.
What now?
Most CEOs will have imagined what comes after.
There may be a six-month break in mind, perhaps a few non-executive positions, some mentoring or advisory work, more travel, time with family, or simply the luxury of allowing the dust to settle before deciding anything at all.
Some already know the next move and step almost immediately into another CEO position.
Others reach the end of the transaction deeply tired and decide that, for a while at least, they want very little demanded of them.
After years of relentless pace, that can sound wonderful. There are holidays that have been postponed, friendships that deserve more attention, books waiting to be read, places they have promised themselves they would visit, fitness to recover and long mornings that do not begin with an inbox full of decisions.
And then, sooner or later, the question arrives.
What now?
A man who has spent much of his adult life with almost every hour accounted for suddenly has an extraordinary amount of freedom and choice, perhaps more than he has had since he was twenty-five.
That freedom is full of possibility, and it can also feel surprisingly uncomfortable.
Many CEOs reach this stage carrying a quiet desire to build something of their own, to invest, sit on boards, mentor younger leaders, become a chairman, support causes they care about or create something that feels more closely connected to the legacy they now want to leave.
There may be ideas that have sat somewhere in the background for years, patiently waiting for a life spacious enough to accommodate them.
And there can be an enormous temptation to fill that space before he has had time to discover what he genuinely wants from it.
The next impressive role solves several problems very quickly. The diary fills again. The status returns. There is purpose, structure, income and, most importantly, a familiar answer to the question, What do you do?
Yet this may be one of the rare moments in his life when there is room to ask a much more important question.
Do I actually want another version of the life I have just left?
And then there is money
Money is one of the more private conversations surrounding life after an exit, and perhaps one of the most revealing.
A successful CEO may have accumulated considerable wealth and still privately worry that one day it could all disappear.
For years, there has been a substantial salary arriving every month, perhaps alongside bonuses, equity, long-term incentives and other rewards. That income has supported a particular home, a particular rhythm of family life, school or university fees, travel, investments, commitments and a standard of living that has gradually become normal.
Then the salary stops.
On paper, there may be no problem whatsoever. His wealth manager may show him projections extending decades into the future, demonstrate that the assets are more than sufficient and calmly explain that he is financially secure.
Yet there is something psychologically very different about living from accumulated wealth when you have spent most of your adult life creating new income.
And so the questions begin.
What if I never earn at that level again?
What if I make a bad investment?
What if what we have accumulated is somehow not enough for the life we have created?
What if I lose it?
I have always found it fascinating that success does not necessarily make those fears disappear. Sometimes the numbers simply become larger while the fear itself remains remarkably familiar.
And this matters because fear can exert enormous influence over what a man chooses next.
A period that could offer genuine freedom, reflection and the opportunity to consciously create the next chapter can very quickly become another race towards income, certainty and the reassurance of being needed again.
Who are you when nobody needs you to be CEO?
The family experiences this transition too.
For many years, they may have lived around the requirements of the role. His partner knows the travel schedule, the late calls, the meetings that move family plans, the phone that appears during dinner and the peculiar experience of having somebody physically at home while part of his mind remains somewhere inside the business.
Then suddenly he is there.
Properly there.
Perhaps for the first time in twenty years, he has nowhere he has to be on Tuesday morning.
That can be wonderful, and it changes the rhythm of a household that may have spent many years evolving around his absence.
His partner has her own life, routines, friendships, interests and independence. His children may be teenagers or adults whose lives no longer orbit around their father in the way they once did. The family has grown and changed while he has been building his career.
So the personal transition following an M&A transaction reaches far beyond the question of the next job.
It opens up much bigger territory.
What does he want from his marriage now?
What kind of relationship does he want with his children?
How does he want to spend his time?
What is money actually for?
What has all this success made possible?
What does he still want to create?
And who does he need to become for the life that follows?
For years, everyone around him has wanted to know what he thinks the company should do next.
Perhaps, for the first time in a very long time, there is room for him to turn that quality of attention towards himself.
What do I actually want now?
My work is with male CEOs, founders and senior leaders, and these are the conversations that have interested me for more than fifteen years, because the end of a significant role has a way of revealing questions that achievement, responsibility and relentless forward movement have allowed a man to leave unanswered.
There may be another extraordinary CEO role ahead of him. There may be a company of his own, investments, board positions, philanthropy, mentoring or work he cannot yet imagine because he has never previously had the space to imagine it.
He does not need to know immediately.
A successful exit has already asked a great deal of him.
The transaction has ended.
The transition deserves some time.
