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The Delicate Matter Of Top Team Off Boarding

Updated: Oct 20, 2021

No-one remains on the top team forever. Everyone who on-boards has to, at some point, off board. It’s a natural law. Over time, inevitably, good top team executives reach a point where they need to start thinking and planning to say goodbye to their colleagues and the business.

As Chief People Officer, you want to make sure that good people don’t leave too early. At the same time, you want to ensure that they don’t outstay their welcome and leave too late. Yet, broaching the subject of stepping out can be a delicate matter. It’s tempting to avoid what could be tricky conversations.

Failing to address off boarding, however, comes at significant cost—for both the individual and the company.

It’s the CPO’s responsibility to get it right.

Off boarding conversations are a delicate matter. In many companies, they occur when people reach their fifties. And being fiftsomething can be a tricky time. It’s an age when even the most resilient can have a wobble in self-confidence.

I have coached 100+ chief officers and big firm partners as they navigated their way out of the top team. At 68, I’ve been through my own transition—successfully, I believe. And I avidly follow the emerging research and global best practice.

What I know for sure is that getting it right shouldn’t be left

to chance. Companies need to help and support their senior

executives to think, plan and execute their stepping out


The cost of getting it wrong—and the benefits of getting it right

Leaving the top team should be a simple task—work out the right time to go, make a plan and execute it. Job done!

The problem is, it isn’t that simple. For many senior executives, a cocktail of negative emotions—like uncertainty and anxiety—can get in the way, along with practicalities such as working out personal finances and deciding upon future options. It’s easy for people to get stuck, always putting it off until tomorrow. ‘Mañana mañana.’

The Goldilocks Dilemma

Let me introduce you to the Goldilocks Dilemma. You don’t want good people to leave too early. You don’t want them to leave too late. You need them to get it just right.

Leaving too early means they go before their job is done—either because others have decided, wrongly, that they are past their sell-by date, or because they, themselves, have decided prematurely to walk-away.

Imran, 53, was good at his job, very good—but he reached the end of his tether. The ever-increasing pressures, the endless schedule, the time away from home and family, and in-company politics were all taking their toll.

Being a member of the top team had lost its sparkle. Imran had made no plan for life after the top team and, as a result, he increasingly felt trapped. As he said, “It’s like being on a never-ending hamster wheel.” Then, two things happened simultaneously—his wife became ill and he had a senseless argument with his CEO. It was enough to trigger him to walk away. He off boarded three months later, without a plan for the future, with his job uncompleted—leaving the business in the lurch and, as a

result, with his reputation tarnished.

On the other hand, leaving too late means people outstay their welcome and outlive their usefulness. They cling on, ignoring the signals, like the unwelcome last guest at the party.

Jenni is 61 years old. She is retiring in two years’ time and has let everyone know. In fact, she has been telling them the same story for the last four years. Jenni wants to leave. She just can’t find the door.

Getting it just right means leaving when they have:

• completed their job well;

• ensured their part of the business is in good shape for the future;

• finished with their reputation intact; and

• created an exciting plan for the future.

Bill Gates got it just right in 2014. He retired as Chairman of Microsoft at 58 years old. Money wasn’t a problem. He had $95b. Yet, I’m sure there were a thousand compelling forces pulling on him to stay. He went anyway, to use his experience, expertise, drive and resources as a philanthropist with The Bill & Melinda Gates Foundation—his new full-time job.

The consequences of bad timing

Getting it wrong, either by leaving too early or too late, comes at a cost.

How much does losing a good executive prematurely cost your business?

• Interruption to leadership, strategic momentum and productivity

• Reduced customer and employee confidence

• Reputation—the optics to the world outside

• Hiring a replacement—recruitment, retained search, on boarding, etc.

How much does it cost your business when an executive stays too long?

• Performance drop off

• Loss of confidence in the company’s leadership

• Frustration and the resulting flight-risk of those below

• Reduced customers and employee confidence

• Reputation—the optics to the world outside.

Getting it right, on the other hand, has obvious benefits. Top team movement creates the space for fresh faces—bringing with them new perspectives, fresh ideas and novel approaches. And satisfied leavers go on to be advocates and ambassadors for the company.

CPO responsibilities

The CPO is responsible for top team off boarding. Well, that’s not strictly true. The CEO, and/or the Company Chairman, holds responsibility for individual performance and the wellbeing of top team members.

However, it is the CPO who needs to ensure that the supporting policy and practices are right:

• Every member of the top team needs to know that they are expected to leave at the right time. As

a CPO friend of mine put it, “Every member of our top team understands that this is not a request,

it’s a requirement. And it’s up to me to ensure that the necessary processes and practices are in

place to make it happen.”

• Of course, age discrimination can raise its ugly head. There’s plenty of evidence that many

companies don’t treat their mature employees well, including the fiftysomethings on their top

teams. It’s your job to eradicate subtle messages that, once you reach fifty, you’re past your sell-

by date. When the hint of age discrimination is removed, the process of off boarding becomes much

more straightforward.

• An effective off boarding process requires ongoing conversations between the organisation and the

individual—not a one-off chat. Conversations need to start early and continue until the point of

departure, if not beyond. The CPO needs to make sure they happen.

In my view, every fiftysomething executive should be offered support for their transition journey. Some will take up the offer enthusiastically, some won’t. It can be difficult to gauge people’s appetite in advance, so it’s safer to include everyone.

It’s a delicate matter

It’s always a delicate matter to address the subject of off boarding, especially with good people who are serving the company well. What adds to the delicacy is another delicacy—being fiftysomething.

People in their fifties seem to proliferate on top teams (the average age of the C-Suite executive in USA is 56 years, according to fresh Korn Ferry research). One CPO defined her top team as ‘a confederacy of fiftysomethings.’ There’s nothing wrong with it, it just happens—good people climb through the ranks and make it, fresh-faced, to the top team—and there they stay. Whilst poor performers get moved on and star performers get the chance of promotion, the good and very good stay, often or a lengthy period. As a result, over time, the proportion of fiftysomthings on the top team grows. While it’s not a problem, it does deserve your attention.

Being 50+ brings its challenges. These are not often discussed in everyday top team life—maybe because senior executives learn that showing any sign of weakness is problematic. So, they stay silent. And, as one person I was coaching put it, “It gets lonely inside your own head.”

James, 55, was a very successful CEO of a large public body. He appeared confident, authoritative, highly resilient, and very comfortable in his role. His track record, over six years, was exemplary. In a quiet conversation, I posed the question, “What is it like leading this organisation?” His answer startled me. He said, “To survive in this job requires 100% of me. As a result it feels like the bridges to all other parts of my life are burning. The bridge to my wife and children, the bridge to my health and wellbeing, and the bridge to my future.” Nobody around him had any idea of what he was going through—and everyone was shocked when, three months later, he resigned.

According to research* many people feel a strange sense of uneasiness in their 50s—the fiftysomething malaise. The causes are many and varied. Here are some insights that people have shared with me:

*The Happiness Curve—Why Life gets Better After Midlife
Jonathan Rauch

• Top Teams are high pressure environments. They bring unavoidable stress and anxiety. But, in their

50s, even the most resilient report that they can start to feel the effects of the pressure like never

before, often along with a wobble in self-confidence.

• After an extended time on the top team, it’s sparkle can tarnish. The excitement of the trappings of

the top team wears off, leaving exposed the immense and continuous hard work needed to survive,

never mind flourish. ‘Why am I doing this?’ is a question asked frequently

• Fiftysomething starts to feel old, in career terms, if not in terms of lifespan. People may well be

living 10 or 20 years longer than their parents, yet, senior roles seem to be moving to those 10

years younger. The bright young things are ready and taking aim at the seats at the top table. ‘For

the first time in my career, I have the unnerving feeling that people are impatient to fill my space at

the top table.’

• Then, consider the emotional landscape for fiftysomethings. A colleague said to me a few years

ago, “At 58, I could already be half way through my life—although, for that to be true, I will need to

live to 116 years.” The realisation of the relentless march of time is often experienced intensely by

people in their fifties. So too, the realisation that life has not delivered and is unlikely to deliver all its

promises. And, in career terms, it dawns that they have probably reached their career pinnacle and

so, when looking forward, they can only see more of the same, or a downward trajectory. It’s not

surprising that the fifties has been shown to be a time when life satisfaction is at its lowest, when

compared with younger people and older people. Fiftysomethings are at the bottom of the Life

Satisfaction U. One senior executive I know referred to a period in her fifties as, “a soft drizzle of


• And, with all this going on, the time arrives when they are meant to plan an exciting future,

negotiate a successful exit, and move seamlessly on to the next phase of their life.It’s little wonder

that fiftysomething executives can get stuck.

New adventures await

In recent years, we have seen the emergence of a new life/career stage between full-on work and full-on retirement. It can last 5, 10, often 20 years, and doesn’t yet have a commonly agreed name.

In the modern world, this phase offers liberation, and is not something to be feared—at least for society’s more prosperous, like senior executives.

If they so choose, senior executives can approach leaving the top team as a liberation opportunity. They can free themselves from whatever is grinding them down (the never-ceasing emails, the commute, endless airports, the politics, the conveyor belt of problems, relentless disruption, the pressures and stressors of a senior role), as well as gaining the freedom to move on to fresh challenges, doing the things they have always wanted to. Great adventures await, along with a different pace of life and a refreshed lifestyle. They have worked hard over many years—so they’ve earned it. Two of the saddest words in the English language are, “If only.” The most common regret for senior executives is not, “If only I had stayed in my role longer.”, it is, “If only I had found the exit door to my new adventures, sooner.”

And senior executive have an intriguing array of choices after stepping out of the top team—often more choices than they realise:

• another full-on, full time position;

• a portfolio of part-time roles—non-executive directorships, mentoring, advisory, freelancing, etc;

• an encore career—i.e. a new role, maybe in a new field, that provides continuing income (or not),

new meaning and the opportunity to make a significant contribution to the greater good;

• retiring to leisure and new, non-work adventures;

• boomeranging—retiring to leisure for a period and then returning to work;


• retiring to the sofa and daytime TV.

A routemap and a travel guide

So, how can you help your fiftysomething executives get unstuck?

Navigating the journey to the exit door and beyond (perhaps for 30+ years) can be daunting. It’s a process that involves self-discovery, deep thinking, the right planning and precise execution. Often, companies leave people to go it alone, which makes little sense—for the individual and the company.

The company should offer each individual the tailored support they need in order to prepare to exit successfully. In my experience there are three key requirements:

• a trigger—to light the blue touch paper;

• a routemap—to outline the terrain ahead and provide directions to the exit and beyond; and

• a travel guide—an experienced person who knows the terrain intimately and can accompany them

as they discover, think, plan and execute. Usually, an experienced coach or mentor.

One big firm I work with does it well:

• At 54 years, every top team executive receives a letter asking them to share their intended plans

and proposed leaving date.

• The letter triggers an ongoing series of discussions between the individual and the company, often

over years.

• The executive is invited to attend a Stepping Out programme—providing information, guidance and

best practice information.

• An external coach is provided to give 1-1 support (the company has learned that their senior

executives are most comfortable with an external/independent coach for such personal and private


Getting it just right

I said in my introduction—what I know for sure is getting it right shouldn’t be left to chance.

Good people will, of course, find their own way to the exit door. But, without a trigger and the offer of support they can easily miss the right moment.

Here is a checklist to help you get off boarding just right. If you aren’t able to tick each affirmatively, you have work to do:

Partner with offboarding experts

There’s plenty that internal teams can do themselves to create quality and effective offboarding programmes for their executives, and hopefully this article has provided you with useful pointers to set you on your way. But if you’d like additional support from a team that has led multiple companies through this process, contact us. ‘Stepping Out’ is a coaching company specialising in top team off boarding. As well as providing highly experienced and accredited Stepping Out coaches, we provide policy advice, workshops, guidebooks and an array of related services.


Oliver Johnston

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