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Stepping Out from the Top Team

Updated: Oct 20, 2021

Oliver Johnston is a coach and teacher. He's the founder of Stepping Out-a coaching practice for senior executives who are thinking about leaving the top team. He has supported the stepping-out journey of more than 100 C-Suite executives and big-firm partners.

If You Stepped In, You Must Step Out

After years of hard work, you made it to the top team -relying on your intelligence, experience, knowledge and skills to get you there and your political nous, creativity, resilience and years of continuous long hours and sacrifice to stay there and flourish. The rewards have been great and well earned. Hopefully it's been fulfilling. There have been financial rewards and, maybe, the appealing business-class life style.

But no one remains on the top team forever. We all reach a point where we need to start thinking about saying goodbye to our colleagues and the business. Stepping out is always a trade-off between what you give up and what you gain. And there is much to be gained. The first question is, when will be the right time for you-and for others (the business, your colleagues, your team, your customers and, of course, your loved ones)?

Once you step out, the next stage of your life will open up, and you have lots of options. Which of these scenarios best describes what you think you'll want to be doing next?

Continuing to Work:

  • A new, full-on, full-time role;

  • A portfolio of part-time roles;

  • 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.


  • Back to study and the academic life.


  • Retired but still doing some work;

  • Retired to active leisure and new adventures;

  • Retired to the sofa and daytime TV.

Pay Attention To Your Daydreams

We all daydream. It's our imagination at work. But are you aware of your daydreams? When you pay attention to them, reflect on them, they can tell you a lot. What do yours tell you?

Do you daydream about the future of your career-more seniority, more money, more status, more top team glitter?

Do you daydream about being free from the daily grind of senior leadership-the never-ceasing emails, the commute, the endless airports, the politics, the conveyor belt of problems, the relentless disruption, and the pressures and stressors of business?

Does your imagination take you beyond your current role to a place of new adventure-a life with better balance and more time for what and who you love. That place may not be a realistic option immediately, but it could be, sooner than you think.

If your daydreams are about carrying-on your career ever-upward, then stepping out is probably not for you just yet. On the other hand, if you daydream about liberation-from your current job and/or the liberation to pursue the next stage of your life, then read on.

The Goldilocks Dilemma

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

Leaving too early means going before your job is done-either because others have decided, wrongly, that you are past your sell-by date, or because you have decided prematurely to walk-away.

lmran, 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 lustre. He had made no plan for life after the top team and, as a result, he increasingly felt trapped. He once told me, "It's like being in a never-ending hamster wheel." When his wife became ill and, at same time, he had a senseless argument with his CEO, it was enough to trigger him to walk away. He off boarded within three months-without a plan for the future, with his job uncompleted and his reputation tarnished.

On the other hand, leaving too late means outstaying your welcome and outliving your usefulness. You 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.

Timing your stepping out just right means leaving when you have:

  • completed your job well;

  • left them wanting more;

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

  • finished with your reputation intact; and

  • created an exciting plan for your future.

Bill Gates got it just right in 2014. He retired as Chairman of Microsoft at 58 years. 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. He timed his exit. He wrapped up his obligations. He ensured a smooth handover. And he had a clear plan in place for what would come next.

Why Wait?

Starting the process of thinking and planning will not bring your departure date closer, if you don't want it to. Rather, it will give you more time to get it right. I've travelled the journey (successfully, I believe) and I've worked with over 100 executives as they have made their way to the exit door and beyond. What I know for sure is that stepping out successfully is a process carried out over time and involves personal discovery, deep thinking, the right sort of planning and deft execution. Here are some key questions for you to consider and answer:

Personal Discovery

  • What is compelling me to go?

  • What is compelling me to stay?

Deep Thinking

  • What do I want to continue?

  • What do I want to be free from?

  • What do I want to be free to do?

  • How do I want the rest of your life to unfold?

The Right Sort of Planning

  • What is the most appropriate planning approach to use?

  • What are my best options after I step out?

  • How will I decide between my different options after I leave?

Deft Execution

  • What actions do I need to take to make it happen successfully?

  • What is the right time to announce my departure?

  • What obligations will I need to honour before stepping out?

A Route Map and a Travel Guide

Getting it right is important. After all, the rest of your life depends upon it. To navigate the journey successfully, you need to build up a map of the terrain ahead. You may also benefit from a travel guide-someone who has travelled the route before and can offer you their insights and experience. At Stepping Out we provide both. A tried and tested guidebook for the journey and a coach to work with you as you travel along-providing just the right balance of support, provocation and encouragement.

Mañana, mañana

So, when is the right time for you to start thinking about and planning to step out? It's easy to put it off until tomorrow­ mañana, mañana. But too early and too late are both costly. It's said that, "If only", are the two saddest words in the English language. 'If only I'd stayed longer' is something I seldom hear when I talk with people who have stepped out successfully. 'If only I'd left sooner', however, is something I hear frequently.

For a conversation or further information please contact -

Oliver Johnston

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