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Coaching People Preparing For Retirement

A client of many decades recently asked Graham if his coaching could be adapted to help them and their senior team to cope with the transition into retirement. The answer is yes! In this edition, Graham discusses how coaching can help leaders prepare themselves for living a great life after work.



I had a really unusual request last week from a client that I have been working with for decades now if I thought our coaching program could be adapted to help him and some of his senior team who are approaching retirement. Whilst I'd never really thought about it in that context, I started to reflect and thought, You know what? I think we probably can.

The interesting thing about retirement is that if you move away from the question of money, can you afford to retire? And can I afford to live the kind of life I choose to, or do I really need to keep working in one form or another? If you remove that question and are on the assumption that money isn't the problem, you start to reflect on what is retirement going to be?

So, having reflected on it, I went back to the client and was chatting it through and started to believe that actually there was a really neat way of helping him and his fellow team members to start to prepare themselves for life after work. And I suppose some of the really interesting aspects of this as a coach is that really is no different.

Whether someone's at the beginning of their career, the middle of their career, or going through a major change in the development program when they're facing it. Another change is leaving what is a career so far, and taking on another phase of life. And so in shaping it up, I began to put together some thoughts as to the questions, the inquiry, and the frameworks a coaching program might take to help people as they begin to think about life after work.

The matters that came up were, are you running away from work or are you positively, actively running into retirement? And whilst that's a glib question, what sits behind it is, do you have things you really want to go and do but have never had the time, and you can now choose to do them in retirement or is it you're just burnt out, tired, fed up with work, and you just want to bury it and then move on? Because that's a different starting point.

Clearly, if you've already got a list of things that you really want to spend your time doing, the work of the coach isn't that difficult. What are they? How are you going to do them? What do you need to do between now and then to be ready? Is there a transition phase? Are you working part-time before you fully give up and so on? That's relatively straightforward coaching, but if somebody's in a different frame of mind and they're just tired and looking to give up work and they haven't yet thought it through fully - what does that then mean? What are they going to do with that time now?

I think it's really a challenge for a coach because the thing about work, as you approach retirement for decades, for the vast majority of your adult life, it's been one of the centrepieces. Of everything that you have done, everything that you are, and all your hopes and aspirations have been bound up largely in your work. And suddenly that's not going to be there. You can summarise it - it's a reason to get out of bed and so on and so on, that's true, but it's deeper and more profound. Certainly in my own personal experience, in my own personal life, I've seen friends and family members who have literally given up work and then thought, Now what?

It's been a fairly lengthy and not inconsiderable disruption to adapt to this new world. And bear in mind, often if you are married or you've got a serious partnership, then that impact on you impacts them too. So the more you are adjusting, the more you are coming to terms with it. So are they.

I started to think about what would I be doing to help someone who is definitely going to give up work but doesn't yet know what they want to do. I started to think about some of the really clever, almost profound sayings that I'd heard from people who'd been asked to think about these things. Michael Palin said something once, which really registered with me and I thought it was a really lovely phrase when I asked about retirement and his view on retirement and the guy's well into his seventies. Now, I believe he said, "Retirement for me is about doing what I love, but less of it". I related to that instant.

Then there was Paul McCartney. Paul McCartney was asked a few years ago when he was going to retire, and his answer was, "Retire, retire from what?". You know the reflection of that is I'm doing what I love. I would do this whether I'd be paid for it or not. What am retiring from? And so when you start to latch onto to the theme between those two quotes; what is it you like doing? What are the things you value? What are the things that are important to you? Can you focus on them? Can you name them? Can you describe them? Are they related to the things that you are really good at? Are they related to some kind of sense of purpose?

When I got to that point, I started to think, how could I help this person or these groups of people start to answer some of those questions? I started to frame it in a different way and said, what would you like your legacy to be? You're coming to the end of your working life and you are looking back and you are deciding what was important to you. You can probably describe your working life, what that was, but what about your retirement life? I mean, it could be a call to review life easily - what would you choose for your legacy to be in that period of your life? It might be very personal things, it might be family, it might be grandchildren, it might be travel - it doesn't matter what it is, what matters is, can you name it? Can you describe it and press another way of asking that very similar question? If you were preparing for a funeral - sounds very depressing, but nonetheless - if you were preparing your funeral and your best friend was gonna read a eulogy, what would things be? What would be the words you'd like him or her to mention? I know that's a bit morbid, but the point is you are helping this person begin to identify what matters.

That can then be the platform on which you begin to build. So, if this is what matters, what are the sorts of things that contain this? Perhaps someone wants to do something that makes a difference to other people. Does that mean working in a charity? Does that mean doing something like working for the Samaritans? Do either of those two things mean you need to do some studying, some learning, some training, and get a qualification?

Perhaps it means you want to do something you want to achieve. I want to write a book - how are you gonna do that? As a coach, how would you help someone prepare to, and even begin to write a book? The question would be what? What kind of book? Is it a novel? Is it an autobiography? Is it a factual reference book? What is it? Then you can go forward, What sort of subject? When are you going to write it? How many pages a day are you going to write? When do you think you're going to get it finished? Are you going to self-publish? You don't know about publishing, so how are you going to find out about publishing? And so on and so on, and so on.

As you start to help them coalesce around the things that really matter, the things that are important, you can help them build a job list. You can help them build a work program, you can help them begin to think about and plan and put into action what they're going to do with their life after work. As you start to work with them, it becomes increasingly important. As they get near and nearer to retirement - or put another way the excitement, the interest, the energy of being able to do these things in retirement, replaces the energy, the commitment that they're currently in have historically given to their career.

So, coaching someone to prepare for retirement. It's all about the future, which sounds ridiculous, doesn't it? It's all about what you're going to do now, and it's got nothing to do with whether that physically fits. It's got nothing to do with whether they've got lots of money. It's got nothing to do with burning ambitions to travel the world because all of those can be brought into the context of what priority things are for them to be doing and what they're choosing to do in their retirement.

So, as I said, I was reflecting on this and discussing it with my client and basically, we both became really excited about the prospect of doing this for him and his team. And I could see the relevance of this. It's not really different to any other kind of executive coaching, except it's pretty well targeted at people in a certain demographic.


That was the latest edition of The Coaching Conversation. I hope you found it interesting. I hope you found it useful. You can find out more about our coaching programmes at

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