Playing to Win: *rethinking risk and failure in business decisions* \\The Dyson blog

In his latest blog, Professor John Dyson reflects on why some organisations play to win while others play not to lose – drawing on a footballing analogy, the psychology of fear and failure, and the logic of portfolio investment theory to argue that treating risk as part of a broader portfolio, rather than a single high-stakes bet, is what allows ambition to survive contact with setback.


Forgive my ignorance, if my footballing story causes pain both in rekindling a painful memory and in making an analogy which is keenly disagreed with. The same day that I looked at the news before going to bed and saw the headline about England’s 6:4 win over France, was the day I had been discussing the idea of playing to win and not playing to lose. In the context of mental health, the metaphor is stated differently: if you are riding a bike and you want to avoid the tree, don’t look at the tree, look at the gap, the space. In England’s previous match with Argentina, the headlines suggested that the manager had played it defensively, played not to lose, and lost. When the pressure was off, the same team played to win with impressive results.

The question I keep coming back to in repeating conversations is how and why do companies, organisations, teams and individuals come to a point where fearing failure overcomes the excitement and ambition of success. In the book Design to Value I talked about how companies or projects often started with ambition and optimism; however, they quickly become entrenched in the rigid fear of failure. In the footballing analogy, we fear failure, so we lose; when we do not fear failure, we can win.

I try to work with my clients to build their own sense of value and worth, to a level where they do not need the continuous validation of things going right to feel okay and if things go awry, which they will, they can learn and move on, rather than feeling crippled by it. The process is not straightforward, requiring experimentation and reframing, though it does work. In the poem ‘IF’ by Rudyard Kipling there is the line ‘If you can meet with Triumph and Disaster; and treat those two impostors just the same…’ this was voted the UK’s favourite poem in a BBC poll and yet how many of us and  our organisations are close to thinking and working in this way?

I wonder if one of the problems is a developed reductiveness, a myopic single-issue focus. In a piece of research I led, I came back to the concept of the efficient frontier theory in portfolio investment. Devised by Harry Markowitz who received a Nobel Prize for it in 1990, it looks at the relationship between risk and gain, suggesting there is a line which plots the optimum level of risk vs gain which can help an investor make decisions about their investment portfolio. There are doubts that he actually used such an approach himself, maybe because nothing in economics or life for that matter can be described so definitively. The point is, however, that an investor does not overly focus on each investment except in the context of the portfolio. Some may lose money, some may make meagre returns, while others will do better than expected. You manage them as fluidly as you can, weighing up risk and return.

My sense is that this idea is altogether absent or has been lost. I understand that some moves or investments are significant and therefore their partial failure can be very damaging – often, though, that is because we design them that way. I am often amazed at the size of projects many companies undertake, making huge long-term decisions in very risky times, when there were options to phase investments allowing change to happen more quickly and easily as the ecosystem changes. We set up every project as a World Cup final rather than an ongoing series of games which demonstrate strengths and depth of performance, while also uncovering areas to improve.

There is much we can do both in the way we organise our work and investments and set our culture which would allow us to feel like we can play to win and be less concerned about setbacks on the way. Business and people’s lives have fewer knock-out rounds.

Professor John Dyson

John Dyson spent more than 25 years at GlaxoSmithKline, eventually ending his career as VP, Head of Capital Strategy and Design, where he focused on developing a long-term strategic approach to asset management.

While there, he engaged Bryden Wood and together they developed the Front End Factory, a collaborative endeavour to explore how to turn purpose and strategy into the right projects, which paved the way for Design to Value. He is committed to the betterment of lives through individual and collective endeavours.

As well as his business and pharmaceutical experience, Dyson is Professor of Human Enterprise at the University of Birmingham, focussing on project management, business strategy and collaboration.

Additionally, he is a qualified counsellor and executive coach who looks to bring the understanding of human behaviour into business and projects.

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