When my coach asked me this question it truly floored me. I actually froze in the chair! I can’t really say why he asked it, how it hit home or indeed if I 100% understood it at the time. And yet, hit home it did!

My take is simply as follows:

  • Playing to win is about being clear how you are going to win and going after it. It is about dreaming big and making bold calculated moves to achieve that vision. Without it, there is no creativity or innovation.
  • Playing not to lose is more defensive. The priority is ultimately to avoid failure. Winning would be nice but only at certain costs. By design, this limits opportunities (to succeed or fail).

Neither approach is inherently right or wrong. Each has its benefits and drawbacks depending on the situation. Indeed, it may well make sense for us to play differently in different games. The key point is being aware of our mindset in any particular game.

If you playing to win, ask yourself:

  • What exactly do I want to win?
  • What would winning mean?
  • How willing am I to lose?

If you feel you are playing not to lose, ask yourself:

  • What am I doing so as not to lose?
  • What do I not want to lose? (status, power, money, relationships…..)
  • What am I protecting?
  • What would losing mean?

In ways, this playing to win mentality is at the heart of the Art of Opportunity approach I developed. This is about dreaming big and ensuring complete clarity around what it is you want to win. Afterall, there is no point winning if the game means nothing to you.

Question in the Image:

  • Am I playing to win or not to lose?

Want to Read More Around This Topic?

Playing to Win: How Strategy Really Works by Roger L. Martin and A.G. Lafley (link to Amazon.co.uk). This is an intriguing book that describes itself as “a playbook for winning”. Blurb aside, it likely will help you build a stronger strategic process and put the numbers more on your side.

Nurturing Curiosity – Daily Practice: This is part of the Nurturing Curiosity series of tools, insights and questions designed to help nurture curiosity as part of our daily practice. In point of fact, every interaction we have is an opportunity to question what we are observing and how we and others are seeing the world. Also remember that questions come in many forms throughout our day. For example, the above discussion brings back Roger L Martin’s strategy questions of: What game are you playing? And how are you going to win? These are two truly powerful questions that are highly connected with this topic. I always have these questions by my side.

About Tom O’Leary

My mission is to help others think differently – meaning more broadly and deeply – and thereby make better decisions. The key to thinking differently lies in our curiosity.

The more we question, the more possible answers we uncover, and the more we expand what we thought possible. Life has taught me that possibility lies not so much in seeking answers but in learning to ask better questions – the ones that help prioritise what is truly essential.

And yet, in a culture obsessed with efficiency and productivity, the paradox is that much energy and resources are wasted by a bias towards action over contemplation. If you are answering the wrong question, it doesn’t matter how ‘hard’ you work, you are still answering the wrong question.

That is why I am a big advocate of nurturing curiosity and innovative thinking at all ages, particularly amongst leaders because of the impact they have on us all. In my vision, leaders aren’t boxed in by traditional thinking or established playbooks. They are curious, open to fresh ideas and diverse perspectives, fostering a culture of exploration and learning.

What Thoughts Would You Like to Share?

I welcome your thoughts, feedback, or personal experiences related to these questions or any insights they may have sparked.