This may feel like an edgy question. For starters, failure obviously depends on how you define success. I co-founded a start-up over 20 years ago that, despite a solid business idea and incredible effort by the whole team, failed to get to market and died after 2 years. On any measure (both intent and outcome) it was a failure.

And yet, the lessons learnt in that failure were instrumental in bringing me to where I am right now, so I no longer think of failure as bad and success as good but rather in terms of learning. That isn’t the same as deluding ourselves that we didn’t fail. We did and we failed badly. The important thing for me was that we were ambitious, and we learned so many valuable lessons.

However, for a while this led me to become more risk averse and I remember being shocked when my own coach asked me:

Are you playing to win or not to lose?

It was one of those questions that stopped me in my tracks and made me realise that I was playing it safe and no longer putting myself in situations where I might fail badly.

I made a vow to myself to follow my heart and my gut wherever they lead regardless of the outcome and continue to do so. It also made me appreciate process (how it is done) more than outcomes (what is done). If I do everything I can on a daily basis to deliver the vision and still fail badly, that is fine in my book.

  • So, how badly have you failed?
  • If you haven’t failed badly – how ambitious do you feel you have been?

Questions in the Image:

  • How badly have I failed?
  • How ambitious have I been?
  • Where am I afraid to fail badly?
  • 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 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 – a discussion with colleagues around accountability raised the question of “If I am accountable to myself, to whom am I accountable to?” I have a voice of perfectionism in my head. He isn’t as loud as he used to be but he is still there. I certainly don’t want to be accountable to him and he isn’t always reasonable. To whom then might I be accountable?

What Thoughts Would You Like to Share? My name is Tom O’Leary, and I envision a world in which curiosity shapes leadership. In this world, leaders aren’t boxed in by traditional thinking or established playbooks. They are open to fresh ideas and diverse perspectives, fostering a culture of exploration and learning. My mission is to shift leadership focus from authority, over-measurement and control to curiosity, learning and innovation, empowering leaders to prioritise the essential. My journey, lived in a number of countries and through various languages, has always been driven by a profound sense of curiosity. In fact, 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. I welcome your thoughts, feedback, or personal experiences related to these questions or any insights they may have sparked.