Life is a journey of continuous exploration that is paved by the questions we ask. As someone who relishes the thrill of deepening conversations and expanding horizons, I find myself growing restless when conversations stagnate.

The one constant in the world around us is change and, in many spheres of life, it is true that every day you are moving further ahead or falling further behind. Surely then there are always questions to be asked, greater insights to be gained?

I have seen this stagnation in the most unlikely places across my life and work. I say unlikely because in many instances individuals or organisations can seem incredibly dynamic but in truth it is often busyness hiding the fact that no time and energy is being set aside to ask bigger questions.

In the case of organisations, this can be a focus on the day-to-day activities with little real regard to strategic challenges that may even threaten an organisation’s future. In the case of individuals, this can be busy doing to cover up the fact that there is no larger purpose or vision.

So, in every interaction, every activity, I challenge myself: Can I see fresh questions here?

It isn’t always about responding to new challenges. In fact, sometimes, it is about delving deeper, looking at the familiar from a different perspective, challenging our assumptions and breaking our own moulds.

This isn’t to say that there is no value in familiar questions. They have their place, and they can offer comfort and clarity in certain situations. And yet, if we’re not careful, they can also lure us into a sense of complacency, where we stop challenging ourselves and cease to grow.

An example at present, in a number of organisations with which I am involved, is around metrics. Because of quantification bias, there is a tendency to use metrics to drive strategy: we want to increase X by Y%.

  • That is fine in theory but in practice what do these metrics really mean?
  • What is not being measured that might be important?
  • What are the numbers hiding?
  • Are these indicators of busyness or impact?
  • What behaviours are the numbers incentivising?

So, the next time you find yourself in a conversation, participating in an activity or even just mulling over your own thoughts, I challenge you to ask yourself: Can I see fresh questions here?

Remember, the value lies not in the answers we find but in the questions we dare to ask.

Questions in the Image:

  • Can I see fresh questions?
  • Am I blind to the questions?
  • Do the questions interest me?
  • Are they deepening the conversation?

Want to Read More Around This Topic?

A More Beautiful Question: The Power of Inquiry to Spark Breakthrough Ideas by Warren Berger (link to This book delves into the importance of questioning in life and work, exploring how the most creative, successful people tend to be expert questioners. It offers practical insights on how to cultivate the art of asking more and more effective questions.

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 sense of having too much on your plate might be a prompt for How might I lighten the load? Who put all this on my plate? What is truly important? What will have the greatest impact in a year?

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.