To my mind, we should not think of conversations just in terms of what is said. Conversations are in truth built on a deeper human connection. Without this, no manner of words will bridge the gap and we simply talk at or past each other.

Personally, I do not so much remember what people say but more the experience we create together. Every aspect of how we turn up, hold our bodies, our faces, how we listen and speak. In short what goes unsaid as much as what is said!

It all stems from our conscious or unconscious intention when entering a conversation. Deep conversations do not happen by chance – each person has to bring a willingness to engage.

Think back to a deep conversation you had – hopefully recently. Bring it to life in every way you can!

  • What exactly do I remember?
  • What feelings does it evoke?
  • What makes this conversation memorable?
  • What contribution did I make to the conversation?
  • What does this conversation say about me?

My experience is that a transformational conversation is always just out of awareness. A conversation that will open the door to insights that are so striking that we wonder why we had not seen them earlier.

The question then is what conversation do I most need right now?

It may well be obvious in this moment. Is it?

  • Why this person / group?
  • Why this conversation?
  • Why now?
  • How am I being asked to show up?
  • What needs to be said?

“All those years listening to those who had nothing to say.”
David Whyte

As David Whyte hinted, we may be drowning in rivers of words but is anything meaningful actually being said?

How then do we move beyond this to something deeper?

To open ourselves up to the possibility of such conversations, it helps to slow down when interacting with others. To bring our full attention to the invitations in the air.

Remember, the depth of a conversation is not connected with what is being discussed. We can have deep conversations about anything – it all goes back to the connection we establish.

This is followed by our intention. Depth comes from being honest, from giving ourselves over to the conversation. From not having an agenda beyond what is being discussed.

Agendas both prevent us from fully listening to the other person – it is a little more about us than them – and often trigger defences because the agenda becomes obvious at some level.

The invitation therefore is to practice the art of deep conversation the next time you interact with another human. And the next and the next. Listen with your whole body. Become more aware of the invitations being made. Of the doors being opened. Of the possibility wafting around you.

In essence, ask yourself:

How might I contribute powerfully to this conversation?

Questions for Reflection

Questions in the Image:

  • How might I deepen the conversation?
  • What do I contribute to conversations?
  • What conversation do I need right now?
  • How might I invite deeper conversations?

Want to Further Explore This Theme?

Fierce Conversations: Achieving Success at Work and in Life One Conversation at a Time by Susan Scott (link to This book focuses on the importance of having open, authentic, and effective conversations in both professional and personal settings. The author presents techniques and principles for engaging in meaningful conversations that can lead to improved relationships, increased understanding and better results.

Next Steps – From Reflection to Action: These reflections model pausing and thinking, and hopefully show how this can quickly translate into fresh insights and decisive actions. They are centred around three “archetypal” questions:

  • What have I learnt?
  • What do I need right now? and
  • What are my intentions?

The aim is to practice translating newfound insights into viable options.

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.

Just now, as I see a figure walking into the distance with a small bag on his back, I am curious as to the horizons he is uncovering. I wonder: What new horizons may be waiting for me?

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.