Conversations, at their core, are exchanges – but how often do we load them with unseen baggage?

While they inherently involve an exchange of information, with a significant portion being non-verbal, we often complicate them by adding layers of expectations and preconceptions, describing them as “difficult“, “tough“, “potentially upsetting“.

However, the less we bring to a conversation in terms of expectations, the more open we can be to simply listen and sense what the other people are saying and equally importantly not saying.

Compare the simplicity of thinking “I am going to talk to John about his performance at work” versus “I need to talk to John about his performance and I’m concerned he will react negatively. He can get very defensive when he feels his position is threatened. This might be tough!

The essence of insightful conversation lies in creating a frame that fosters genuine connection without triggering defensive barriers. The first pivotal step is recognising the expectations and biases we carry into each discussion. It is about cultivating awareness. With awareness comes power.

Armed with this awareness, we can then explore:

  • What concerns might John have?
  • How might I make this a positive interaction?
  • What support might John need?
  • What possibilities might this conversation have?

Questions in the Image:

  • What am I expecting from this conversation?
  • How might I think about it differently?
  • What do I truly want to accomplish?

Want to Read More Around This Topic?

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.

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. I just came back from holidays last week and my daily routines from before the holidays are all coming to me in the form of questions. How is this of benefit? Is this truly the most important thing I might do now? It also reminds me of how fascinating the conversation between short-term and long-term considerations is. An activity may not pay off today but doing it repeatedly over time may offer significant compounded returns. Beginnings – like coming back from holidays – are wonderful opportunities to question everything we do.

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.