This question goes to the heart of what it is to have a conversation. Conversations can sometimes feel more like a series of loosely connected monologues than a true dialogue of peers. How then are you contributing?

In order words, what is your purpose in having a particular conversation? I have been in a series of conversations lately where one of the participants simply wanted to badger the others to agree with them. There was no listening on any side. In other situations, conversations have ultimately been about status and power – about people using them as informal (and often ineffective) therapy sessions.

Becoming more aware and intentional about what we are bringing to the conversation is particularly critical leaders looking to improve team meetings and one-on-ones. Ask yourself:

Why am I having this conversation?
What assumptions am I making?
What is this really about?

The next source of information is turning to the other person or group for clarification in the form of “What do we hope to accomplish here?” I know that in many settings and cultures this may feel uncomfortable so you may want to come at it indirectly:

  • What is the deeper issue here?
  • What is your concern?
  • What do we want to find out?
  • What is the real question?

Whilst this will allow you to dive a little deeper, it may still not come close to a sense of the true purpose. This is because so much human behaviour is both unconscious and embodied and not immediately available to the conscious mind. And yet, much of it is in plain sight in the form of body language, spoken or unspoken assumptions and individual values.

In working with a client recently around improving one-on-ones with a particular manager and more broadly with the whole management team, it became clear that whenever issues arose with the individual it was because there was an unacknowledged conflict of values between the two. They simply didn’t see the world in the same way. This led back to the need for clarity around shared values and ground rules governing particular types of conversations. It also opened the door to the possibility that the manager in question wasn’t the right fit for the management team.

The invitation therefore is to become more comfortable taking a step back from the conversation and observing what is truly playing out before your eyes. In every encounter, ask yourself:

  • How am I contributing here?
  • What might I do differently?
  • How might that change the dynamic?
  • And ultimately what purpose is the conversation serving?

Questions in the Image:

  • How am I contributing to the conversation?
  • Indeed, why am I having this conversation?
  • What is my intention?
  • What do I truly want from it?

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. Just now I am holding a question for which I have no words. I simply know that I am being asked a question and that if I want to hear it on some level, I need to slow down enough to allow it to catch up with me. It reminds me of the benefit of an ongoing practice of reflection (even 5 to 10 minutes a day).

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.

How Might Tom Help?

  1. My first invitation is to take maximum advantage of the free content on this site.
  2. I also endeavour to answer every email so if you have any queries do reach out – you will find my address if you are curious. Your future self will thank you!
  3. If you would benefit from a face-to-face conversation, consider signing up for a Decision Coaching package (initial call plus follow up call).
  4. If you feel you would benefit from a chat without having to sign up for decision coaching, click on the button below to join the waiting list for the opportunity to speak face-to-face. No charge! You just need to make a case as to why we should speak.