What Am I Looking for Today?

To explore questions about time?

To practice my curiosity?

To create impact? Explore these two free programmes:

To learn more about Tom?

For a deeper Dive on Tom himself, Tom’s Journey might provide some insights. Otherwise, just keep on reading this page!

Why Is Curiosity Key to Empowering Leaders?

There can be a tendency in our busy world to jump straight into a quest for answers rather than a quest for questions. Indeed, vast amounts of energy, resources and opportunities are wasted pursuing the wrong answers. So much more could be accomplished if we simply had greater clarity on what questions we are actually answering. That is why my mission is around empowering leaders to see beyond answers.

As Einstein said, “
If I had an hour to solve a problem and my life depended on the solution, I would spend the first 55 minutes determining the proper question to ask…

That is why I advocate curiosity-inspired leadership, where leadership isn’t about having all the answers but rather about asking better questions and fostering an environment of exploration and innovation.

This is about empowering leaders to become crystal clear about desired outcomes, make smarter decisions, conserve energy and resources, and accomplish more of what truly matters.

It is also about fostering leaders’ self-leadership as they become increasingly curious about their own actions, decisions, thinking and motivations.

Want to dive deeper? Read Curiosity: A Short Manifesto!

Want to Boost Your Curiosity?

Sign up for the Nurturing Curiosity: Weekly Practice emails for a thought-provoking question each week.

What have you got to lose?

Sound Like You?

  • Are you a leader with big ideas but unsure how to make them real?

  • Are you so busy with daily tasks that you can’t find time to stop and think?
  • Do you feel you are at a crossroads and unsure which path to take?
  • Are you looking to lead from deeper inside yourself in alignment with your core values?
  • Are you eager to nurture your curiosity and ask the essential questions that will shape your legacy?
  • Are you looking for a partner with whom you can explore what might be possible?

If you answered ‘Yes’ to any of these questions, let’s talk.

My name is Tom O’Leary. My journey, lived in a number of countries and through various languages, has always been driven by a profound sense of curiosity – a trait that has remained consistent from childhood. If anything, it has been reinforced through my experiences as a project manager, start-up founder, manager and entrepreneur for over two decades.

The need for tangible outcomes is paramount and yet 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. This is the heart of self-leadership.

I remember a pivotal moment in my life while working as a manager in Belgium. Despite the fulfilling nature of the work, I felt life was stagnating. These questions began to float around me:
  • What do I want from life?
  • Is this it?

Together with my (now) wife, we began questioning our lifestyle:

  • How can we live differently?
  • How can we work differently?

Acting on these questions, we left our well-paying jobs, left Belgium, moved to Spain to live on the beach, started our own businesses and made our family the priority.

This lifelong fascination with questioning and curiosity led me to a Masters in Personal and Management Coaching. This gave me the tools to translate my decades of self-coaching, specifically around more insightful decision-making and self-leadership, into an offering I could share with others.

My ongoing journey of learning, coaching and educating – particularly around what I call bigger questions – has been focused on expanding horizons by exploring how we may have made our worlds and our thinking too small.

Decision Clinic: What Issues Are on Your Mind?

Are you grappling with a particular decision? Feel stuck?

Not sure where to turn?

Why not book a call?

I offer a number of free slots every week so book one now!

Our conversation will allow you to unlock insights as to what is truly important and move you towards a smarter decision.

Rest assured, our conversation will remain completely confidential, providing a safe space for you to say what needs to be said.

Don’t remain stuck. Book a call and get clarity on what truly matters!

What Can I Offer You?

I empower leaders like you to:

  • Nurture your curiosity;
  • Prioritise the essential;
  • Improve your decision-making;
  • Foster your self-leadership;
  • Become stronger leaders.

In many ways, before we can truly lead others, we first need to lead ourselves. I therefore invite leaders to filter out the noise and ask bigger questions about all aspects of who they are as individuals and as leaders.

Such questions open the door to greater possibility and also to discerning what is truly essential right now.

This allows for a much deeper form of decision-making and leadership in life, work and business.

Let me illustrate with an example. When I started working with John, he was spending 6+ days on the startup. Even on rare weekends away with his family he would spend time alone in the hotel room engaging with clients. He felt guilty not doing so.

We looked at his vision – not his vision just for the business – but rather a larger vision that involved the young kids he wanted to see grow up, his wife, friends, even time for himself to exercise. The result? Now, John balances caring for his children and himself with 3 1/2 days working on the business. And every hour he is working he is asking himself:

  • What is important now? and
  • How can I have the most impact?

If you would like to explore how you or your organisation might benefit from such an approach, please click here: What Might a Partnership Look Like?

To continued curiosity,

Tom O’Leary

P.S. If you are grappling with a particular decision, why not book a call to chat through it and unlock the insights that will move you towards a smarter decision?

Ask yourself: If I pass on this offer, with whom might I have this conversation?

In Tom’s Words

Hear from Tommaso

Are You Tired of Having to Have the Answers?

“Wisdom in decision making is vastly more important — not just practically, but philosophically — than knowledge.”
— Nassim Nicholas Taleb

To my mind, wisdom is not just about focusing on what we know but rather about becoming increasingly curious about what we don’t know. This can dramatically shift how we approach decision-making and leadership.

In our early years, we are surrounded by voices talking at us. Parents, guardians, teachers, friends and indeed society tell us how to think, what to believe and set limits on what we should aspire to.

As we age, we start finding our own voice, but it often lacks confidence and may be accompanied by whispers of doubt as to what others may think of us. As a result, we play roles, projecting what we believe the world wants to see, continually looking for outside validation rather than trusting the wisdom that lies within.

But true growth, the journey to wisdom, begins when we embrace our vulnerabilities. It starts with recognising our imperfections and understanding that our deep inner strength is built on accepting who we are, warts and all.

In leadership, this means admitting we don’t have all the answers.

This means accepting that our decisions and our leadership may be less than perfect.

And that is OK. Yet, this courageous step is only the beginning!

Empowering Leaders to Shift Their Energy and Attention

This allows us to shift our energy and attention away from defending what we know to the perspectives and bigger pictures we may not have considered.

To removing distractions and interruptions.

To prioritising accomplishment over mere action.

To becoming more attuned to learning where to look and what to ignore.

To building organisations and systems that are more robust and resilient.

I would invite you to join me in this today. There is a host of free content on the site to help everyone nurture their curiosity and increasingly tap into their inner wisdom.

Remember, like most of us, you probably know both more and less than you think.

My invitation is to take a moment to reflect right now. Ask yourself:

Where might I benefit from embracing what I don’t know?

If I can help in some way just email me.