Leadership is tough. It is lonely, daunting, and overwhelming.

I help leaders feel heard, gain clarity, take action, build confidence and thrive.

👉 I highly recommend anybody give it a go❞ – Tommaso


Don’t Stop Questioning!

As Einstein reminds us: “The important thing is not to stop questioning. Curiosity has its own reason for existing.

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Why Are You Here?

  • I need to feel heard.
    Leadership can be isolating. I offer deep listening, ensuring you feel genuinely seen and heard.

  • I need some clarity.
    Challenging your own ideas is tough. I will challenge your stories and assumptions, helping you think differently and gain clearer insights.
  • I need to take action.
    Feeling stuck is frustrating. I help you unearth actionable insights that offer decisive steps forward.
  • I need to build confidence.
    Overwhelmed by planning next steps? Let’s build confidence in your decision-making.
  • I want to thrive.
    Continually refining ourselves is key. I will nudge you beyond your “limits” to thrive in every aspect of your life.

Identify with any of these? WHAT NOW?

Regardless of which statement resonates most, my sense is that the key to evolving how we experience the world is nurturing our curiosity at all levels.

Take maximum advantage of the free content on this site to become more curious and expand how you think. 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. I’m not claiming to have any answers. Instead, I offer questions, which open the door to infinite possibility.

Please also share this content. My view is that humanity could solve most of its problems by simply thinking differently and, as a species, it seems like we certainly have created a series of not only major problems but potentially existential crises.

This is collectively known as the metacrisis. A key component underlying the metacrisis is a thinking (or sensemaking) crisis – how we think and what we allow ourselves to think as constrained by the stories we tell ourselves. To survive and thrive, we are being called to evolve every aspect of our thinking – even how we think about thinking. All of this requires curiosity.

Who is Tom O’Leary?

Tom O'Leary 🤝 I empower leaders to thrive as they shape a brighter future

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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.

I remember a pivotal moment in my life while working as a manager in a Nasdaq-listed company 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, made our family the priority and embraced our inner Zen. This meant fostering a more mindful, present and reflective approach to all aspects of our lives, including the inevitable challenges.

The lifelong fascination with questioning and curiosity led me to a Masters in Personal and Management Coaching and a thesis on Play in Coaching, which explored more creative and playful ways of supporting coaching clients.

This particularly gave me the tools to translate my decades of self-coaching and dedication to mastery of core soft skills such as self-awareness, empathy, problem-solving, decision-making and thinking environments, into an offering I could share with others.

My vision is to continue thriving each day no matter what life throws at me. In terms of my work and volunteering, my vision is to within a decade work with leaders and boards of global organisations who are working on aspects of the metacrisis. Visions only become real when you share them with the world!

I continue to hone my craft and my vision through my membership of the Institute of Directors Ireland, the Charities Institute of Ireland, the Wheel as well as the Association for Coaching and the British Psychological Society. I also hold a number of governance positions in the non-profit sector.

What Is My Unique Voice?

I coach, mentor, and teach leaders to thrive as they build thriving organisations that shape a brighter collective future.

Leadership is tough. It is lonely, daunting, and overwhelming.

I help leaders feel heard, gain clarity, take action, build confidence and thrive.

The first step? Becoming more curious. I see curiosity as the key, allowing us to unlock deep insights that directly enhance our ability to think, act and lead.

This means spending time contemplating what might be possible so that when we take action, we can bring all our energy and power to bear.

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. Humans are very good at solving problems but less so at ascertaining the right problem to solve. Afterall, if you are answering the wrong question, it doesn’t matter how ‘hard’ you work, you are still answering the wrong question.

The focus of my work is thus helping clients to think differently and question more. This starts with how we think about the challenge right in front of us right now (aka decision coaching). The mindset here is that every choice matters; every decision compounds.

This builds into longer-term thinking partnerships (aka mindset coaching or thinking partner) that truly provide the scope to foster curiosity about every aspect of what we do, how we do it and indeed why we do it in the first place. This progressively allows the client to nurture their own self-coaching skills and build a high-performance mindset.

That is why I always emphasize that while some of this may seem fuzzy or theoretical – “Am I right in saying that we will basically talk?” – it is by its nature highly practical. This means that, as we move from call to call, you should feel the benefits and experience immediate impact by thinking differently, behaving differently and doing things differently as a result of what you have experienced.

Let’s Illustrate with an Example!

When I became John’s Thinking Partner, 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. He has also become his own coach, applying a coaching mindset to all aspects of his work:

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

To continued curiosity,

Tom O’Leary

P.S. Curious About Possibly Working Together?

If you are curious then this page may be of interest: Thriving Together!

If not, what are you curious about right now?

David Whyte’s poem Start Close In may inspire!

As I said earlier, I coach, mentor and teach leaders so that they feel heard, gain clarity, take action, build confidence and thrive. Remember, I am just an email away!

In Tom’s Words

Hear from Tommaso

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. Vast amounts of energy, resources and opportunities are wasted pursuing the wrong 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 is not so much about seeking answers to specific questions or accumulating knowledge, but rather about fostering a deep, open-ended awareness and attentiveness to the present moment. It is more about asking better questions and fostering an environment of exploration and innovation.

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

It is also about fostering aspects of leaders’ soft skills as they become increasingly curious about their own actions, decisions, thinking and motivations. It is ultimately about changing how we think and taking broader perspectives. In many ways this approach echoes the basic tenets of Zen, where questions are valued more than answers.

Want to dive deeper?

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 do not 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 do not 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.
  • Removing distractions and interruptions.
  • Prioritising accomplishment over mere action.
  • Becoming more attuned to learning where to look and what to ignore.
  • 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 do not know?

If I can help in some way just email me.