We all fail. We all lose focus. We all make poor choices. We all let our standards drop at times. That is part of the journey. The key thing is what you do next – the next choice you make. The next question you ask!

I coach, mentor and teach leaders so that they feel heard, gain clarity, take action and build confidence.

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


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Why Are You Here?

  • I often feel isolated as a leader.

    Having a trusted sounding board is crucial.

  • Being stuck with no clear way forward is frustrating. I am looking for fresh perspectives to overcome challenges.
  • I often feel overwhelmed. I need support in focusing and prioritising what truly matters.
  • Assessing progress and planning next steps can be overwhelming. An outside perspective could be invaluable.
  • Challenging my own ideas is tough. I need a partner who is not afraid to push back and explore blind spots.
  • Personal and professional growth is a priority for me. I aim to connect more with others, inspire my team and thrive across every aspect of my life.
  • I love continually refining how I am and what I do. I need someone to keep nudging me to go beyond my current limits.
  • It is time for bigger conversations about my organisation’s capacity to grow and sustain itself over time.

Identify with any of these? WHAT NOW?

Regardless of which statement (if any) resonates most, my sense is that the key to evolving our thinking towards a high-performance mindset is continually nurturing our curiosity.

My invitation is thus to 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. Your future self will thank you!

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 ton of major problems of late.

Who is Tom O’Leary?

💡I believe curiosity drives high performance 🔍My passion is helping clients find deeper questions that unlock next level thinking 🤝My clients feel heard, gain clarity, take action & build confidence

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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 work with leaders and boards of global organisations who are shaping a brighter future within a decade. Visions only become real when you share them with the world!

What Is My Unique Voice?

I coach, mentor and teach leaders who are shaping a brighter future.

Leadership can be lonely and the challenges daunting. I help leaders feel heard, gain clarity, take action and build confidence.

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. If you are answering the wrong question, it doesn’t matter how ‘hard’ you work, you are still answering the wrong question.

My work thus ranges from writing and mentoring to deep coaching around particular issues and decisions (aka decision coaching). I am, however, increasingly gravitating towards longer-term thinking partnerships (aka mindset coaching or thinking partner) that, in addition to providing ongoing decision-making support, provide the scope to foster critical thinking skills and mindset so that the client ultimately becomes their own mindset coach.

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 learnt.

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?

Curious About Possibly Working Together?

If you would like to explore how you or your organisation might benefit from working together, this might help: Working Together: What Do You Think?

To continued curiosity,

Tom O’Leary

P.S. Decision Coaching Immersive

If you are grappling with a particular challenge or decision, I offer a number of decision coaching immersives every month for new clients who are grappling with a particular issue or set of issues and want to think it through.

Our conversations (initial call plus follow-up call) will allow you to unlock insights as to what is truly important and move you towards a more insightful decision.

P.P.S. Want to Chat but Not Ready to Sign up for Decision Coaching?

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. Make my decision an easy one by telling me a powerful story!

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.