🎯 Facing Tough Choices?

🎯 Struggling to Achieve Key Results?

Finding the Right Answers Means First Ensuring We’re Asking the Right Questions!

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


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Sound Like You?

  • A leader who is so busy that you cannot find time to stop and think.
  • At a crossroads and unsure what path to take.
  • Eager to explore key questions that will shape your future, including the ones you wouldn’t dare ask.
  • Looking to turn ideas into decisive action.
  • Seeking to tap into and deepen your wisdom.
  • In search of a thinking partner with whom you can explore what might be possible.

If you see yourself in any of these, what now? What is the next step?

Decision Coaching: Facing Tough Choices?

I offer a number of free decision coaching 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 more-informed decision.

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

Do not remain stuck. Book a decision coaching call and get clarity on what truly matters!

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 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. It is ultimately about changing how we think and taking broader perspectives.

Want to dive deeper?

Who Am I?

Tom O'Leary: Decision Coaching ¦ Self-Leadership ¦ Leadership Development

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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 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 and a thesis on Play in Coaching, which explored more creative and playful ways of supporting coaching clients.

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 has been focused on expanding horizons by exploring how we may have made our worlds and our thinking too small.

What Can I Offer You?

I work with leaders to:

🎯 Make more insightful decisions

☝Stay focussed on the bigger picture

🌝 Foster self-leadership

⚡️ Become more powerful leaders

And yet, it all starts (and ends) with the decisions we make. In practice, we make decisions all day every day. Some echo for minutes, others for months, whilst a few echo throughout our lives. How do we distinguish and decide accordingly?

That is why I am a big advocate of nurturing curiosity and innovative thinking at all ages. If you are a leader, you will no doubt already know that continually nurturing curiosity in leadership is absolutely key.

In many ways, leadership begins with self-leadership, which is in turn built on a deep sense of curiosity about who you are as a person and as a leader and at its core about how you make decisions.

Such questions open the door to greater possibility and also to discerning what is truly essential right now. That is the heart of my work, which ranges from coaching around particular issues and decisions (aka decision coaching) to a true thinking partnership encompassing all aspects of your mindset, behaviours and habits and even beyond to the environments you inhabit.

Let’s 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. He has also become his own decision coach, applying a decision coaching mindset to all aspects of his work:

  • 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 decision coaching or self-leadership and leadership development, please click here: What Might a Partnership Look Like?

To continued curiosity,

Tom O’Leary

P.S. If you are grappling with a particular challenge or decision, why not claim your free slot 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 fact, who is your thinking partner?

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 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.