My sense is that we need to ask deeper questions:
– What is the role of humanity within the web of life?
– How might we build human societies that live symbiotically?
– What duty do we have to future generations of all species?
– What if, instead of rushing to solve problems, we learnt to ask better questions?

A Call for More Curiosity!
My name is Tom O’Leary and curiosity has defined my life to the point that my strength is not that I am a specialist in any one area but rather that I am an ardent generalist.
My formal studies – which cover law, IT, applied psychology – only represent a small fraction of my interests. If my varied studies have taught me anything it is how siloed information and thinking can become. The age of the polymath certainly seems to be fading and yet the magic lies in connecting seemingly random ideas.
I have seen the limitations of our formal education system up close through my involvement in a self-directed democratic school. Seeing the children and the facilitators follow their collective curiosity without regard for traditional “subjects” was continually inspiring.
One wonders, what might our societies be like if more children and adults were exposed to such environments?
This siloing means that we see parts more than wholes. Tightly defined problems with specific solutions are preferred to real-world messiness. Whatever happens outside the problem statement is essentially irrelevant. This hides no end of issues, not least of which the negative costs of our choices.
If I can make any small contribution, it is hopefully to encourage us all and particularly those in leadership positions to think more broadly and incorporate these three questions into every aspect of our daily work:
- How can my organisation shape a brighter future for all life?
- How can the organisation’s stakeholders thrive?
- How can I thrive?
My sense is that it is only by focusing on these three levels – and expanding well beyond these opening questions – that we will build organisations that shape a brighter future for current and future generations of all species.
Please 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 am not claiming to have any answers. Instead, I offer questions, which open the door to infinite possibility.
To continued curiosity,
Tom O’Leary
Why Is Curiosity Key to Empowering Leaders?
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.
