About Tom O'Leary - Empowering Leaders to Be Curious

Tom empowers leaders to be curious, and thereby make more insightful decisions, foster their self-leadership and become stronger leaders! He invites 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. Know anyone who might benefit from exploring and embracing bigger questions in life, work or business? Nurturing Curiosity. Curiosity-inspired Leadership. Self-Leadership.
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25 09, 2023

How Can I Be More Productive?

2023-09-25T14:32:48+01:00

It is important to step back and ask: Why do I want to become more productive?What exactly do I want to accomplish? Always remember that there is a risk that we may become productive at tasks that truly don’t matter. Productivity therefore doesn’t exist in a vacuum. Before you consider becoming [...]

How Can I Be More Productive?2023-09-25T14:32:48+01:00
18 09, 2023

I Am Not Curious About Anything. How Can I Become More Curious?

2023-09-18T06:58:53+01:00

I was recently asked this question and here is my answer: I would suggest that you are already more curious than you think. Otherwise, why ask this question? And becoming curious about how, where and when you are or aren't curious is a great place to start. Ask yourself: What [...]

I Am Not Curious About Anything. How Can I Become More Curious?2023-09-18T06:58:53+01:00
14 09, 2023

I Have Wasted Too Much Time. What Do I Do?

2023-09-14T15:09:43+01:00

I was asked this question recently and here is my answer: If you feel you have wasted too much time, then you have wasted too much time. It is your choice. On the other hand, you could think: “How wonderful! Every minute I have spent on this planet has made me [...]

I Have Wasted Too Much Time. What Do I Do?2023-09-14T15:09:43+01:00
4 09, 2023

What in Your Opinion Is the Pursuit of Happiness?

2023-09-04T15:56:29+01:00

I was recently asked this question and here is my answer: Interesting question. My sense is that the “pursuit of happiness” (as we currently understand that word) is an illusion. A pursuit implies that we don’t yet have whatever it is we are chasing. This striving for something we don’t have [...]

What in Your Opinion Is the Pursuit of Happiness?2023-09-04T15:56:29+01:00

Boost Your Curiosity!

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What Might be Possible If We Believed It Were Possible?

Questions have a strange power. They can release us from what we believe to be true by offering us glimpses of something different. Indeed, there are times in that brief moment after a question is asked when it feels like anything is possible.

Questions have certainly given me the freedom and permission to pursue my passions and live a life I would never have thought possible. That is why I am a big advocate of Nurturing Curiosity at all ages.

If you are a leader, you will no doubt already know that continually nurturing curiosity in leadership is absolutely key. Indeed, that is why I started the Bigger Questions Project around one key question: How might we empower more people to explore and embrace bigger questions? Learn more about the Bigger Questions Project.

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?

What Might be Possible If We Believed It Were Possible?

Questions have a strange power. They can release us from what we believe to be true by offering us glimpses of something different. Indeed, there are times in that brief moment after a question is asked when it feels like anything is possible.

Questions have certainly given me the freedom and permission to pursue my passions and live a life I would never have thought possible. That is why I am a big advocate of Nurturing Curiosity 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.

Indeed, that is why we started the Bigger Questions Project around one key question: How might we empower more people to explore and embrace bigger questions? Learn more about the Bigger Questions Project.

Tom’s innate ability to listen and empathise enabled me to relax and really explore the issues that were causing me some anxiety. Our sessions provided me with an enhanced sense of self-awareness and a considered plan of action. The benefits in terms of relationships and self-confidence this process has given me are invaluable, in both work and life in general!
Testimonial from Sean
I went for coaching with Tom, without knowing what I wanted but knowing that I needed some help after having a number of setbacks with interviews. By the end of the first session, I was beginning to realise my problems. By the end of the second session, I was beginning to realise what I wanted. In our final two sessions, Tom helped me to identify a strategy for achieving my goals.

I thoroughly enjoyed our sessions. Tom listened without judgement, guided without being opinionated and ultimately helped me to help myself. You can’t ask more from a coach.

Testimonial from Paul

I didn’t think I had a specific need for a coach, however, having met Tom outside of our professional roles we decided to set up a coaching programme. I’m delighted we did. Tom’s approach is based on taking it slow, listening first and asking questions you won’t have thought of second. The latter always result in positive actions to take away and implement immediately. Now, I’m really looking forward to continuing our working relationship.

Testimonial from James Crothall, Account Director at AMO DIGITAL

I’ve been catching up with Tom for now, over three years. It is a moment where I’m able to create space away from the noise and the busyness of my life to really tackle whatever is top of my mind. This can be on the professional side and can be on my personal side. My conversations with Tom are really conversations we have dialogues that we have, and a walk away from these meetings with clarity around ideas of how to convey pragmatically and practically tackle some of the challenges and the issues which I wanted to discuss with Tom. But I think more importantly, with a greater degree of confidence in my ability to solve for these topics. I’ve been really enjoying my catch up with Tom I hope to continue to do so in the future and I highly recommend anybody to give it a go.

Testimonial from Tommaso
Tom’s innate ability to listen and empathise enabled me to relax and really explore the issues that were causing me some anxiety. Our sessions provided me with an enhanced sense of self-awareness and a considered plan of action. The benefits in terms of relationships and self-confidence this process has given me are invaluable, in both work and life in general!
Testimonial from Sean, Ireland
I went for coaching with Tom, without knowing what I wanted but knowing that I needed some help after having a number of setbacks with interviews. By the end of the first session, I was beginning to realise my problems. By the end of the second session, I was beginning to realise what I wanted. In our final two sessions, Tom helped me to identify a strategy for achieving my goals.

I thoroughly enjoyed our sessions. Tom listened without judgement, guided without being opinionated and ultimately helped me to help myself. You can’t ask more from a coach.

Testimonial from Paul, Ireland

I didn’t think I had a specific need for a coach, however, having met Tom outside of our professional roles we decided to set up a coaching programme. I’m delighted we did. Tom’s approach is based on taking it slow, listening first and asking questions you won’t have thought of second. The latter always result in positive actions to take away and implement immediately. Now, I’m really looking forward to continuing our working relationship.

Testimonial from James Crothall, Account Director at AMO DIGITAL

Calilogia Ltd., t/a Bigger Questions Collective, is registered in Ireland. Registered office: Woodfield, Inchicullane, Killarney, Co. Kerry, Ireland. Company No. 531734. Privacy Policy

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