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

If you are looking for a traditional blow-by-blow account of what I have studied or where I have worked, my LinkedIn profile may be of some assistance. As regards my volunteering, my BoardMatch profile (login required) may provide some additional answers.

However, my view, echoing the words of the Irish poet John O’Donohue, is that there is always a risk that identity will be reduced to biography. This can become a soulless recounting of milestones without any sense for who we have become along the way and that surely is key.

So who have I become?

  • A loving dad to 2 teenagers.
  • A loving husband to a wonderful and inspiring woman.
  • A friend to some extraordinary souls.
  • A concerned ancestor to future generations.
  • A professional who coaches, mentors and teaches leaders who are shaping a brighter future. My art form is contemplation. My preferred tools are boundless curiosity, unorthodox thinking, soulful listening, deep conversation and empathy.

Someone who loves:

  • Deep slow conversations and connections and who sees more to unite us than divide us.
  • Seeping himself in the wisdom of others through books, audiobooks and podcasts.
  • Ag machnamh ar an saol (Irish for contemplating and reflecting on life).
  • Seeing others become curious.
  • Being outdoors and active (running, hiking, rowing).
  • Play and comedy.
  • Music of all kinds. Here is my 2023 Spotify list.

In truth, my story is one of joy and sadness, of ups and downs and successes and failures. They have all contributed to making me who I am – warts and all!

The sections that follow offer a form of alternative CV told through a series of themes close to my heart.


As far back as I can remember, I have been insatiably curious about how things work and about the world. As a young child, I got into ‘trouble’ for taking things apart and, once I discovered the joy of reading, books were my constant companion. In those early days it was more about facts. The old encyclopedias were a particular favourite and I read them cover to cover. I’m not sure I got through the entire alphabet, but I do recall making a fair impression on it.

This ongoing curiosity meant that I was never going to be contented with just a single domain and have ultimately studied in a diverse range of fields from law to IT and coaching. However, I found increasingly that the fun was not only to be found in acquiring new information or indeed new ways of seeing the world but in using this new knowledge to question myself and the world around me and to generate fresh thinking. It is, as Frans Johansson argued in The Medici Effect, at the intersection of ideas that we find the truly exciting breakthroughs.

Nevertheless, I found the world wasn’t always particularly interested in being questioned. Questions can trigger fear as the illusion of certainty cracks. Certain cultures and groups also struggle more with questioning. Indeed, obedience to the party line is standard in most organisations, meaning it can be difficult for leaders to think in unorthodox ways.

And yet, if we are to build more sustainable societies and businesses and live the lifes we want to live we have little choice but to question the status quo. One thing is certain, it won’t question itself!

Tom’s Journey of Curiosity

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Conversations Can Change Your Life

Conversations were the currency of my childhood so always present, but I truly learnt this lesson when I was at university. There was an exchange programme that allowed us to spend our 3rd year in another university somewhere around Europe. This meant the degree would take 4 years rather than 3 and our classmates who didn’t go on the programme would have finished up by the time we got back. There was therefore some grieving around the fact that we would no longer get to study together.

Anyone interested had to apply by the middle of the 2nd year. One day a couple of months after the deadline for applications, I was at home studying when a friend called over and basically said “Dude, we have to study together in our final year.” When I regretfully countered that I would love to go but that it was a little late now, he just said “Go to the professor running the programme and tell him that you would truly love to go and see what happens.” After that conversation, it truly felt like I had fresh options – which in truth I did and I didn’t. I did, because the conversation with the professor was now an option, and yet I didn’t, because the deadline had closed months previously.

Seeing as I am telling you this story, you have no doubt guessed that I did go to the professor, bared my soul and ultimately got a place. A number of those who had applied dropped out and I got offered the last spot. As a result, I spent an amazing year at college in Switzerland, met my future wife and the whole trajectory of my life was changed.

All of this from one conversation that gave me the impression that I had different options. That is the power of continually reassessing possibilities — one moment of insight, one conversation, one chance meeting can open doors you never even realised were there.

My Story of Time

I have been fascinated with the concept of time my whole adult life. It started right out of college when I took a job as a Project Manager. Managing large teams for multinational clients across a host of time zones meant being in early and leaving late. Weekdays were intense. In that role, I scheduled every minute of every working day. I was so exhausted by Friday that the weekend was basically to recover for the next week.

Then I got promoted and took on more responsibility and other people’s pressures. Weekends got that bit shorter. I invested significant time in becoming Mr. Productivity but it still wasn’t enough. To-do lists got longer and never-ending. I lived under the impression that time had to be used at full speed, always. I really didn’t have anyone to call on to chat through what might be right for me and ultimately elected to speed up.

That was when an idea for a start-up with some friends came along. With the time to market monkey on our backs there was rarely any downtime. Weeks now had seven workdays. We became less creative, more stuck in our ideas and ultimately less productive. It also took a toll personally, but the treadmill kept moving so I kept running.

Until one day I realised that I had control over the speed of the treadmill. That was a good day! In fact, my wife and I embraced every cliché possible and went to live on a beach and raise our kids in an environment where we could spend meaningful time with them. That didn’t mean life didn’t have its deadlines or time pressures. In fact, in the meantime, I have founded and managed a number of businesses with my wife, but we always kept the lens of “why are we doing this” close by and a keen sense of how to use time to create as many moments as possible each and every day. It is an ongoing journey of judging when it makes sense to slow down and when to benefit from speeding up.

Befriending Change

Change has been my constant companion since an early age. Like another member of the family. Living in 5 countries, studying in widely different fields (Law, IT and coaching) and working both within large organisations and for my own company across different industries, change has always been in my backpack. Most of this was by choice. Rather than be a prisoner to a set path through life I have continually sought freedom and reimagined the rules as the need arose.

I have also had unwanted change thrust upon me. There were times it wasn’t easy, like losing my dad at a tender age, and I have been lucky to have some great people help me bridge the gaps. It has also helped that I am pretty committed to play and to board games in particular. This extends from Chess to Catan and Risk and plenty in between. You may wonder, what relevance does play have for change? Play is a gateway to a separate universe where different rules apply – a threshold between the current reality and future possibility. Children are particularly good at tweaking these rules to make the play more interesting. Adults a little less so. And yet we all live by rules.

My Coaching Story

I first encountered coaching as a young manager in the late 90s in a global localisation firm when I led a team of project managers, most of whom were older and had more project management experience than I did. It quickly became apparent that a top-down management approach wouldn’t work and that they were in essence the experts. My job was thus to unlock their potential. It amazed me how when they came to me with issues that they also brought the answers but just needed me to help unearth them (their inner wisdom so to speak). This sowed the seed for a life-long fascination with coaching. What I lacked, however, was a really good coach to turn this fascination into a clear plan. Indeed, it was almost two decades before I finally resolved to bring the power of coaching to others, in the meantime continuing to run my own business, managing projects, people and translations.

My journey formally started when I was sent on a Leadership Programme relating to my volunteering work. This developed my inner coach and gave me the impetus to take my journey to the next level and sign up first for a Certificate in Coaching and then to UCC’s 2-year Personal and Management Coaching Masters. This has added a strong understanding of coaching approaches and psychology. It has also allowed me to embark on journeys with clients that have been both humbling and satisfying. More recently, I completed Dr. David Drake’s Integrative Development Practitioner program at the Moment Institute. Dr. Drake is a proponent of serious play that allows clients to have new experiences rather than collect more explanations. Seeing the power of this approach first hand and how people can get a better sense of themselves and their next steps in life and business never ceases to excite.

Being a Maverick

For me, a maverick is someone who is able to demonstrate independent thinking and creativity, rather than simply conforming to the expectations of others. Indeed, as someone who has never bought into status and power dynamics, I am happy to shine a light and ask the “silly” questions.

Anyone who knows me will know that I have always taken a slightly different path. At first, such paths were chosen by my parents in deciding to send me to schools where I knew nobody rather than just pick the local school like everyone else. Once I reached adulthood, the ability to pick whichever path felt the most appropriate regardless of the company meant that I continually chose challenging environments in which I had to prove myself time and again, rather than relying on some reflected credibility (for example parental status in society).

This also applies throughout my life in what I read, how I dress and how I choose to live more broadly. None of this is done from the position of rebel, to somehow be different, but rather from embodying the ideas at the heart of the Art of Opportunity in creating a vision for how I want to live my life. I am now in the third decade of a 40-year plus vision for a balanced lifestyle that allows me to continually nourish all parts of my being and contribute to the world around me.

I also bring my outsider perspective to my work and volunteering in service of the individuals and organisations I work with. It means that when I curate or join a community it is because I truly choose to be part of it rather than coming from a place of need.

My Life in Food

I never intended to become vegetarian or plant-based. Both just happened. It all started when I was 21. I had spent the summer travelling around Central & Eastern Europe with my future wife. We were poor students so we decided to save money by not buying meat or fish, both of which were so much more expensive than the fruit and vegetables we could source in local markets. The priority was having enough money to stay together to end-August, so we were happy to make the sacrifice.

My return journey by bus from southern-Poland to Cork, in Ireland, took over 2 days and when I got off the bus early that morning my wonderful aunt Chrissie was waiting for me. It was actually my uncle’s 50th that day so that was why I had wanted to be back on the island. Sensing that I hadn’t eaten properly during the trip, Chrissie took me for a full Irish breakfast. I was so excited as I tucked into my sausages and rashers and yet by the time I had finished the meal I felt really poorly. I knew then and there that meat wasn’t for me but I was happy to keep eating fish, eggs and dairy products.

Over the subsequent years, I went through periods when I also gave up fish, but it was really only around 5 years ago that I decided to make that permanent. Once I was there, it was really an easy step to experiment with going fully plant-based, initially for a couple of days a week. In fact, the step to a wholly plant-based diet only happened when my wife started complaining of serious knee issues. A possible operation was on the cards. I had read of the impact of dietary inflammation and suggested we try going fully plant-based for 2 weeks. I had read that she should see results by then and if she didn’t nothing was lost. It went even quicker than that and both she and I were so impressed with the results that we have been primarily plant-based as a family ever since.

Full disclosure: I will make an occasional exception and eat some egg and dairy if I’m out for dinner or on holidays, but it is exceptional. I therefore hesitate when using the term vegan as it can be so loaded.

Minimalism in My Life

My first encounter with minimalism was over 25 years ago, long before I had even heard the word itself. My girlfriend and I were students in Switzerland, and we decided to go camping around Eastern Europe for a couple of months. After a full year of living and studying, our bags were full to the point that we could hardly lift them. Within days of lugging them around we started asking ourselves the question: How much of this stuff do we really need? Our bags got lighter week by week as we spent less energy lugging stuff around and more energy on the experience.

I’m not going to claim that I’ve been on a minimalist journey since then – far from it. There were periods in the following years when we accumulated lots of stuff, something that didn’t fit well with our semi-nomadic lifestyle. So, the question kept coming back: How much of this stuff do we really need?

What really hit me as I began to spend more time reflecting on minimalism was the amount of energy that was tied up in all this stuff. There was not only the time spent working to pay for it but all the time managing it (moving it, cleaning it, fixing it….). The more I let go, the more obvious it became that I had much more mental baggage than physical baggage so with the support of some great people around me I started working through that too. That’s when the sense of lightness became more embodied. Not only was my knapsack lighter but so too were my mind and body.

I’ve found it is a process that is solely about the next step. When my mother died a few years ago, I was only ready to move things to the attic for a number of years. Then gradually, as the grief resolved itself, I could start letting go. In fact, I’ve worked with clients who couldn’t go into their sitting rooms because they were so full of clutter. Even setting a goal of filling one rubbish bag was a step too far. The first step was simply unlocking and opening the door and sitting in the doorway. It is all about what you are ready to do next!


Because of the time I spent living in France, Belgium and Catalonia, I have lived and worked in French and Catalan. I also have very good passive understanding of Spanish along with lower levels of German and Irish from my school days. I even studied Latin and Russian back in the day but knowledge of both has faded over the years.


I’ve been subject to a range of psychometric tests over the years. Whilst I don’t completely buy in to the idea that a person can be reduced to a test result, they do at least provide a snapshot of how we see ourselves or perhaps how we want others to see us at a particular point in our lives.

For Kolbe fans, my Kolbe A Result is 8-5-5-3.

Kolbe A Results