Hot 100 career quiz: Lewis Silkin’s Stephen O’Flaherty

What’s your most vivid memory from being a trainee?

When I undertook my commercial seat, I was constantly in fear of being put on the spot by the partner I worked with. The lift stopped outside his office and he always got to work really early, so I used to get out of the lift a floor early and walk the final flight of stairs to avoid detection. He’s a really nice man and someone I’m still in touch with, but commercial litigation wasn’t my strong point.

Who has been the most influential person in your career? Why, and how have they helped you?

My parents first and foremost, but in a professional capacity I’ve been really lucky to have worked with some really inspiring people. They have all been influential in different ways from encouragement to pursue a career in law to trying to emulate how they work.

Prior to becoming a lawyer I worked in business development and my first boss, and now good friend and mentor, Ger Teahon, had so much belief in me he convinced me to go back to university rather than continue working for him. Thankfully my second career is going okay…

Prior to my training contract I worked at Kennedy Cater Legal with Peter Morel, Leo Fattorini, Davinder Virdee and John Halpin. I learned so much about how law firms work and the business side of providing legal services. We also had a lot of fun along the way too.

When I joined Lewis Silkin, Andrew Osborne and Owen Eastwood were joint heads of the sports group and Alex Kelham (currently joint head of sports group) joined shortly after. Their individual approach to their careers and the work they have done as sports lawyers has been the basis for my approach. The team meetings were really interesting and I didn’t say much in the early days, which is rare! 

What is the thing in your professional career that has terrified you or taken you out of your comfort zone the most?

When I started working in the Immigration team at LS,  I shared an office with two associates. I was so impressed by how they engaged with clients, working with clients to really understand what was important and offering firm and sage advice rather than a range of different solutions. I remember thinking about how much the client will invest in recruiting their international talent on the back of this advice, but the team instilled such confidence and trust that they went with it.

Initially, it’s terrifying to take on that responsibility and back yourself to be able to get the result a client wants. When I started to work with Andrew Osborne on football transfers and professional sports recruitment the stakes grew substantially. It definitely took me some time to gain confidence in my abilities and experience to give straight forward simple advice.

What is the wisest thing anyone ever said to you (and who said it)?

My mum (who is always good for a wise word or two) bought me a set of espresso cups when I qualified – it’s always reassuring when your lawyer takes their inspiration from kitchenware! One of them said ‘no one has it all figured out’ which really resonates with me, it’s quite a simple message but also very reassuring.

What advice would you give to someone who wants to get to where you are/do the job you do?

Take your time and follow the path you want to take. However, don’t overthink it and don’t put too much pressure on yourself to get to a final destination too quickly. It’s all a journey anyway and I’m not sure you ever get to a final point, you have to take one day at a time and always consider what’s next. You have to enjoy the journey too.

What’s your best friend from law school doing now?

I met my wife on the PSC at College of Law so although not technically law school, it’s absolutely the right answer here. Orla currently works for Baker McKenzie in Belfast, but right now spends most of her time negotiating with our two-year-old (her toughest opponent yet).