This is Allens

Phil O'Sullivan

Phil is a partner specialising in technology, media and telecommunications, with experience working on major procurement, data and business transformation projects for both commercial and government clients.


I spent the first part of my career working in the healthcare sector, as executive officer for the Australian Medical Council (AMC). While I was there we had a few interesting cases for which I acted as a conduit between the law firm and the AMC executive. It really clicked for me then that I wanted to sit on that side of the fence, helping clients through difficult processes as an external adviser.

There are some obvious similarities between doctors and lawyers – commitment to excellence and perfectionism stand out – but in some ways doctors as a group are more predictable than lawyers. I found particular medical specialties tended to attract similar personality types. Pathologists are quite different to surgeons, paediatricians are the nicest people on earth and it is hard to make an anaesthetist laugh. I haven't found that's the case with lawyers – practice area doesn't help you predict what you're up against.

What I loved about the medical world was the direct connection to real-world outcomes. I was worried about losing that when I came into commercial law because it's broader, but I've been able to steer my career towards fields where I can see real-world impact, including in defence and aerospace as well as healthcare. My clients have deep experience in high-growth, heavily regulated sectors, and I love learning about the detail of their work as we navigate critical issues together.

If there's one thing I don't miss about working in the healthcare sector, it's being the butt of lawyer jokes from a roomful of doctors. It's nice to feel like you've found your tribe rather than being the black sheep in the room, although I still enjoy a well-aimed lawyer joke.

A day in my life

My current remote working routine looks a little different to the usual routine outlined below, but I'm looking forward to injecting back in some elements of my old routine as restrictions ease. 

0630 Alarm goes, and I ease into the day. Intensive morning exercise is generally out of the question.

0700 Quick brekky at home with the kids, and a babycino at the local café before day-care drop off.

0730 I'm a rare type – a Sydney resident that enjoys the daily commute. I get the ferry into the city from Neutral Bay, which is a truly beautiful way to start the day. I generally keep my phone and papers in my bag and enjoy the sights on the way in.

0900 Regular catch up with Bianca, my practice assistant. I use my inbox as a task list so the day will start with us scanning the latest and working out what will be done, in what order for the day ahead.

0915-1230 Mix of scheduled calls, document work and conversations with colleagues. We are a collaborative team, so I rarely am working alone on any task or matter. I'll make sure there's a junior lawyer on each key client call or negotiation – it is the best way to develop talent and it always leads to valuable questions/discussions after those calls or meetings.

1230 It borders on a miracle if I make it this late in the day to eat lunch. Thoughts of food start presenting around 11 and I try to hold them off. On a good day, I'll eat early and then set out for a lunchtime run on a five to 10 kilometre loop and often with Ian McGill who maintains a very consistent pace (other than a regular pause at the Opera House to check for his favourite seal). If I don’t get a run in at lunch, I'll try to jog home at the end of the day.

AFTERNOON I like to schedule junior feedback, mentoring and similar tasks for the afternoon, when you can clearly focus on each session and some of the morning rush and priority allocation has subsided. Other than that, it is work as usual. On Fridays it's cake corner with the TMT team which is a real highlight (especially when it is my turn to bake and cheese scones are produced to (mostly) glowing reviews).

1630 Flexibility is a real feature of work at Allens. This means I am generally able to schedule my day around a 530 or so departure, so I can get home, do bath time with the kids and read them a book before bed. Remarkably, given the current levels of construction around us, the clear favourite for bedtime reading is 'Diggers'. I've found the best way to manage this is to take stock at around 430 and divide the remaining tasks into those that can be completed before my target departure, and those I can complete working from home later in the evening when the kids are in bed. Some days it doesn’t happen, but having a quick assessment in the afternoon and reallocation of tasks usually means I make it home.

1730-1930 On a good day, time with the kids. Frantic, but bliss. 

2000-sometime It will either be working from home on the remaining tasks for the day, or if nothing is required that evening then a meal with my wife and inevitably the streaming of something. Better Call Saul and Billions get a good run on Stan, Succession is great on Foxtel and pretty much every stand-up comedy special will be viewed on Netflix. Then sleep, at any old hour. 

10 quick questions

  1. What was your childhood career dream? To be a pilot. I've made it in to a flight simulator.
  2. Who would play you in a movie? Hugh Jackman.
  3. Name a book/film that changed the way you see the world The Rainmaker by John Grisham – that set me on the path to law. More for the against-the-odds victory than the insurance law aspects!
  4. What’s your go-to office lunch? Last night's dinner, and if I've forgotten that then a peanut butter sandwich.
  5. What three things could you never live without? Coffee, holidays, wife + kids (in no particular order).
  6. If you could switch lives with someone for a day, who would it be? Ricky Ponting, to feel that level of talent pulsing through my body.
  7. What’s the best career advice you’ve ever received? Build a team, bring them with you and train them to be better than you.
  8. When do you feel happiest? On the bike leg of a triathlon, having survived the swim.
  9. What’s the last show you binge-watched? Schitt's Creek.
  10. What was your first job? Front desk and maintenance at Canberra's finest Go-Kart Track.