Driving justice for those who need it most

As Global Head of Pro Bono at Herbert Smith Freehills, Brooke Massender brings an extensive experience in social impact, using advocacy for systemic change, and bringing together cross-sector stakeholders to achieve tangible outcomes for disadvantaged communities.

Brooke is an experienced solicitor with particular expertise in access to justice and working with Aboriginal and Torres Strait Islander clients. She provides strategic and legal advice for several non-profits, including as a board member of Justice Connect, the Justice and Equity Centre and the PILnet Pro Bono Leadership Council. Read on for our interview with Brooke!

Describe your career trajectory and how you got to your current position?

I grew up in the North of England and fell into law by accident having applied for 8 different courses at 8 different Universities (careers advice at our local public High School didn’t stretch to tertiary admission intel). I ended up studying Law with European Law in the UK and Germany at a time in the 90s when the European Union was developing at pace. It was a genuinely exciting time in European history. I had no interest in corporate law whatsoever but was drawn to the commercial firms on graduation of necessity (covering College of Law fees and starting salary to tackle student debt). Nonetheless, as the start of my Magic Circle career in London approached I felt increasing queasy. So I did what any self-respecting 22 year old would do and ran away to Australia to backpack around and volunteer at the Sydney 2000 Olympic Games. I managed to swing a paralegal role at what was then Freehill, Hollingdale and Page and the rest, as they say, is history…

I spent close to 10 years learning how to be a disputes lawyer and taking on every pro bono opportunity I could get my hands on, with a particular interest and passion for Aboriginal and Torres Strait Islander rights. A 6 month pro bono secondment to The Shopfront Youth Legal Centre came at a pivotal point and showed me that I needed to make pro bono more of an explicit focus in my career. I took a gamble on a parental leave contract in the Freehills Foundation to try to get close enough to the then Head of Pro Bono (my dear friend and mentor, Annette Bain) to make a convincing pitch for a new pro bono strategy role with responsibility for developing a Reconciliation Action Plan. I’ve been in national, regional and now global pro bono roles ever since. In 2020 I joined the partnership at Herbert Smith Freehills as the firm’s inaugural pro bono partner, hopefully the first of many in our future.

I’ve worked closely with Justice Connect in my various day job roles over the past decade or more and was thrilled to be invited by former Chair, Marcia Neave AO, to join the Board in 2023. It is an incredibly dynamic and impactful organisation both in Australia (and beyond through its pro bono portal technology footprint). I’m looking forward to working with the Board, CEO and senior leadership team to support the next chapter in Justice Connect’s evolution.

Take us through a typical day of work for you.

Ha! I wish. It is a diverse role and you always have to expected the unexpected and be prepared to shift gears in any direction.

That said, there probably are some general trends. I’ve spent the past decade in a global Head of Pro Bono role, supervising very talented colleagues across time zones. So I generally wake up to a series of emails from London based colleagues relating to the UK and EMEA practices. After I’ve addressed anything critical from the UK (and get my teenage son off to school fed and watered) I typically head into the office to connect with Sydney based team members and our Australian clients. Asia comes online later in the day and so I generally catch up with those team members and projects in the late afternoon before the UK come online in the early evening. It is fairly relentless and very much a team effort.  I’m really incredibly proud of the talented and committed global pro bono practitioners in the global team and how well they collaborate as a team supporting our clients across regions.

I also make a very conscious effort to spend as much time as possible with NGO CEOs and Principal Solicitors of community legal centres to listen and problem solve together. Sometimes they are looking for support with strategy development, having people challenges or simply exploring their own unique style of leadership. Sometimes they value a sounding board from someone independent and non-judgmental who is not an immediate stakeholder in the day to day decisions they need to make. Talent development of purpose driven leaders, and particularly supporting diverse talent, is very satisfying and possibly my favourite aspect of the role.

We’ve recently made a strategic decision to align our Australia and Asia practices into more of an APAC and we’re already enjoying taking on some meaty cross regional matters as a combined team. I don’t often get my hands on the drafting pen these days, but when I do I still really enjoy being on the tools.

What is the biggest challenge you’ve encountered in your career, and how did you overcome it?

I haven’t always managed myself as well as I need to. There are so many rewarding aspects to having a purpose driven role that you are deeply passionate about. It is very easy to fall into the trap of being “always on” and taking the approach that nothing is too much trouble. Whilst that is my natural inclination it is simply not sustainable over the long term. I’ve learned the hard way that I need to put my own oxygen mask on first.

I now have to be pretty disciplined about looking after myself and encouraging my colleagues to do the same by role modelling sustainable practices. Compassion fatigue and burn out are ever present risks in purpose driven pro bono careers. I try to schedule relatively regular meditation, yoga or pilates classes and make a better effort to switch off properly during leave periods.

If you could go back in time, what piece of advice would you give yourself as you first embarked on your career?

Trust your gut and follow your instincts.

We’re so tuned in to our rational head brains that sometimes we forget to pay attention to our heart and gut brains as well. Whenever my head and heart are at an impasse I can usually trust my gut instincts. That may sound a bit “woo woo”, but when I think of the major life decisions I’ve made that have served me well, gut feel has always pointed me in the right direction. Studying in Germany at 19, moving to Australia at 22, staying in Sydney to qualify at Freehills rather than returning to a Magic Circle firm in London, prioritising pro bono and community participation and moving full time into a pro bono career at 32. These are not text book “head brain” career decisions. I couldn’t necessarily see it at the time, but it is pretty clear with hindsight that on each of those occasions I was following my gut to step out of the norm and take a path less travelled.

How do you unwind after work?

Our son usually has a TV show that he is bursting to show me. He collects DVDs from Vinnies (and I progressively sneak them back to Vinnies again). Last school holiday we did a journey through British comedy from Monty Python and Fawlty Towers to the absurdism of Vic Reeves and The Mighty Boosh. It was fun to re live some of the old favourites I used to watch with my (late) Dad and see them through the wonder of 13 year old eyes. It also prompted some great conversations on how much societal expectations have shifted and how some of the so-called  ‘classics’ have not stood the test of time in terms of what is and isn’t fair game in comedy.

I’m also a Sydney Swans tragic and get to as many games as possible, I made it to my first ever AFL grand final in 2024…and I’m still recovering. I also take the occasional surf lesson which is always an exercise in focus and humility as I am very very bad at it. I’d hate to calculate the wave to wipeout ratio.