Bossing It: Pippa O’Regan on Navigating the Leadership Merry-Go-Round
DDB’s mantra is ‘Unexpected Works’, and that’s proven to be true for DDB Melbourne’s managing partner Pippa O’Regan. Leadership was never something she consciously pursued or expected in her career path – instead it was thrust upon her when her boss suddenly quit, leaving her in charge of a small agency.
Originally from the UK, Pippa moved to Australia in the early 2000s, honing her skills at agencies like BMF and Clemenger BBDO. Pippa moved to DDB in April 2021 – meaning her leadership really came to the fore as she helped support the team as they navigated the pandemic and its many challenges. For Pippa, honesty and empathy are cornerstones of leadership – here she talks about the joy of mentoring people on their own journeys toward leadership, the importance of tackling unconscious bias and DDB Group Melbourne’s accelerating momentum.
LBB> What was your first experience of leadership?
Pippa> My first experience of leadership wasn’t part of my career plan. It happened unexpectedly and I was completely unprepared. I was working for a small agency and had taken some annual leave. While I was away, my boss called me and pretty much said, ‘I’ve resigned, so you’re in charge now!’ When I got back to Australia, I took the reins of running the agency day to day and managing the team.
LBB> How did you figure out what kind of leader you wanted to be – or what kind of leader you didn’t want to be?
Pippa> Trial and error is probably the best way to explain it. I’ve been lucky enough to have worked for several great leaders who have inspired me over the years, but it’s been a journey for me. I’ve made (and still make) mistakes along the way, which continue to shape me as a leader.
LBB> Did you know you always wanted to take on a leadership role? If so, how did you work towards it and if not, when did you start realising that you had it in you?
Pippa> I’m definitely an ‘accidental leader’ – I never really had a leadership role in my career plan when I was younger. My approach was to keep my head down, work hard, and gain experience. It was only when I moved to Australia from the UK, and through the support of some incredible clients and colleagues, that I started to recognise my potential.
LBB> When it comes to 'leadership' as a skill, how much do you think is a natural part of personality, how much can be taught and learned?
Pippa> I do believe some are born leaders and others discover their path to leadership through education and experience. I was thrown in the deep end, so it was sink or swim, but I had the desire to learn to be a better leader. I looked to those around me to learn from, both good and bad. Today, we have access to so many leadership development tools that I wish I could have tapped into earlier in my career.
LBB> Have you ever felt like you've failed whilst in charge? How did you address the issue and what did you learn from it?
Pippa> I’m not a big fan of the word “failed”, I prefer the term “letting the team down”. There are many occasions where I feel I have “let the team down” and this is all part of the leadership merry-go-round. My biggest leadership learning is that no matter how hard you try, you will never make everyone happy. I tend to lean into the issue by owning it, learning from it, and moving forward.
LBB> In terms of leadership and openness, what’s your approach there? Do you think it’s important to be transparent as possible in the service of being authentic? Or is there a value in being careful and considered?
Pippa> 100% I believe that openness and honesty is such an important approach, along with bringing yourself to the role. As a leader, I do believe you need to give part of yourself to the team to build a strong connection and demonstrate empathy.
Don’t get me wrong, my team doesn’t need to know everything about my personal life. But I do think that knowing about me as a person and what motivates me outside of work helps build respect and a stronger relationship, and ultimately delivers better outcomes.
LBB> As you developed your leadership skills did you have a mentor, if so who were/are they and what have you learned? And on the flip side, do you mentor any aspiring leaders and how do you approach that relationship?
Pippa> I’ve not had a mentor as such, but over the years there have been a few people who have guided me in my career.
One in particular was my client for five years and my boss for two years. John made everyone feel important, he took time to listen, and people wanted to work for him. He knew how to get the best out of his team to deliver results.
I’ve mentored a few aspiring leaders in the past. I approach these mentoring relationships differently and take my lead from the mentee rather than trying to lead them. It’s been really rewarding seeing them go on to achieve success, and knowing you played a small role in their journey.
LBB> It's been a really challenging couple of years - and that's an understatement. How did you cope with the responsibility of leading a team through such difficult waters?
Pippa> It’s fair to say the past two years have been the most challenging of my career and tested every aspect of my leadership.
It’s been even more important to be yourself and be authentic as a leader, as your team looks to you for support beyond just the work.
I joined DDB Melbourne in April 2021, and fortunately had a few weeks of freedom in the office, getting to know the team and working face to face with them before we went back into lockdown (and Melbourne became the most locked down city in the world!).
Showing up with a positive outlook day after day in lockdown, and keeping the team motivated and supported, was personally hard and I often found myself sharing my vulnerable side, which I believe helped my new team relate to me.
LBB> This year has seen the industry confronted with its lack of action/progress on diversity and inclusion. As a leader how have you dealt with this?
Pippa> I’ve been taking a good look at my own unconscious bias, in order to take responsibility for how I’m personally contributing to the lack of progress. We all need to be part of the solution, and we all need to do a much better job at promoting the industry as an inclusive and fulfilling career choice.
LBB> How important is your company culture to the success of your business? And how have you managed to keep it alive with staff working remotely in 2021?
Pippa> DDB Group Melbourne has been really focused on building momentum over the past year – growing our client base and head count. That growth inevitably shapes our culture, and we couldn’t take our foot off the accelerator during lockdown. Now that we can head back to the office, I’m really excited to see how our culture keeps evolving to fuel us through the next phase of growth.
