5 Questions with Cathy O'Connor

After a career built over decades, Cathy O’Connor announced she will be departing as the CEO of oOh!media towards the end of the year or the beginning 2026, after nearly five years. She spent 17 years at Nova Entertainment including 12 as CEO, and before that held several management roles at Austereo. She sits on a number of boards, including as Chair of the Sony Foundation, and has been inducted into the Commercial Radio Hall of Fame and won the Telstra NSW Business Women’s Award and Centenary Medal for Service to Australian Society in Business Leadership.

Q1. What was your first leadership role, and what did you learn from it?

I stepped into leadership earlier than expected, managing a team with more experience than I had. That fast-tracked some big lessons: that good leadership isn’t about having all the answers, it’s about setting clarity, listening closely, and making space for others to do their best work.

Q2. What has been your best career move?

Taking on the Nova role was a defining moment. I didn’t feel 100% ready, but I saw the opportunity to help build something from the ground up. Growing a challenger brand meant thinking creatively, taking smart risks, and putting trust in people, and it set the foundation for smoothfm’s success later on. That experience gave me the confidence to lead at a broader level and showed me how powerful a strong, lived culture can be. Jumping into the Out of Home sector with oOh! (outdoor and public advertising) was another pivotal choice. It pushed me into unfamiliar territory and reminded me that reinvention isn’t just for businesses, it’s something leaders need to embrace too.

Q3. Given your time over, what would you do differently?

If I had my time again, I’d probably stop waiting to feel “ready” and lean into big opportunities earlier. Like a lot of women, I had a habit of wanting to tick every box before saying yes. But growth usually shows up after you take the leap, not before it. Earlier on, I was very outcome-driven - get the results, hit the targets. Over time, I’ve realised the “how” matters just as much. Building trust, growing people, creating clarity, that’s what actually drives sustainable success.

Q4. What’s the best advice you’ve been given?

Back yourself, but stay open. Confidence and curiosity can (and should) co-exist. And when you’re stuck, ask better questions - that’s what good leadership often comes down to. My advice to others? Be useful. Bring energy, solve problems, and people will want you on their team.

Q5. What do you think the media will look like in 10 years?

It’ll be faster, more personalised, and I think trusted brands will matter more, not less. As AI and automation take over some parts of the value chain, human creativity and good storytelling will become even more valuable. In Out of Home, I think we’ll see smarter, more context-aware formats, dynamic creative, more data-led planning, real-time relevance. But the fundamentals won’t change. It’s still about reaching people in the right moment, with the right message, in a way that earns their attention. And I think media companies that know how to balance innovation with integrity - who can move fast but still stand for something - will be the ones that thrive.

Interview by Susan Horsburgh