When Caroline Register took ownership of Holmwood Property Management in 2006, it was her compelling enthusiasm that set her apart. Today, she’s as chipper and passionate about property management as ever. Caroline has grown the business to lead a team of 28 dedicated property specialists and has established herself as one of New Zealand’s foremost experts in the field.
At the heart of Caroline’s ethos is her unwavering and undeniable energy and her motivation to provide an experience centred on the pillars of kindness and care. However, Caroline backs this with strong, effective leadership and resolute attention to legislative detail. As tenancy law goalposts rapidly shift, Caroline’s superior knowledge plus having her finger on the pulse ensures she’s always ahead of the game. Combined with the latest technological innovation she has introduced to Holmwood Property Management alongside her willingness to share information and intellectual property, Caroline’s place as an elevated and aspirational trailblazer is firmly cemented.
However, Caroline doesn’t get it all her own way! At home, the two pre-schoolers rule the roost, ensuring her feet are well and truly grounded and merry mayhem enriches her life.
Sessions
Panel: People, Pathways and Leadership
Property management has a people challenge — attracting great people into the industry, growing them, and keeping them. But too often, the conversation happens in one direction: leaders talking about what they need from the next generation, without asking what the next generation needs from them.
This panel brings both sides to the table. What do younger people entering the industry actually want from their leaders — and what do leaders genuinely need from the people coming through? Where do expectations align, where do they clash, and what does a career pathway in property management need to look like to keep the best people in the room?
Facilitated by Sarah Cincotta, this honest, two-way conversation features Caroline Register (Harcourts Holmwood), Sam Hewetson (Aspire), and Britney Ross (Bayleys Wanaka) — voices from across the industry and across career stages, sharing what they've learned about leading, being led, and building teams people don't want to leave.
Q&A
What do you do for a living?
I look after my Property Management team, so they look after each other also and our owners, tenants and tradies.
How did you get into your line of work?
I purchased a rental portfolio back when I was 26, after having worked in Australia in Property Mgmt.
What drives you in your business?
My team first and foremost feeling great about what they do, enjoying our workspace and other team members, and excellence results within the industry.
Biggest challenge in your career?
Navigating the earthquakes as their impact morphed over time - it wasn't just the earthquake and the immediate results, it was all the aftermath too.
How impactful will AI be?
Impactful fairly heavily in many ways, and certainly not as heavy at all in others. It will streamline what we do. The human element will not change - the relationship with owners and tenants must be at a human level.
What do you do to unwind?
I head to Twizel. Hang out with my six and seven year old and my partner. The kids are super active - I can't play soccer, but boy do I give it a good nudge.
Favourite holiday destination?
Twizel, and abroad of course.
Advice to your 18-year-old self?
Do it now, all of it, take the risks early - they're always calculated anyway so just do it. You win and you learn. I bought my first investment property at 19 and my second at 20.