Q - First of all, can you tell us a little about yourself, your career so far, and what you do now?
A - I started my career in corporate (Finance @ American Express, Consulting @ PwC/KPMG) but didn't love it as I was recommending lots of things, but never got to do the implementation. So I joined two of the largest Australian marketplaces MadPaws, a marketplace for pet sitters, and Expert360, a marketplace for independent consultants. I loved startup life as I got to work on real customer problems, seeing the smiles on people's faces. After taking Expert360 through a $14m Series B I joined Startmate, Australia's most ambitious accelerator, as Head of Operations where I'm now CEO. I took it from an Accelerator to a household name for Aussie and Kiwi founders, investors and operators.
Q - What are some of the key lessons you've learned from your experiences with managers, both good and bad?
A - Bad managers. We've all had them, likely, we've even been a bad manager for someone else. I've had dozens of small and big interactions where I hated something my manager did (ie not explain things properly, not greet the team in the morning), equally often I loved things my managers did (ie give me the context before explaining the task). I've collated all these micro-moments from my first job onwards in a google sheet called "Manager Insights" so these scars stay with me and remind me to either never be like the bad manager I had, or do the things I loved about my managers. There is nothing that shapes you more as a manager than your previous managers (and your parents!).
Q - Can you share a pivotal moment in your career that led you to where you are today?
A - I loved my time at Expert360 where we grew a team of 7 to 60 people and raised $14m in VC funding. I could have easily stayed with the great team and have a fun journey! Instead, I quit my job without another one lined up because I knew that I wanted to scale myself - work with hundreds of startups, not just one. It was a big risky move. I travelled around the world, spent all my money and was stuck without a job. It forced me to go really deep into what I really wanted and do the hard work. The hard work was to cold email ~200 accelerators across the whole world to see if anyone would hire me. 180 of these emails never even got a reply. 15 of the replies wanted to sell me something rather than hire me. But through doing the hard work, I found my role at Startmate, where I've now been for 7 years.
Q - How have mentors and continuous learning played a role in your development?
A - Exec Coach - I've been working with an Executive Coach for 4 years now, initially I saw him every 6 weeks, now it is roughly once a quarter. Here are my favourite lessons from his coaching. Mentors - I've always surrounded myself with mentors, they can change over time. For the last few years, I've had regular check-ins / mentoring from Robyn Denholm (Chair of Tesla / bi-monthly), Niki Scevak (Founder of Startmate / fortnightly) and Rachael Neumann (Founder of Flying Fox Ventures, bi-monthly). Books - I read a lot. My Kindle is my most-prized possession. As I forget books too quickly though, I summarise them on my blog so it solidifies the lessons when I write the summary and I can come back to my summary at any time. Podcasts - I listen to them when I run. I bookmark my favourite spots with Snipd. Then summarise them on my Twitter and a Whatsapp group with friends where we share lessons - here are all my summaries.
Q - How do you incorporate feedback and set boundaries in your work culture?
A - Micro-feedback. It is baked into our culture. Feedback doesn't start at performance conversations - that's when it is way too late, people are reluctant to give feedback or it comes as a surprise and won't be well received. Instead, we share feedback weekly in every single manager/managee 1:1. We ask two questions (1) What did I do well? (2) What could I have done 10% better?. Why? Because it normalises giving small pieces of feedback which can be by themselves useful, but even more importantly it makes everyone much more comfortable passing on the big painful feedback in the regular 1:1s or in our bi-annual 360 surveys. Boundaries. Work is never-ending. The funniest quote here is "great work is rewarded with more work". Don't get me wrong, I love my work, but it can get overwhelming. The way I deal with the pressures is to set clear boundaries. For me the morning is sacred, before 9am it is "me" time - I'll eat breakfast with my wife, exercise and go for coffee. I will never have a meeting, nor let that be interrupted by work. At 9am, I'll be there, fully present and deal with all the fires - until then, I have time for myself and my family.
Q - Can you explain the "Elephants" framework and its impact on your personal and professional life?
A - Elephants. It is my favourite framework to (1) stay close with my best friends and (2) push each other to greater heights. In short, you bring your 2-4 best friends together, you set goals for yourself for 1, 3 and 10 years across work, health, family, financial, intellectual, spiritual - whichever dimensions resonate. Weekly you check back in on your week and update your goals quarterly to get closer. It is the ultimate mechanism to stay close to your friends' lives whilst supporting and pushing each other on the most important aspects of life and go way beyond just work goals. Here is the full framework if that inspired you.
Q - What is the most essential question to ask yourself as a manager, and how has it influenced your management style?
A - "What's my boundary of responsibility?" the most essential question to ask yourself as a manager. It is so easy to overstep your boundary of responsibility. Always clarify the boundaries and hold yourself and the other person to them. Here is the full content on my lesson
Q - How has the 80/20 rule influenced your approach to work and decision-making?
A - 80/20 Rule - this was early in my career. I built this stunning financial model that took me day and night for days on end to build. Only for my manager to come up and ask me about something I hadn't built... which was an instant kick to the gut. But the advice stayed with me forever which was to not build the "perfect model" but apply the "80/20" rule. What is the 20% of the work which will provide 80% of the value? Instead of overcooking the model, I could have saved myself many sleepless nights by focusing on what's actually important.
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