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Scaling, Sales Teams & Sanity: A Real Talk Leadership Ep with Courtney Hill
We’re jumping straight into the juggle—leading teams, raising kids, scaling careers, and still trying to have a life that feels like yours.
Joined by the brilliant Courtney Hill—tech leader, mum of three boys, and freshly obsessed guitar learner—we talk about what leadership actually looks like behind the scenes. No fluff. No corporate spin. Just honest convos about performance, burnout, boundaries, and what it takes to do big things without losing your mind.
This ep is full of big truths, bigger laughs, and permission to not have it all figured out.
We asked:
- What does good leadership actually look like in 2025?
- Can performance management not suck?
- How do you scale when you’re raising a young family?
- Do you really need to be a natural-born leader?
- How do you make time for joy (when you barely have time to pee)?
- And what's the deal with travelling the country 70 flights a year?
Chapters:
[00:00] Welcome, Courtney! Catch-ups & Career Throwbacks
[05:00] From Music to Property to Tech—Courtney’s Wild Career Path
[13:00] Building a Biz Inside Someone Else’s Biz
[18:00] Leadership, Culture & Giving Your Team a Voice
[25:00] Performance Plans That Don’t Feel Like Punishment
[35:00] 70 Flights, 3 Kids & Making It All Work (Sort Of)
[44:00] Picking Up the Guitar at 40 (and Not Giving a Shit Who’s Watching)
[53:00] PottyBot Wild Card: If You Gave a TED Talk on Something Not Business?
If you’ve ever wondered how other women actually “do it all” (hint: they don’t), this one’s for you. Pour a drink, take a deep breath, and settle in for a masterclass in real-world leadership and letting go of the pressure to be perfect.
With your hosts:
Jessica Whatman – founder of AgentSync, the best VA company in Australia
Hermione Gardiner – real estate biz coach and founder of Sidekick, the best property management consultant in Australia
✨ Connect with us:
🎧 The Podcast: here
📱 AgentSync: www.agentsync.com.au
📱 Sidekick: www.sidekick.net.au
Free Download
The Ultimate Personal Branding Blueprint
A free guide for agents, PMs and BDMs who want to stand out, get noticed and grow their business.
👉 Download the guide
The Brand Lab
Marketing made easier for real estate pros
Brand Lab is your shortcut to better content, stronger branding and more leads.
👉 Join now
With your hosts:
Jessica Whatman, founder of AgentSync
Hermione Gardiner, founder of Sidekick
View all episodes
By Jess Whatman & Hermione GardinerWe’re jumping straight into the juggle—leading teams, raising kids, scaling careers, and still trying to have a life that feels like yours.
Joined by the brilliant Courtney Hill—tech leader, mum of three boys, and freshly obsessed guitar learner—we talk about what leadership actually looks like behind the scenes. No fluff. No corporate spin. Just honest convos about performance, burnout, boundaries, and what it takes to do big things without losing your mind.
This ep is full of big truths, bigger laughs, and permission to not have it all figured out.
We asked:
- What does good leadership actually look like in 2025?
- Can performance management not suck?
- How do you scale when you’re raising a young family?
- Do you really need to be a natural-born leader?
- How do you make time for joy (when you barely have time to pee)?
- And what's the deal with travelling the country 70 flights a year?
Chapters:
[00:00] Welcome, Courtney! Catch-ups & Career Throwbacks
[05:00] From Music to Property to Tech—Courtney’s Wild Career Path
[13:00] Building a Biz Inside Someone Else’s Biz
[18:00] Leadership, Culture & Giving Your Team a Voice
[25:00] Performance Plans That Don’t Feel Like Punishment
[35:00] 70 Flights, 3 Kids & Making It All Work (Sort Of)
[44:00] Picking Up the Guitar at 40 (and Not Giving a Shit Who’s Watching)
[53:00] PottyBot Wild Card: If You Gave a TED Talk on Something Not Business?
If you’ve ever wondered how other women actually “do it all” (hint: they don’t), this one’s for you. Pour a drink, take a deep breath, and settle in for a masterclass in real-world leadership and letting go of the pressure to be perfect.
With your hosts:
Jessica Whatman – founder of AgentSync, the best VA company in Australia
Hermione Gardiner – real estate biz coach and founder of Sidekick, the best property management consultant in Australia
✨ Connect with us:
🎧 The Podcast: here
📱 AgentSync: www.agentsync.com.au
📱 Sidekick: www.sidekick.net.au
Free Download
The Ultimate Personal Branding Blueprint
A free guide for agents, PMs and BDMs who want to stand out, get noticed and grow their business.
👉 Download the guide
The Brand Lab
Marketing made easier for real estate pros
Brand Lab is your shortcut to better content, stronger branding and more leads.
👉 Join now
With your hosts:
Jessica Whatman, founder of AgentSync
Hermione Gardiner, founder of Sidekick