AI can write your emails, hype you up, and tell you you’re right. The problem is that real leadership and real relationships are built in the moments that don’t feel good. I’m joined by Kyla Colbin, founder and CEO of Boma, TEDx Christchurch pioneer, Singularity University advocate in Aotearoa New Zealand and Australia, and a certified Dare to Lead facilitator, to unpack what courageous leadership looks like when the world is noisy and the stakes feel personal. 

We talk about resilience as practice, not personality, and why the biggest shift is stopping the habit of “fixing” other people first. Kyla shares how values-based leadership shows up in daily life, from guiding stressed clients through major decisions to building cultures of trust and accountability. We also dig into the Crusaders Leadership Programme and why elite sport is such a clear mirror for teamwork, standards, and belonging, even if you’ve never watched a match. 

Then we go straight into the hard stuff: money stories, asking for a pay rise, and the real cost of avoiding tough conversations. Kyla’s Courageous Communication framework makes hard conversations less mysterious and less scary, and we explore how AI “sycophancy” can quietly rob us of the interpersonal friction we actually need to grow. We finish with a powerful reframe on success, purpose, mortality, and the simplest advice Kyla is willing to give: forgive yourself everything. 

If this resonated, subscribe, share it with someone who’s avoiding a hard conversation, and leave a review so more New Zealanders can find the show.

https://www.kailacolbin.com/

https://nz.boma.global/kaila-colbin

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