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Key Takeaways

  • • Hire for a “we’ll figure it out” attitude, not just skills – early-stage chaos demands it
  • • You can’t reliably assess for chaos tolerance until someone’s in the fire
  • • Use probation honestly: define success early, measure it, and have the hard conversation in month one, not month seven
  • • The role that gets founders into the most trouble: sales before the product is ready for market
  • • Big-company experience doesn’t guarantee startup success – and vice versa

The Chaos Tolerance Test

Nobody can reliably predict who will thrive in the chaos of an early-stage startup. The panel is blunt about this: you can put someone through every competency-based interview in the book and still not know how they’ll respond when the plan falls apart on a Tuesday morning.
What you can look for is attitude. The “we’ll figure it out” mindset. Generalists who don’t need a playbook to get moving. People who see ambiguity as a feature, not a bug. Michael Delaney puts it simply: you’re hiring for resilience and adaptability, not a CV full of logos. Big-company experience can actually work against you if the person needs structure that doesn’t exist yet.
The panel agrees on one thing above all: use the probation period honestly. Define what success looks like in the first month, measure it, and have the hard conversation early. Waiting until month seven to address a bad fit is the most expensive mistake a founder can make. And the hire that gets founders into the most trouble? Sales. Selling a product that isn’t ready burns revenue projections, customer trust, and the team. Align your go-to-market with what engineering can actually deliver.

Often the right answer is I don’t know the answer, but I will find out the answer as we go along.

— Anthony Meek, Chief People Officer, Edrolo

Featured People Leaders

Michael Delaney – Head of People & Culture at JET Charge. Ex-Preezie. Blends people-first leadership with AI-driven strategy to build teams that scale. Former professional ballet dancer with 20+ years in talent and culture at Salesforce, DocuSign, and high-growth startups. Co-hosts the Talent Savvy podcast and leads diversity initiatives with Jobs for Humanity.

Sarah Sherriff – People Experience Manager at Factor House. The Melbourne-based engineering-led software house behind Kpow and Flex. Builds people and culture in “by engineers, for engineers” environments. 13+ years in talent acquisition and people operations across high-growth scale-ups. Joined Factor House after their $5M Seed round to support scaling from 15 to 30+.

Pavi Iyer – Head of People & Talent at Fortiro. Purpose-driven people leader with a background in medicinal chemistry and experience across global organisations, startups, and co-founding a coffee business. Champions workplace cultures that enable individual and organisational growth, and advocates for empathy, mentorship, and supportive networks in the Victorian talent community.

Anthony Meek – Chief People Officer at Edrolo. Australia’s leading edtech. Reformed teacher and people-and-culture champion with an MBA and background in organisational psychology and therapy. Has led Edrolo through two CEO transitions while scaling the team to 200+ and speaks widely on burnout, trust, and building teams you can rely on.

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