CyberWins ANZ Episode 3: Craig Hayes – Find a Way or Make One

What if the nicest thing you could do for your team was stop being nice? In this episode, host Hayden Loader sits down with Craig Hayes, a global executive currently driving a 50,000-SEAT MICROSOFT 365 UPLIFT ACROSS MULTIPLE COUNTRIES, with a career spanning MASTERCARD, G4S, and large-scale payment platform transformations. Craig's core expertise sits at the intersection of STRUCTURAL CHANGE, COMPLEX RISK MANAGEMENT, and building RESILIENT OPERATING MODELS FOR THE AI ERA. Craig's standout story: a global payment platform consolidation where his team documented the worst-case failure scenarios for a legacy system nobody wanted to call end-of-life. Six months later, ALMOST WORD FOR WORD, every scenario came true. Multi-database failure. Multi-site failure. Weeks of cleanup. Months of financial reconciliation. The win? NOBODY ASKED HOW THEY GOT THERE. Because the risk had already been communicated, clearly and honestly. His philosophy, borrowed from Hannibal: "I SHALL EITHER FIND A WAY OR MAKE ONE." When the path forward is blocked, your job as a leader isn't to push through the rock. It's to FIND THE WAY AROUND IT. Chapters: 0:00 – Intro: Meet Craig Hayes 1:30 – Nice vs Right: Why Transparency Beats Comfort in Transformations 3:00 – The Legacy Platform Story: Documenting the Worst Case 6:00 – Words Matter: Why "Legacy" vs "End-of-Life" Changes Everything 8:00 – The Credibility Win: When Risk Communication Pays Off 11:00 – Find a Way or Make One: The Hannibal Philosophy 13:00 – The River and the Boulder: A Masterclass in Leadership Navigation 15:00 – ANZ Cyber Landscape: Data Sovereignty, Compute and Skills 19:00 – The BYO AI Risk: What Happens When Staff Use Personal Subscriptions 23:00 – Agentic AI: From Email Summaries to Core Business Processes 28:00 – The Ethics Problem: Why a Global AI Framework May Be Impossible 33:00 – Multi-Model Validation: How Microsoft Is Tackling AI Bias 36:00 – Final Takeaway: Agile and Resilient — The Two Skills That Will Matter Most #CyberSecurity #DigitalTransformation #RiskManagement #AIStrategy #CyberWinsANZ #TechLeadership #DataSovereignty #AgenticAI #CyberResilience #infosec Join the CyberWins community on LinkedIn:   / cyberwins-anz