What’s keeping tech leaders up at night? According to CIO Simon Sayegh, it’s not just AI hype. It’s legacy systems, missing skill sets, and unclear outcomes. 

Segmented Discussion Points: 

1. Outcome-Driven Architecture, Not Agile Theatre 

• Why “agile in name only” is no longer good enough 

• The rising demand for capability-based partnerships 

• How CIOs can enable business outcomes without owning everything 

2. Simplify or Sink: The Case for Fit-for-Purpose Tech 

• The hidden risks of going “best in class” vs. “fit for purpose” 

• Why modular and hybrid architectures are the new normal 

• Lessons from consolidation trends across enterprise tech 

3. The AI Reality Check 

• Why “guardrails first” is Simon’s golden rule for AI adoption 

• What boards should really be asking about AI projects 

• The difference between solving a problem and chasing a trend 

4. Partner Ecosystems and Trusted Networks 

• The modern CIO’s secret weapon is who they can call at 5pm on a Friday 

• When to outsource, near-source, or in-source (and how to decide) 

• The underrated art of asking, “Help me understand the value you bring” 

5. Culture Isn’t Motherhood Stuff. It’s a Strategy 

• Why work teams are more like sporting teams than families 

• The cost of keeping your “best performer” with the worst behaviour 

• How shared KPIs can transform internal relationships 

6. Two-Speed Tech Teams and Career-Defining Projects 

• Why CIOs must deliver quick wins while building long-term foundations 

• The uncomfortable truth: most organisations don’t know what’s going on under the hood 

• Reframing AI as “just another project” but with way more risk 

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