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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