Ep 37: Simon Sayegh on the CIO’s Balancing Act - People, Platforms, and Progress
Tue Jul 29 2025
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
👋 Follow ThunderLabs on LinkedIn for more sharp, human takes. Or subscribe to our newsletter for fresh episodes and smarter thinking.
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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 👋 Follow ThunderLabs on LinkedIn for more sharp, human takes. Or subscribe to our newsletter for fresh episodes and smarter thinking.