Lessons learnt from CISO Singapore 2025: The Top 7 Questions Every CISO Will Have on Their Minds in 2026

As cyber risks continue to intensify at breakneck speed, understanding the insights from today is essential for preparing for tomorrow. This article distills the key lessons learned from CISO Singapore 2025 and highlights the top questions every CISO will be considering as they navigate the risks, opportunities, and strategic decisions of 2026.

Read on to discover how the role of the CISO is shifting from defending systems to designing trust.

The pace of change in cyber security requires ongoing reflection and preparation. Understanding today’s challenges is essential to navigating tomorrow’s risks. Lessons learned from CISO Singapore 2025 made one thing clear: the role of the CISO is evolving from defending systems to designing trust.

Looking ahead to 2026, based on these lessons, here are the top seven questions every CISO will be asking:

1. How do we embed “security everywhere” rather than just “shift left”?
   Security is no longer a checkpoint; it’s a mindset. CISOs are moving away from rigid gates toward guardrails that enable speed while maintaining protection. Policy-as-code, automated SBOMs, and integrated security practices make protection invisible but indispensable. In 2026, CISOs will ask how to extend accountability across all business functions, making security part of every decision.
2. How do we secure identities in a perimeterless world?
   The modern cybersecurity perimeter is identity itself. From cloud-native to hybrid environments, protecting users, devices, and third parties is non-negotiable. The lesson from 2025: yesterday’s tools won’t secure tomorrow’s world. In 2026, CISOs will focus on unified identity fabrics, context-aware access, and AI-driven anomaly detection to ensure trust across the digital ecosystem.
3. How can cyber security be positioned as a strategic enabler, not just a technical function?
   Boards now demand risk-informed narratives, not just technical reports. The most effective CISOs translate complex threats into business outcomes, showing how security investment drives growth, resilience, and trust. From 2025, it’s clear that business fluency is critical: CISOs must speak the language of performance, innovation, and opportunity, not just compliance.
4. How do we balance AI as both a threat and a tool?
   AI is a double-edged sword. Malicious actors use AI to amplify attacks, while defenders use it to enhance detection and response. The lesson from 2025: AI is changing the scale, speed, and sophistication of threats. In 2026, every security strategy will need clear approaches to leveraging AI responsibly while defending against AI-driven attacks.
5. How do we manage converging risks across cyber, physical, and societal domains?
   Modern threats no longer exist in isolation. Economic pressures, geopolitical tensions, climate risk, and AI-driven threats collide in ways that amplify impact. Lessons from 2025 underscore the need for a converged security mindset - considering how digital, physical, and societal risks intersect to protect the enterprise holistically.
6. How do we strengthen the human element in cyber security?
   Despite automation and AI, people remain the weakest, and strongest, link. Burnout, mentorship, and culture shape resilience. From 2025, CISOs saw that human readiness is just as critical as technological defenses. In 2026, the question becomes: how do we cultivate teams capable of thriving under constant change and sophisticated attacks?
7. Are we investing in the right tools, talent, and AI ecosystems for measurable impact?
   AI adoption isn’t only for large enterprises; small, targeted initiatives can drive outsized results. The lesson from 2025: focus on meaningful ecosystems and initiatives that deliver tangible security and business value. In 2026, CISOs will evaluate whether tools, people, and partnerships are truly driving measurable outcomes.

Conclusion
If 2025 was about redefining the CISO role, 2026 will be about redefining trust itself. Cyber security is no longer just protection — it’s enabling innovation in a world where AI, identity, and integrity intersect. Learning from the lessons of CISO Singapore 2025 ensures leaders are ready for the risks, and opportunities, of tomorrow.

Don’t miss your chance to be part of CISO Singapore 2026 (19–20 August) at the Equarius Hotel, Sentosa.

You can also join our other flagship events happening in the same space: AppSec & DevSecOps Singapore 2026 and Cloud Security Singapore 2026 (both on 20 August).

If you’re interested in sharing your expertise and insights at any of these events, get in touch with Vanessa Jalleh to explore speaking opportunities.

Photo by BoliviaInteligente on Unsplash