The world of cybersecurity is not just about code and firewalls, but above all about people, processes, decisions made under pressure, and visionary thinking. On 29 January 2026, at the CyberSG TIG Collaboration Centre in Singapore, Digital Club / Cyber organised an international edition of “The CISO Game”: a strategic simulation scenario devised by Andrea Guarino. Digital Club / Cyber has developed a format of interactive and educational conferences, aimed at fostering exchange among C-level executives, strengthening the culture of cyber awareness and promoting the development of cyber talent. Launched in Italy with over 50 events to its name, it has made its debut in the technological heart of Asia in partnership with Division Zero (Div0), the Singaporean cybersecurity community which is entirely voluntary and open to all professionals in the sector.
What is ‘The CISO Game’?
The format is a serious game in which participants — CISOs and Security Managers — tackle a cyber incident in real time, balancing technical decisions, communication with the board, business continuity and reputation management. The scenario is the same for everyone, but features four decision points with 32 possible outcomes. The text and plot of this interactive story were created by Andrea Guarino.
The event in Singapore fostered collaboration between the academic and business worlds, thanks to the support of the Cyber Security Agency of Singapore (CSA) and partnerships with strategic partners such as GreyInt, Bernoni Grant Thornton, Digimetrica, Redface and CREST.
The role of Cyber Mentors
Crucial to the success of the exercise was the presence of the Cyber Mentors, industry experts who led the discussion groups. Their role was not to provide answers, but to encourage critical thinking, prompting participants to ask themselves: “Why this choice? What would I do if this actually happened to my company?”
The mentors observed with great interest how, despite the information on the scenario being incomplete (just as happens in real life), the teams managed to collaborate successfully to complete the mission, thanks in part to the support of a select few strategic partners such as GreyInt, Bernoni Grant Thornton, Digimetrica, Redface and CREST.
Participants’ reflections
The feedback gathered at the end of the day paints a consistent picture: the CISO Game struck a chord – both professionally and personally – that few other formats manage to achieve.
‘The CISO Game provided an extremely realistic simulation of the pressure we face every day: not just technical challenges, but managing communication with the board and making critical decisions under immense time pressure. The opportunity to compare notes with colleagues was incredibly valuable. It’s an exercise every security professional should undertake to test their skills and psychological resilience. Singapore needs more initiatives of this kind.’
‘What struck me most was the game’s ability to break down the silos between different departments: it wasn’t just a challenge for IT experts, but a genuine exercise in business risk management. We had to balance security, business continuity and brand reputation, just as we would in the real world. This format is essential for teaching leaders to view cybersecurity not as a cost, but as a vital component of business resilience.’
‘One thing makes this format unique: its ability to transform abstract concepts into tangible, immediate scenarios, where every decision has a direct impact on the simulation. The turnout was incredible and demonstrates just how much demand there is for practical training in our sector. Events like this serve above all to build the trust and shared language among security leaders that are essential for tackling global threats.’
‘What sets the CISO Game apart is the way it replicates the uncertainty and speed of critical decision-making during an attack: it’s not just about knowing what to do technically, but how to communicate it and how to prioritise actions when resources are limited. This event has shown that cybersecurity is a team effort. We’re leaving with a greater understanding and practical tools that we can put into practice immediately within our organisations.’
The organiser’s thoughts
‘Bringing the CISO Game to Singapore was an interesting experiment, not least from a social perspective. We discovered a different approach to resolving issues arising from cyber incidents: a focus on following procedures, a desire to protect reputation, and a willingness to seek external help were the key aspects that emerged. In Europe, the search for the most efficient solution usually prevails, always in compliance with regulations, but geared towards minimising technical damage to the company, placing reputation on a level that is still important but slightly less of a priority. From the perspective of interpersonal relations, we witnessed a significant evolution: in Singapore, people tend to be very reserved and quiet, just as the room was at the start of the conference. By the end of the day, that audience had transformed into a bustling gathering of CISOs deeply engaged in conversations on the topic raised by the tabletop exercise. My greatest surprise, and source of satisfaction, was discovering that, in a country as cutting-edge as Singapore, the CISO game proved to be a huge success, proving to be extremely innovative.”
– Andrea Fumagalli
Conclusions
The success of the Singapore event confirmed that cybersecurity is, above all, an exercise in open-mindedness. Knowing how to manage uncertainty, coordinate the human factor and think in terms of scenarios remains the greatest challenge for CISOs — regardless of culture or geographical context. Digital Club / Cyber continues its international growth with a clear mission: to build a culture of cybersecurity that is not merely technical, but strategic, human and shared.
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