Organisational ResilienceWargame to Gameday NYC: Practicing the Strategies for an Adaptive Future

What do you do with a threat that learns faster than you do?

This was the question posed at our recent Wargame to Gameday event in NYC.

The ever-changing threat landscape is evolving at an unprecedented pace, with the emergence of new and concerning risks. A recent example of this is the alarming potential of fast-learning AI capabilities, which can present severe, prolonged, and multifaceted impact to business operations. An example of the potential malicious application of Artificial Intelligence capability was highlighted in a recent scenario orchestrated by 60 Minutes, where an ethical hacker utilized AI to mimic the voice of an unsuspecting colleague, illustrating the alarming potential for misuse of digital identity and wide-scale deception in AI-driven attacks.



With these threats in mind, iluminr organized an in-person event gathering business leaders, technologists, and advisors for an unforgettable experience diving deep into the world of Artificial Intelligence and exploring the challenges posed by rapid-learning adversaries.

The event was an opportunity for business leaders to try their hand at severe but plausible simulated events, employ game-based strategies for building the muscle memory of risk and resilience, and learn from proven resilience-building techniques leveraged by the likes of athletes, surgeons, astronauts, artists, and the military.


Bringing to life decades of research, showcasing emerging technologies, and leveraging immersive engagement techniques, the event focused on how executive leaders can create context, capability and connectivity to create more agile companies.

Learning from trusted industry leaders from some of the world’s most innovative organizations, we all walked away with a new perspective on leadership and team development in crisis, along with practical tools and techniques for driving sustained resilience.

This summary delves into the core components of the Wargame to Gameday workshop experience, exploring strategic considerations when confronted with a threat that learns faster than we can respond, all within the context of operational and digital resilience.


Threat Evaluation

We kicked off the workshop with a threat evaluation exercise, a captivating group simulation that aimed to assess the possible dangers that could arise from a fast-learning AI cyberattack. The simulation was designed to provide an interactive and immersive experience, allowing participants to actively engage in identifying potential risks and evaluating their implications on organizational systems.

The first task assigned to the participants was to thoroughly analyze the capabilities of the simulated AI cyberattack. They explored various aspects such as its ability to learn and adapt, the potential techniques it might employ to infiltrate systems, and the extent of its potential impact. This exercise encouraged the participants to think critically and anticipate the attack’s potential strategies, enabling them to gain a deeper understanding of the threat at hand.

Next, the participants were required to assess the impact that the AI cyberattack could have on the organization’s systems. They evaluated the potential consequences of a successful attack, including the disruption of critical services, compromise of sensitive data, and damage to the organization’s reputation. By examining the potential repercussions, the participants gained insight into the potential magnitude of the threat and the importance of addressing it effectively. Simultaneously, the participants focused on identifying potential vulnerabilities that the AI cyberattack might exploit. They examined various aspects of the organization’s infrastructure, systems, third parties, and processes, seeking weaknesses that could be targeted. This exercise helped highlight the significance of proactive security measures and the need for robust defenses to mitigate potential vulnerabilities.

Throughout the simulation, the participants recognized the adaptive nature of the adversaries behind the AI cyberattack. They realized that traditional response mechanisms might be insufficient to counteract the attack’s agility and speed. This realization emphasized the critical importance of continuously evolving and improving response strategies to stay ahead of the threat.

Participants were required to prioritize their actions and allocate resources effectively, ensuring that the most critical aspects of the organization’s systems were protected. They also assessed existing response processes, identifying potential gaps and areas for improvement. Lastly, the participants recognized the significance of having a skilled and knowledgeable team capable of responding to an unseen adversary, highlighting the need for continuous training and talent development, as well as skilled legal and compliance personnel, advising the organization on how to respond within established guidelines and policies.

Overall, the threat evaluation workshop provided participants with a practical and immersive experience to assess the potential risks associated with a fast-learning AI cyberattack. By actively engaging in simulations and exercises, the participants gained valuable insights into the adversaries’ adaptive nature, the vulnerabilities that may be exploited, and the importance of agile and proactive response mechanisms to mitigate such threats effectively.



Source: Preview of iluminr Feedback Reporting

After Action Reporting

After the threat evaluation exercise, the participants took part in a feedback reporting session, which served as a crucial component of the workshop. This session provided a platform for participants to engage in a constructive debriefing based on what actually had happened, allowing them to share their insights and receive valuable feedback from both facilitators and their peers.

The primary objective of the feedback reporting session was to foster collaboration and promote a culture of open communication. Participants were encouraged to express their thoughts, observations, and perspectives regarding the threat evaluation exercise. They had the opportunity to reflect on their experience, discuss their findings, and articulate their understanding of the potential risks associated with a fast-learning AI cyberattack.

Just as during a live after-action report, facilitators played a crucial role in the feedback reporting session. They provided expert guidance and offered constructive, outside-in feedback based on their knowledge and experience in the fields of security, legal, and effective response. Their insights helped participants refine their strategies, identify potential blind spots, and gain a deeper understanding of the complexities involved in countering advanced cyber threats.

Peer feedback was also an essential element of the session. Participants had the opportunity to receive input and suggestions from their fellow participants, who may have approached the exercise from different perspectives or possessed unique insights. This peer feedback helped participants broaden their thinking, consider new angles, and discover innovative approaches to effectively counter the simulated AI cyberattack. In this way, the feedback reporting session served as a catalyst for continuous improvement, as we moved into the next phase of the workshop on simulations and wargaming.



Source: Wargame to Gameday NYC Simulation

Simulations and Wargaming

The workshop incorporated lectures and discussions that emphasized the importance of simulations and wargaming in the context of emerging threats. These sessions were designed to provide participants with practical insights into utilizing simulations and wargames as effective tools in preparedness and response.

The lectures and discussions shed light on how simulations can replicate real-world attack scenarios, offering participants a controlled environment to explore decision-making processes and test their response strategies. By simulating different attack scenarios, participants were able to gain hands-on experience and develop a deeper understanding of the challenges posed by fast-learning AI cyberattacks. Participants learned how simulations and wargames can facilitate the development of adaptive response strategies. They understood that traditional static approaches to cybersecurity may not be sufficient to counter dynamic and evolving threats. Simulations allowed participants to assess the effectiveness of their existing strategies, identify areas for improvement, and develop personalized approaches to enhance operational resilience.

The practical guidance provided in the workshop equipped participants with the knowledge and tools necessary to design their own simulations and wargames for their teams. They learned how to tailor these exercises specifically to the challenges posed by fast-learning AI cyberattacks.

The practical application of simulations allowed participants to bridge the gap between theory and practice, equipping them with the skills and knowledge necessary to address emerging threats proactively.

Overall, the lectures and discussions on simulations and wargaming provided participants with a comprehensive understanding of these tools in the context of emerging threats. By incorporating practical guidance and emphasizing the dynamic nature of AI adversaries, participants were empowered to design tailored simulations and wargames that enhanced their operational resilience and preparedness.


Source: Wargame to Gameday NYC 

Effective Coaching

Recognizing the importance of effective coaching in high-stakes and rapidly evolving environments, the workshop dedicated a specific session to delve into coaching strategies. This session aimed to equip participants with valuable skills and techniques that would enhance their ability to navigate and thrive in such dynamic situations. The workshop emphasized the significance of coaching in fostering adaptability, facilitating sound decision-making under pressure, and promoting effective teamwork.

During the coaching session, participants were introduced to various coaching approaches and methodologies, including reflective coaching. These approaches encompassed both individual coaching, focusing on personal growth and development, as well as team coaching, emphasizing collaboration and collective performance.

Participants gained insights into the importance of adaptability in fast-moving environments. They learned how to leverage effective coaching to help individuals and teams embrace change, adjust their mindset, and navigate through uncertainty. Coaching strategies such as encouraging flexibility, promoting a growth mindset, and providing constructive feedback through reflective coaching were explored as tools to foster adaptability.

Another key aspect of effective coaching covered in the session was decision-making under pressure. Participants learned how to coach individuals and teams to make informed and effective decisions even in high-stress situations. They explored techniques for enhancing critical thinking, managing emotions, and leveraging collective intelligence to make sound judgments in fast-paced environments.

The workshop also emphasized the role of coaching in promoting effective teamwork. Participants discovered strategies for building trust, fostering open communication, and enhancing collaboration within teams. They learned how to coach individuals to leverage their strengths, embrace diversity, and work cohesively towards shared goals. These coaching techniques aimed to improve team dynamics and enable teams to perform at their best in challenging circumstances.

Throughout the coaching session, participants had the opportunity to engage in interactive exercises and case studies. They practiced applying coaching techniques, received feedback from facilitators and peers, and gained firsthand experience in coaching scenarios. This hands-on approach enabled participants to internalize the coaching strategies and develop their coaching skills in real-time.

By focusing on effective coaching, the workshop aimed to empower participants to support themselves and their teams in high-stakes and fast-moving change. It recognized the crucial role that coaching plays in enabling individuals and teams to adapt, make informed decisions, and collaborate effectively. Equipped with coaching strategies, participants were better prepared to navigate complex environments and drive positive outcomes even in challenging circumstances.



Adaptive Response and Continuous  Learning

The workshop culminated in a final response drill, designed to put the new knowledge and skills gleaned during the workshop to the test.

During the exercise, participants were confronted with a series of realistic scenarios and challenges related to the theoretical attack. They were required to analyze new information, adapt their strategies accordingly, and make timely and informed decisions. The drill aimed to replicate the pressure and uncertainty often associated with real-world cyber threats, allowing participants to experience the complexities of managing an evolving situation. By engaging in the response exercise, participants had the opportunity to demonstrate their preparedness and apply the knowledge and skills acquired throughout the workshop. They were able to put their understanding of threat evaluation, adaptive response strategies, and effective coaching into practice.

This drill was designed to uncover areas for improvement and identify any gaps in participants’ response strategies. It allowed participants to evaluate the effectiveness of their approaches and tactics in real-time, highlighting potential weaknesses and areas where further development was needed. This feedback-oriented approach aimed to foster a culture of continuous learning and improvement.

Furthermore, the drill reinforced the importance of operational resilience in countering evolving cyber threats. Participants experienced firsthand the challenges posed by an attack that adapted and evolved, underscoring the need for organizations to develop robust response capabilities. The exercise emphasized the significance of agility, adaptability, and a proactive mindset in effectively responding to dynamic cyber threats.

By culminating the workshop with a drill, participants were able to apply their knowledge and skills in a realistic and challenging setting. The exercise provided a valuable learning experience that allowed participants to identify areas for improvement, refine their tactics, and reinforce the importance of operational resilience in countering evolving cyber threats.


Source: © Team Coaching International 2012. All Rights Reserved.

Reflections and Commitments

As a capstone to the experience, participants spent some time in reflection and making commitments towards enhancing their teams’ resilience. This segment aimed to create a space for individual introspection, enabling participants to contemplate their experiences throughout the workshop and consider how they could apply their new knowledge and insights to their respective organizations.


Wargame to Gameday for a More Resilient Future

Wargame to Gameday NYC provided a comprehensive and immersive experience in navigating the challenges posed by fast-learning AI cyberattacks within the context of operational resilience. By engaging in the simulation, participants gained valuable insights into the adaptive nature of AI adversaries and the importance of staying ahead of evolving threats.

In a world where cyber threats continue to evolve at an alarming pace, threat intelligence, simulations, wargaming, and adaptive response are quickly emerging as the essential platform for organizations to test their capabilities, strengthen their defenses, and develop the resilience necessary to navigate the unknown. By investing in this new frontier of capability, organizations can position themselves at the forefront of Resilience, ensuring the protection of their operations and maintaining trust in an increasingly volatile world.

Are you interested in learning more about our Wargame to Gameday series? Watch for the next installment of the blog that outlines the key learnings and insights from the collaboration, as well as more information on where we are taking the experience next! Or, visit us at to learn how to bring Wargaming to Gameday to life at your organization.



Paula Fontana

VP, Global Marketing, iluminr