Cyber Choices & Consequences: The 'Would You Rather' Security Showdown with Dan Haagman

Would You Rather: Cyber Edition” – Absurd Scenarios, Real Cyber Lessons

In cybersecurity, every decision has consequences—but what happens when the choices are hilariously terrible? In this special interview, Prof. Dan Haagman, CEO at Chaleit, sits down with Corinium’s Vanessa Jalleh to take on a series of outrageous “Would You Rather” dilemmas. It’s all fun and games… until they have to explain why they chose the lesser evil.

Through laughter, logic, and a few existential groans, Prof. Dan gives us a candid look at the mindset behind tough calls in security leadership. What would you choose—and more importantly, how would you defend it?

Some of the impossible choices include:

• Would you rather explain “zero trust” to the board every week for a year — or patch that one legacy system that breaks something new every time you touch it?

• Would you rather accidentally reply-all to the whole company with a phishing test — or have your CEO post their password on LinkedIn thinking it’s a motivational quote?

• Would you rather have your next audit conducted by a room full of interns — or by your most vocal internal critic from Marketing?

• Would you rather every cyber threat be named after a fruit (“BananaRAT”, “PineapplePhish”) — or have to sing your incident reports to the tune of a Taylor Swift song?

• Would you rather defend your network from a nation-state attack with only free trials and open-source tools — or present a security roadmap to the board with nothing but a whiteboard marker and pure charisma?

   

Why watch?

Behind each absurd scenario is a serious insight into how cyber leaders think about communication, culture, and control in an ever-evolving threat landscape. Expect laughter, sharp takes—and a fresh perspective on security leadership.

Prof. Dan Haagman is speaking at CISO Singapore 2025, this August. If you would like to share your experience and insights at CISO Singapore, reach out to Vanessa Jalleh for CISO Singapore.