PANEL – CISO Regrets & WTF Moments: Lessons Learned and What I’d Do Differently

The role of the modern CISO is one of the most high-stakes, high-pressure positions in the enterprise and no one steps into it without a few hard-learned lessons along the way. In this candid, unfiltered conversation, seasoned security leaders share the moments that made them say “WTF?”, the decisions they’d take back if they could, and the insights they wish they’d had on day one. From career pivots to cultural clashes, budget battles to breach response blunders, this session offers an honest look at the realities of the job.

This is the perfect way to close out the day; equal parts entertaining, relatable, and loaded with takeaways that could save you from learning the hard way.

In this session, we’ll explore:

• The biggest surprises and blind spots in the first year as CISO
• Career-defining missteps and how to recover from them
• “I wish I’d known…”: advice seasoned leaders would give their past selves
• Dealing with political landmines and stakeholder clashes
• When the business ignores your warnings and you’re proven right (too late)
• How to turn a mistake into a leadership moment

Why attend:
You’ll leave with laughs, lessons, and a sharper playbook for navigating the CISO role, plus a few stories you probably won’t hear in any other session.