#266 - Why CISOs Miss The Next Big Security Challenge (with Richard Stiennon)

CISO Tradecraft® · Jan 5, 2026 · 44m

CISOs are expected to anticipate the next major security failure, yet the cybersecurity market is moving too fast, too fragmented, and too noisily for any leader to clearly see what’s coming next.

AI is accelerating vendor sprawl, threat models are shifting mid-year, and every product claims to be “critical.” CISOs aren’t missing threats because they’re uninformed; they’re overwhelmed. By the time a risk is obvious, it’s already budgeted, deployed, and exploited. Boards ask “How did we not see this?” while CISOs are left defending decisions made with incomplete signals and outdated market…