In this episode of The New CISO (Episode 136), host Steve Moore speaks with Carl Cahill, CISO, about a deliberate, methodical approach to career growth—and why every leader must “pick their pain” to progress.

From combat arms in the U.S. Army to Active Directory engineering and large-enterprise incident response, Carl shares the pivotal choices that shaped his leadership. He opens up about moving from certifications to business fluency, using a personal gap analysis to chart his path to the C-suite, and how feedback like being called a “propeller head” pushed him to translate geek speak into the language of finance, law, and strategy. Carl also explains his five-phase 100-day plan, why IR readiness comes first, and how “radical collaboration” defines the modern CISO.

Key Topics Covered:

• Early career pivots: Army leadership, perseverance, and precision → IT foundations
• Certifications as a fast track (then) vs. blended learning and passion projects (now)
• The “pick your pain” decision: staying comfortable vs. returning to school to advance
• Building a CISO gap analysis from job reqs and targeting stretch assignments
• Upgrading the lexicon: finance, legal, and general management (e.g., Wharton GMP)
• Turning tough feedback into growth: from geek speak to boardroom dialogue
• Consulting variety vs. ownership: when to switch for long-term impact
• The 100-day plan: assess → plan → act → measure → adjust (with IR first)
• Stakeholder mapping, team SWOTs, and making strategy stick beyond 90 days
• Metrics as a “health language” and why today’s CISO must be a radical collaborator

Carl’s story shows how intentional trade-offs—education, language, and leadership style—compound into career momentum. His roadmap helps CISOs and aspiring leaders navigate transitions with discipline, communicate across the business, and build resilient teams that lead with clarity.