Pick Your Pain: A Methodical Approach To Career Growth The New CISO podcast

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Pick Your Pain: A Methodical Approach to Career Growth

3d ago 45:20

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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.

136 episodes

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