Pick Your Pain: A Methodical Approach to Career Growth

About this episode

Steve Moore interviews Carl Cahill about a methodical approach to career growth and the importance of making deliberate choices in leadership.

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…

People in this episode

Host: Steve Moore

Guest: Carl Cahill

Topics covered

• career growth
• leadership
• CISO
• feedback
• incident response
• methodical approach

Keywords

• career development
• CISO
• leadership
• feedback
• 100-day plan
• gap analysis
• radical collaboration

Mentioned in this episode

Organizations: U.S. Army, Wharton GMP

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