The most sophisticated security tools fail when leaders don't understand the business context they're supposed to protect. Michael Freeman, Head of Threat Intelligence at Armis, learned this lesson during a major security incident where his team had the intelligence from day one but missed the breach because they didn't understand what was important to the business. The most effective security leaders aren't just technical experts, he tells Ben, they're business translators who understand that at the core of every decision lies human motivation.
Michael discusses his evolution from pure technical execution to leadership through strategic energy management rather than time management, scheduling his calendar around the types of thinking required rather than random meeting distribution. He also shares his hiring methodology: he gives candidates real problems, not to test what they know, but to observe how they approach what they don't know, because the questions people ask reveal more about their leadership potential than their technical answers.
Stories We’re Telling Today:
- How missing a security breach despite having day-one intelligence taught the critical importance of understanding business context.
- The evolution from hands-on keyboard work to leadership through energy management rather than time management.
- Building trust and credibility in high-stakes environments by demonstrating curiosity and humility.
- A hiring methodology that evaluates how candidates think and approach unknown problems rather than testing existing technical knowledge or credentials.
- Balancing deep technical expertise with leadership responsibilities through a structured 80/20 approach where leaders handle strategy and validation while teams execute core work.
- Why understanding human motivation and business drivers creates more effective security outcomes than purely technical approaches.
- The transition from individual contributor to leader requires fundamental shifts in what defines success and personal value creation.
- Mentoring approaches that build foundational understanding from assembly language up.
Too busy; didn’t listen:
- Michael's team missed a major breach despite having day-one intelligence because they didn't understand the business context, fundamentally changing his approach to security leadership.
- Michael's hiring process focuses on how candidates think through unknown problems rather than testing technical knowledge, revealing leadership potential through question patterns.
- Energy management trumps time management for leaders — Michael clusters similar meeting types together rather than randomly distributing them throughout the week.
- Building trust in high-stakes environments requires demonstrating curiosity and humility rather than asserting technical superiority.
Skip to the Highlight of the episode:
[25:23-25:42] “Another thing I've found to help me manage that is not managing my time, but manage my energy. So in the past, it'd be really hard to contact switch where I'm on one meeting, where I'm doing sales for two to three meetings, then I'm in three deep technical meetings, and the first one or two, I'm like, wait, my mind is not there just yet..”
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