What happens when the plan hits the wall, the clock is running, and nobody's reading the manual? For Michael Gips, that's not a hypothetical: it's Tuesday.
With over 30 years navigating the intersection of security, risk, and leadership, Michael is Managing Director at Kroll, one of the world's foremost global risk advisory firms. He's a Certified Protection Professional, a Chartered Security Professional, and the author of It's Not In the Manual: Real World Leadership For Security and Risk Professionals, a title that, as Dr. John Dentico notes, may be the most honest thing anyone in leadership has said out loud in years. He also writes a monthly leadership column for Security Magazine.
In this episode, Michael pulls back the curtain on what leadership actually looks like when the crisis doesn't follow the playbook, which, as it turns out, it never does. He shares the counterintuitive reframe that has defined his career: great security leaders aren't the "Department of No." They're the "Department of KNOW" know the people, know the processes, know the business deeply enough to be an indispensable partner, not just a gatekeeper.
From the post-9/11 breakdown of public-private trust to the modern reality of perma-crisis (where a ransomware attack, a geopolitical flashpoint, and a natural disaster can land simultaneously), Michael maps the terrain of 21st-century security leadership with clarity, candor, and a wry humor that only comes from having survived enough chaos to find it funny in retrospect.
He and Dr. Dentico also dig into one of the most under-discussed leadership questions of our time: what does it take to develop the next generation of leaders, not just the ones who already look the part?
This is a conversation packed with hard-won insight, zero fluff, and the kind of grounded wisdom that doesn't come from a textbook. It comes from showing up in the room when things go sideways; and knowing what to do next.
0:00 Welcome & Introduction — Who Is Michael Gips?
1:55 From New Rochelle to Kroll: The Creative Roots of a Security Leader
4:00 When the Manual Runs Out — Leading on Principle, Not Plans
7:30 Mission Clarity: The One Sentence That Guides Every Decision
12:30 The Department of KNOW: From Gatekeeper to Strategic Partner
16:30 Building Influence Without Authority — Getting a Seat at the Table
17:30 Post-9/11 Lessons: When Public & Private Sectors Finally Started Talking
20:00 Perma-Crisis & Poly-Crisis: Welcome to the New Normal
23:00 Technology, Privacy & Geopolitics: Even Simple Problems Are Now Global
28:00 Developing the Next Generation: Leaders Who Grow Leaders
32:00 Leadership Is a Process, Not a Personality Type
36:00 Adaptive Leadership: Why One Size Never Fits All
40:00 Embracing Doubt — The Counterintuitive Key to Collaboration
43:00 The Ego Trap: Humility, Self-Awareness & the Ongoing Work of Leading
45:30 What's Next: Michael's Vision for His Second Book
47:00 Closing Thoughts & Farewell
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