The one security practice most teams skip: tabletop exercises with Jeff Fields

Most security teams aren’t underprepared because they lack tools, they’re underprepared because they haven’t rehearsed what happens when humans, systems, and pressure collide. Jeff Fields says that the single most important thing teams can do is run tabletop exercises.

Fresh off a 20-year FBI career, Jeff explains why the most damaging incidents aren’t caused by “unknown threats,” but by breakdowns inside the organization, alerts going to the wrong people, missing owners, and teams operating in silos. Tabletop exercises expose those weak points early, forcing engineering, HR, legal, leadership, and comms to operate as one security team. The result is a security posture that assumes human error, limits blast radius, and lets teams ship faster with confidence.

Topics Covered

* Why “there’s no separating the digital from the human” in modern cyber attacks

* Nation-state motivations: how PRC, Russia, North Korea, and others target differently

* The “geopolitical layer cake” and why every builder is in it (whether they like it or not)

* Security as a team sport: breaking silos between engineering, HR, legal, physical security, and leadership

* Why basic information sharing is the cheapest “upgrade” most companies aren’t doing

* The Sony hack lesson: when the alerts won’t stop… and someone turns them off

* “Humans be humans”: designing systems that assume mistakes will happen

* Bake security in from the start vs. bolting it on after launch

* Zero Trust explained in plain English and why it can accelerate innovation

* Why table top exercises/war games separate resilient teams from chaotic ones

* Planning for the least likely, most catastrophic scenario (and why it covers everything else)

* Where to get government resources: fbi.gov, dni.gov, and National Counterintelligence and Security Center (NCSC) support for private sector

About Jeff Fields

Jeff Fields is a newly retired FBI leader, most recently serving as Assistant Special Agent in Charge of the FBI’s Counterintelligence Branch in San Francisco, with 20 years of experience spanning counterintelligence, national security, and the defense industrial base including emerging tech and the innovation ecosystem. Now advising VCs, startups, and universities, Jeff brings a rare operator’s perspective on how real-world adversaries move and how builders can design security that supports speed instead of fighting it.

In addition to being a technical advisor, Jeff is also a Senior Fellow of Practice at the Berkeley Institute for Security and Governance where he serves as a “Hacking for Defense” (H4D) instructor. H4D teaches students how to work with the government to rapidly address the nation’s emerging threats and to solve mission-critical problems at the speed of a startup. In his free time Jeff enjoys hiking with his two Belgian Malinois, volunteering with the non-profit Girl Security, or checking out a live opera or hip-hop show.