No Perfect Information: Leading Under Pressure with Jeremy Boss
Jeremy Boss (bio below) has spent much of his career making sense of situations most of us would prefer to watch safely from our couch. China. Afghanistan. Yemen. The Houthis. Gray-zone conflicts. And apparently, dynasty fantasy baseball. After joining the National Geospatial-Intelligence Agency, Jeremy expected years to learn the ropes. Instead, it was basically: Glad you’re here. We have a crisis. Jeremy went on to monitor Chinese military activity, support combat operations in Afghanistan, and work the Yemen-Houthi crisis, where a 12-hour shift could mean 11½ hours of boredom followed by 30 minutes of sheer terror. One of his biggest lessons? When pressure rises, leaders often pull decisions toward themselves. Jeremy believes the better move is frequently the opposite: stay calm, trust the expertise around you, distribute authority, and stop believing the person with the biggest title needs every answer. That thinking led Jeremy to create Black Horizon, where leaders are dropped into live crisis simulations and forced to make decisions with incomplete information and real pressure. Think leadership development without 74 PowerPoint slides and awkward role-playing. Jeff and Jeremy talk about uncertainty, trust, ego, geopolitical risk, decision-making under pressure, and Jeremy’s concept of collective cognition: using the expertise of the entire team instead of expecting one heroic leader to know everything. jeremy boss-jeff Because eventually every leader faces the same reality: You won’t have perfect information. You still have to make the call. This episode is brought to you by... Pelaccio & Partners. Ever wish your company updates could be less “quarterly earnings report” and more “late-night talk show”? At Pelaccio & Partners, we help leaders stay connected to their people as their organizations grow. We create internal podcasts that make leadership communication more human, give employees a voice, and help build a more connected and engaged workforce. Think less corporate broadcast. More conversation people actually want to hear. Whether your employees are across the hall or across the country, an internal podcast can keep leaders visible, employees connected, and important messages from getting buried in the inbox. Curious what one could look like for your organization? Connect with Jeff on LinkedIn or schedule a 15-minute call with Jeff . About Jeremy: Jeremy Boss is the founder of Black Horizon, an experiential leadership training company that puts leaders inside live, unscripted geopolitical crisis simulations to build their capacity for decision-making under real pressure. Jeremy spent 14 years at the National Geospatial-Intelligence Agency, where he worked on grey-zone conflicts in the South China Sea, supported combat operations in Afghanistan, and ultimately led the analytic team tracking the Yemen-Houthi crisis — one of the most consequential regional escalations of the past decade. Before founding Black Horizon, he spent roughly a decade co-running Waymark Intelligence Solutions, designing and delivering geopolitical simulations for intelligence analysts. Black Horizon grew directly out of that experience. After years inside high-stakes crisis work, Jeremy noticed that the skills that mattered most — decision-making under pressure, leading through ambiguity, thinking clearly when information is incomplete — almost never got trained deliberately. They got stumbled into. Black Horizon exists to close that gap. Simulations run inside a proprietary 2035 universe spanning 20+ nations, using a DIME (Diplomatic, Informational, Military, Economic) framework with live human adjudication — meaning participant decisions genuinely cascade and shape what opposing teams face next, with no scripted outcomes to game. Jeremy holds a Master's degree in Government and Politics from the University of Maryland.






