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Learn why you can’t eliminate technical debt until you tackle executive debt—and get the playbook for spotting it before it sinks your security program. Decisions made (or not made) in the boardroom create hidden liabilities that no patch cycle can fix. Drawing on audits of 400+ companies and his new book Executive Debt, Mark Dallmeier explains how to trace risk back to leadership blind spots—and how security teams can drive change without getting “shot as the messenger.” Key takeaways Executive Debt vs Technical Debt – how short-term, ego-driven choices create long-term cyber-risk. Common executive-debt patterns – risk avoidance, single-view leadership, siloed communication. Debt-Sherpa exercise – an in-session game that maps debts to practical fixes. Influence tactics – turning business impact, revenue loss, and personal coaching into catalysts for change. Free toolkit – Excel scorecard, heat-map spider chart, and survey to measure executive debt in your org. 00:00 Speaker introduction & background 00:20 Topic overview: technical & executive debt 02:04 Defining executive debt vs technical debt 04:00 Understanding risk creation & decision impact 05:10 Accountability gap: why executive debt persists 06:01 Visualizing exec debt: resistance to change 07:28 Interdependence: executive debt & technical debt 12:54 Introducing the Debt Sherpa game 14:09 Debt Sherpa gameplay: pick your risk card 23:13 Game debrief & self‑assessment overview 24:10 Closing reflections & key takeaways 24:40 Q&A session begins #ExecutiveDebt #technicaldebt #CISOLeadership #cactuscon13 #riskmanagement