
Diagnostic Investigation
Cascade Labs: Diagnosing Organizational Dysfunction
An incoming VP has one morning to investigate cross-functional tension at an AI-pivoting SaaS company before briefing the CEO.
Protagonist
Erin Brennan
Format
Diagnostic investigation
Estimated time
~90 minutes
How this one works
You interview AI characters to diagnose a problem inside an organization, then brief a decision-maker on what you found.
What students practice
- Recognize that organizational problems are often symptoms of deeper structural patterns
- Resist the temptation to diagnose prematurely or propose solutions before understanding the system
- Hold multiple competing explanations simultaneously without collapsing to a single narrative
- Distinguish between interventions that address symptoms vs. structural drivers
- Notice how incentives, information flows, decision rights, and path dependence shape organizational behavior
- Reflect on your own sensemaking process — where you felt certain, where you were wrong, and what you missed
Themes
Organizational DiagnosisStakeholder InterviewsIncentive AnalysisStrategic Communication
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