The Red Team Pressure Test: Using AI to Stress-Test Strategy

Speaker: Doug Langille

Every AI-assisted strategy document carries a hidden risk: the model that helped you write it is also disposed to agree with it. The result is polished prose that confirms existing assumptions, papers over weak logic, and reaches your steering committee looking better than it deserves. Higher Ed IT has enough failed projects. We don't need AI accelerating the pipeline to the next one.

This session introduces the Red Team Pressure Test: a structured adversarial review workflow that forces AI to argue against your plans before implementation does it for you. We've watched well-intentioned IT initiatives collapse under pressures that were visible in hindsight and invisible at approval. Drawing on real examples from IT governance and project planning, we'll walk through how targeted adversarial prompting can simulate critical stakeholders, expose logical gaps, and surface the implementation risks that internal review consistently misses.

The same adversarial framework that pressure-tests a strategy proposal also protects against the subtler failure: AI-smoothed prose that strips institutional voice, local context, and the specific judgment that makes a document actually yours.

This is not a prompt engineering workshop. It's a decision-quality framework that slots into planning processes you already run.

If your institution is using AI to support strategic planning and you haven't built in a mechanism to challenge what it produces, you're not managing risk. You're automating it.

Learning Objectives:

  • A three-step adversarial prompt sequence applicable to any policy brief or project proposal
  • Recognition of the three most common LLM bias patterns that generate false strategic confidence
  • A structured review template ready to use before your next steering committee meeting

Speaker Bio:

Doug Langille (he/him) is Manager of Digital Innovation, Staff Training and Development at Nova Scotia Community College, where he leads Microsoft 365 Copilot deployment, faculty AI adoption, and the eternal institutional question of whether we can just use Excel for this. With 25 years at NSCC and a front-row seat to every wave of workplace technology, he brings a practitioner's honesty to conversations about AI integration and digital change. He publishes Digital Doug weekly on AI in practice, productivity systems, and higher-ed innovation: documenting the experiments, the failures, and the occasional wins. No thought leadership theater. Just the rubber meeting the road.