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Trust, Risk & Governance

AI & Emerging Technology

The Context Between the Clicks

AI agents use interfaces designed for people who bring context and learn through experience. What happens when they arrive without either?

AI & Emerging Technology

What If We Can't Keep Up?

Chicago's Deep Tunnel offers lessons for investing in AI defense, finding bottlenecks, and adjusting when future demands exceed our plans.

AI & Emerging Technology

What Kind of Fires Does AI Start?

Alex Cannella applies familiar problem-solving methods to active AI incidents, smoldering problems, and conditions that could fuel future failures.

AI & Emerging Technology

Digital Pair Therapy

Use disagreement with a coding agent to uncover missing context, preserve decisions, and improve how you work together.

AI & Emerging Technology

Kirk, Raccoons, and the Trouble With Rules

Kirk, raccoons, and AI agents offer a humorous look at how persistent learners discover gaps between intended rules and the possibilities a system actually permits.

AI & Emerging Technology

Can You Recover Your AI Work?

Backup copies are a starting point. Recovering AI work also means restoring the conversations, instructions, connections, and context that make a project usable.

AI & Emerging Technology

Why Aren’t Skills Namespaced?

Understand how flat skill names create ambiguity, and reduce friction and risk through source tracking, reviewed revisions, and deliberate updates.

AI & Emerging Technology

Can I Trust an LLM With Business Math?

How to trust AI-assisted business analytics by defining the metric, inspecting the calculation, and following the number back to its source.

AI & Emerging Technology

Human-Shaped, Not Human

Human-shaped model behavior raises choices about usefulness, safety, and the friction people face when those patterns are suppressed.

AI & Emerging Technology

AI Is Only Magic When We Close Our Eyes

When AI systems behave in unexpected ways, senior leaders need to examine the objectives, tools, permissions, monitoring, and organizational capacity surrounding the model.

AI & Emerging Technology

The Race Condition with Reality

A systems-thinking article explaining why AI adoption feels chaotic when capability, understanding, governance, resilience, human adaptation, and scale all move at different speeds.

Systems Thinking

Resilience Debt

A reflection on how convenience, efficiency, and automation can quietly remove the alternate paths an organization needs during disruption.

AI & Emerging Technology

Where Second Brains Break

A practical article on stress-testing AI-powered second brains for retrieval, source authority, calibration, and safe operating boundaries.

AI & Emerging Technology

Where Is the Panic Button?

A practical reflection on why every GenAI user should know how to stop an agent before handing it work.

AI & Emerging Technology

The Coverage We Forgot

AI-accelerated delivery needs a broader definition of coverage before teams can release with confidence.

AI & Emerging Technology

AI Reaches Far Beyond Its Users

Like many technologies before it, AI is spreading into more and more of the systems that shape modern life. History reminds us that technologies often become deeply embedded in society long before we fully understand their long-term consequences.