Skip to main content

3 posts tagged with "Decision Making"

Writing about decision quality, evaluation frameworks, choice architecture, and avoiding analysis paralysis.

View All Tags
Prompt Fragility: Why Your AI Workflows Break When Models Update

Prompt Fragility: Why Your AI Workflows Break When Models Update

· 11 min read

You built a workflow that works. A prompt that produces clean, structured output. A pipeline that runs daily. A system prompt that keeps the assistant on track across hundreds of interactions.

Then the model updates. Nothing dramatic — no announcement, no changelog entry that affects you. Just a quiet weight tweak in layer 37.

Your output format shifts. The structure loosens. Edge cases that were handled cleanly start leaking through. The workflow still runs — it just produces subtly worse results, and nobody notices for two weeks.

This is prompt fragility: the hidden coupling between your workflow and a specific model's behavior at a specific point in time. It is the most under-discussed risk in AI-augmented work, and it gets worse as you build more dependencies on AI output.

This essay maps why prompt fragility exists, why it compounds as you scale, and a practical resilience framework for building AI workflows that survive model changes without silent degradation.

The Autonomy Spectrum: A Practical Framework for Deciding What to Delegate to AI

The Autonomy Spectrum: A Practical Framework for Deciding What to Delegate to AI

· 15 min read

The language around AI is drifting toward a single word: agent. Every major lab is shipping "agentic" features. Every startup pitch includes autonomous workflows. The promise is seductive — describe what you want, and the machine handles the rest.

But autonomy is not a switch. It is a spectrum. And treating it as binary — either you do the work or the AI does — leads to two symmetrical mistakes: delegating too little, leaving productivity on the table, and delegating too much, ceding judgment you cannot afford to lose.

This essay builds a practical framework for navigating the autonomy spectrum. It is not a taxonomy of AI products. It is a decision tool for deciding what to hand off, what to supervise, and what to keep — organized around a single question: what breaks if the AI gets it wrong?

Decision Debt: When AI Research Produces More Options Than You Can Evaluate

Decision Debt: When AI Research Produces More Options Than You Can Evaluate

· 13 min read

Every new AI capability is sold as a way to make better decisions.

Better research. Better comparisons. Better summaries. Better recommendations. The pitch is consistent: give the AI more data, more context, more edge cases, and it will surface the right answer faster than you could on your own. The tools get better every quarter, and the pitch gets louder.

There is a quieter problem that almost nobody talks about. When you make research cheaper, you do not just get better answers. You get more questions. More leads. More options. More paths to evaluate. Every AI-assisted research session that used to take a day now takes twenty minutes — and generates five times as many things to think about.

The bottleneck shifts. It used to be finding enough information. Now it is deciding which of the things you found actually matter.

I call this decision debt: the accumulating backlog of options, leads, and research threads that your AI pipeline has surfaced but you have not yet evaluated. It compounds silently. It shows up as a feeling of being busy without making progress. And it is one of the most underdiagnosed failure modes in AI-augmented work.