Craig Stanley
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AI trolley problems

Sixty dilemmas about AI at work, in five tracks. Pick the track closest to your job, make twelve calls, then read a short report on where your choices leave you.

How it works

Pull the lever, or don't

  1. Pick a track

    Boards, leaders, operations, agent builders or users. Each track has its own twelve dilemmas and its own six things to score.

  2. Make the call

    Most dilemmas are a lever: pull it or do nothing. The rest are open thought experiments where you choose between two positions. After each one you see what happened, and what would have happened the other way.

  3. Read your report

    An archetype, six scores, takeaways drawn from your own calls and what to put in place first. Print it or copy it. Your answers stay in your browser.

Five tracks · 12 dilemmas each

Choose your track

Question to take awayWhich of these calls is your organisation already making without anyone deciding it?

Inspired by Neal Agarwal's Absurd Trolley Problems. The dilemmas, scoring and reports here are new, written for AI at work.

About me

Craig Stanley

Microsoft AI consultant and technical architect, based in Whitley Bay. Over the last few years I've delivered Microsoft 365 Copilot, Copilot Studio agents, Azure AI Foundry work and governance for UK public sector and financial services organisations.

What interests me is the decision underneath the tool: what it costs, what it risks, and whether a small, transparent model can make it better. I write the methods up here and on Substack so anyone can use them.

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