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Derek Featherstone

Accessibility × AI Strategist & Builder


Thinking out loud about accessibility, inclusion, and AI — observations, early reads, works in progress, delivered to your inbox.

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Jun 12

I made AI build the same modal 2,340 times. Here's what I learned.

Last time, I left you with a question I couldn’t answer cleanly: how do we build a human-centered, AI-driven accessibility model that keeps lived experience at its core? The truth is… in order to answer THAT question, I need to be able to answer a lot of other smaller questions first. And in order to do THAT, I’m going to get under the hood and figure out what AI does do well, where it fails, and learn how to shape it towards the right outcome. And so began my experimental AI & accessibility...

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May 20

When roles collapse, so does judgement.

Apr 30

What I learned from office hours conversations

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