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Sarah O'Keefe

Things Sarah Says on Podcasts

Where to Find Them

Sarah O'Keefe has been a guest on Content Strategy Insights (2 times) and Pragmatic AI with Matt Stauffer .

Recently: “Why AI Fails at Technical Documentation (and How to Fix It)” on Pragmatic AI with Matt Stauffer (November 2026); “Sarah O'Keefe: AI in Technical Communication and Content Strategy” on Content Strategy Insights (November 2023); “Sarah O'Keefe: The Evolution of Technical Content Strategy” on Content Strategy Insights (March 2023).

What They Said

Matt Stauffer asked for her most controversial take on AI in the closing speed round. She says companies adopted AI hoping for savings, and now none will be the first to pull back.

Pragmatic AI with Matt Stauffer · 2026-11-04 Permalink → Listen →
Pragmatic AI with Matt Stauffer Around 41:32 into the episode
Sarah O'Keefe

Honestly, whichever one is lying in front of me, I don't care. They're all terrible.

Matt Stauffer

Okay. Wow. You are the first person who's answered that way. I'm not supposed to comment on your answers here as a speed round, but wow, I'm fascinated. All right. Second question. Have you ever cussed out an AI?

Sarah O'Keefe

No, I point and laugh a lot and take screenshots and share them. You know, when you ask the AI Fails question, this is the experiment I would ask people to do. Ask the AI Fails question about something that you are an expert in. Maybe it's knitting, maybe it's video games, I don't know, something, right? Ask it a question. Nearly always the first answer you get is pretty good, and then ask it for more details. And as you go down that rabbit hole, it'll get worse and inaccurate. Okay. And then ask it a question about something you don't know anything about and do the same thing. And notice that as you go down the rabbit hole, you think it looks okay.

Matt Stauffer

Yeah.

Sarah O'Keefe

And then think about that carefully.

Matt Stauffer

That's so good. I'm going to make my kids do that. Thankfully, my kids don't do a lot of AI, but still I'm like, I need the baseline understanding, you know, about that. All right. What is one pro usage of AI more people should be using?

Speaker names come from our own diarization. The position is estimated from where the line sits in the episode.

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