Hi Reader
Most conversations about AI are about what it can do.
Very few are about who pays when things go wrong.
This week on Reframing Perspectives, I sit down with Catharine Montgomery — Founder and CEO of Better Together Agency, creator of TogetherAI, and one of the most important voices in the country on AI bias and inclusive technology. Catharine has spent the last several years asking — and answering — one quietly radical question:
Who bears the cost when the systems we build get things wrong?
Her answer isn't a moral position. It's a structural one. She calls it born-inclusive technology — building with diverse voices from day one, rather than auditing for bias after the harm is already done. And the communities already overlooked by every previous system are the ones who can't afford to be overlooked again.
A few of the moments we sit in:
- The mammy moment — the day she asked ChatGPT to generate content and watched it return a full historical stereotype, and what it taught her about who needs to be in the room
- Why AI doesn't go neutral — it reverts to how it was originally trained (and the Othello reference that names it: I am not who I am)
- The annual Biases in Generative AI survey — the first consumer-focused study of its kind from a communications agency
- Inside TogetherAI: a private AI platform built for nonprofits and mission-driven organizations, trained only on a client's own voice and values
- Why asking for help is one of the strongest things a leader can do
Catharine also opened up about what building all of this has actually cost her. She brought a rare honesty to this conversation, and it stayed with me long after we stopped recording.
A question to sit with this week:
If someone asked you what your work has actually cost you — and whether it's been worth it — what would you say?
