Adoption First: Designing a Legal AI and Data Strategy That Sticks episode artwork

EPISODE · May 29, 2026 · 45 MIN

Adoption First: Designing a Legal AI and Data Strategy That Sticks

from Overruled by Data · host Tom Baldwin

What does it actually take to get 70-80% of attorneys using AI every month? In this episode, Tim Fox, Chief Data and AI Officer at Ogletree Deakins, makes the case that adoption isn't a byproduct of a great tool - it's a strategy in itself.Tim shares his journey from mailman to litigator to C-suite AI strategist, and breaks down how Ogletree Deakins moved past the hype cycle to hit usage numbers most firms only dream about. His thesis: if people aren't using the tool, it wasn't worth building. That philosophy shapes everything from how they evaluate vendors to how they staff their AI program.He explains why AI requires dedicated people (not just platforms), why early adopters can only carry you so far, and why the buy-vs-build debate misses the real question - which is whether anyone will actually show up to use what you deploy. Tim also gets honest about what attorneys really think about time savings, and why "five hours saved" doesn't land the way technologists expect it to.Timestamps:(00:00) Intro(01:50) Mailman transitioning to legal AI leader(06:09) Transforming firm data into strategic advantage(07:45) Settlement data extraction insights(09:09) Leveraging external data for competitive advantage(10:32) Four key barriers to AI adoption(15:31) Training staff for effective AI usage(18:55) Buy and build AI strategy explained(21:33) How to run vendor demos successfully(25:36) Managing legal tech ecosystem sprawl(36:27) Regulatory data insights for labor law(39:10) Sequencing data strategy and governanceConnect with our guest:Tim Fox on LinkedIn: https://www.linkedin.com/in/tim-fox-legal/ Learn more about Ogletree Deakins: https://ogletree.com/ Connect with Tom:Tom Baldwin on LinkedIn: https://www.linkedin.com/in/tombaldwin/ Learn more about Entegrata: https://www.entegrata.com 

Episode metadata supplied by the publisher feed · Published May 29, 2026

Embed this episode

NOW PLAYING

Adoption First: Designing a Legal AI and Data Strategy That Sticks

0:00 45:14

No transcript for this episode yet

We transcribe on demand. Request one and we'll notify you when it's ready — usually under 10 minutes.

No similar episodes found.

No similar podcasts found.

Frequently Asked Questions

How long is this episode of Overruled by Data?

This episode is 45 minutes long.

When was this Overruled by Data episode published?

This episode was published on May 29, 2026.

Can I download this Overruled by Data episode?

Yes. Use the download control on the episode player to save the publisher-provided media file.
URL copied to clipboard!