AI’s got everyone thinking legal work will become cheaper, eventually. But is that belief grounded in reality? Tim Fox is not so sure. In this episode of Between the Briefs by Steno, Adrian Cea and Joe Stephens sit down with Tim, Chief Data and AI Officer at Ogletree Deakins, to unpack what AI adoption actually looks like inside a major law firm. Tim breaks down why legal AI adoption is notoriously difficult, the hidden maintenance costs of building tools in-house and why the real value lies in superior work quality rather than simple cost cuts.
Everyone wants AI to make legal cheaper. But what if that’s the wrong promise?
In this episode of Between the Briefs by Steno, Adrian Cea and Joe Stephens sit down with Tim Fox, Chief Data and AI Officer at Ogletree Deakins, for a sharp, practical conversation on what AI adoption really looks like when you are trying to scale it across a large law firm.
What You’ll Learn:
- Why build vs. buy is rarely as simple as “building is cheaper”
- How internal tools create long-term support, maintenance and upgrade costs
- Why legal is not a rational economic actor when it comes to technology adoption
- How firms can measure adoption through actual use and attorney feedback
- Why shadow AI, hallucinations and privilege risks make governance non-negotiable
- How peer-to-peer learning moves lawyers faster than another mandatory webinar
- Why law schools need to teach AI literacy before students arrive at firms
- Why AI may increase quality, capacity and profits without reducing legal costs
This episode gets into the messy middle of legal AI: not the hype, not the doomsday predictions, but the actual work of making attorneys use tools responsibly, strategically and well.
Highlights:
00:00 Introduction
01:17 Tim’s Journey From Technology to Law
04:01 How Legal Tech Led to “Legalmation”
06:21 The Build vs. Buy Question in Legal AI
09:46 Why Legal Tech Vendors Struggle to Sell to Law Firms
10:30 Legal Is Not a Rational Economic Decision-Maker
14:41 How Vendors Should Actually Pitch Lawyers
18:50 What a Chief Data and AI Officer Really Do
19:02 Scaling AI Strategy Across Ogletree Deakins
23:36 Why Product Demos Beat Pitch Decks
26:59 How Tim Measures AI Adoption
29:00 Balancing Leadership With Hands-On Innovation
31:28 What Law Schools Are Getting Wrong About AI
36:03 Building AI Governance at Scale
39:12 The Hallucination Risk That Keeps Firms Awake
42:52 Why Peer-to-Peer AI Education Works
46:39 Tim’s Hot Take: The Truth About Legal AI Costs
48:25 Closing Thoughts
Quotes:
- “Building it yourself isn’t always cheaper. It’s not always easier. It’s almost never faster.”
- “Legal is not a rational economic actor. You can have the best tool, the best solution out there, and attorneys can still say, no, we don’t want it.”
- “Show me your product. I don’t want to just see your PowerPoint.”
- “I don’t think anybody has cracked change management in law firms, and AI is change management.”
- “AI doesn’t always save time. It makes the work better and it allows you to do more.”