The Legal Data Intelligence Podcast with David Cowen (Episode 28)

In this episode of Careers and the Business of Law: The Legal Data Intelligence Series, host David Cowen speaks with LDI architect Stacy Lettie, chief of staff to the general counsel at Organon; LDI founding member Scott Milner, a partner at Morgan Lewis; and James Vinson, senior director of eData at Morgan Lewis.

This episode, inspired by a panel discussion at Legalweek 2026, explores why design thinking remains critical in an AI-driven legal landscape. It emphasizes slowing down to clearly define problems before jumping to solutions, especially amid pressure to adopt new technology. A human-centered approach — prioritizing people, process, then technology — is key.

To bring this to life, the group briefly gamifies the discussion with a simple scenario: being told to plan a vacation with a fixed budget. What seems straightforward quickly reveals deeper questions — why take the trip, what outcome matters and what constraints actually define success?

The exercise underscores a central point: The real challenge isn’t choosing a destination — it’s defining the problem itself.

Listen to the full episode and read a partial transcript below.

David Cowen: Scott, your panel at Legalweek was incredibly well received. Why do you think it resonated so much?

Scott Milner: Because it was practical. It wasn’t consultant-speak or buzzwords—it was real-world application. We focused on human-centered problem solving, sharing how we actually use these tools—sometimes without even realizing they were part of design thinking. That authenticity really resonated with the audience.

Stacy, you mentioned Simon Sinek’s book “Start With Why”. How does that connect to this moment that we find ourselves in legal?

Lettie: Yeah. I think about a year ago, all our conversations were very AI-focused—what it can do, how exciting it is. And people were being told: “Go get AI. Implement AI.” But there wasn’t enough thought behind why. So now we’ve taken a step back. Technology is great, but if you don’t have a problem, it’s just a shiny tool. We’re now redefining: what’s the problem? How do we solve it—maybe even without technology first? Then we go look for the right tool. And honestly, people are overwhelmed. There are hundreds of legal tech vendors reaching out constantly. Most people don’t know where to start—and are too embarrassed to admit it.

Let’s say we all want to go a vacation. There are four of us in the group. We all want to go on vacation. Ready, set, go. Where are we going? How are we going to get there? What’s the problem? So let’s start with, as Stacy said—what’s the problem we’re trying to solve here?

Vinson: We want to go on vacation. Let’s go on vacation, everybody. There are four of us in the group. We all want to go on vacation. Ready, set, go. Where are we going? How are we going to get there? What’s the problem? So let’s start with, as Stacey said—what’s the problem we’re trying to solve here?

Cowen: Here’s how I’m feeling: my boss came to me and said, “Here’s $10,000—go spend it on vacation.” Which is like: here’s $1,000,000—go spend it on AI. That’s the parallel I’m trying to draw. I didn’t wake up wanting a vacation—my boss said I had to spend the money.

Milner: How long did he give you for the vacation?

Vinson: And I know this is tough because it’s your boss—but did you ask your boss why?Why do you have to spend $10,000 on a vacation?