I should have asked AI to argue against me

Field Note #1 — Week 3 back as GC at Worksome

Three weeks back into my role as General Counsel and VP of Compliance at Worksome. I'm building an AI-first legal function, and I'm sharing what I'm learning as I go. This includes the wins, the mistakes, and the stuff nobody's talking about.

Here are three things on my mind this week:

1. Flip your prompting perspective

A few of us were working through a genuinely complex legal question this week — the kind that feels like a law school exam. We had ChatGPT, Gemini, Wordsmith, and Claude all open. Everyone prompting, everyone asking questions with the same set of facts.

Here's what I noticed: I was framing everything from my legal risk perspective. And AI was giving me exactly that answer back.

When I flipped it, came at the same question from the business's perspective, asked AI to prove the business's case, an exception to the rule surfaced that wasn't coming out in my prompting or analysis at all.

AI delivers what you're looking for. That's the thing. So if you only ask it to confirm your risk assessment, that's all you'll get.

Try coming at it opposite to what you think the outcome should be. Stress test it. Poke holes in that position. And then verify by going to direct sources — which is what we did.

2. Sometimes you don't want generative AI

At Worksome, I'm building out worker classification. We already had a deterministic tool built pre-AI, and I've been working through whether to replace it with gen AI.

The answer? No.

Gen AI needs verification. For classification, you need defensibility, control, and explainability. We're using weighted questions, which is better because we can control it and it creates a much more defensible position.

Here's the bigger point for legal leaders: understand how different types of AI work and when they should or shouldn't be applied.

Not everything needs gen AI. The question that should drive your decision is simple — is 80–90% accuracy good enough for what you're doing, or do you need 100%?

3. Querying our own codebase

One thing that's been really cool coming back is seeing how much AI has changed how our engineers work. We've now set it up so we can query our codebase and get information directly from our platform.

I can ask questions about our code and get answers — which is powerful on its own. But what I'm trying to do now is connect that to Wordsmith through MCP, so that when I'm making legal recommendations or risk assessments, I can pull actual product data to back them up.

We're not just doing this for legal — we're rolling it out across the company so people can make genuinely data-backed decisions. I'll share how this goes as it unfolds.

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Welcome to Fields Notes from a GC

I’m Laura Jeffords Greenberg. I'm the General Counsel and VP of Compliance at Worksome, and I'm building an AI-first legal function.

This is where I share what that actually looks like,week by week, in real time.

Not theory. Not predictions about how AI will change legal "someday."

The actual work: what I'm building, what's breaking, what tools I'm testing, what's working, and what I got wrong.

Why I'm doing this

I spent the last year at Wordsmith AI, where I built their Academy and trained over 3,000 legal professionals across the UK, Europe, and the US on how to implement AI into their legal practice. Before that, I built the product counsel function at Unity Technologies and made their first legal operations hire.

Every time, I was building something new, figuring it out as I went, learning by doing.

What I kept hearing from other legal leaders was the same thing: "I know AI is going to change how we work. I just don't know where to start."

So I'm showing you where I'm starting. Right now. In public.

What to expect

Every week, I'll share what's on my mind — usually three things I learned, noticed, or got wrong that week. Short reads. The kind of stuff I'd tell you over coffee if you asked me how the build was going.

If you're a GC, a legal ops leader, or an in-house lawyer trying to figure out how AI fits into your function — this is for you.

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And if you ever have questions or want to follow up on something I've shared, hit reply. I read everything.

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