
Hi there! It’s Heather Stevenson.
Happy Wednesday and thanks for being here! Here’s what’s covered in today’s issue:
The moment I realized AI might be making me a worse lawyer;
Why this matters more than most people are saying out loud;
Four practical strategies to stay sharp in an AI-powered world;
Links you’ll want to read;
And More.
Let’s dive in.

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Deep Dive
Thriving in an AI World (Without Letting It Make You Worse)
A few months ago, I was reviewing a contract.
I fed the document into our AI tool, watched it surface the key terms, flag the risk provisions, and spit out a clean summary. It was useful and incredibly efficient—the tool did exactly what it was supposed to do.
And then I noticed something that scared me.
My eyes had glazed over the actual contract. I hadn't really read it. Not in the focused way I know I need to as a lawyer. I thought I had, in the way you think you're listening to someone when you're actually just waiting for them to finish. The words had passed in front of me, but I hadn't engaged with them. Because I didn't technically need to. The AI had it covered. And that, it turns out, is exactly the problem.
It was a yikes moment.
I work for an AI incubator. We build AI startups. AI is woven into my team's workflows in ways I'm proud of, and our legal work is better for it. We're finding new use cases every week, recovering time, operating at a level that wouldn't have been possible a few years ago. I am not a skeptic. I am a true believer.
But that moment with the contract rattled me. Because I realized that if I'm not careful, all this efficiency could cost me skills and capabilities I've spent years building.
That's what this issue is about.
The Risk Nobody’s Talking About Enough
Most of the AI conversation in legal circles is about adoption: which tools to use, how to use them safely, what policies to put in place for your team. That's all important. We've covered some of it here.
But there's a conversation happening behind closed doors and among friends that I think deserves more airtime. It's the one about what happens to us as lawyers when AI handles more and more of the work.
My worry isn't that AI will get something wrong (though it will, and you should always check).
And it's not about AI taking my job.
It's about what happens to our skills when we stop exercising them.
As we work to automate more of our processes and build out agents, I think about two categories of risk. The first is technical legal skills like the ability to read a contract carefully, spot the thing that doesn't fit, catch the clause that looks standard but isn't. The second is critical reasoning; it’s the ability to engage with a hard problem, think it through, and arrive at a well-advised judgment.
Both require practice and both atrophy without it.
The scary thing about atrophy is that you usually don't notice it happening. The muscle just gets gradually weaker, until one day you need it and it isn't quite there.
What To Do About It
I want to be clear that I'm not suggesting you use AI less. I'm suggesting you use it—and decide when not to use it—more intentionally. Here are four strategies I've been actively trying to build into my own practice.
1. Always take a first stab yourself.
When a complex question lands on your desk, resist the urge to start by asking AI. Take the time to process and think it through. Do the things you used to do, like go for a walk or brainstorm with a colleague. Then sketch an answer before you consult with AI.
This is about keeping the part of your brain that does hard legal thinking in good working order. Using AI to pressure-test your analysis after you've developed it is very different from outsourcing the analysis to AI and signing off on the result. The outcome may look similar. The skill-building is not. (And often, the outcome doesn't look similar for complex problems involving human judgment—that's part of why AI won't replace you any time soon).
For repetitive work, you absolutely can and should use AI. First-pass review of a routine NDA, summarizing a long document against a known checklist, or generating a first draft of a policy you've written a dozen times are exactly what these tools are for. They free you up for the higher-stakes work where your judgment is the whole point.
But when your judgment is the value-add, exercise it.
2. Schedule regular digital detoxes.
This one is simple in concept and harder in practice. Periodically do a task the old-fashioned way—and while you're at it, put the phone down too. Better yet, spend a weekend day without a cell phone, or a week without social media.
To be clear, this one is about more than just closing the AI chat window. I mean stepping away from the screens for a bit. Try going for a walk without a podcast, sitting with a hard problem and a legal pad instead of a laptop, or just letting your brain be bored for a few minutes before it starts doing something interesting.
There's growing evidence that our always-on, always-connected habits are changing the way we think—shortening attention spans, making deep focus harder, training our brains to expect constant input. Fortunately, there’s also evidence that even a short digital detox can undo meaningful amounts of damage (from WaPo: This detox may erase 10 years of social media brain damage, researchers say).
So pick a contract and read it yourself, without feeding it anywhere first. Draft a memo from scratch. Work through a legal question before opening a chat window. And when you do, leave your phone in the other room.
Think of it the way a surgeon still drills technique after years in the OR. Better equipment doesn't mean you let your hands forget how to operate. The skill matters. The practice maintains it. And when something unusual shows up, you want to be the person who catches it.
You don't have to do this constantly. But you should do it regularly enough that your brain remembers what it feels like to do hard, focused work without a shortcut. That's a capability worth protecting.
3. Stay close to the details your agents are handling.
This is the one I think about most as we build out more automation. When an agent is managing a piece of your process, it's easy to stop paying attention to the details of that process. And for a while, that's fine. It's efficient.
The risk shows up later. When something changes or when a new edge case appears. Or when you need to explain to a senior executive why a contract says what it says, and you realize you haven't actually looked at one of those contracts in months.
Periodically audit what you've automated to stay fluent in the process and catch anything that needs adjusting. Know what your agents are doing and why. Keep enough of a handle on the details that you could step in, catch a problem, or explain the logic if you needed to.
You don't want to be the lawyer who can't explain their own contracts.
4. Use AI to learn, not just to execute.
This is one of my unexpected favorite parts of using LLMs.
Instead of just asking AI to produce an output, ask it to show its reasoning. Push back on its conclusions. Ask it to take the opposite position and see how it defends it. If it drafts a contract clause, ask it to explain why it structured it that way, and then ask what the strongest argument against that structure would be.
Treat it like a smart junior associate who needs your supervision, not a vending machine you load prompts into and walk away from.
When you engage with AI this way, you're both gaining efficiency and sharpening your own thinking in the process.
That's good lawyering. It just happens to involve a robot.
The Bigger Picture
I am convinced that the lawyers who thrive long term will both use AI regularly and work intentionally to keep their skills and judgment sharp alongside it.
AI is changing what in-house lawyers are expected to do and how much volume we're expected to handle. But the same things that have always made great in-house lawyers—judgment, credibility, the ability to look someone in the eye and give them an answer they can trust—hold true.
You built those skills over years of doing hard things, making mistakes, and learning from them. They're worth protecting, even when that costs you a little time.
None of what I'm suggesting here means going backward. It means being intentional about how you move forward. Use the tools and embrace the efficiency. Just don't let the efficiency become a reason to stop growing.
The goal is to be a better lawyer in five years than you are today. AI should help you get there, not get in the way.

That’s it for today.
But before you go, here are a few links I think you will enjoy.
Each week, I share content from across the web that will help make your life as an in-house lawyer better. Let me know your favorite.
The NDA That Made Me a Better Lawyer - On my first day back as an in-house lawyer — after a few years away building a company — my new boss handed me a three-page NDA to review. I spent nearly two hours on it...Early in my career, I thought my job was to find every problem. Turns out, cataloging every conceivable risk isn't the same as being useful. Here's what I learned about what it actually takes to get a seat at the table.
GC Communication & Influence in the Boardroom - Adrian Moffatt makes a point that all in-house lawyers need to be aware of: there's a gap between being right and being trusted, and brilliant legal advice gets ignored every day not because the law is wrong, but because the lawyer across the table felt like an adversary instead of an ally. The cheat sheet he's built to close that gap is worth saving.
When Your Colleagues See Your Name in Their Inbox - When your business colleagues see you're calling, what's their gut reaction? If it's dread, that's a problem . . . and it's probably costing you more influence than you realize.
Thanks for reading! Look out for the next issue in your inbox next Wednesday morning.

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