After six months of installing AI systems inside other law firms, plus a couple of years running one inside my own, I can tell you where lawyers actually get stuck. It is not using the AI. Once the system is built, talking to it is the easiest part of the job. You type a sentence. It does the work. You review it.

The part that breaks people is setup.

The panicked emails taught me this

When I first started working with firms, I sent a tidy email before our first session: here are the things to do to set up your Claude before we start. Reasonable. Organized. A checklist.

What came back were panicked calls and emails. Some version of: I have no idea what this means, I feel incompetent, maybe this isn’t for me.

These were not people who struggle with hard things. They were trial lawyers and mediators who run businesses, manage staff, and handle the worst weeks of other people’s lives. They were stalling on folder permissions and connector screens. The vocabulary is new, and lawyers are trained to be afraid of doing something wrong. Put those together and a short setup turns into weeks of avoidance.

The owner has to understand the build

I hold one position firmly. Every law firm owner needs to understand how their AI is set up and why. You do not hand your firm’s brain to someone else and stay in the dark about what they built. If a vendor or consultant installs a system you can’t explain, you don’t own that system. You’re renting it, and I’ve written about why renting your own firm’s knowledge is a bad trade.

Understanding the build means you know what your AI can read, where it saves things, what rules it follows, and what it is not allowed to do without asking. That’s the same level of understanding you’d want about any employee with access to your client files.

The owner does not have to install it

Here’s what changed my approach. Asking lawyers to do the installation themselves was creating more problems than it solved. They got so buried in the setup steps that they lost the big picture of what we were building and why.

So with a few of the firms I coach who were struggling, I stopped sending checklists. I said: give me an hour on your computer. Go away. Let me get the basic stuff done.

Once the foundation was in, the stress went with it. They could see a working system and learn it by using it, instead of learning it by configuring it. Understanding came faster, not slower, because they were learning on something that already worked.

Different firms, different starting points

Not everyone wants the same thing, and that’s fine.

• Some owners just want it to work. Build it, show them how to drive it, and get out of the way.
• Some want to know how to build it themselves. They want to see every step and eventually make their own changes.
• Most are somewhere in between, and where they land depends on their tech comfort, their budget, their time, and frankly their personality.

I run this the way I’ve always run my law firm: lots of options, so the engagement fits the person instead of the other way around. What doesn’t change is the destination. Every firm ends with a system the owner understands and controls.

If you’re stuck right now

If you’ve opened Claude, stared at the settings, and closed it again, you are not behind and you are not bad at this. You hit the hard part first, which is where everyone hits it.

Three things that help:

1. Separate learning from installing. You can learn what the system does by watching it work. You don’t have to learn it by building it.
2. Get hands-on help for the first hour. A screen share with someone who has done it fifty times beats a week of tutorials.
3. Start with one real file. The moment you see your AI read an actual case folder and tell you something useful, the setup stops feeling abstract.

AI for law firms is a firm-management project before it’s a technology project. I wrote about that in data in, data out, and it’s the reason I call this coaching instead of installation.

Want to see it on your own files? Open Office Hours run every Friday from 2:00 to 3:00 PM ET, and any lawyer or paralegal is welcome. Join on Zoom. If you’d rather map out your firm’s build one-on-one, book a custom build strategy session.