Wrong question.

The better question: why does this keep happening to lawyers who’ve been careful their whole careers?

The old deal with technology

For decades, tech taught lawyers a simple rule: if something’s wrong, you’ll know.

• The software would crash

• The file wouldn’t open

• The error message would pop up

• Spellcheck would flag a typo with a red squiggle

• Something would freeze, stall, or clearly refuse to work

Lawyers learned to trust those signals. If the tech didn’t blow up, it probably did the job. If it did blow up, they’d feel the friction right away — and often stop using it out of frustration.

That pattern held for 30+ years. Word processing, email, e-discovery, document management, cloud storage, e-filing. Broken tech looked broken.

AI doesn’t play by that rule

AI flips the script. When it’s wrong, it doesn’t warn you.

• The output is clean

• The formatting is perfect

• There are no typos

• The reasoning sounds measured and sensible

• The citations look exactly like real citations

Nothing in the response says, “Hey, I made this up.” Because nothing in the system knows it did.

It’s a mirage. And it’s going to keep tripping up lawyers — especially the ones who aren’t using AI often enough to spot the seams.

The perfect storm

Here’s the setup that catches even careful lawyers:

• They’re under time pressure (when aren’t they?)

• They don’t use AI often enough to have calibrated instincts yet

• They ask a legal question and get a polished, confident answer

• The answer passes every pattern-recognition check they’ve built up over a career

• They don’t have the minutes to verify every citation

• So they go with it

They’ve heard the warnings about hallucinations. Those warnings just don’t feel relevant in the moment, because the output looks too good to be wrong.

What to do

You can’t un-condition decades of experience with old tech. But you can build a new habit:

• Treat every case citation from AI as unverified until you check it in a real database

• Do the check before the draft leaves your hands — not after

• Don’t rely on AI’s confidence level. It has no idea what it doesn’t know.

• If you’re rushed, that’s exactly when to slow down on citations. AI is at its most seductive when you have the least time to vet it.

The lawyers who’ll get burned aren’t the reckless ones. They’re the ones whose instincts from the old tech world are still running the show.

Adjust your instincts. The rules changed.

;-)

Ernie

P.S. In the Inner Circle, we practice spotting AI’s failure modes together — so you’re not relying on old instincts that don’t apply anymore.

→

https://innercircle.ernietheattorney.net/

Early on, AI was a tool. You gave it a command, it did a thing. Summarize this. Rewrite that. Clean up the formatting. Useful, but basic.

That’s not where we are anymore.

What it can actually do now

I had Claude (the latest model) analyze my website and a lead magnet page recently. It didn’t just check grammar or spot typos. It flagged things that were off-brand in ways I’d have to work hard to explain to a new employee.

Some of what it caught:

• Tiny copy issues most humans would miss — a stray space before an em dash, a lowercase “l” that was actually the number “1”

• Bigger strategic issues about positioning and tone

• Subtle places where the writing drifted from how I actually sound

Was it perfect? No. A few suggestions didn’t match my sensibility. But when I told it I’d made a change, it registered that and updated its own notes. Next time, it remembered.

The employee analogy

Think of AI as a capable new hire. Smart, fast, can spot things you’d never notice. But still a new hire.

A new hire needs guidance. They need to know how you think, what you care about, why something matters. They need dialogue — not just commands.

AI works the same way.

Who’s going to struggle with this

My hunch, based on watching people try to adopt AI over the past few years: some people have never been good at giving guidance. They’re trapped in their own perspective. They can’t imagine how someone else thinks. Delegating to a human employee has always been hard for them, and their employees usually don’t last long.

I suspect those same people are going to struggle with AI. Because AI now demands the same skills:

• Explaining what you want clearly

• Giving examples, not just rules

• Correcting it when it’s off, instead of giving up

• Being patient enough to have a real back-and-forth

If your style is to bark vague orders and expect perfect results, AI will probably disappoint you. Same as humans do.

What this means for lawyers

Solo and small-firm lawyers have an advantage here. You’re already used to doing everything yourself, which means you know your own standards. You know what “good” looks like.

The question is whether you can put that into words. Whether you can guide.

That’s the skill that matters now. Not prompt engineering. Not picking the right tool. Just the basic human skill of explaining clearly what you want and why.

;-)

Ernie

P.S. In the Inner Circle, we practice this together every week in the AI Lab — working through real tasks, refining how we talk to AI, building the skill of guiding it.

→

https://innercircle.ernietheattorney.net/

They’re not behind. They’re just missing a piece of infrastructure that big firms have, and small firms don’t: an R&D department.

What R&D is

In a big company, someone gets paid to test new tech and report back. They try tools. They compare notes. They figure out what improves operations and what’s just no…

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“Writers must therefore constantly ask: what am I trying to say? Surprisingly often they don’t know.”

That was written about …

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So you ask around. You hire a consultant. You talk to the IT person someone recommended. And you get advice that sounds reasonable.

But here’s the thing nobody warns you about: the people giving you tech recommendatio…

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ChatGPT won in a landslide — 57%.

No surprise there. It’s the most well-known, most accessible option. It’s where most people start.

But the comments told a more interesting story.

The “all-in on one tool” trap

One lawyer wrote: “I’ve been all in with ChatGPT and not dabbling w…

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Paperless offices. Cloud systems. Automation. Now AI.

Every wave looks different on the surface. Underneath, the resistance is always the same.

It’s not what you’d expect.

It’s not “I don’t understand it.” Most lawyers are smart enough to learn any tool.

It’s not “It’s too expensive.” ChatGPT cost…

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But if I’m honest, the single technology change that made the biggest difference in my own practice wasn’t AI.

It was documenting my processes.

I know. Boring.

Nobody gets excited about writing down how they onboard a client or how their VA handles phone inqu…

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The lawyers getting the best results from AI aren’t the ones with the fanciest prompts or the most expensive tools.

They’re the ones who treat AI like a new associate.

What that means in practice

When you hand work to a new associate, you don’t say “write me a brief.” You say:

• Here’s the issue

• Here’s th…

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Which one should lawyers believe?

The debate

Allie K. Miller broke down both reports in her newsletter. Here’s the short version:

The Citrini Report (doomer view): AI will cause intense disruption by 2028. White-collar workers face the biggest risk. Institutions won’t ada…

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His clients look a lot like solo and small firm lawyers: knowledge workers running lean operations, juggling client work with everything else, struggling to stay consistent on the non-billable stuff t…

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You don’t need a leap. You need a stepping stone.

The real problem

Hourly billing is convenient for firms, not clients.

Clients don’t want your minutes. They want clarity, protection, and momentum. They’ll happily pay for those—if you deliver them quickly and confidently.

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Here’s why NotebookLM matters to practicing lawyers.

Where NotebookLM shines

• Research and synthesis: pulls from…

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That works on law school exams and with hyper‑rational judges.

It works less well with real people.

Beyond mere logic

Rory Sutherland observed:

Not everything that makes sense works. Not everything that works makes sense.

Consider th…

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It was never about client value. It was about internal management.

Here’s the short history—and the practical takeaway for your firm.

Before hours: outcomes, relationships, fixed fees

For most of legal history, lawyers charged for judgment and results, not minutes.

• Fixed fees…

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There’s a better way: record once, let others watch when it fits their workflow.

What Loom is (and why it matters)

​Loom​ lets you capture screen + voice (+ camera if you want) and share an insta…

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Zoom and Teams can record every call by default.

So the question isn’t can you record—it’s should you, and under what conditions?

Here’s what lawyers need to know before they record conversations.

Why Lawyers Record (and Why It’s Tempting)

• Better than scrib…

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The real problem

Lawyers often make snap judgments about tools—“good” or “bad.” That’s a trap.

• Tools aren’t universally good or bad; they’re useful for specific jobs.

• A few tools are easy wins.…

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• Agents that do multi‑step work (not just drafts)

• “Context engineering” + memory that lets AI work inside your files and systems

• Clients finding lawyers through AI assistants, not Google

If you want mo…

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Here’s the list that I shared with my online lawyer community of tech that consistently moves the needle—for communication, automation, and sanity.

Core stack (start here)

1. ​Zoom​ — video meetings and ​online workspaces​ (about $150/year).

2. ​ChatGPT (Paid)​ — your $20/mont…

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