The 80/20 Principle

Before you put client data into an AI tool, ask these questions

Ernie the Attorney — Fri, 30 Oct 2026 12:01:03 GMT

One of the ClioCon sessions I flagged ahead of time was Privilege, Supervision & AI in the Modern Law Firm. It turned out to be one of the most practical hours of the conference.

The speakers came at it from two sides. Georgia Horstman is a compliance analyst at Clio who works on AI. John Hendricks is a cyber law litigator in San Francisco who’s licensed in California and as a solicitor in England.

AI is a very capable first-year associate

John opened with a framing he credited to Clio’s Ed Walters. Treat generative AI like the world’s most capable first-year associate. Not the best one, the most capable.

It’s fast and never gets tired. But it sometimes makes things up, sometimes misreads your instructions, and it has no judgment. So your job is the same as always: train it, instruct it, and supervise it. Georgia added that this associate never becomes a second-year. You supervise it forever.

A court already tested this

In February, a federal court in New York decided United States v. Heppner. A CEO facing fraud charges used the consumer version of Claude to analyze his case, on his own and without his lawyers directing it. The court held those documents weren’t privileged and weren’t work product.

Part of the reasoning: the AI provider’s privacy policy undercut any expectation that the conversations were confidential. It’s one district court ruling, and it didn’t address enterprise tools or AI use directed by a lawyer. But it shows that the tool’s terms matter.

Five questions to ask any AI vendor

Georgia asks every AI provider these:

Do you train on my data?
How is my data kept separate from other users, and can you honor my ethical walls?
Do your staff read my files or outputs? For many lawyers, that’s a deal-breaker.
Where is my data processed, not just stored? Does it leave my jurisdiction?
What happens to my data when I leave? Can you give me a certificate that it’s destroyed?

Where to find the answers

The vendor’s trust website. Many vendors have one at trust.vendorname.com. Clio’s is trust.clio.com.
The SOC 2 Type 2 report. It’s an outside audit of the vendor’s security controls. Ask what’s changed since it was issued, and read the section near the end that lists what the vendor expects you to do.
The subprocessor list. It shows which other companies get your data and where they keep it.
The contract. Georgia’s sharpest point was that a help center article isn’t a contract. Look for zero data retention in writing, for the vendor and its subprocessors. And keep a dated record of what the vendor told you.

In the loop, or on the loop?

The second half covered what comes out of AI.

Human in the loop means the AI stops and asks for your approval at each key step. John’s example was drafting a reply brief, going back and forth to find and test authority.
Human on the loop means the AI acts on its own. Think of an AI that talks with a prospective client and books the consult. That’s fine for low-risk work, as long as the tool keeps a log you can review.

Either way, the responsibility is yours. A contract can shift some financial risk to a vendor. It can’t shift your professional duties.

What I’d take from it

Write down which AI tools your firm uses, and for what. John keeps a register of the tools he’s vetted. It also catches the tools people use without telling anyone.
Ask Georgia’s five questions before you sign up. Then check the answers against the contract.
Make checking AI’s work easy. Georgia’s view is that if verifying is a hassle, people skip it. Ask for inline citations you can click, and tell the AI to say when it isn’t sure.

The room was split when Georgia asked whether people could confidently tell a client where their data goes when it’s put into an AI tool. That’s a good question to be able to answer before a client asks it.

;-)

Ernie

P.S. In the Inner Circle, members compare notes on which AI tools they’ve vetted and what they found, so you don’t have to read every vendor’s fine print alone.

→

https://innercircle.ernietheattorney.net/

Your AI chat gets worse the longer it runs

Ernie the Attorney — Fri, 23 Oct 2026 12:03:48 GMT

I’ve written about context rot before, but it’s worth another look. Mike Taylor at Every just published an exceptional clear explanation.

What is context rot?

Context rot is what happens when a long AI chat starts giving you worse answers. The model hangs on to old instructions, repeats earlier mistakes, or skips details buried in the middle of the conver…

Best sessions to attend at the upcoming Clio Conference

Ernie the Attorney — Tue, 20 Oct 2026 16:41:58 GMT

ClioCon takes place October 26 and 27 in Boston. You can watch sessions online for free (see link below). If you register and miss a session you can also watch the recording, so I recommend registering with the link below.

In this episode I discuss why the keynotes will be especially helpful for solo and small firm lawyers, and recommend a few key sessions that will be well worth your time. I also explain how you can participate in a virtual discussion of the conference sessions with other lawyers like you.

Information about conference

Keynotes sessions

Malcolm Gladwell, “Weak Links, Strong Links: How AI Will Reshape Justice” (closes Day 1, Monday)
Ethan Mollick, “From Disruption to Opportunity: Embracing the AI Revolution” (opens Day 2, Tuesday)
Mechele Dickerson, on access to justice and the economics of legal services
Jack Newton, Clio’s CEO, on where Clio is headed

Recommended sessions

Taking On Clients Who’ve Already Asked AI (Oct 26)
How to Automate Your Firm End-to-End as a Solo Practitioner (Oct 26)
AI in Action: What Early-Adopting Law Firms Have Learned So Far (Oct 26, also virtual)
Pricing with Confidence: 4 Steps to Charging What Your Work Is Worth, with Molly Kremer (Oct 27, also virtual)
Promise and Perils in the Judicial Adoption of AI (Oct 27, also virtual)

Resource Links

ClioCon 2026 (October 26–27, Boston)
Free virtual ClioCon (register to watch a selection of sessions live or later)
Full ClioCon agenda
The Inner Circle (try it for 30 days for just $1)

The best part of ClioCon isn’t on the agenda

Ernie the Attorney — Fri, 16 Oct 2026 12:04:11 GMT

It’s in Boston, October 26–27. You can also attend virtually for free, even if you don’t use Clio.

ClioCon is less than two weeks away, and I’ll be there. So will at least 12 members of my Inner Circle.

I’ve got some history with this conference. I spoke at one of the first couple of ClioCons, back when it was in Chicago. Now it’s at the Hynes Convention …

Stop emailing your team about email

Ernie the Attorney — Tue, 13 Oct 2026 12:04:13 GMT

A lawyer I work with asked me a simple question last week. The team lives in email, and they spend a lot of time emailing each other about the emails. Is there a better way?

There is. And many solo and small-firm lawyers do not know it exists yet.

The problem every small firm knows

A client email comes in. The lawyer needs the paralegal to pull a document.…

Running with scissors: what lawyers should know about AI security

Ernie the Attorney — Fri, 09 Oct 2026 15:11:34 GMT

Ben Thompson is one of the most tech-savvy writers I follow. He used to work at Microsoft, and his Stratechery newsletter is one I pay for and recommend. So when his latest issue opened with the news that his Mac had been hacked, I paid attention.

If it can happen to Ben, it can happen to any of us. So I made security the topic of yesterday’s AI Workshop.

Before you turn on an AI agent, check who can see your folders

Ernie the Attorney — Fri, 02 Oct 2026 12:02:44 GMT

Last week Microsoft launched a redesigned Copilot app. It bundles chat, a coding agent, and a new agent called Autopilot. This new tool is a persistent agent that keeps working even when you’re not at the keyboard.

An agent like that works with the access you already have. Microsoft’s documentation for its Copilot agents says they respect existing Micros…

The best use of AI right now isn’t buying an app. It’s building your own.

Ernie the Attorney — Fri, 18 Sep 2026 12:03:45 GMT

Ben Thompson writes the tech newsletter and podcast Stratechery. Last week he interviewed Joanna Stern — a longtime tech journalist, formerly at the Wall Street Journal, who now runs her own YouTube channel and newsletter. The headline topic was Apple’s new folding iPhone.

I skipped past that part. The second half of the conversation, where two people wh…

The habit that makes AI worth using

Ernie the Attorney — Fri, 11 Sep 2026 12:01:13 GMT

This morning I saw a tweet claiming China now produces more solar power than every power plant in the United States combined.
That’s a big claim. If true, it says something important about where energy production is headed.
So I copied the tweet, pasted it into ChatGPT, and typed: “Validate this.”

What ChatGPT told me

The claim was false. It mixed up instal…

The AI agent that shows up before you ask

Ernie the Attorney — Tue, 08 Sep 2026 12:01:53 GMT

I have been testing a tool called Viktor. It is an autonomous AI agent that integrates with your Slack or Microsoft Teams workspace and works alongside the people already there.

I heard about it from a lawyer in the Inner Circle who is normally reserved about software. She was not reserved about this one. So I installed it, expecting to be underwhelmed.

T…

The Big Thing Your Small Firm Needs but Can't Yet Name

Ernie the Attorney — Fri, 04 Sep 2026 12:02:56 GMT

There is a job that almost every small firm needs and almost no small firm has. It has no standard title, so nobody goes looking for it. Owners feel the absence as a vague sense that things are slipping, and they blame themselves.

I recorded a podcast episode with Sarah Persich about this. She has a name for the role. She calls herself a fractional integ…

Before you add an AI agent, get the hub right

Ernie the Attorney — Tue, 01 Sep 2026 12:02:01 GMT

The tool doesn’t matter as much as where it lives.

I’ve been testing an AI agent called Viktor that plugs into Slack or Teams and works alongside your team inside the channel. It’s impressive. But the thing I keep coming back to isn’t Viktor. It’s the fact that none of this works if you don’t have a hub in the first place.

The real barrier isn’t capability

Build your own AI memory, or rent someone else’s

Ernie the Attorney — Tue, 25 Aug 2026 12:01:55 GMT

Harvey — the legal AI that big firms pay serious money for — launched its next generation this week. The headline feature isn’t a smarter model.

It’s more robust memory.

Their system can learn a firm’s lawyers’ word choices, their drafting style, how they structure their work, and then use all of that as context inside the firm’s workflows. You can read t…

Mark Cuban’s advice to doctors might be a good business idea for lawyers

Ernie the Attorney — Fri, 21 Aug 2026 16:15:54 GMT

Mark Cuban posted a suggestion for doctors in private practice: sit down with the patient and configure their AI assistant. Custom instructions, a set of saved prompts, and a recurring task that asks the patient the same questions every day at 5pm and sends the results to the doctor. The doctor emails over new questions, and the patient’s AI picks them …

I’ve been wearing two AI recorders. Only one belongs near a client.

Ernie the Attorney — Fri, 21 Aug 2026 12:03:36 GMT

I’ve been wearing two AI recording devices side by side to see which one earns a permanent spot.

The Plaud is a meeting recorder. You start it, it captures audio, you get a transcript and a summary. The Fieldy is a small disc you wear on a lanyard or a wrist strap, and it’s always on. It tries to figure out on its own when a new conversation has started,…

I fact-checked that iPhone theft warning going around

Ernie the Attorney — Tue, 18 Aug 2026 12:04:35 GMT

A story has been circulating online: someone’s iPhone gets stolen outside a bar, and within minutes their Apple ID password gets changed — from their own phone. By the time they notice, a thief is inside their email, banking apps, and photos.

I checked the story’s claims against the settings on my own phone. Most of it holds up. One part needed a correct…

Kara Swisher unintentionally helped unpack interesting hype regarding Harvey.ai

Ernie the Attorney — Fri, 14 Aug 2026 12:03:47 GMT

I heard an interesting mention of Harvey AI on Kara Swisher’s Pivot podcast recently. Swisher’s a well-known tech and business journalist worth paying close attention to, because she’s good at sussing out when tech founders are making hyperbolic claims.

She’s never discussed the Harvey.ai tool before, as far as I know, so my ears perked up when I heard h…

The AI law firm’s best feature isn’t the AI

Ernie the Attorney — Tue, 11 Aug 2026 12:01:03 GMT

A writer spent two weeks inside Crosby, a New York law firm built around AI from day one. They call themselves a “neofirm.” Half the staff came from Kirkland & Ellis, Wachtell, and Sullivan & Cromwell. The other half are engineers from Ramp and Stripe. They’ve raised $85 million.

The piece ran in late July in a publication called New Ontologies. It’s wor…

AI didn’t ruin your writing. It removed your reason to edit.

Ernie the Attorney — Fri, 07 Aug 2026 12:01:55 GMT

Film cameras had a built-in constraint: every frame cost money. That cost forced you to think before you pressed the shutter.

Phone cameras removed that ceiling. Now you can take two hundred photos of the same sunset and sort them out later.

That shift explains something that’s been bugging me about AI writing, and I think it applies directly to how lawye…

Everyone I recommend on AI is optimistic. Except Cory Doctorow.

Ernie the Attorney — Tue, 04 Aug 2026 12:03:05 GMT

When I started blogging in 2002, one of the first signs it was working was a link from Boing Boing. Cory Doctorow was co-editing it then.

I’m sure he has no memory of me. But I’ve read him ever since, and I’ve heard him speak a few times along the way.

I bring it up because he’s the odd one out on my list of people worth following on AI. Nearly everyone e…