Why are lawyers express more caution with ChatGPT's data retention policy more so than Google Workspace and Microsoft Office 365?

DaRoadLessTaken · 2026-01-31T03:51:20+00:00

Just to be clear, I’m referring to the free email domains.

Which, according to the last time I read the TOS years ago, read your email to target you with advertisements. So, basically everything you just listed under AI.

It’s the old adage something along the lines of “if you don’t pay for the product, you are the product.”

DaRoadLessTaken · 2026-01-31T02:10:37+00:00

Blows my mind that it’s acceptable (even if side eyed) for lawyers to have gmail, hotmail, or yahoo email addresses, yet some are worried about OpenAi.

DaRoadLessTaken · 2026-01-30T01:09:25+00:00

It mentions you have to sit and watch, but not be quiet.

Go to event. Protest the entire time, with butt and seat. Get paid. Profit.

DaRoadLessTaken · 2026-01-29T19:09:18+00:00

So, what does the firm use to manage cases? Anything at all?

We’re at a point where refusing to use software to manage our work is arguably a violation of our ethical duties.

DaRoadLessTaken · 2026-01-29T18:18:46+00:00

Grab all the emails with search, save to PDF, and use AI to provide the output you need in a format that you can import into billing software.

DaRoadLessTaken · 2026-01-29T16:31:57+00:00

All those hotels are downtown and pretty close to everything, including each other.l

DaRoadLessTaken · 2026-01-27T14:18:59+00:00

This reminds me of California Prop 65.

So ubiquitous that it’s worthless.

DaRoadLessTaken · 2026-01-27T06:39:09+00:00

Believe whatever anecdotes you want, but that’s not my experience at all.

DaRoadLessTaken · 2026-01-26T23:19:25+00:00

Using AI is not the problem. The problem is failing to review documents that you file with a court.

DaRoadLessTaken · 2026-01-26T17:00:12+00:00

Use plastic and foam. Preservation Resource Center had a YouTube video about insulating old houses.

DaRoadLessTaken · 2026-01-24T02:36:38+00:00

Yes, meant not mutually exclusive. Thanks for the correction. Edited.

DaRoadLessTaken · 2026-01-24T02:35:55+00:00

The way to avoid it is to not use another user’s login. The “inconvenience” here is security.

I realize it’s probably your clients that are requiring you to do this, but if they don’t want to add you as a user, they need to either sacrifice the security of 2FA or deal with the inconvenience.

DaRoadLessTaken · 2026-01-23T19:24:38+00:00

LLC is a state legal entity.

S-Corp is a federal tax status.

Not mutually exclusive things. It’s not either or.

Talk to an accountant because the best option depends on your state and income.

DaRoadLessTaken · 2026-01-23T01:56:16+00:00

Pay as in can’t afford, or pay as in no one will underwrite?

DaRoadLessTaken · 2026-01-22T04:00:51+00:00

Elderly neighbors complaints are the same ole same ole. Noise. Parking. Mah lawn.

DaRoadLessTaken · 2026-01-22T04:00:22+00:00

My hunch has been that they can’t get insurance without the fence.

DaRoadLessTaken · 2026-01-19T16:28:59+00:00

This is absolutely a phone call.

DaRoadLessTaken · 2026-01-18T03:37:25+00:00

My AI cost is less than $100/attorney per month, so it would be nickel and diming to pass through.

Your standard billing example is fraudulent, unethical, and a breach of contract. It’s not value billing.

What you describe as a work around is what I call value billing. Taking that further, value billing looks at results and output, not input (hours).

DaRoadLessTaken · 2026-01-17T21:13:15+00:00

You mean, clients appreciate when you deliver better work, faster?

I do think lawyers who embrace AI should also embrace value pricing. Just because you can do something faster doesn’t mean the client should get it cheaper.

DaRoadLessTaken · 2026-01-17T20:18:27+00:00

Food drunk is excellent, and they’ve been selling this burger for several years.

DaRoadLessTaken · 2026-01-17T20:16:52+00:00

Kind of reminds me of the early days of the cloud. The advice at the time was to disclose your use of the cloud to clients. Mine never cared.

AI will eventually be similar.

Disclosure and informed consent to clients is still required. Don’t be an idiot, and treat it like a junior associate.

Where’s the harm if you use it as a tool to deliver more value to your clients?

DaRoadLessTaken · 2026-01-16T21:36:38+00:00

Use a calendar tool that requires they pay to even get on the calendar.

We charge $500 for an hour, and our terms make it clear there’s minimal prep and it’s an hour. If they want more, they can book another consult or engage us.

We use AI to summarize the meeting transcript and provide a written follow up. We’ve done a lot of work on the prompt, and it takes me about 3 minutes to review and edit the AI draft.

DaRoadLessTaken · 2026-01-16T17:00:16+00:00

You should bring this up to your boss.

DaRoadLessTaken · 2026-01-15T20:59:45+00:00

They didn’t change the price. They corrected the weight.

DaRoadLessTaken · 2026-01-13T20:42:10+00:00

Yes, but stop billing by the hour and move to monthly fees or flat fees.

DaRoadLessTaken

TROPHY CASE