A new Washington Post analysis of 47,000 ChatGPT conversations reveals a troubling pattern. People are sharing deeply personal information, getting advice that tells them what they want to hear (not necessarily what’s accurate), and creating potential discovery goldmines for future litigation.

The study found users discussing emotions, sharing PII and medical info, and asking for drafts of all sorts of stuff. Whatever is asked, ChatGPT says ‘yes’ 10x more often than ‘no.’

As lawyers, we have an ethical duty to understand technology risks. The question isn’t any longer whether GenAI will impact our practices. It’s whether we’ll educate our clients about these dangers before they create their own smoking guns. Here’s my post for Above the Law. 

The grade school game seemed simple enough. Grab the other team’s flag without getting tagged. But for a kid like me with not much athletic talent, the chances of being a factor other than getting quickly tagged out were pretty remote. Or so it seemed.

One of the questions I am often asked by young lawyers is how I get to where you are and develop a successful practice and career. 

It All Started With Capture the Flag

I tell them it all started with Capture the Flag.  For the uninitiated, Capture the Flag is a school yard game where the playing area is divided into two territories. Each team has a flag placed somewhere within their side of the field. Players try to grab the flag but if they cross into the other side’s territory they can be tagged and are out. To win you have to get the flag.

Continue Reading Thinking Outside the Fence: What a Grade School Game Taught Me About Legal Innovation

Two AmLaw 100 firms are doing something unusual: sacrificing billable hours to train associates in AI.

Ropes & Gray lets first-years spend up to 400 hours (20% of their requirement) on AI training. Latham & Watkins flew 400 associates to DC for a two-day AI Academy.

The revenue hit? Probably minimal. First-years aren’t profit centers anyway, and clients often won’t pay for junior associate time.

The learning boost? Likely significant.

As Thomas Suh from LegalMation told me: mastering AI requires giving lawyers the “grace to dabble” , time to experiment and fail without billing pressure.

Most firms are still wringing their hands about AI’s impact. Smart firms are training lawyers to leverage it.

Here’s my post for Above the Law.

New research from Disco and Ari Kaplan reveals a striking contradiction in legal’s relationship with AI and eDiscvovery. While 70% of legal professionals recognize AI’s efficiency benefits, only 35% have actually incorporated it into routine processes.

Even more telling: 42% of law firms report zero external pressure to adopt AI solutions. .

The reasons for resistance? The usual : billable hour concerns, “perfect vs. good” thinking, and the classic “we’ve always done it this way” mentality.

Here’s why this matters: eDiscovery has historically been the proving ground for legal tech adoption. When court deadlines force efficiency over billable hours, innovation happens.

With 96% reporting increasing eDiscovery workloads and new data sources (including AI prompts and outputs), the pressure for change is building.

The irony? The same factors making lawyers resist change like time constraints and risk aversion, may ultimately force the adoption they’re avoiding.

Here’s my post for Above the Law.

Small firm lawyers keep telling me they can’t afford the AI tools big firms use. They’re not wrong, I’ve heard vendors literally laugh at affordability concerns. So when I came across Descrybe, a legal research platform with free core features (and paid plans at only $10-20/month), it got my attendtion and I dug deeper. Here’s my post for Law Technology Today.

New study from Thompson Hine: 95% of in-house counsel see little innovation from their law firms. But clients might be part of the problem. When they reward the status quo with an average 7.4% rate increases year after year while claiming innovation is “crucial,” what message are they really sending?

The gap between what clients say they want and what they actually demand reveals a lot. Law firms aren’t going to change much unless and until their clients demand it. Here’s my post for Above the Law.

When we talk about GenAI for the legal profession we frequently focus on the risks. But Comment 8 to Model Rule 1.1 requires us to also the understand the benefits. Sometimes we make AI a little too complicated.

Two fundamental rules: Don’t put client confidences in prompts and check the output for accuracy. Here is my post for Above the Law.

I was recently at a charity benefit reception and dinner. An acquaintance (and I stress acquaintance) came up to me, took one look and out of the blue asked, “you’re retired, aren’t you”? For some reason that question was both galling and irritating. It took me a bit to figure why even though I’m sure the acquaintance didn’t mean any ill will and was just trying to be polite.

The short answer: I may not practice law full time but I’m far from “retired” and the assumption that I am just because I changed careers is disappointing. I’m not going gently into the night.

Do not go gentle into that good night,

Old age should burn and rave at close of day;

Rage, rage against the dying of the light.

Do Not Go Gentle into That Good Night, Dylan Thomas

Perhaps some background is illustrative.

Some Background

As many know, I practiced law full time for over 30 years as an equity partner in a large law firm. Most of that time, I defended companies involved in mass tort litigation. My work took me all over the country and was challenging and cutting edge. It was a wonderful career, and I don’t begrudge any of it.

But long about 2017, I discovered a new interest in writing and speaking about legal technology. It’s no secret why: since I was always on the road practicing my cases near and far, I had to have the best technology to help me do that.

I enjoyed writing about legal tech and in 2017, made the decision to pursue a second career as a legal tech journalist full time. I was frankly ready for the new challenge. I wanted to see if I could achieve success doing something different than practicing law and for which I had no formal training and little experience. I wanted to see if I could do it.

Here’s what my “’retirement” actually looks like.

How’d That Turn Out?

Since then, here’s how it turned out:

  • My blog Techlaw Crossroads is a well-respected and well known legal tech blog.
  • I write regularly for Above the Law, also a well-known and respected legal tech outlet.
  • I write for an ABA publication, Law Technology Today.
  • I am a regular panelist on the Legaltech Week Journalist Roundtable composed of the leading journalists in the community.
  • I’ve won awards for my writing and my contributions to CLE.
  • I am on the faculty of a trial technology training program.
  • I chaired the ABA Law Practice Division composed of over 30,000 members.
  • I co-chaired the ABA TechShow, one of the leading legal technology conferences.
  • I am co-chair of the Kentucky Bar Association Law Practice Management and AI Committees.
  • I host a podcast consisting of interviews of legal tech vendors and movers and shakers.
  • I regularly attend and speak at conferences, trade shows and other legal tech and even standard tech events.

All in all, I think I’ve done pretty well.

A Part Time Hobby?

As for the part time nature of what I do, I have kept track of the hours I actually work on my second career. (Old habits are hard to kill). Last year I worked close to 1800 hours. This year I am on track to work even more. I regularly hit between 1700-1800 hours. That’s pretty close to my billable hour output the last few years I practiced full time.

And while I use the word “work” it’s really not work-work. I love every minute I spend on my new career. It’s a challenge; I wouldn’t trade it for anything.

But one thing it ain’t is retirement and the insinuation that it is strikes me as insulting.

Still Fighting for Every Inch

But the deeper issue isn’t just about hours worked, it’s about assumptions and ageism. The idea that leaving my legal career means I’m just dabbling, not really working hard or trying my best, is what irritated me most about the question.

I reject the notion that when you reach a certain age and decide to do something different, you can’t or won’t contribute meaningfully. That you need to go gracefully out to pasture, endlessly watching TV while thinking about the good old days. That you’re of little value and expected to just slowly fade into the sunset. That’s not living, that’s slow death.

I am not fucking retired

So no, despite what my well-meaning acquaintance assumed, I am not fucking retired. As long as I have life in me, I’m going to pursue my new career, or maybe even my next one, just as hard and as long as I can. Like Coach Tony D’Amato (played by the incomparable Al Pacino) in the movie Any Given Sunday said:

“I know if I’m gonna have any life anymore it’s because I’m still willing to fight and die for that inch — because that’s what living is.” 

Either that, or like Paul Simon, maybe I’m just still crazy after all these years.

A lot of lawyers think AFAs will save them from AI disruption. They’re wrong.

I’ve been using alternative fee arrangements since the 90s, so I’m not anti-AFA. But the current rush to AFAs as a solution to AI’s impact on billable hours misses the point entirely.

The real issue isn’t how we package our fees. It’s that AI is fundamentally changing what legal work looks like and what it’s worth. You can’t just slap a flat fee on the same old work and call it innovation.

Here’s my post for Above the Law.

At its Inspire Conferance, NetDocuments assembled some of legal tech’s sharpest minds to talk about AI’s real impact on legal practice. Zach Abramowitz, Nicola Shaver, Zach Warren, and Jennifer Poon didn’t hold back on the hard questions: Why traditional ROI metrics fail for AI, how ‘AI-first’ firms are disrupting the leverage model, and why many lawyers are still ignoring what’s coming. But we might be just one economic downturn away from widespread AI adoption in law. Here’s my post for Above the Law.