I was on a panel discussion at ILTA last week and we were asked why do law firms have so much trouble measuring the ROI on their AI investments. It’s an interesting question. And after I thought about it, it occurred to me that, at least on the substantive side, the ROI for law firms’ investments really inures to the clients through lower fees. But I’m hardpressed to find a direct ROI to the law firm that bills by the hour. It’s a paradox.

I explore this paradox and a potential solution in my post for Above the Law. It may require on both side some soul-searching, asking some hard questions and having some heart to heart talks. Which lawyers and their clients often are reluctant to have.

I’ve read and seen a lot about all the money flowing into the legal tech space these days. I can remember when the big tech news was that some firm was thinking about going to the cloud. And now this.

And despite that, I have to admit I was not prepared for what I saw at ILTACON 2026. The extravagence and money being spent was so far over the top it’s hard to describe. But I thought I would try. Here’s my thoughts for Above the Law. And my musings as to what could happen if and probably when the bubble actually bursts

The last day of any big conference. I’m always a little sad to see things ending. Crowds thinning. Exhibitors breaking down booths. People with roller bags stacked in session rooms. A closing reception that somehow lacks the excitement of the opening one.

On days like this, I always think back to the opening day. The energy and excitement of not knowing what exactly would happen. The expectation of seeing old friends, learning new things. I can’t help thinking I wish it was just beginning instead of ending.

But last days of conferences are also a good time to reflect on the conference and what stood out. The most memorable takeaways.  ILTACON 2026 was, by any and all estimations, a record-setting event. Which is not surprising since everyone is riding the AI tsunami. A tsunami which may be at its peak right now. 

And while there are lots of things to talk about when it came to this year’s conference, five things stood out to me as the most meaningful. Here they are: 

I keep hearing rumblings about AI pricing. So far most vendors seem content on charging on a subscription basis. Under that model you can input as much as you want at no increased cost. But a lot of the providers are losing money. And at some point they will have to turn a profit. To do that they may turn to a consumption based model. With that model, the more you search and the more tokens you use, the higher the cost. Sort of like the billable hour ironically.  

And it will beg for an ability to undertake a cost benefit analysis. So when Net “we arent rock stars” Documents came up with a tool to determine how to measure how increased content could save costs, I was interested. It’s a step towards undertaking the kind of analysis that may be needed in the future. Here are my thoughts for Above the Law. 

There have been several surveys and reports of late that suggest law firms are spending a lot of money on AI but they haven’t yet figured out how use to benefit their clients. Or themselves.

The consulting firm Harbor recently came out with their own report. It’s a little short on statistics and methodology but the conclusions seem simialr to that of others. As I’ve talked about before, I think that the law firms’ failure in this regard grows out of some systemic issues inherant in law firms. Here’s my post for Above the Law where I discuss the findings and the issues.

So next week starts the annual ILTACON. It’s one of the biggest legal tech shows. Maybe the biggest. And like everything over the top it’s a love hate relationship. To paraphrase a famous authort “Until you go to ILTACON and behold it with your own eyes, you ain’t never been nowhere and you ain’t seen nothing.”

The 2026 version starts next week in NashVegas. It’s four days of nonstop sessions, sales pitches, demos and of course a few parties thrown in. 

Here’s my preview and what I love. And hate. But I’ll be there trying to keep up and letting you know what I see and hear.

For some time, I have been concerned about the amount of AI slop that’s being offered. It’s all over social media and seeps into marketing and advertising. I hate it.

But I fear that the more people read AI slop, the more normal it becomes until it becomes, God forbid, the accepted and expected way to communicate. Already there is some evidence that people prefer AI generated content to that of humans.

And for those of us in the business of communicating with and persuading others, we may have to face a reality we don’t like and change some things about how we communicate. But some things, like the ability to tell stories convincingly and to decide what facts resonate, will for the time being fall within the human domain. At least I hope so.

Here is my post on this subject for Above the Law

For years, I have been concerned that cybersecurity and the risk of data breach does not get the attention they deserve at many law firms. Part of it is becasue law firm leadership often does not understand cybersecurity and part of it is cybersecurity is just a cost drain.

That’s why the new IBM study of today’s data breach landscape is important reading even though it does not look at the problem for the legal business. The study clearly shows that AI is enabling cyber attacks to occur incrementaly faster and take less time and cost for the bad guys. And for the good guys, the attacks will on average cost some $1 million more than they used to be. The study confirms many of my worst fears. Here’s my discussion for Above the Law.