Lawfront CIO: Why AI Is Under-Delivering in Legal Tech

Jim Merrifield (00:01.116)
Well, welcome back to the info gov hot seat, the podcast where we put tech leaders in the hot seat to talk real world data, AI and innovation. So no no buzzwords, fluff. So today I'm excited to continue our CIO series with someone operating right at the intersection of law technology and AI transformation. Joining me today is Tony McKenna, CIO at Lawfront Welcome Tony.

Tony McKenna (00:28.558)
Thanks, Jim. Great to see you. Can't believe this is my first meeting of 2026. How cool is that?

Jim Merrifield (00:35.812)
I know it's awesome. Me as well. Me as well. so Tony, let's, I know, let's start with a fun, I know you've answered this question before, but let's start with a fun question. So as a CIO, what tasks do you secretly hate? You know, the one that you're absolutely thrilled AI might steal from you in 2026.

Tony McKenna (00:58.062)
For me, that's a really easy one. I'm looking forward to the point where AI can just read your emails and actually respond to all the nonsense that you get on a daily basis with something that's courteous. And actually, the AI sort of understands the context of you and how you...

how you operate, your email is constantly coming in, you're looking at it, you're doing certain things with it, you're doing very repeatable things with certain types of emails. So therefore, I can definitely see, sometime 26, 27 where that type of auto response based on some thresholds and some learning,

If you've ever had the luxury of having a human EA, you know, a really good executive assistant who works alongside you, you, lives inside your inbox, helps by reading through and actually delegating tasks out to people and stuff like that, which makes you infinitely more productive. Why can AI pick up that task and really be that digital assistant that instead of having

150, 200 emails that land in your inbox and then the day you think, well, I'm going to do it all that. It just gets done, filed out and all the important stuff that, you you can see it at the moment a bit with the focus and other tabs inside Outlook, which are amazing. That really helps. But actually doing the filing and getting rid of them would be the cherry on the cake.

Jim Merrifield (02:49.189)
No, it would. But let me ask, here's a follow up question to your answer. If AI nailed that one, is that a productivity win or like a personal victory?

Tony McKenna (03:02.714)
I think that's, I think it's both. Personal victory for me, brilliant. know, as I've told you many times, I'm dyslexic, you know, so it takes me infinitely longer to read the emails and decide what I'm going to do with them, right? But I think productivity across the piece, because everybody gets so much nonsense, yeah? And I think that would be a huge productivity gain. I think people would gain back hours in the day, not just minutes, because I think...

You think of the volume of messages that goes in and out of your business today. And if you can cut a wheat from the chaff as we say here in the UK, then that would be brilliant.

Jim Merrifield (03:43.193)
And we're all drowning in email these days.

Tony McKenna (03:46.348)
Yeah, it's all about collaboration, isn't it? So we just collaborate more. But that's not, the productivity gain is outdone by the volume of collaboration. if we can get through that, I think that's a big one.

Jim Merrifield (04:03.365)
Yeah, absolutely. Well, here's another one. When it comes to AI adoption in law firms, what do you think really slows things down more? Messy data, nervous partners, lack of talent, or just money?

Tony McKenna (04:19.622)
I think all of them are relatively easy labels to stick on things, particularly the kind of people and talent and cost of fortune. Both you and I know that you can go into the market with really cost effective solutions, partner with organizations that have got, you partner with them, they partner with you and you can develop a product together.

and they've got all their skills and expertise, you've got all the knowledge of the legal world. So I think those labels that people put on them, know, say, adoption's poor because of nervous partners or cost or whatever, are just ways of hiding behind the fact that people don't really want to change. And even the change agents don't want to change. And the number of people that I know that are in change roles, that if you want to move them from one side of the office to the other, they're the first one up in arms. It's like you were the change professional, right?

But yeah, think the other, the kind of one thing that I think really is, has some kind of validity is it's kind of got to be in your workflow. know, AI is sitting outside of your workflows. You've got to come out of the thing you're doing and do something else and then come back into that. That's the modern world doesn't really work like that.

You could have gotten away with that in the 90s and stuff like that, but now the world is much more, it's all in my workflow. It's on my phone, it's easy. Everything feels logically. One step follows the next one. So I think that's where the adoption, the slowness is to adopt, is because it's not really integrated well enough into the individual workflows. It's a bit like over the Christmas period, over the festive season,

I watched the Blackberry movie. For all of us boys and girls who remember the original smartphone in 2001, 2002, the 50, 10 or whatever it was that we were very fortunate to get. The adoption of that was a proper hockey stick because it was just right in your workflow. just extended your connectivity.

Tony McKenna (06:43.544)
to being away from your computer, you know? And you could then have emails and messaging and calls all on one device. And so that's when AI, I think, will just be, or is being, naturally adopted, you where it's inside that workflow that you always do. So if it's sitting inside, you know, the copilot browser, you just type something and it just feels more natural. And I think that's where...

For me, that's where the adoption barrier is at the moment. It's still not quite in the logical world.

Jim Merrifield (07:21.393)
Yeah, that's a great point. mean, you mentioned BlackBerry, so I have to comment on this. I'm still waiting for I wonder if BlackBerry level skyrocket again, you know, with their stock. I don't know. You know, it's I'm still waiting.

Tony McKenna (07:28.226)
Thank

Just hoping, you you bought stock in 2008 and now you're...

Jim Merrifield (07:35.026)
Long time. You know, hey, listen, I remember where Apple was, you know, before they skyrocketed. But, you know, one, one will have to wait and see, but, let's talk about the, yeah. Yeah. Let's talk about the elephant in the room, right? It's the financial aspect here. so what do you think by 2026, does AI finally mess with the billable hour or does the model somehow survive?

Tony McKenna (07:42.446)
Absolutely, yeah.

Tony McKenna (07:46.606)
They keep me a

Jim Merrifield (08:02.423)
everything we throw at it because we've been talking about flat fees, alternative fee arrangements for quite a while in the law firm world. Do you think AI pushes the needle here?

Tony McKenna (08:09.559)
Absolutely.

I think it does. think actually the way that I see the bill of the law is, you know, you've got that kind of value pyramid and where the advice is specialized at the top of the pyramid. And as you get down, it becomes more commoditized. And you can see that the commodity area is the area to go up first, you know, automation, just via whatever pushing up through that pyramid.

that value pyramid to get to that kind of specialized stuff. So I think the billable hour will still remain for those, you know, those more complex or areas where just people need to talk to someone. You know, so it's as simple as, it can be as simple as divorce, right? You know, do you want to talk to any AI bot about your divorce? Or do you want to talk to a person who's sympathetic and has a view and understanding?

and take you through stuff. So I think that the billable hour still have some value for the next three, four, five years. And those specialist transactions for those things that are just complicated and require people to touch. But as I said, those more automated or commoditized parts of those processes will become more...

AI orientated or have that in that workflow and therefore the billable hour will have to change. It'll have to incorporate and it'll have to inflex to reflect the new ways of working. But I don't think that's significantly different to what probably happened in the 2000s and when emails and stuff like that started to be really prevalent and automation then started and litigation support and all that kind of stuff as things just become

Tony McKenna (10:09.294)
available then the model starts to reflect that. So yeah I think the billable hour will remain for a wee while yet at least.

Jim Merrifield (10:17.753)
I will. We'll have to wait and see. We'll have to wait and see for sure. Well, listen, here's an uncomfortable question. When AI gives bad advice and client work. And it will. We all know we've seen the news. Who's holding the bag in 2026? Is it the lawyer, the firm, the CIO? The vendor? What do you think?

Tony McKenna (10:42.254)
Well, I think the answer is pretty straightforward from a regulatory point of view. It's definitely the lawyer in the firm, right? Okay, we're at great pains. You and I and other enlightened professionals who understand information governance and how to use these technologies are still impressing all of our lawyers and...

professionals, risk professionals, that actually the buck still stops with the lawyer and the law firm controlled by how you regulate it. And I think that in time, regulation will catch up with technology. We all know that regulation like everything, right? So regulation will catch up with technology, the technology will improve and the disclaimers will be

maybe written differently to reflect the new world. So that an informed buyer of service needs to really understand. If you want something quick and cheap and a level of accuracy with a level of risk, then as long as you're an informed buyer of service and you can sign up to that, then yeah, you can maybe push some of that kind of

and some of your kind of rights or some of kind of things that you as a lawyer or a law firm have today and hold close, you can allow the client to make some of those decisions, you know. But I think it's important at this moment in time we're not there yet, you know, we still need to make sure that the lawyer understands and the law firm understands that, yeah, the buck stops with them.

Jim Merrifield (12:33.167)
Yeah, for sure. We're seeing more more law firms and their clients are working closer together, probably than ever before on AI and different work products. So probably expect that to continue in 2026.

Here's another question for you. What's CIO skill will matter most in 2026 that nobody was hiring for? You know, years ago, probably years ago, you're looking for like an infrastructure, you know, really techie CIO. But is that still is that still the case?

Tony McKenna (13:08.376)
think it's really changed significantly in the last, even the last four or five years. I think the skill set that CEOs would be looking for and CIOs today are all about how can you make the technology, sorry, stepping back. The thing working is just table stakes. It's just, you just.

It all has to work, it has to be stable, reliable, and it has to be available to me and my colleagues wherever I, you know, that's table stakes now. So, you your infrastructure stuff, you know, however you configure the backend to present a desktop image to colleagues on our phone or our smart device or whatever, that's just a given, I think the CEOs...

of the future or today are looking for CIOs who are about to say, well, how can I transform this into revenue? How can I support the firm in its endeavor to delight clients and really understand what it is to be in a law firm, what clients' expectations are, what regulatory requirements there are, what governance there is, and actually be able to articulate that as part of a business leader.

I would suggest that 30 % of your job is just making sure that stable and reliable and secure. 30 % of your job is making sure that everything fits strategically within your team and within your law firm and within your organization. And the other 30 % is how do you delight clients, understand the marketplace? How do you drive the industry forward? And I think CEOs are looking for CIOs at that level in the modern.

you know, and, and, know, to come up with those ideas about revenue generation, we were talking about it earlier, you know, how can you turn what you're doing and the advances that you're making in technology into revenue streams for, for, for the law firm? So I think that will be, I think that would be what the skills that they'd be looking for that, you know, a few years ago, wouldn't be.

Jim Merrifield (15:25.957)
Makes perfect sense. So, all right, Tony, listen, it's time for the lightning round. Quick answers, no overthinking. So you ready?

Tony McKenna (15:37.408)
I am prepared

Jim Merrifield (15:39.087)
All right, here we go. All right. Don't overthink it. So AI and law by 2026 overhyped or under delivering. What do you think?

Tony McKenna (15:51.376)
I think it's still under-delivering.

Jim Merrifield (15:57.234)
Okay, okay. One word to describe most law firm data today.

Tony McKenna (16:03.308)
Messy.

Jim Merrifield (16:05.105)
Here's another one build AI in-house or buy it from a vendor

Tony McKenna (16:11.768)
Buy it Buy it.

Jim Merrifield (16:15.237)
biggest AI risk firms worry about that actually shouldn't be their top concern.

Tony McKenna (16:24.366)
hallucination.

Jim Merrifield (16:28.345)
What's one role in the firm that changes the most because of AI by 2026?

Tony McKenna (16:36.6)
secretarial, you know, administrative support, that type.

Jim Merrifield (16:44.625)
And here's the last one, actually second to last one. CIOs in 2026, more technologists or more of a translator?

Tony McKenna (16:54.382)
Business translator, definitely.

Jim Merrifield (16:57.02)
All right, finish this sentence. If law firms don't get AI right by 2026, they risk what?

Tony McKenna (17:04.556)
not existing.

Jim Merrifield (17:08.561)
That's awesome. Well, listen, Tony, this has been a great conversation. It's honest, practical, very real. Before we wrap up, what's one piece of advice you give to CIOs or tech leaders in law firms who are building their AI roadmaps right now?

Tony McKenna (17:25.708)
I think the most important thing is to really understand your organization and strategy, what you can then bring to the party around, know, innovative technologies, whether it's AI or just automation or just being really good at scaling. My organization is all about scaling. So, you know, we are looking at how we do that and how we introduce that to our partner businesses. So I think understand the business you're in.

That's the most important thing that you can do as a CIO.

Jim Merrifield (17:56.731)
Yeah, that's fantastic advice. Now, CIO, Tony McKenna, CIO of Lawfront, thanks so much for stepping into the InfoGov Hot Seat. Today was great to catch up with you. And to everyone listening, if you've enjoyed this episode, please subscribe, share it with your team, and check out the rest of our CIO series. And until next time, I'm Jim Merrifield, and this is the InfoGov Hot Seat.