Don't Miss Out on ILTACON 2025 INSIDER Secrets
In this episode, Jim Merrifield hosts Tony McKenna and Jason Dirkx to discuss ILTACON 2025, a pivotal event in the legal tech industry. They explore the conference's pirate theme, networking opportunities, standout keynote speakers, and the importance of community engagement. The conversation also delves into reflections on leadership, advice for the incoming president, and aspirations for the future of ILTA. The episode emphasizes the significance of preparation and connection at the conference, highlighting that ILTACON is not just a conference but a vibrant community. Join Jim Merrifield as he explores ILTA Con 2025, a key event for legal professionals. Discover the future of law and legaltech through collaboration and innovation. This conference is set to be a pivotal gathering for those in the legal industry.
Jim Merrifield (00:01.608)
Well, hello and welcome to the InfoGov hot seat where tech leaders get candid and we get curious. I'm your host Jim Merrifield and today we're diving into one of the most anticipated events in the legal tech world, ILTACON 2025. Now, if you're like me, you know, ILTACON isn't just another conference. It's the place where innovation, collaboration and community come together to shape the future of legal technology.
And this year it's happening from August 10th to the 14th at the stunning Gaylord National Resort in National Harbor, Maryland. So whether you're a seasoned attendee or a first timer, this is the event to be at. So to give us an exclusive preview, I'm joined with two incredible leaders from ILTA. First, Tony McKenna, president of ILTA, and Jason Dirkx the incoming president of ILTA. Welcome to you both.
Jason Dirkx (00:58.446)
Thanks, Jim.
Tony (00:58.472)
Thanks, Jim.
Jim Merrifield (01:00.328)
Yeah, I know I introduced you, but Tony, let's outside of Ilta. What's what's your day job like?
Tony (01:08.68)
Well, hectic as always, particularly in the current climate. But yeah, I'm the director of technology and change at Howard Kennedy. the change element for me is the most exciting. We get a load of stuff done. We've got a stable and reliable platform. But getting in around the lawyers and working with them on a regular basis around what's coming down the pipe is the fun bit of the job.
Jim Merrifield (01:35.324)
Love it. Thanks, Tony. Jason, how about yourself?
Jason Dirkx (01:38.264)
Sure, I'm Jason Dirkx I'm director of AI product management at Sidley. And as you can probably imagine in the climate right now, my day job is pretty hectic. I'm getting questions from all sides, partners, clients, vendors, everybody. So it's pretty intense.
Jim Merrifield (02:02.216)
Yeah. You're the popular one in law firms, right? Yeah. And managing those AI products. I love it. Well, thanks to you both for joining me today on the hot seat. Tony, let's start with you. What's the overarching theme or vision of ILTACON 2025?
Jason Dirkx (02:03.79)
Right now.
Tony (02:21.884)
It's a fantastic conference at a wonderful venue this year. I can't wait to get to National Harbor in a few weeks time. We're going with a pirate theme. And yeah, where's the link there? Not just the fact that it's on the waterfront, but obviously information is the treasure in our industry at the moment and how to get that treasure. We're using a pirate theme and in the conference itself, you'll see a lot of connections back to pirates.
it seems you'll be seeing a lot of army gym lad and stuff like that. But it's all about the information and in an event like Iltacon, there's going to be so much peer to peer networking, education sessions, that whole information, that really topical day to day information that people really thirst for and you can take back to your firm is what the whole theme of the conference is all about.
Jim Merrifield (03:21.316)
So I'm sure there's some first time attendees, right? So what advice would you have for first time attendees? Maybe Jason, you can answer that question first. And of course, throughout this conversation, if anyone of you want to jump in and kind of banter a little bit, that's fine too.
Jason Dirkx (03:41.016)
Sure. Yeah, I've got the same advice that I pretty much give every first time attendee, which is find some of the stuff that's maybe a little bit outside your comfort zone or maybe a lot outside your comfort zone and just pop in. That was something I did my first couple of conferences and it really helped expand my horizons into areas like law firm finance and legal project management and pricing that I had no idea about.
And also it's a long week, so definitely pace yourself.
Tony (04:16.485)
Yeah, I agree with that. That pace yourself great, great bit of advice there. One of the things, one of the other things Jim for newbies is this whole idea of the buddy system. We've, there's a fantastic thing that ILTA set up a few years back where if you're new, you're going to the buddy system, you get connected with a seasoned ILTACON attendee and they can really open up the doors really quickly and get you to the right.
Jim Merrifield (04:16.86)
Yeah.
Tony (04:44.264)
places that you wanna be and things you wanna see. And there's loads of information on the ILTACON website and actually that's one of the things that we pride ourselves on in my tenure in the board is we've kind of improved the ILTACON website. So get onto that and have a look at the Know Before You Go. There's a kind of what to expect webinar coming up this Wednesday at 12 to 1 p.m. Eastern time. So just really take that half hour.
to invest in looking at what content is there so that you can map out and do exactly as Jason says, look at all those sessions that are a bit outside of your comfort zone that you kind of want to learn about.
Jim Merrifield (05:26.866)
Yeah, there's a lot going on and wear some comfortable sneakers, right? Or some sneaker shoes. Because you're going to be walking a lot for sure. But hey, it's good to get some exercise because most of our days, I'm sure, at our firms, our butts are in the seats. Maybe we're at a standing decks like Jason is right now, pacing around. most of the time, we're kind of in our offices on call. as you mentioned, there's an opportunity.
Jason Dirkx (05:30.51)
For sure.
Jim Merrifield (05:55.824)
so many opportunities to connect, not just in sessions, but to have lots of conversations. So speaking of sessions though, Tony, are there any standout keynote speakers or sessions that you would personally recommend?
Tony (06:11.304)
So yeah, definitely, I love the keynotes. I make sure to get in there after a nice hearty breakfast, wherever that may be, across the campus. But I think the most important thing is getting in and getting seated and listening to these guys. ILTA does a lot of research, particularly the ILTACON committee, there's a lot of research into themes and topics that are hot. And this year we've got Ryan Campbell coming and talking about the power of prioritizing joy.
I'll let Jason tell you what whether that's joy or chief executive in terms of happiness. But we've got sorry, Ryan's on on the Monday. Really looking forward to his talk in that whole bit around mental health and as a saber prioritization, which is a challenge for all of us in our day to day lives. And then we've got Reena SenGupta She's joining us on the Wednesday.
talking about sustainable digital transformation. Sustainability is a hot topic as is digital transformation. So both of them are great sessions. The other session I'll let Jace talk about is the Thursday morning, the kind of G100, G200 wrap up session, which I think getting to hear what the top leaders in the legal field are working on is fabulous.
Jim Merrifield (07:38.79)
Absolutely. Jason, how about, how about you want to talk about that G 100, 200 session or, or even, don't know, Joy's not on the call right now or on the podcast right now. So you could add some insights into, I saw that title of the opening keynote. was like, is it about joy or is it, know, or something else?
Tony (07:46.142)
Thank
Tony (07:53.19)
Okay.
Jason Dirkx (07:55.724)
I think the ambiguity is intentional. But yeah, no, I agree with Tony. The G100, G200 is really great. It's really interesting to hear what that group is sort of chewing on and deciding to focus on over the day that they have earlier in the week. And it gives you, particularly if you're in those departments, in those structures in law firms,
Or if you work closely with law firms, it gives you really good sense of where those leaders' focus are.
Tony (08:33.736)
I think the great thing is the kind of closed room session, the G100 and G200 sessions, the full bay sessions, but actually the wrap up on a Thursday really lifts the highlights out of them and shares it with the whole community. And as Jason said, you can go back to your firm with some really decent insight on what's going on on those, particularly those mega firms and some of the things they're doing.
Jim Merrifield (09:00.796)
Yeah, yeah, I mean, I the opportunity, as you know, last year to attend the G200 and, you know, been part of that community for the last year. It's been really enjoyable knowing what's being able to connect with you all and know what's top of mind on CIOs. And there's definitely a lot going on. you know, to be able to translate the overview or the recap for the entire community to let the ILTA community know that.
what the one of the top conversations that everybody wants to know about, I think is, is awesome. So, Tony, here's a question for you. I know you've been Ilta president for two years, right? So your, your reign's coming to a close and in a couple of weeks, right at, at ILTACON so as you, as you reflect back on the last couple of years, what, what have been like your proudest moments, and even some, some lessons learned.
Tony (09:59.518)
It's been an amazing super quick two years. I can't believe it's two years already. Yeah, Jason, you've got it all in front of you. Yeah, there are whole bunch of things that I've learned. And I suppose the most surprising thing was how much I've learned over the last two years. Being the chair president of an association isn't like any other volunteering role. It's a real full-time commitment.
and you're involved in all of the aspects of that organization and where the organization is going. So I think the biggest thing was the lessons that I've learned that I'll take back into life and actually I take back into my work every day. It was way more intense, a lot more effort than I anticipated. Sorry Jason, I should have told you this.
But on the other side, was just amazing and probably one of the standout things in my career, which has been pretty long from the early 80s. So scary stuff. Proudest stuff, I think the financial stability. I mean. ILTA is in a wonderfully strong financial position that allows us and has allowed us as a board over the last couple of years to really invest in improving the kind of
day-to-day experience of our vast membership across the globe. So I think that is the standout thing from the real dark days of 2020 through to 2021 when the previous boards were really dealing and grappling with some real challenges. To come out of that in such a strength is all about Ilta, the community and really the last...
sort of two boards have really put in play a fabulous platform for us to invest in. I think that's probably the proudest thing is that financial stability that gives us the opportunity to improve how we work with our business partners, improve our web experience, improve our mobile. Whoa, woohoo, we're gonna have a mobile app at last. Oh, jeez, but it's amazing. These things all cost money and it's been real tough.
Jason Dirkx (12:16.194)
Yeah
Tony (12:23.728)
and the tends to get to that situation. Whereas now we're in a great position in the twenties where we can invest in stuff like that. You'll have seen we've done an international road show this year. So we've been in places that we've never been before and we're getting incredible attendance. So there's a huge stuff for ILTAs education in places like Italy where we had about 500 people attend a session. We were down in Spain as well and across some of the Nordics in the coming months. So yeah, brilliant. That's kind of really my proudest thing.
Jim Merrifield (12:54.984)
That's awesome. And obviously in this time, we've got to know you. We've probably crossed paths a few times, but we got to spend some time on the G200 and even being the ARMA of chair, ILTA president, that partnership. So it's been nice to work with you. And of course, looking forward to working with Jason as well. before we...
you know, pass the torch to Jason to comment. Tony, as you pass the torch to Jason, what advice would you give him? I mean, you told him that, you know, was more than you anticipated, which I think, you know, any board member would probably say on any, you know, any board level. But what advice would you give Jason as he steps into his role as president of ILTA?
Tony (13:43.592)
Well, I mean, Jason and I started our volunteering career at similar times, know, albeit I'm nearly twice his age. But I was late to the party. But Jason knows the challenges around the time and the commitment and the effort. I think the big thing for me is, as I know Jason is and will be, is be kind to your boss, because at the end of the day, the effort and the commitment, you'll nourish yourself,
Jason Dirkx (13:55.502)
you
Tony (14:13.416)
the work that you need to put in. Be kind to obviously your family, know, so Miss and Dirkx's and the kids and all that kind of stuff, need to be over kind to them because you're going to be dragged away for weekends and stuff like that, which everybody thinks is great fun. And they are, but they're great fun in a work pace, you know, so you're not sitting on a deck chair somewhere, you know, you're sitting in a dusty meeting room in a hotel. And, you know, friends, colleagues, you know,
Take every bit of advice, every bit of feedback that you can get and translate that into how you deliver your presidency. That's for me. I've had an immense amount of advice, guidance, and never shy away from feedback, because I firmly believe it always comes from a good place.
Jim Merrifield (15:08.808)
Excellent advice, right? Stay humble. so Jason, what are your hopes for Iltas future in the direction that you'd like to take the organization? I know it's a loaded question, what do you think?
Tony (15:11.262)
Yeah.
Jason Dirkx (15:22.978)
You mean assuming I'm still here after everything that Tony just said, right? Yeah, you know, I've thought about this a lot and beyond, we kicked off talking about ILTA, which is this premier conference and it's great. But in reality, the vast majority of our membership and business partners and constituents that are part of ILTA don't.
Tony (15:26.866)
Thank
Jason Dirkx (15:51.31)
ever go to conference or only go to conference very infrequently. But by the same token, ILTAs is real differentiator from a lot of the other conferences and other things that have started to spring up is the community that surrounds the organization. And so what I'm hoping that we can continue to do is Tony sort of outlined some of it that we started during this last term, but I'm hoping we can continue to really strengthen our
our experiences for members and constituents at the local level. So both in the US and globally, and also continuing to strengthen our digital platform, our digital presence to support those relationships digitally online where everybody is these days as well.
Jim Merrifield (16:43.642)
I think that's excellent, excellent advice. So, Tony, we're like two weeks away, right? And so...
Tony (16:51.934)
Okay, unbelievable. I'm so looking forward to the G200 session because I know you're doing a bit of moderation of that group this year, aren't you?
Jim Merrifield (17:00.808)
That's what they tell me. I'm MCing. You just got to keep me focused on the themes. And I think we're doing a session together too. We're co-moderating. So that should be fun, be able to banter a little bit. No, it's always fun to hang out with some CIOs on the G200, have some laughs, learn some stuff.
Tony (17:03.518)
Yeah.
Tony (17:24.264)
I think that G200 community is just such a great community, such an open collaborative environment because that group's, the resources at the disposal of that group is nothing in comparison to the G100. So therefore they've got to make so much more with what they have and that peer-peer community is so important. And occasionally, Jason, hopefully you'll be able to attend
those sessions that she or his party or presidency. I think that a great thing for the president to be involved in. What you get is you get you see some of the G 100 guys and girls sneaking in the back door of the G 200 just to hear what's going on. it's and they're a massively welcome addition to that community. As is Jim from his own experience in innovation side, obviously.
from the ARMA side, it just brings that information governance and it's hugely important to have experts in the room from outside of the legal tech space and really more in that kind of process and governance space has been fabulous over the last couple of years. yeah, looking forward to, really looking forward to spending the day on Tuesday and having a bit of fun.
Jim Merrifield (18:43.664)
Yeah, yeah, it's been amazing to be a part of it. Looking forward to seeing both of you in a couple weeks. So I know we talked about a lot here. I know we could probably go on and on, but final thoughts. Maybe we'll start with you, Tony. What's your message to the ILTA community as we gear up for ILTACON 2025?
Tony (19:02.994)
Well, a couple of clear messages for me. Anybody want to bring their sneakers, we'll be doing a better running when we get there. yeah, always a fantastic location, Washington, to do a better running. And it's only a 20 minute Uber ride down to the monuments. but yeah, not real important messages. It's been an honor and an absolute privilege and I'll tell colleagues at the AGM that to be a President and serve on the board and serve the community.
and really just do the research before you get there. Really look at the agenda, what's going on in the business partner hall, which will be absolutely fabulous. There'll be over 25 newbie startups there, which will be amazing. So really do your research, do the speed work before you get there so that when you arrive there, you really know where you want to go. And just an adjunct to that is ask people.
You'll see people going about with badges with loads of stickers on them. Just look, any of those people, anybody with a badge on in that community is going to give you a bit of support. yeah, that's what I'm thoroughly looking forward to being stopped loads in and around the place.
Jim Merrifield (20:16.378)
Excellent. Jason, how about you?
Jason Dirkx (20:19.508)
you know, I, the, the part that I'm really excited about is, we, I think for the first time we're taking, we're basically taking over national Harbor. So the, the entire area is, is. Ilta stuff going on. and so much so that we're spilling into Alexandria as well. So I'm really looking forward to seeing how all that kind of plays out and, seeing the energy.
Not just at the Gaylord, but throughout that that little area of National Harbor So I think it's gonna be a fun time
Jim Merrifield (20:56.37)
Yeah, it's gonna be a blast, know, for sure.
Tony (20:58.398)
Absolutely. think, you know, one of the standout things for me is the size of the American flag, the US flag flying in National Hall. It's just amazing. I just love that sight. I just wondered if we could get an Iltacon flag up that mast. You never know.
Jason Dirkx (21:07.373)
Yeah
Jim Merrifield (21:19.196)
Hey, you never know. So to the listeners, that's the ask for the next two weeks. That's what Tony's at the helm. So he wants an Ilta flag in National Harbor. So maybe one of the business partners can make that happen. You never know. lot of connections in DC. seriously, Tony, Jason, thanks so much for joining us today. It's been a pleasure to having you on the hot seat gearing up and hearing.
Tony (21:36.776)
never
Jim Merrifield (21:47.976)
about what's in store for ILTACON 2025. Looking forward to seeing both of you in National Harbor. Just to everyone watching ILTACON 2025, it runs August 10th through 14th at National Harbor. So whether you're an attendee, a business partner, or just passionate about legal tech, this is the place to be. Right smack in the middle of the summer, right? Come down and learn about some more legal tech.
And here's some personal advice, come ready to learn, connect, and be inspired, because there's a lot that ILTACON has to offer. It's more than just a conference, it's a community, and there's no better time to be a part of it. Of course, too, visit ILTAnet.org for registration, full agenda. And again, until next time, thanks for joining us on the hot seat. I'm Jim Merrifield. Enjoy the rest of your day.
Jason Dirkx (22:42.574)
Thank
Tony (22:43.358)
Nice show.

Tony McKenna
Director of IT & Change
At Howard Kennedy, a full-service international law firm, Tony is responsible for Technology Services & Innovation, Business Change and Information Security. Tony is President of ILTA, a twenty-five thousand strong, volunteer-led international legal technology association, chairing the Board. Over his 40 year career Tony has delivered significant change programs and maintained the highest level of technology service across Utility and Legal sectors.

Jason Dirkx
Director, AI Product Management
Jason Dirkx is the Director of AI Product Management at Sidley Austin LLP, where he leads the development of AI-driven legal technologies that enhance service delivery and client value. With prior leadership roles at Paul Hastings and Littler, Jason has deep experience in legal innovation, product strategy, and emerging technologies. He is the incoming President of the International Legal Technology Association (ILTA) and a frequent contributor to the legal tech community on legal tech, AI and innovation.