LegalTechTalk 2026: Legal Careers, Networking and the Future Lawyer - Oliver Haddock - E06

0:00Oliver Haddock:What happens when the brightest minds in legal, technology and innovation come together to shape the future of our profession? Welcome to the Legally Speaking Podcast Legal Tech Talk 2026 miniseries. As the UK's number one legal podcast and show ranked in the top 1 % of podcasts globally, we're delighted to be returning as the official media partner for Legal Tech Talk for the third time. Having supported this event since the beginning, we've witnessed firsthand how it has become Europe's largest legal technology conference, bringing together the people, ideas and innovations transforming the legal industry.

0:37Oliver Haddock:Across this special series, we'll be speaking with some of the world's leading legal professionals, founders, technologists, change makers to explore what's next for law. Because our mission remains the same, inspiring legal minds, transforming legal futures. Let's get into it.

0:58Oliver Haddock:Hello everyone and welcome to the Legally Speaking podcast sponsored by Clio, recording live here at Legal Tech Talk 2026 in London. Joining me now is a very special guest. Please kindly introduce yourself, name, title and organisation. Well, firstly, it is fantastic to be back. It is Oli Haddock here. I am no longer, since the first time or the last time I was on this podcast, a full-time fee earner. So I now split my time between innovation and, indeed, a little bit of fee earning still at Waitmans. And I also run and am founder of the Careers Edit. You absolutely are. And, yes, Oli was the very, very first guest of the Legally Speaking podcast.

1:36Oliver Haddock:So please go back to the very first episode of the show. Still the most listened to episode. I will have that on my gravestone. Absolutely. and we in all seriousness we appreciate your support and collaboration back then and we've stayed good friends and this stuff you've been doing is incredible and love what you're doing with the careers edit and highly encourage folks to go check it out and we'll share the links at the end i would also say so that first episode was about legal community i think was kind of the title yeah and what i would say is since then yourself and you know a wider group of names that will know if they're listening to this have supported each other so much through our careers we've all kind of shifted slightly i think everything that we were doing back then you We've all developed our careers slightly from then, and we've definitely supported each other through.

2:14So that community that we talked about five years ago has stayed very strong.

2:18Oliver Haddock:Absolutely. We is greater than me, as many of our guests will know. Okay, this conference is a lot around transformation. So in your view, what's the single biggest shift happening right now in the legal industry that leaders can no longer afford to ignore? I don't know whether this is the single biggest shift, but this is certainly the one thing that I flag whenever I'm having conversations with my innovation hat on, which is we're all here listening to hundreds and hundreds and hundreds of talks about AI, legal AI. For me, culture and people are, if not as important, but more important than the tech.

2:48So part of my role, we call it the firm Hearts and Minds. So just educating someone on a piece of tech is not good enough. You have to try and change the culture. And lawyers, for very good reason, are set in their ways. We're risk averse. And that's for very good reason. So a corporate lawyer has built their systems to avoid making a mistake. A litigator has built their systems and their processes to avoid missing a deadline. So that's why we don't like change, and that's very sensible. So when a new piece of tech comes along, obviously the initial instinct is eek. So as I say, for me, we can all sit and listen to all these talks about the great features that all these programs have, but the big bit that we need to get hold of, or as a law firm owner or as someone in the innovation team, we need to help or start changing that culture get people open-minded to it make people feel as though they can try it without feeling pressure all that sort of thing yeah absolutely really

3:39Oliver Haddock:well said and this i think i think is your first year at legal tech talk so it is it is i was sadly well i'll say sadly i was away but i was on paternity leave so i was very happy about it um but i was i missed last year sadly and what's been your highlight of it thus far and what's brought you here and so many people from whitman's well i think that's exactly it there's a great crowd from the firm here there is it's one of those lovely things the legal tech space obviously there's so many people in the law or the law affiliated industries as it now is um but when you come to one of these conferences you basically spend your whole time bumping into people you know and the chat is just as important as the actual sessions and what are you going to learn yeah very very true and this is a legal question but you can take it broader if you like because your phone book will have a lot of strong entrepreneurs people that are really solving problems you spend a lot of time at the forefront of the legal industry specifically what's the legal problem or challenge you're most passionate about solving right now and why does it matter a great question um i think i would go back to that point of proving roi and and by that let me dig into that because that's a sort of buzzword that everyone is going to be discussing here.

4:48But my general hunch is trying to run pilot schemes, short-term pilot schemes, even if it's up to six months, you're not going to see real meaningful data in that time because it probably takes a lawyer six months at least to try and change their habits, change their systems. So my big point is trying to discuss open-mindedly what ROI looks like when we are investing in this. And there's all these discussions about where the prices are going to come down, whether legal fees are going to come down. Well, at the moment, we've got firms investing millions and millions and millions into some of these systems, depending on the size of the firm.

5:24And we're at a stage where we're still educating our lawyers on how to use them. So you're not going to see that yet, and people need to be aware of that, and we need to educate people around that. And as I say, it's all about trying to change that culture, trying to get people more on board. There's a really interesting dynamic around, I guess you'd call it generational divide. traditionally the more senior members of staff will be imparting their legal wisdom onto the more junior members of staff i think the interesting dynamic here is if you're looking as an innovation team around your firm for innovation champions whatever you want to call them ai champions that are likely to really take to these sort of systems like ducks to water and unlikely to lead them forward in your firm they might not be the senior partners so that's a dynamic we need to look at how are your senior partners going to react when perhaps a more junior member of staff is trying to educate them support them help them to adopt these pieces of tech so that's an interesting dynamic we're going to have to look at yeah and i think an interesting one

6:21Oliver Haddock:indeed but also very exciting i think if you look at it from a growth mindset perspective i know this question will resonate with you i talk a lot about we're no longer in b2b b2c it's h to h human to human connection so let's go on to human impact now um we're talking a lot about technology information innovation automation but if we get this right what's the real human impact how does this improve life for lawyers legal teams clients and overall society well i heart back to a point that i was making many many years ago which is all about well-being you know there are many ways you can take this question um i don't want to bring the mood of the podcast down too much but i had a friend uh that i was at law school with who very sadly took his life um that was devastating to his family but also and those that knew him but also all of us that knew him in the industry because had we noticed what he was going through could we have done more all those things go through your mind um many years have passed since that moment but it still hangs with me and i know that so many are you know that that's obviously a very extreme example but i know so many people that are going through whether it's burnout or whatever it might be that are stepping back from the industry brilliant minds talented minds are stepping back from the industry because it's a difficult way of earning a living.

7:32The stresses are unique. They're unlike any other industry. The conversations that I overhear juniors having about, will I get struck off? Will I get struck off? Oh my god, I missed this or I forgot this. And then they're kept up all night because they forgot to send an email. Have they missed a deadline? All those sorts of things. They are pressures that I genuinely don't believe that any other industry faces. So I suppose in a perfect world, perhaps incoming innovation could relieve stresses, could make work-life balance slightly easier for people within the industry.

8:03Oliver Haddock:Really well said. We talk a lot about on the show tech for good, and it's one of the reasons we partner with Clio as well in terms of hopefully improving people's lives. But also I would encourage folks to go back to one of our recent episodes. We were out in Ibiza earlier this year as the official media partner for Lawyers Retreat, and we spoke to Ryan Hopkins who specializes and delivers an incredible keynote on well-being and tips, strategies beyond the buzzwords and things you can do to improve your overall well-being. So go and check out that episode as well. Let's fast forward a few years, Ollie, now.

8:29Oliver Haddock:What would seem obvious in maybe 2030 that many legal professionals perhaps are still underestimating today? The obvious answer is that we might need fewer individual human rights. And I don't want to get into the computers are coming for our jobs a bit, but that probably will be the case to some extent. Yeah. The other point is that a law firm will look very different. And those two points are obviously related. At Waitmans, we are real market leaders in the innovation space. It's amazing. We are a top 40 law firm at the moment, very much aspiration to be a top 30 law firm. And perhaps at some of the big, big, big legal conferences, there might not be names and faces from Waitmans on those panels.

9:10But I tell you what, at places like this, we've got our managing partner and our innovation lead on a panel downstairs. That will be a packed house because they are right at the top of their game. Waitmans are doing some amazing things. and I'll get back to the answer now after pitching Waitmans. And that is to say, look, so what we do in the product team, there's the internal element, which is what a lot of law firm innovation teams will look at. That is adoption of XYZ platform. How can we speed up our processes? How can we be more efficient? What Waitmans do particularly well is the external element of product and innovation, which is building products that actually create revenue.

9:45So we license and sell products to clients to make our clients' lives easier, not just our own. We have a team of engineers. I'm not sure how many firms can say that. So a really good example is an award-winning product called Transport Manager Comply. So if you have a fleet of vehicles, and a fleet of vehicles can actually be anything from about three or four. It's a much smaller number than you might think. There are all sorts of regulatory requirements for you to check the tyre pressure, the brakes, the this, the that. You know, all the things that you should be doing if you have vehicles on the road.

10:16There is, for good reason, very strict regulation around that. Now, if you have a fleet, it's often quite complicated to keep track of, you know, have you checked X on vehicle 200? So we built a system, a platform that not only is being constantly fed and updated with the current regulations, but it's tracking what you're doing. It's giving you a reminder, you know, have you done this? You know, when you have to do it. And then if the regulator comes in, by the way, you can press print, thanks very much, and you're all clear. So the reason why I give that example is that is the law firm of the future.

10:44So if access to the information, i.e. there will be an AI platform out there where you can plug in what regulations do I need to worry about if I have a fleet of vehicles, if access to that information is becoming far easier, what's the thing that adds value? Well, we've created a system that does all of that for you, that tells you when you need to do something. It's the sort of human-facing element of the regulations. And that, I think, is the future. It's not just simply telling people the law or advising on the law. It's how to get into their businesses, how to help their businesses in practical ways based on your legal knowledge.

11:19Oliver Haddock:And it's going up a level, isn't it, in terms of that value add? OK, an action question for you now. If you had the attention of every law firm leader, managing partner, general counsel, legal professional, legal ops person, listening or watching to this podcast right now, what's one action they should take in the next 90 days to prepare for a better future? One action. We've discussed the well-being, but if I hadn't have just talked about it, to about five minutes, that probably would have been where I went. I've got a big theory that certainly some of the bigger firms, I've always said employ a third more people and pay people a third less, they'd still be very wealthy and they'd all go home and sleep at night.

11:55So that would be one, that's a sort of easy one that I always like to go for. What else? I would say I think we need to start opening up KPIs. I think we need to stop focusing so much on simply the billable hour because what you do is you undermine your staff's ability to test iterate develop all that sort of thing um i know that some firms do do this and i would encourage all organizations to do so is to encourage within kpis within trackable units whatever they do as their targets um encourage time spent researching innovating coming up with ideas have kpis that really encourage you to come up with innovative solutions for your clients not just sit at your desk and bill because those firms that have their staff just sat at their desk billing they'll suddenly realize they were doing the wrong thing and what they were doing

12:49Oliver Haddock:was suddenly outdated very very very true wise words okay what's one belief about the legal profession legal technology or future law that you hold strongly that most people will disagree with it's not going anywhere anytime soon i don't know if many people disagree with that but This comes back to that argument we were saying earlier. There is a back and forth across the whole industry about this. I have worked with small business owners that have come to me with contracts, with correspondence, whatever it might be, and said, this will do, can you just touch up, whatever it might be. They've clearly generated bits from various AI platforms.

13:29I don't think that stuff is... Well, certainly I'll stay busy as a litigator, let me put it like that, because if they're going to use those contracts, if they're going to use those agreements, if they're going to correspond in that way, they're going to get things wrong and they're going to get things wrong for a long time. We've all heard the success stories of AI platforms. I think the more we use them, the more we realize they're fabulous in many things, but they're still not there yet. And of course that will change and develop, but I still think, I hold out hope that a skilled mind will have a place in this industry for a little while yet.

14:00Oliver Haddock:There we go, I like it. Okay, the Legally Speaking podcast, as you know, is all about inspiring legal minds transforming legal futures so my final question is this what skill mindset or behavior do you believe will separate tomorrow's leaders from everyone else well we've got this far and i haven't even mentioned networking yet so there we go that's an obvious one so rob and i originally know each other through the london young lawyers group which is a division of the junior lawyers division of the law society bit of a mouthful apologies um but so from very very early on in my career i was running legal events networking events um Rob and I have been to many of those together.

14:34We worked on incredibly successful ones, including the Supreme Court. Yes. Not many people that could say they've hosted an event there. That was a serious memory. But look, business development, and I would put personal brand into that. I would sort of lump them together because I think building a personal brand involves networking as well. So that's what's going to separate people because, as I can sit here and very proudly say, not all careers in legal are linear anymore. There are so many options available to people. There are hundreds of roles now as legal engineers. There are innovation teams that are growing, growing, growing, growing, growing.

15:08So when I say networking, I don't just mean find the next client, find the next client. It is spread your net wide, get to know as many people as possible, find out what they're doing, how you can help each other, whether that's a role, whether that's a pivot in your career, understanding what other roles exist in this industry, which I don't think is educated well enough. at uni you know the law schools want to push you towards trading contracts so so yeah as i say when i say networking i don't simply mean you must find the next client for your law firm it is building your brand and it is understanding where your career is going yeah and i think with

15:44Oliver Haddock:all of that you suddenly become a magnet not a chaser the more you invest in that and build your network the more opportunities will start coming to you as well yeah it's the old john linux advert is enjoy giving presents rather than just receiving because let me tell you the more you do that the more incomings you will start to get absolutely okay finally if people want to learn more about yourself the careers edit which is fantastic by the way um feel free to share any websites any social media handles and we'll share them as episode free too absolutely so anyone here listening welcome to find me on linkedin oliver haddock um the careers edit is my cross-industry networking organization as i said i i've sort of born and raised as a legal networker running events for lawyers and then about when i qualified i decided that actually we should be networking with other industries, funnily enough.

16:26So the careers edit is a nod towards that. We host lots of events. You can find that. The handle is simply just the careers edit and you can plug that into Google and you'll find us as well. Come along. And as I say, welcome to get in touch with me if you have any questions. Absolutely.

16:38Oliver Haddock:So, and don't forget to go and check out the first ever episode of the Legally Speaking podcast, which was also recorded live in London at one of my former offices. So it just leads me to say, thank you so much for welcoming and joining me back on the Legally Speaking podcast, recording live here at Legal Tech Talk 2026. Maybe we'll see you again in another five, 10 years on the show. But from all of us here on the Leads Being Podcast, sponsored by Clio, wishing you lots of continued success and future collaborations, I'm sure. Over and out. Thank you for listening to this week's episode. If you like the content here, why not check out our world-leading content and collaboration of the Legally Speaking Club over on Discord.

17:12Oliver Haddock:Go to our website, www.legallyspeakingpodcast.com. There's a link to join our community there. Over and out.