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

You can hear Rob and Oliver discussing:

Connect with Oliver Haddock here: 

https://www.linkedin.com/in/oliver-haddock-2b316a106

Transcript

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 Ollie Haddock here. ⁓ I am no longer, since it’s the first time or the last time I was on this podcast, a full time fianer. So I now split my time between innovation and indeed a little bit of fianning still at Waitman’s. ⁓

Founder of the Careers Edit. You absolutely are. And yes, Ollie was the very, very first guest of the Legally Speaking podcast. So please go back to the very first episode of the show. Still the most listened to episode. I I will have that on my gravestone. Absolutely. And we j 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 w 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 know, we’ve all developed our careers slightly from then and and we’ve definitely supported each other through. So that community that we talked about five years ago has stayed very strong. 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. No, no, no, honestly. I I think 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. So 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. We have to try and change the culture and and and lawyers for very good reason are set in their ways, we’re risk averse, ⁓ we have and that and that’s for very good reasons. 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 a very sensible.

So when a new piece of tech comes along, obviously the initial instinct is eek. So as I say, it is 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 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 no, I’ll sadly, I was

Way, but I was on paternity leave, so I was very happy about it. ⁓ 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 Whitemans? Well, I 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. ⁓ 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 you’re gonna 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? Great question. I think I would go back to that point of

moving ROI and and by that let me dig into that because that’s a sort of buzzword that everyone is gonna be discussing here. But my general hunch is trying to run pilot schemes, short term pilot schemes, even if it’s up to six months.

You’re not gonna see real meaningful data in that time because it probably takes a lawyer to ⁓ six months at least to try and change the 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 whether prices are gonna come down, whether legal fees are gonna 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. And 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 on 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 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 H2H, human-to-human connection. So let’s go on to human impact now. 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 wellbeing. ⁓ th you know, there are many ways you can take discussion. I don’t want to bring the mood of the podcast down too much, but I had a friend ⁓ that I was at law school with who very sadly took his life. that was devastating ⁓ to his family ⁓ but also and 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 just things go through your mind. ⁓ many years have passed since that moment, but it it is still

Hangs with me and I know there’s so many you know that that’s obviously a very extreme example, but I know so many people that are going through whether it’s burnout, 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. The stresses are unique, that unlike any other industry, ⁓ you know, the conversations that I I overhear juniors having about will I get struck off, will I get struck off, you know, my god, I missed this or I forgot this. ⁓ and you know, 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 in a perfect world, perhaps

Incoming innovation could relieve stresses, could make life, work life balance slightly easier for people within the industry. Really well said. We talk a lot about on the show, Tech for Good, and that’s one of the reasons we we we partner with Clio as well in terms of you know hopefully improving people’s lives. But also I’d encourage folks to go back to one of our recent episodes where we’re out in Ibetha earlier this year as the official media partner for Lawyers Retreat. And we spoke to Ryan Hopkins, who specialises and delivered 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. ⁓ what would seem obvious in 202 maybe 2030 that many legal professionals perhaps are still underestimating today?

I feel like there’s the obvious answer, which is

No, I’ve I’ll take this in a different direction. The obvious answer is that we might need fewer individual human rights. And I don’t want to get into the, you know, computers are coming for our jobs a bit, but that 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 Waitemans, we are real market leaders in the innovation space. It’s a it’s amazing, you know. We are a top 40 law firm at the moment, very much, aspirations to be a top 30 law firm. And perhaps some of the big, big, big legal

conferences, there might not be names and faces from Waitemans on those panels. But 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 the game. Waitemans are doing some amazing things and I’ll get back to the answer now after pitching Waitemans. And that is to say look, so what we do in the product team, there’s 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?

We’d be more efficient. What Waythmans do particularly well is the external element of product and innovation, which is building products that actually create revenue. So 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 tire pressure, the brakes, the this, the that, you know, all the things that you should be doing if you have vehicles on the on the road. And there is for good reason very strict regulation around that. Now, if you have a a fleet, it’s often quite complicated to keep track of, you know, have you checked X on vehicle 200? So we’ve 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 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. So 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 it’s the sort of human facing element of the regulations. And and that I think is the future. That it’s not just simply telling people the law, 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. And it’s going up a level, isn’t it, in terms of that value adds. Okay, 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.

That is a a really, really good question.

One action they could take. we’ve discussed the well-being but bit that if if I hadn’t have just talked to you about for five minutes about that, that probably would have been where I went. ⁓ I I’ve got a big theory that certainly some of the bigger firms, ⁓ I’ve always said employ peop 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. ⁓ so that would be one that’s a sort of easy one ⁓ that I always 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. ⁓ I know that some firms do do this and and I would encourage all organisations to do so is to encourage within KPIs, within trackable units, whatever they do as their targets, ⁓ 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 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 I don’t know if there’s many people disagree with that, but this comes back to that argument we were saying earlier, that you know, there is there’s 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, you know, this’ll do, can you just touch up whatever it might th that they’ve clearly generated bits from ⁓ various AI platforms.

I don’t think that stuff is well, certainly I’ll be I’ll stay busy as a litigator, let me put it like that. Because if they’re gonna use those contracts, if they’re gonna use those agreements, if they’re gonna, you correspond in that way, ⁓ they’re gonna get things wrong and they’re gonna get things wrong for a long time. ⁓ we’ve all heard the success stories of of AI platforms. I think the more we use them, the more we realise they’re fabulous so many things, but they’re still not there yet. And of course that’ll change and develop. But I I still think I I I hold out hope ⁓ that a skilled mind will have a place in this industry for for a

There we go, I like it. Okay, ⁓ the League of Speaking Podcast, as you know, is all about inspiring legal minds, transforming legal futures. So my final question is this. What skill, mindset or behaviour 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 a division of the junior lawyers division of the Law Society. Bit of a mouthful, apologies. ⁓ but so from very, very early on in my career I was running legal events, networking events. Rob and I have been to many of those together. We 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 and I would put personal brand into that. I I would sort of lump them together y because I think building your personal brand involves networking as well. So that that’s what’s gonna separate people because a 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. So 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 I know ⁓ I don’t think is educated well enough. you know, you know the law schools want to push you towards training contracts, da da da da da 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 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, see, I’ll join Luna Server is it’s 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, ⁓ feel free to share any websites, any social media handles, and we’ll share them as episode three two. Absolutely. So anyone on here listening, welcome to find.

Me LinkedIn, Oliver Haddock. ⁓ the Careers Edit is my cross industry networking organization. As I said, I I 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. ⁓ so 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. So, and don’t forget to go and check out the first ever episode of the Legally Speaking Podcast, which was all

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 LeadSpeed Podcast, recording live here at Legal Tech Talk 2026. Maybe we’ll see you again in another five, ten years on the show. But from all of us here on the Leeds Beam Podcast, sponsored by Clio, wishing you lots of continued success and future collaborations, I’m sure, over and out. Good man. Thanks so much.