Free strategy advice for law firms with Andy Cooke

Andy Cooke is General Counsel at TravelPerk, the world’s leading B2B travel management platform. We meet on a sunny day in Harewood Park, a place primarily of interest to Andy’s dog Chief, because it’s where he gets to meet other dogs. While Andy and I talk about why law firms aren’t the centres of innovation they could be, Chief sniffs absolutely every blade of grass in our path. He also becomes best friends (forever) with Legal OS co-founder and CPO Jake Jones, who periodically lifts him up single-handedly to protect him from oncoming cars and other (considerably larger) dogs. 

Andy Cooke: The question that I get asked most is What does AI mean for law firms?

Lilian Breidenbach: And you get asked that by law firms?

AC: They ask me in a quiet voice, but they ask. There are strategy people in law firms for whom this is front and centre in their thinking, but the incentives of the people actually in charge are against bringing in this technology. 

LB: So, what do you tell them? 

AC: I started writing a LinkedIn post about this the other day, like a real loser (haha), but here’s some free strategy advice for law firms: Get the ten most annoying associates, typically the ones who won’t do exactly what they’re told, who don’t want to do the same thing forever to become the number one expert in it. Take those people and a PSL (Professional Support Lawyer). Put the PSL in charge of the naughty lawyers and take off all shackles regarding what products they can or can’t use. We still have law firms that can’t get access to Google Docs, so you’ve got to clear away all those restrictions. Then let them start with a blank piece of paper and very heavy customer outreach, real needs analysis. Of those ten naughty lawyers, eight are on pure tell us what your pain points are customer discovery for at least six months before they start building anything. Then that neo firm just gets to run, no partners involved, very little reporting or oversight. 

LB: No billables…

AC: 100% no billables. But the brilliant thing about it is the cost. If you look at an NQ salary for a US law firm, it’s like a rounding error. And eventually, if you truly give it that blank sheet of paper, allow it to take on clients and run with a wholly different model, it will eat your bigger firm. But first you have to create an environment where people can do that without additional oversight, without having to give weekly reports in terms of outdated metrics, like how many clients they landed or billables they created. 

LB: I imagine that would make a huge difference. Think how every scale-up or even just technologically minded person would flock to these law firms, if they actually used AI and it wasn’t just a marketing ploy. 

AC: That’s it. Everybody wants the magic trick, so they can say they’re innovative, but it’s not about that anymore; it’s about the future state of your law firm. How do you create a genuine experiment that can offer a different way?I once worked in this privatisation of various airline assets in a country where, if you got to 25 years of service, you basically got your final salary forever. So when this privatisation started, there were a bunch of people on 21 or 22 years who decided to put the brakes on. 

LB: Sure, they just need four more years. 

AC: Exactly. So we were trying to build a vendor data room, and they’d be like, Since you were last here, we found ten documents, but bad news, we’ve only got one page of that one. If you come back in a month, maybe we’ll have found some more. Occasionally they would accidentally disclose a new document and then get really upset with themselves. It was an unending process. Of course, once those people get to 25 years, there’s a bunch of others who also need just four more years. That’s why it has to be a separate thing and can’t happen within that law firm structure. 

LB: Do you see law firms stalling like this when it comes to AI? 

AC: Yes. We’ve done a few demos where we took data sets from law firms, ran them through Legal OS, and told them This is the kind of thing we’re doing with your data, and you could be doing this as well, at zero cost. The data’s already out there. But it raises a bunch of really uncomfortable issues that the political structures of law firms, in my limited experience, are not well geared to resolve. 

LB: For how long did you work in a law firm? 

AC: I did about ten years in a law firm and was an annoying associate. 

LB: Oh, you were one of those! 

AC: They just kept punching me around the firm, which was great, because I had loads of very unusual experiences. I worked post-qualification in both litigation and M&A, and I worked in loads of different countries on the ground, all of which was amazing. It was also great training for my first in-house job as a sole counsel. Having been in Syria doing the third mobile licence auction in December 2010, there’s very little now that still fazes me about new projects. 

LB: So you grew up here in Yorkshire. What made you want to become a lawyer? Were there lawyers in your family?

AC: Not at all. I grew up on a pretty remote farm. My parents completed higher studies, but my dad went to agricultural college, my mum to teacher training college. My sister studied as a nurse, so she was the first person in my immediate family to go to university. It was a fantastic home. My dad was very keen for us to get ahead, to get big jobs, go to London and travel, because of what he wasn’t able to do as a kid. Also, when you live somewhere remote, you develop an interest in travel. So when I ride my bike, I tend to ride long distances, because there’s that desire to explore. There’s something else out there, beyond the fields around your house. 

LB: Why law school though? Were you just like, This is interesting? 

AC: Actually, I did a test when I was about 15, at school, and they were like, You should be a lawyer. They might as well have said that I could be an ice cream man or astronaut, that’s how proximate it felt. But I did know that lots of law firms have offices overseas, so if I could get into a law firm with overseas offices, I’d be able to work overseas, which I wanted to do. 

LB: So it was your doorway to travel. 

AC: It was my doorway to travel. So I did all that, went straight to law school, hadn’t lived or worked in London at any point during this period, and then travelled a bit before going to Norton Rose. That was my first time working in London, and it was pretty rad, to be honest. 

Chief lovingly interacts with some members of the British public. Simultaneously, around a bend in the road, a spaniel comes into view. Because Chief’s got a bit of a record with spaniels, Andy temporarily puts him on a leash and we pray he won’t go into attack-mode (to the extent a cat-sized Schnauzer can ‘attack’ anything). 

AC: I moved to London and, specifically in the law firm, instantly felt like I was crossing loads of social boundaries that I had no idea existed. Everybody else seemed to understand the rules of how to get ahead, and I genuinely had absolutely no idea. One of the reasons why I qualified as litigator was that, in the distribution of seats, I got put with someone who was really creative. I could have been put with absolutely anybody, but this was the kind of person who would come up with 100 ideas a day. And maybe 98 of them were not that good, but one was good, and one was really good. A lot of the other people I dealt with seemed to be very sort of staid. Of course that makes sense, because it’s a law firm and conservative. Meanwhile, I was literally getting sent home for crimes like wearing brown shoes, something which still rankles with me to this day. I was wearing all kinds of ridiculous suits, and there were some fashion crimes committed, but nevertheless…

LB: …none that would warrant sending you home! 

AC: I was constantly smacking into these unknown walls. I don’t think the firm knew entirely what to do with me, so they sent me off to various places. I worked in a bank for a bit. 

LB: But you made it for ten years. 

AC: Yeah, but more just by coming up with new, interesting things to do. 

LB: So you didn’t follow the partner track. What made you want to transition to in-house, and why that particular first job?

AC: Well, ironically, I was travelling. Be careful what you wish for. I was travelling a lot, and not to places where you would necessarily want to hang out a whole lot, particularly as a business traveller. I remember standing on the street in Saudi, in this really thick suit, because the air-conditioned offices would be completely freezing, then outside it would literally be 54 degrees or something insane, like Death Valley temperatures, just on the street, sweating. It’s a very high-touch way of doing business over there, and you build fantastic relationships with people, but it’s a lot of legwork. I was coming back to the office with people who weren’t really getting out into the region, and I just sensed a disconnect, so I thought it was probably the right time to get off. And it’s weird, I don’t want to get all Deepak Chopra on you here, but the universe delivers when you plant the seed. A job came up with one of the largest promoters in the world, doing music and sports events. I thought that sounded more like me. 

LB: And how was that different? Was it quite a culture shock?

AC: Yeah. Once you’ve attuned yourself to the ways of private practice, you’ve got to unlearn a lot of stuff, particularly this idea of having to insert yourself into absolutely everything, because that’s how you get ahead, by gatewaying solutions. Even now we see this. We’ll be onboarding a new law firm, and they’ll say something like,

What we’re going to do is get all our associates together and have a day with you guys to really understand your business. I mean this in the nicest possible way, but you can read our website. We’ll give you any briefing materials you want. Do you not see how inefficient that is? We just had a tangle with one of our law firm partners, who loaded a bunch of people into a call, none of whom said a word, and then billed us for everybody at rack rates. This is like end of empires stuff. If you accept the idea that the current version of the billing model for law firms is past its peak, then these kinds of practices are on the downslope and we’re heading towards the earth. This kind of stuff is going to annoy people more and more. As AI makes everyone’s lives more convenient, the gap between those two things is going to get bigger and bigger. So that sort of stuff really upsets me. 

In hopes of seeing some deer and maybe cooling off a bit on a scenic bench, we push further into Harewood Park. Free again and scampering ahead, Chief is having the time of his life. 

AC: Anyway, I had to unlearn a lot. Far less face-time, far less being-in-the-room type stuff. I started to play with very early-days tech, mainly because we were doing risk management for big football tournaments with a million tickets for sale. You can do that with paper forms, but it’s a nightmare, particularly if your contractors are speaking Arabic or Hindi or Urdu. You’ll have like 10,000 contractors. So we started to do some experiments. Can we do that with an iPad? Can we create ways for people to self-serve? Initially that meant doing things in Word Developer and trying to connect that in. It came pretty late there, but I think in 2014 we started using e-signature. It sounds crazy now, but the one criteria we had was that it had to be on premise. No cloud, because the cloud is not secure. 

LB: I have to say, I haven’t heard that one in a while, even from law firms. 

AC: Yeah, it was like health provider-grade security, like on server. So anyway, we started to put some things together and explore the benefits of tech. 

LB: I think it’s going to be very interesting. 

AC: There’s a period of uncertainty now. What we’ve seen from working with Legal OS is the importance of knowledge to building great models for informational self-serve. There’s a potentially really interesting pathway right now, which is something like super PSL + technology. You can add a huge amount of value to any legal environment like that. Lawyers could be really good at dealing with far more uncertain risks, rather than churning out contracts. You can train a monkey to do that sort of thing. There’s so much value to be released in curating and managing knowledge in a way which is really customer-centric. 

LB: 100%. We had some funny moments when we released the trailer for our product. I got a few replies on LinkedIn that were like, Sorry I didn’t get back to you, I’ve just been swamped with high-frequency legal requests. So I’m definitely your person to talk to, I’ve just had no time. They saw the video, connected with it instantly, and considered starting a conversation. Then, very often, about 50% of the time, mostly in smaller teams of up to eight people, they have no documentation. They have no time to develop documentation, because they’re firefighting. 

AC: When we started building the team in TravelPerk, that was one of the toughest things, a tough initial message. It’s much easier to do this at the start of a relationship with a new company than to change course midstream. But to say, I know you think that you’re already working about as hard as you can, but you’re going to have to work harder, because we’ve got to build a future state in parallel to serving existing customers. Ironically, it’s easier if your relationship to your internal customer is awful, because they’re already upset, and if you just stop doing the stuff you don’t want to do…

LB: …in six months they’ll be really happy. 

AC: Exactly. In just six months they’ll be happy. 

 Check out Part Two of the conversation with Andy here.