21 min read

Giles Thompson on challenging the status quo

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Giles Thompson is the Head of Growth @ Avvoka, former lawyer at Kirkland & Ellis and Herbert Smith Freehills,  Agriculturalist & Foodie, and tech investor & entrepreneur.

Giles left practice a year ago to join the world of legal technology, and during this conversation we discuss:

  1. How the culture has shifted from his days in practice vs what he hears today
  2. The challenge of collaboration and different approaches firms are taking
  3. Pertinent skills/thoughts for future and newly qualified lawyers, and when to challenge the status quo

We covered a number of other topics as well such as the importance of mentors, the increasing levels of interest in innovation-type functions, and more.

You can connect with Giles on LinkedIn. During the show, we discussed the Avvoka Academy – it can be a great resource and a good place might be to explore the Ultimate Guide to Document Automation.


Ab: [00:00:00] Hello everyone and welcome again to Fringe Legal. Today I’m excited to have Giles Thompson on the show. Before we dive in, I thought I would do something slightly different and give his life narrative in a chronological order. Giles is the son of a farmer, which naturally turned into him becoming a foodie, he went and did political science , which led to going into law school and actually practicing as a lawyer. He was formerly at Kirkland and Ellis, and then at HSF Herbert Smith Freehills.

[00:01:29] And now he is a tech investor and an entrepreneur. And the head of growth at Avvoka based in the UK. Charles, thanks for joining me. Welcome.

[00:01:39]Giles Thompson: [00:01:39] Thank you. The pleasure is mine. I thank you very much for having me.

[00:01:42]Ab: [00:01:42] I guess a good place to start would be you practice as a lawyer and now your work for a legal tech company.

[00:01:49] As you speak to law firms that you speak to it in house councils and corporate, what are you seeing from a culture point of view from your days in practice to now? Are the other trainees associates, partners, leaders, are they asking for different types of things to when you were in practice or is the conversations still the same?

[00:02:11]Of course there’s no one size fit all, but  what’s that spectrum look like from your conversations?

[00:02:15]Giles Thompson: [00:02:15] I’d always say be interested in your perspective in a moment as well as to what’s changed and actually whether you disagree or agree with me, but Yeah, certainly I do see some differences.

[00:02:25]I’ve not been long out of law. So even in the kind of that short intervening period, actually a lot has that has changed as a result of the pandemic. The main thing I’ve really seen in actually and this quite a granular answer, but is an increasing desire for collaborative tools.

[00:02:43] That is a result of the sort of physical collaboration and interface between lawyers being pulled away actually. So the, I certainly remember when I was particularly when I was a trainee, because I was the one carrying the physical bit of paper, but actually the process of, having a physically printed out document and then marking that up and maybe three or four people at layering on their amendments on, onto a markup.

[00:03:04] And actually, the biggest trend that I’ve seen since I’ve left is people wanting to use tools that are akin to something like a Google docs and everybody being able to chip in on a document and work on it together rather than working on divergent drafts. And I do genuinely think that a good degree of that is because of that physical process being pulled away.

[00:03:23] I think the other thing, and maybe it hasn’t really changed since I left, but maybe I just didn’t realize quite the extent of the interests that lawyers and probably lawyers who are more senior than me when I was in practice who wants to have one foot in that camp of innovation.

[00:03:42] And so I think that there’s definitely even in the last sort of 18 months, there’s been a huge proliferation of innovations secondments  within law firms. So senior lawyers seeing it as a potentially, even as a stepping stone towards partnership, actually spending some time in that innovation part of the business.

[00:03:57] And then maybe specializing in that area full-time or taking their skills back and actually then improving the revenue of wherever they came from initially. So I’m meeting a lot of those people and really enjoy meeting those people. But I think that they seem to be proliferating and I constantly see job ads for peoples in those kinds of divisions. But they’re not asking for technologists all the time. Now that they’re specifically asking for the lawyers of all the time.

[00:04:20]Yeah. What’s your experience.

[00:04:21] Ab: [00:04:21] Yeah. I think I’d agree with most of that. Probably the distinction I would make is absolutely  the collaboration point of view is true.

[00:04:30] The meaning of the word seems to differ greatly, right? From firm to firm or individual to individual. I’m not sure if the vast majority of, and I’ll speak from the law firm perspective, that’s the conversations I have the most think of it as working together with their clients. I think what I hear a lot now, and especially since COVID 19 last year, how can we replicate the environment where we could all sit in a room and work on a draft together to doing so digitally.

[00:05:02] And there’s nothing wrong with that. And it’s the, the approach of taking a offline practice online. That’s one angle to that. The other side is. How do I collaborate better with clients? How do I give them more transparency and actually for what its worth,  it’s the clients are asking more for that, right?

[00:05:19] They don’t want to keep emailing or calling just to get an understanding of, Hey, where’s my matter at? Who owns what, are we on target and other things. So those are probably the two things.

[00:05:31] The innovation point is. Yeah, absolutely. There’s a huge proliferation of that. I do catch myself sometimes because the view from inside the bubble, and I think both of us certainly are inside the bubble is very different because when you go and speak to probably 90% of the firms they’re not thinking in that way. And you talked about innovations to continents, and I know some of your previous firms do absolutely do that.

[00:05:54]In my view, and I’m happy to be wrong, I don’t think that’s the norm. I don’t think most firms have innovation secondaments. Very few do. I do think that there is a higher level of desire to go into innovation or something else, that’s not just practice. And that as a pathway to both partnership, and also as a lot of the practitioners think about want to stay in Legal, but maybe I don’t want to practice, all the time.

[00:06:20]And in the past one common route was maybe I’ll become a PSL and that’s not the only route, of course. But now it’s, while I could be a technologist, I could be a innovation manager.

[00:06:30] I could be X. I could go in-house and work for a legal tech company as the case with both of us. So there’s a whole bunch of routes now that weren’t available before. So  those would be some of the things I’m seeing.

[00:06:41] Giles Thompson: [00:06:41] Yeah. And I’ll pick up on the point around collaborations because I think you’re completely right.

[00:06:46] But just before that, I think the other thing as well is I certainly received a lot of phone calls,  a lot of messages from people having made that, the venture that in certain legal tech that I have made. And I think  there’s a lot of people that are thinking very openly at the moment about what type of role might be suitable for them.

[00:07:03] And, the main fear that I hear from people when I’m speaking to them is. Can I ever go back? And I think that’s one of the beauties of these kinds of comments. And I think you’re absolutely right to call me out there and say that is the likes of the Herbert Smith Freehills  offering that kind of thing, and I think, that those people that I speak to are perhaps smaller firms they don’t have that kind of halfway house option.

[00:07:23] And actually one of them really inspiring things as people who create those kinds of positions and themselves, and, I find myself trying to recommend people to do that, knowing full well, all of the difficulties of doing that.

[00:07:34] And actually on that sort of collaboration point that you mentioned,  you’re totally right.

[00:07:38] And that there’s very good reasons why. Actually it’s easier to replicate that into lawyer collaboration versus client lawyer collaboration. And I don’t think it’s easier tools to replicate either really. But the client point is harder because there is a very good reason for it.

[00:07:54] But lawyers have a tendency towards perfection and, anything that you type in a shared document with a client, That’s it’s possibly legal advice. And so you end up in a bit of a sticky situation where maybe you have to put a new engagement letter that, if we’re using so-and-so application until X stage has been reached, you can’t deem what we’re putting in there is legal advice because everything needs to be signed off.

[00:08:18] So if you have a, and I know this is going out around the world, but in the UK context, if you have a trainee lawyer typing in a document and a client seeing that they certainly shouldn’t be relying on that, but how do you. Yeah. How do you rationalize that process? Yeah and replicate that situation where a trusted advisor is sitting in a meeting room with a client and actually going through something line by line.

[00:08:38]Ab: [00:08:38] I had this conversation recently with probably about eight to nine different KM leaders. And that was the number one take for them. I think people are generally open to the idea, but there’s that management of risk compliance, data, integrity, all of those things that come into play.

[00:08:54]Which I mean, it is not an easy problem to solve and I don’t think anyone has it figured out yet, but I think those discussions are now happening more and more. The other part, and this probably goes into the second topic I wanted to chat about is I think there is a link to transparency as, because at the moment, A lot of the work that’s being done by law firms.

[00:09:15] A lot of it not all is done behind closed doors, right? You go in with your problem or you’re seeking advice and eventually out comes a response in  the form of a draft or opinion or whatever it might be. As you start working in a more multiplayer environment where people can see what you’re doing, then you have to, get your clients comfortable and get yourself as the lawyer comfortable with people. Seeing the initial subpar work that you may be doing right? The end. It’s not that it’s bad. It’s just, there’s a degree of changes that will happen as the draft goes from, the first draft all the way through to the eventual final delivery.

[00:09:56] And do you really want to really let your clients see how the sausage is made? Not just from, Hey, maybe I will need to rewrite this 20 times or maybe there is a trainee working on it and an associate and a senior associate, not just the partner. So all of those things come into play and I don’t think we have that figured out and how that works while yet.

[00:10:17] Giles Thompson: [00:10:17] No, and actually it’s quite funny. I look by the way, I love the phrase with when we were playing multiplayer. I think that’s an amazing phrase –  love it. But I think the other thing is, you can’t win as a law firm  from in a sense, because if if you’re using document automation software or something, and you’re creating a draft in seconds and you’re charging a good amount of money to do that clearly there’s a lot of IP that has gone into you getting to that point.

[00:10:40] So query whether time is the relevant thing anyway, in terms of the value, but actually, the inverse, you’re also not winning because if there’s tons of work going in and you’re trying to make it look like every single stage was easy. And not  iterative and everybody working all hours on a document and yeah, I guess it’s a little more comfortable and a lot safer.

[00:11:02]Having this sort of wall in between you and where you can wrap up the package and then deliver it in a particular context. I think one thing that’s quite interesting Ab is I’ve seen in a slightly different take on this really take off.

[00:11:15] And it’s something that’s connected with, the sort of more commoditized, outsourced Legal advice, offerings that a lot of these big firms are doing. And actually the it’s funny because in a different context, the client and lawyer collaboration can work really well. So I, and I’ll expand on that. So I’ve seen where corporates are doing routine contracting works.

[00:11:36] If something like a know procurement function. And I’ve seen where certain risks franchise and that kind of thing are exceeded at that point, then lawyers get added to documents or get added  to a document repository and then asked to advise on particular documents if they have certain property.

[00:11:52] So that’s kind of collaboration. It’s actually been around for a fairly good while. It’s funny to see how, where it’s quite clear, who’s got responsibility for blocks and where advice has actually been deemed delivered. You can get around those things and actually people can work in pretty good harmony in that sense.

[00:12:09] Ab: [00:12:09] Yeah. And I think that’s right.  A lot of these things are big changes for those that have been around and have been doing this work for any amount of time. So it’s just making people feel comfortable by having some incremental things. So they’re used to the process, right?

[00:12:24] If you are warming them up by, as you said, if you’re using something like doc auto and, you’re able to turn things around quickly, but helping them in a way, Hey, you need to give this to your client or your in-house teams need this great, how we created and delivered this very quickly. Next time, when you do that, they become a bit more accustomed to paying for efficiency rather than inefficiency, which has been the case in the past, because efficiency doesn’t have to mean that you’re cutting corners or the level of thought hasn’t gone into it.

[00:12:56]It is in fact the opposite where you spent probably a lot more work upfront to make sure you’re thinking through a lot of that. And, you are spending more time problem solving than you are producing things.

[00:13:10] Giles Thompson: [00:13:10] Yeah, no I completely agree. And it’s definitely a mindset shift needed.

[00:13:14] And I suppose, actually in a scenario where you’ve got a first draft, that’s completely spat out and thinking is, has happened in the background so that it’s literally a hundred percent automated when it gets to that point, you actually get around a lot of these issues. Almost entirely because you’ve got that first draft.

[00:13:32] And then at that point it does become a sort of true collaboration. But I, and I especially always probably run into species again when you go in and tear up that initial first draft.

[00:13:40] Ab: [00:13:40] Yeah, exactly. Yeah. I don’t think the initial first draft offer often looks exactly the same by the time it has signatures on it.

[00:13:47]One of the things that I thought that certainly you’d be good to take it your view on that: as a lawyer, that’s just joining the workforce today in house or in private practice, so let’s say you’re either a trainee or two, three, four years PQE, what do you think are the skills that they should be focusing on?  And part of that is I know part of your interest came from your work with IP lawyers. And not saying everyone has to go out there and learn to certainly code or even be an expert in using tech. But what do you think are some of the things they should at least be keeping an ear to the ground about?

[00:14:19]Giles Thompson: [00:14:19] This is a huge can of worms and I’m really glad that you’ve asked me about it. Because it’s something I’m fairly passionate about.  This is perhaps a bit of a controversial thing to say, but I think that the skills that often junior lawyers at this point in time get rewarded for, and indeed they can absolutely set out and move up and doing are not necessarily the skills that, junior lawyer are gonna need to have in 10 years, or indeed those junior lawyers who are starting or working now are going to need by the time that they’re looking at partnership . And actually one of the reasons I left practice myself was because I was doing IP litigation and thoroughly enjoying it.

[00:14:56] But a large part, of course I did was taking precedent information and then reshaping and, sometimes that was deleting and filling out square brackets. Sometimes it was a fair bit more complicated. And I wouldn’t want to undersell how hard some of that can be, but ultimately I was the most junior person on the team.

[00:15:14]So I was doing a lot of the more monotonous and square bracket literally filling out or deleting. And I, and actually I got pretty good at it. And I’m  dyslexic. To avoid those comments about sort of attention to detail. I actually got quite good at creating almost algorithms in my brain around how to use, find and replace how to perform checks and all this kind of thing.

[00:15:34] And I thought, hang on, I’m getting good at this. And people are clapping and applauding me for getting better at this stuff, but actually. This, isn’t why I got into the law. But also this is stuff which is probably not going to serve me that well in the future. And this is not stuff.

[00:15:47] When I look at the people who are more senior than me, that really impresses me about them. Obviously when I was a trainee, I was really impressed by people who knew every Word function, but that’s slowly changed. To that end, what skills would I say to build and I, again, a bit controversial, but this negative feedback I often got in practice was.

[00:16:05] Why do you always try and find a different way of doing things or why, why do you always over complicate things, Giles? And so I would actually say that people don’t lose that. I think that’s ultimately a, I had it to a, such a degree that I thought I, she wants to change the way that certain things are done for the better, so I’ve moved, but I think there’s always a healthy element of that mindset, I think is really important to preserve.

[00:16:27] And I think it’s important to remember, especially when you’re on the junior end people who are more senior don’t necessarily have an incentive for  you to keep asking those questions. And you might set yourself apart as someone who is able to innovate and challenge the status quo and actually maybe even generate new forms of revenue for the business, but will say for yourself and you’ll face in the partnership.

[00:16:47] So I’d say, hold on to that kind of. Challenge things mentality. Obviously there’s a time and a place probably like 3:00 AM when you’re trying to put the transaction. It’s not the time. But yeah, I think T take advantage of the opportunities that are available to exercise that particular muscle.

[00:17:00]And definitely. Network with tech, the technologists in your firm and network with people like ourselves out, because, frankly, we’re grateful from the attention from private practitioners or in-house lawyers. But actually, because we might be able to  teach something and give them a tool that will also help them stand out.

[00:17:19] Ab: [00:17:19] Yeah. And I love so much of what you were saying, because I think there is an element at different stages of your career, regardless of what you’re doing. And certainly a technical career like legal practice, you will need to have different skills, right? What you need to be good at when you’re a trainee in your first month is probably going to be very different to when you’re a partner and you need to be able to learn a lot of those things along the way.

[00:17:42]The frustrating things, from everyone’s perspective,  there isn’t a rule book for a, Hey at three months, learn about these things. So you can be ready in another three months time. So you do have to do a lot of work because it will change and it will differ both based on the firm or the company you’re aware as well as your practice and what you may want to do in the future.

[00:18:01] For sure. You should be able to question and challenge things. And sometimes if only to understand why something is being done in a certain way, and it doesn’t mean that it’s right and it shouldn’t change, but at least it’ll give you the context and the background, because some things, which frankly seems quite absurd because it doesn’t.

[00:18:20] In a particular way, maybe because it makes sense from the client’s perspective based on what they may need to do with a document or information. And if you don’t have that context as someone who’s sitting there at 3:00 AM , doing control F searches for square brackets, you would think this is definitely not a good use of my time.

[00:18:37]But there may be a reason for that. Doesn’t make it okay. But there may be at least a reason that’ll give you some solace. And the last point I’ll say is. The incentive piece that you talked about right there, often isn’t an incentive for a partner let’s say, or someone at a high level in the firm.

[00:18:54] To get you to sit there and improve how you’re getting the work done. I think that’s true. For what its worth  I do think is starting to change very slowly, but it’s starting to change. And one of the conversations I’m having in a few weeks is around how a lot of the partners and senior associates, they’re ultimately managers, but they don’t see themselves as that.

[00:19:12] And often they’re not even trained to that. So that does create a gap in, personal development and team development and people development that you might expect. And I think this is where in-house teams. So generally a lot better because at least they have for better or for worse, a corporate structure who is aware of that.

[00:19:27] And there is some programming there. And the very last point I’ll make, I realize I’ve been talking for awhile.  There’s a big difference in someone who practiced as a trainee 10, 15 years ago, really getting a full understanding of what it’s like for you today. And I mentioned that because it’s actually important and helpful for your partners or your supervisor to understand some of the ways in which you’re doing things, because they may not know that anymore.

[00:19:55] Because if the last time you did that kind of work was 12 years ago, you would hope some things have changed and that’s not on your radar. So actually you may, again, time and place important but you may actually be helping the whole process, but just being a little bit more vocal around that.

[00:20:10] Giles Thompson: [00:20:10] Yeah, and I think that’s right. And one of the things that, I do a lot of and without direct it back and get is the sessions. But what we do is we educate people on what our tech does. And we actually do have a large focus on the student population as well and not trainees because.

[00:20:28] We went away that, it’s not actually that much of a long play to those people that are basically deciding what technologies companies use. And, I certainly was in that, the pair of shoes, where I had to explain to a partner that You could use a PDF compiler as opposed to printing the document off, manually compiling it and then scan it, scanning it back in.

[00:20:50] And in fairness, I don’t know how long Adobe has been able to do that in a way that most people know, but I don’t know. Is it, has it been 15 years? Has it been as long as a lot of those partners have been at this time? Probably not.

[00:21:04] Ab: [00:21:04] Yeah, and that’s right. And I’ll give you guys a shameless plug.

[00:21:07]Yeah, I would, if you’re a student, please do check out Avvoka  Academy. And otherwise as well, I think it’s a good resource to start learning some of these things. And if you’re listening to this podcast, I already appreciate it because we do talk about these things quite a lot, too. Awesome.

[00:21:19] So I just had one more, one more thing to talk about and conscious of time as well. And it touches on the sort of trust element we talked around, having transparency with your clients.

[00:21:29] The partners or supervisors that you worked really well with, where you felt like you were being heard or are you were learning a lot what did they do well to to basically enable you to go out there and learn things and, take an interest in technology and all sorts of other things.   I’m thinking of this as, how do you encourage someone who’s in your team who you’re working with?

[00:21:50] To come forward and say those things, because there is a trust deficit element where people feel afraid. It’s look, if I go and tell them, I don’t know, something, will this look back for me? I think that sent me prevalent in law firms and in my experience as well. And in my discussions, how do you overcome that?

[00:22:05]   Giles Thompson: [00:22:05] There were definitely some fantastic mentors that I had. And I think the ones who were great were basically if I would do it was proposing to do something a slightly different way, they’d say, okay before you go and actually spend the energy doing that. Can you go away and explain to me, what’s wrong with the current process and also what what the benefits of your process and how do we actually get there and then we’ll make an assessment on that basis.

[00:22:29]And I think what that did is it forced me to have a degree of empathy with the way things currently were. And actually, even if they weren’t ideal, there might be very good reasons, a little bit, slightly crazy ones. Why it was a certain way. And I’ll just use that example. I remember that in a particular context, absolutely losing my mind because I was dealing with signature pages, which have been signed on pages, which have different document numbers.

[00:22:54] And until you realized that was when I was training, until you realize the risk associated with that for a large transaction, you don’t really understand it, yeah. Just doing that loyalty thing of using your in term anxiety, that’s been drilled into you to unturn overturn every rock and really look at the negatives of moving away from the standard.

[00:23:14] And then thinking about actually. To be honest, that doesn’t really match up with the potential benefits of change. And I think actually those supervisors really helped me to, in my comment real. So having that level of empathy where people say to me, okay yeah, I’ll have style. We need to make sure that had to matches up three millimeter away from the robot level or something.

[00:23:37] I get why that’s super important because if you have two signature pages and one of them. It’s three millimeter difference to the other. That’s a big problem. So yeah, I think the recommendation would be. Actually sit down and make time to talk through proposals like this and take them seriously.

[00:23:53] But I think the beauty of that is it also forces the person instead of coming out with a proposal to think seriously about it as well, because it’s all very, I think a lot of this stuff comes from a place of frustration or, frankly just being fed up and tired which is a situation I was in a lot as a private practitioner but actually putting together a concrete proposal, Yeah.

[00:24:10] That’s about much more helpful  rather than an emotional outburst. It’s an emotional output.

[00:24:14]Ab: [00:24:14] That there’s a great example of there’s some of these things that happen in the moment. You’re like, why does this even matter? Why are we, why are we making these sort of micro adjustments and moving things by millimeters?

[00:24:24] It matters to the clients and it matters overall to the practice sometimes. Yeah, it’s important to take a breath every now and then, and just think about it. And actually when you do see the potential repercussions of that, it makes everything seem real. And it’s okay, now I understand why that was the case. So awesome.


[00:24:39] Wonderful. Giles , thank you so much. When I publish this and with the show notes, you’ll find link to Giles, his LinkedIn page. He’s very he’s very prolific on LinkedIn and Twitter.

[00:24:47] So I’ll link that link out to that. Please do reach out to him. I’ll also link to a Avvoka Academy. And if there’s anything else that we can help with, please, don’t be shy to reach out to either one of us. I know we are. Very happy to connect with both private practitioners and in-house folks because yeah, it’s wonderful to learn.

[00:25:02] And actually, certainly if you disagree with anything, we said, it would be wonderful to hear your perspective too.

[00:25:09] Giles Thompson: [00:25:09] Yeah, Def definitely and Ab thank you so much for having me really appreciate it. And, I would say we’ll invite you on to the podcast that we do at Avvoka as it, when that’s released, but maybe it will be, maybe it’ll be clubhouse now,

[00:25:20] Ab: [00:25:20] yeah, exactly. I need to get an iPhone for that though. Awesome. Thank you so much. It’s wonderful having you on have a good day. Thank you everyone.

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