Jack Shepherd on the transition from legal practitioner to legal technologist

Legal Practice Lead at iManage, Jack Shepherd, discusses his experiences making the jump from practicing lawyer to building legaltech products and offers his key pieces of advice and learnings on product development, collecting data and how to incentivise lawyers to adopt new tools.

Jack Shepherd combines his knowledge of legal technology with his experience working as a restructuring lawyer at an international law firm. He has a focus on the processes lawyers do in their day-to-day working lives, and how technologies and processes can feed into these and actually become adopted on the ground. He has particular expertise in transaction management, e-signatures and knowledge management. 

In this Transaction Management episode of Shieldcast, Jack and Geoff discuss:  

• Customers as the driving force behind iManage's recent acquisitions to expand their product offerings
• Why the transition from legal practitioner to legal technologist was the "challenge of a lifetime"
• How to incentivise lawyers to become interested in and adopt new tools
• The tension between technology pushing standardisation and a lawyer's inherent want to offer client-centric services
• What to do about data - the collection process and the insights to be extracted

Listen to this Transaction Management edition of Shieldcast to find out more!

You can learn more about iManage and the services they provide on their website: www.imanage.com

Jack contributed to our recent Transaction Management eBook. You can read his insights on whether technology has fundamentally changed how we close transactions by downloading the book here. 

Find other episodes in the series on our website: Shieldcast library

Podcast brought to you by Shieldpay - learn more: shieldpay.com

Transcript

Geoff: On today's episode of the Shieldcast, we welcome Jack Shepherd Legal Practice Lead at iManage.  Welcome Jack. 

Jack: Hi, Geoff.Good to be here. 

Geoff: Jack is another lawyer turned legal techie. Having been trained and practiced as a solicitor at Freshfields, he jumped across the corridor to join the innovation team as a legal tech associate. It was in this role that I first met Jack, a long time ago now, but since then Jack has gone full tech and now is Legal Practice Lead at iManage. 

Jack describes himself as being interested in the human side of legal tech and actually getting technology used. I want to delve into that a lot more, a little bit later. A career to date that spans Freshfields, a firm that sort of defines what precedent is in terms of how deals are handled to iManage, a legal tech company on a journey for being known as an email and document management provider to today, a company that touches pretty much every part of the transaction management life cycle.

So, you are absolutely uniquely placed to provide some insights on the topic of this series and I'm very much looking forward to one of our conversations finally being recorded so that posterity can listen to it…or maybe that's a bit too grand.

 To begin with Jack, it'd be great if you could tell us a little bit about iManage  in your own words and your role as Legal Practice Lead and kind of what you're doing.

Jack: First in iManage, as you say, you teed it up quite well. Most lawyers that have spent time in a reasonable sized firm will know iManage’s risk document management system, email, filing, all that kind of stuff. But iManage is an incredibly exciting company to work for.    It made the acquisition of Raven a few years back, which introduced some AI capabilities to the company, which is kind of where our contracts intelligence solution. It’s all about clause extraction, things like that and our Knowledge Unlocked solution which is knowledge searching. That's where some of those two solutions come from. More recently also with the acquisition of Closing Folders, which introduces a transaction management angles to what the company offers. So, you can really think of iManage now as sort of a full stack legal technology company that provides capabilities pretty much for every part of the legal technology framework that we should need. 

My role specifically at iManage, as you say, Legal Practice Lead. I really bring with me my experience of being a lawyer from Freshfields. I think it's incredibly important in any legal technology company, and I don't think you necessarily have to have been a practicing lawyer to bring that experience in, you can do it by having conversations with people and asking the right questions.

But I think fundamentally what iManage's philosophy is about is getting really close to the end users. How can we produce technology that doesn't work in a vacuum, but it just works for the people that need to use it. And it's very much where the company positions itself -being, you know, for knowledge workers, being for people that who's primary asset is knowledge. How can we deliver solutions to them? That really transformed the way they work. That's what we're all about really. 

Geoff: It's an interesting transformation, really. I mean, in a very short period of time, Raven was bought maybe a couple of years ago and Closing Folders even more recently than that. So, it's clearly jumping on an opportunity they see or demand from their clients. Do you think that progression for iManage, being driven directly from what their clients have been telling them, and so direct client feedback has been we want you to have everything?

Jack: Yeah, exactly. When we talk about law firms, it's from different people within these law firms and everyone's saying the same thing, from IT directors to innovation people to the end-users and the lawyers, is we want a software stack that speaks to each other nicely. We don't want to go to one vendor for one solution and another vendor for another solution. That's why APIs are so important in legal technology. So look, knowledge is that the products don't just fit within a silo, but they fit within a framework and a set of processes that touch upon other solutions as well.

The great thing about iManage is that we've now got so many solutions that fit across so many different process areas. And, as you say, that the acquisition's relatively recent and you know, pretty high up the company's agenda is how are we going to squeeze all of these products together, working harmoniously, sharing data between them, in a way that really works for lawyers.

So, yeah, to answer your question, it is directly responding to that kind of feedback.

Geoff: That you know that sort of segways nicely to ask you questions around tech design that actually works. Cause I know you're passionate about that, and you know what you've just said about making everything seamlessly work together.

It's interesting your path has been from a fee earner to internal technology development within a firm. How easy was that, or how difficult was that should I say. Because there's a multifaceted, and I'll let you get onto it, but it's, for me, it's fascinating being a former lawyer myself. I jumped out of the firm rather than trying to see what I can do internally, but there's a very different mindset being a fee earner dealing with billable hours, then being the legal technologist that's tried to transform the way that the legal practitioner works. So how did that come about? How did it feel and talk to us a bit about that. 

Jack: Yeah. I mean, I would say it's the challenge of the lifetime. And one of the reasons it's such a challenge is because you don't think it's going to be a challenge. And one of the things that I had going into my innovation role was we worked for a law firm, a big  law firm, most people that work for those kinds of firms have pretty good academic records that they are used to people heaping praise on them. And then they actually think that they're pretty good at what they can do. And I think in the case of lawyers, there's this impression among most lawyers, that they have, rightly or wrongly, but they could probably turn their hands at pretty much anything and give it a good crack. That's definitely a mindset that I had. 

And, in many ways for me, it was exacerbated because I have experienced working in development teams, you know, hands-on with code and that kind of thing. So, I've always had very keen interest in technology. I do a bit of programming in my spare time. So, I was coming into my innovation role with his mindset, I'm a lawyer I've done relatively well, and I can turn my hands at pretty much anything, but especially technology because I know how to code and that's going to put me in a really good place.

I started doing this innovation secondment with that kind of mindset and looking back on it,  I adopted what I'd now describe as like a tool centric approach or a technology centric approach to innovation. Which I found out soon enough is pretty much the wrong way of doing things. You don't start with technology. And one of the projects I worked on was a matter management, transaction management product, basically. And I remember designing this and not putting users at the heart of it. But I thought to myself, you know, I'm a former lawyer myself, or I'm a practicing lawyer, I know how these things are done. I don't need to speak to many other lawyers, let's just design the tool that works for me, and everyone's going to come along with it and be fantastic and it's going to be a success.

And found out pretty quickly that people work in very different ways. One example I can give is when you've received comments back from the other side on a document. Now, my approach is always to look at the changes the other side had made and type those into the document. And the product was designed around that workflow. But from day one of launching the products I found out lots of other people did it in a completely different way. They would copy that version they got from the other side and work off that version. They wouldn't do that exercise of manually typing in the comments and they just work off the version the other side sent over. 

And it was kind of really at that moment that I realised that being in technology and providing products for people is so different to being a lawyer. It requires a very, very different skillset because when you're working on a matter for a specific client, the stuff you do generally is tailored to that particular situation, for that particular client. If you're working on any software product really, if you want it to be successful, the chances are your idea is that the product or the solution would be available for more than one person to use, and indeed for multiple classes of people to use, multiple law firms maybe, multiple practice areas. And the problem is that I had started off by designing a product that worked very well for Jack Shepherd, but it didn't work very well for people who weren't Jack Shepherd and that I think is like a key difference between the two. 

Products, you really have to adopt a user centric approach. You have to understand who are the people who are going to be using this products. You have to understand they don't care about the products, they're not like a technology geek, like I am. They don't use technology for the sake of technology. They just want to use the technology to get a job done. So, you've got to find out what the job is, what jobs do they want doing? Is the technology sufficient enabler to get them to do that job? What are the incentives in place to get them to do things differently? These are all the things that kind of really became very clear to me after I started in my innovation role and, and really caused a huge change in mindset for me compared to how I used to operate as a practicing lawyer. 

Geoff: Oh, that's really fascinating insight, actually, Jack. And one of the things that you knew drew out there is that customer centric or user centric approach, which lawyers pride themselves in that approach. And in a way, it's slightly something that stops them adopting technologies to a certain extent, because of that lack of flexibility that a lot of products do have. 

One of the elements that I've found is that people come to lawyers to solve problems, right?  I want you to do my transaction. I don't really care how you do that. I just need you to get to the final product. My problem is solved. And so, from a lawyer's perspective, it's quite difficult because they're so time poor, because they're constantly tried to solve other people's problems, they can't really look at looking at their business from a product perspective or looking at like, how do you productize that? 

How do you manage to find lawyers that have the time to give you to do that and how do you approach it really? Because literally for lawyers, time is money because that's how they bill. 

Jack: Oh, this is a tough question, this one. For me, it all comes down to incentives and I think you've got to start from the premise that no one's going to change the way they work. No one's going to do anything new, unless they've got an incentive to do that. And for people, there's a small minority of lawyers that were like me and love technology and the kind of people that would download an app to their phone just to see what it does. But, in the work context, those kinds of people are very few and far between, but they're very easy to establish incentives for because they're up for trying stuff new. They don't care about whether they get bonus for doing it. They just want to do it. Those kinds of people are very few and far between, but the first step is to find those kinds of people. And they'll be really good at working collaboratively to change and improve processes.

But for everyone else, it really comes down to incentives. And I think when people talk about change management for lawyers and incentives for lawyers, in general, I think people generalise a bit too much. There's different types of lawyers and different types of firms and different types of clients. The incentives in place for an associate, for example, to change the way they work will be very different from the incentives you need to get a partner to change the way they work. And the two very much kind of cross relate in law firms. I think because lots of people talk about the monetary incentives for the associates and introduce things like innovation hours to get them to change the way they work. But my view is that that's not effective. I don't think that's a very effective way of instilling change because people generally no one's auditing those hours. And it's not really a good metric of value. It's a good measure of time, but it's not measuring value. 

What associates do care about very deeply, it goes back to the standard persona of a lawyer is that, I think it was written in the FT a while back that, most lawyers are overachieving, perfectionists that thrive on praise. And the one incentive you can really get is, is a partner telling them that they're good. It's a partner pushing them along the way to, to use a new tool. So that kind of drives you back to, okay, well, let's get the partners on board with what can we do to get the partners on board, right. 

For partners it's two things. It's first of all, profitability. How can you put putting money in their pocket? Can you spot matters that are like hemorrhaging money? Are they losing a lot of money out on a specific type of matter, whether it's a specific type of client? In which case, we can look at those things and there you've got a direct correlation between improving processes and profitability.

And the other thing is like just general client satisfaction. It's a bit more of a difficult thing because you've got to distinguish between client satisfaction and snazzy tech tools because snazzy tech tools that the client doesn't care about, you might as well forget that. But things that solve client problems in a very real way, sell the partners on those. And then, you know, sometimes it trickles down to the associates cause partners get bought into an idea. They really propel their associates along and to instill the change. And then you've got the kind of full part of the party there. 

To kind of answer your question, I think people look at tech for tech's sake far too much. Tech isn't important. The outcomes that tech achieves are the important things and you've got to sell people on the outcomes. And only once you've sold people on the outcomes a tech tool can deliver, can you actually get people to use the technology itself.

Geoff: That's really interesting because it depends hugely on the type of law that you practice as well. Right? Because I think it's a very different thing if you're doing what is considered a slightly more commoditised type of legal practice versus where any efficiency gains are hugely important.

Yeah, I'd take conveyancing as being one of those that, that I still think it's crazy the cost of conveyancing is so low considering it's the biggest purchase that an individual will ever do. It's probably the biggest fee that someone should have to pay really for a transaction.   Versus, where we're at, you know, in a M&A transaction or a structured finance transaction, or a restructuring insolvency transaction, where the nuances are very different. And where I guess the one spectrum, you have total transformation of the process through technology to a certain extent yet, on the other side, you just have slight marginal gains. So, and then in the slight marginal gains category, you have basically e-signatures for example, taking one bit of the transaction cycle, that the e-signature providers just aren't suitable generally for those types of transactions on the whole, because of the way that those deals are structured.

I'll come to a question in, in due course on that, but it's that we haven't got tools really that have really penetrated heavily into those like more complex, higher value deals rather than the commodised side? 

Jack: The kind of thing I usually think about on this issue is how close is the type of work you do to a car factory production line and lawyers don't want to be on this spectrum full stock because many of them take pride in the fact that the work they do is extremely complicated. That's fine, but I think everyone's on the spectrum to some degree. And like I said, the conveyancing stuff is very much in the left-hand side of the spectrum. It's like, I want to buy a car. Okay, here's your car. And then somewhere in the middle, you've got like, you know, you're buying a car and what kind of trim you want? What kind of seat color do you want? What sound system do you want? So, we've got like a standard product with some trimmings. And I think sometimes the mistake people make is that they're in the middle of the spectrum where they've got something standard with some bespoke things. But the conclusion people too easily draw is because it's not completely standard, the whole thing is bespoke. And I'm a very firm believer that no matter how custom the services you offer, however custom you think they are, there are always elements that you can standardise in it.

And I think sometimes people fall into that trap a little bit of thinking that just because it's not, everything's like a, you know, fill in the gaps, fit in the square brackets, you can't standardise certain aspects. And I think the one preliminary question that comes in necessarily before the technology is what are the processes that this technology is going to bite on? Because it's very, very difficult to get technology to bite on processes that are completely inconsistent every single time. There has to be some degree of consistency in all the processes, otherwise you might as well just build a new piece of technology for every single transaction you do, which we should never make sense at all.

And I think maybe we, you referenced this a bit in one of your earlier questions, but I do also think there's a tension between products needing necessarily to push lawyers down in a particular way of doing things, against this resistance from lawyers that they're not on the car production line spectrum, that they want to do things their own way. They don't want to be dictated by the product. And there's this huge tension here because really what we need to be doing is to meet somewhere in between. We shouldn't be giving lawyers free reign and we shouldn't have like one M&A matter being run completely differently from another M&A matter.

But when you talk to lawyers, that seems to be what happens. I mean, I've spoken to a lot of lawyers and done a lot of research on this, on this point. And the conclusion I've drawn is that processes by and large are dictated by the individual preferences of the party that you work for, which I find problematic in a law firm. In any other business, people would look at this stuff top down, they'd look at how can we optimise our processes in a way that enhances the client experience or that enhances profitability. They would take stock of all of the processes people do, and they'd look at ways of harmonizing them and optimizing them.

And that's a fundamental tension. Comes back to processes. You’ve got to map the process, get the processes consistent first and then the technology bites off those. But as I said, there's this huge tension because I don't think many lawyers want to be felt of as like standardised. 

Geoff: Yeah. And I think that's absolutely right. Lawyers are I think we all pride ourselves having something to us in some kind of some secret sauce, and that's what sets us apart from others. Well at least that's the perception we'd like to give to the outside world and why we went to law school and spent loads of time training, is you feel like you need to demonstrate it and flex that somewhat. 

But I think that's why it's interesting seeing new firms coming in that are taking a very different approach. So people who have probably been in larger firms setting up their own firms or joining smaller firms, and really bringing in that kind of process driven approach with that additional nouse to do transactions and really making the whole process or transforming that whole process bit by bit.

But I think we are still for a while in the world of marginal gains rather than in total transformation of processes or how a transaction is done and probably even further away from a total standardisation of how things are done across the industry. We will get there, but I don't think we will get there anytime soon. I think different segments of it have. Again, it's on that spectrum, that conveyor belt spectrum, right, again. It's an interesting place to see where everything is going to evolve to and particularly around the transaction management life cycle. You guys have your e-discovery Raven piece, then you've got document management and you've got closing folders and e-signature and all of that process - sort of what is the end-to-end process but then what happens next? What did you do with all the data and all of that knowledge effectively?

Jack: I think like to answer the data question, we've got to come back to adoption of technology tools, because if I maybe just take one of your other points, which is if we're struggling to get adoption on what you call the marginal aspects, like adoption on things that optimize the existing workflows, if we're still having lawyers refusing to manage multimillion dollar M&A transactions, in anything but Microsoft word, if that's a problem, what hope have we got in getting them to adopt something that's just like a fundamentally different process like that. 

There's lots of people out there that pride themselves, we're going to disrupt, we're going to do the big bang innovation, I think that is a perfectly legitimate way of thinking about things. I find it scares lawyers off a little bit, and it's much easier to build that trust by delivering incremental improvements and then maybe that's a roadmap to something more exotic.

On the data point, this is a very interesting one. So first we start with what outcomes are you going to drive? Why are you even talking about data? But no one wants to just to capture data and have it sit in a load of spreadsheets and databases. What's the purpose of doing that?

And the purpose for law firms, I mean, there's many purposes, but I think the two that will probably resonate mostly with lawyers is first of all, making your advice better. Instead of you looking at something the other side is saying and thinking, oh, well, that doesn't sound quite right, I've never seen that before. And then maybe emailing around the team and asking people like, you know, has anyone seen this before? Instead of doing that, you have at your fingertips a view based on what's happened in the past, as to whether this is market or not. Is this something that we've accepted before? Is this something we should accept? And that's a really good use of data. 

The second use case I just draw out would be like things that are done even more finger in the air. I think more in the process internal side for firms, but especially in a world where all the talk is about moving to more of a fixed price model, most law firms are coming up with this kind of stuff and fee estimates if they're not on fixed price models by way of finger in the air estimate. Wouldn't it be better yeah, if we, if we looked at the data, looked at the characteristics of the matters that we've done in the past- work out how much they cost and, and have a bit more steer rather than just guesstimating.

Those kinds of the two outcomes I think might resonate with, with lawyers as far as data collection's concerned. 

Geoff: Yeah, I think both really interesting points. I think the first one, particularly, and I was talking about this previously with Anthony Rose from SeedLegals, but  they have something called a ‘termometer’ on SeedLegals. It goes, which actually tells them what percentage of people have actually accepted  that term at one point. One of the challenges there, right, is that it does become the internal versus the external market, right. Because then if you're looking at deal terms like that, purely within what's happened within a law firm, then you're like, okay, great, well, that's market on the on the premise of the deals that we've seen, but we only see 1%, 2% of the deals that are there, not what the whole market is. So, we have no idea whether that can go - which might not be an issue because firms tend to operate within certain tranches of business or of a personal thing. So, you can probably feel that your within your market when you've got the deal in terms there. 

But it's interesting, cause then it's not open sourced. Do at some point firms, like yours, end up having that ability to collate all of that information data, obviously anonymised, around that and be able to really use that as a powerful tool?

Jack: I mean, yeah, we would love to be able to do that. I'm sure there's people listening to this should think of a million reasons why we couldn't do it. I think when we're talking about data, like the kind of major blocker you see often in law firms is all of the data hygiene issues that surround them. And I say, let's say we're in a hypothetical world where we were able to collect data from law firms who are happy to give it to us on the basis that we produce insights for everybody. All that data would have to be mapped consistently because think of the spreadsheet. If I'm collecting spreadsheet from five different law firms, the columns have to be consistent otherwise I don't want to have to spend time mapping it against each other. And I think, there's so much data out there and when you say it's internal to law firms, of course it is but... for example, a high yield bond issuance. Prospectuses that are issued, publicly available in the market are fantastic data sources for working out what's market. And law firms already use those, it's just that they employ junior associates to manually trawl through the documents instead of having the data just naturally available. 

Another source would be clients themselves, you know, the big banks, big corporates, they're doing the same kind of deal over and over again. They're looking at contract management systems to track this stuff. I suspect the in-house teams will get there before the law firms do quite frankly. So, I think that's a great business imperative to track this stuff. But I think that that's definitely work to be done around people collecting data consistently, so that the mapping, the data, hygiene issues are reduced.

But back to the question that we're actually collecting the data of course, and that in itself is a huge challenge.

Geoff: No, I thought that that is of course. And then you might be accused of being too central and having some kind of power over what then does become market as a result of holding a position of privilege, which has many moral and ethical issues that can come with that all data conversations end up going to .

So, you know, you rightly point out that you could get data from five different law firms and they are all in different, different formats and different things. But how do you even get it to the point of collecting that data? Because there are certain standard documentations, like the LMA documentation, for example, that's a really good place to start because that's relatively structured data, but how do you extract that from lawyers or even internally from a lawyer or law firm to actually make sense of it and what needs to be captured and what doesn't?

Jack: Option one is the non-technology option. And this is something I've done on myself when I was a lawyer, very junior associate had a client say, you know, Jack, we're interested in tracking how assignment provisions have changed in loans over time. And what I went and did was basically email around the team, so everybody said, please, can you send me all of your finance documents you've executed in the last five years. And I spent a day trawling through them and jotting down on a spreadsheet, what was the assignment provision in this document? What was the date of it? And we were tied in as a timeline of, lots of restrictions and then gradually things were relaxed over time and white lists were introduce, blacklists are introduced and all that kind of stuff. So that's like option one. That's how people would classically do it.

There's an increased desire from law firms to not have to go to that stage of things to track this market intel. And so it's incredibly time consuming and I now have this conversation with law firms, and I can tell you that the best way of getting a partner to walk out the room in the middle of a legal technology pitch  is to tell them that lawyers have to manually tag things or that they'll always have to enter in a spreadsheet at the end of a transaction to say what the key terms were.

My own view is that if he cared about this problem enough, then you wouldn't find that so unpalatable because you know, everyone says, oh, lawyers don't have time to do that. But honestly, at the end of a transaction, how long does it take to fill in a spreadsheet? It's like it's of four or five minutes. You honestly telling me that people don't have time to do that? You know, I understand that people finish a transaction and want to go to the pub and celebrate and that's the reality of things. But, yeah, the reason people say lawyers don't have time to do it is because no one's telling them to, because they don't believe in incentives enough.

But the, the kind of the next option, which I'm a big fan of, is how can you capture this information without people even knowing about it? How can you capture that information as part of processes that lawyers do anyway? There's two things you want to look at there. And this, by the way, applies just as much to collecting example documents as it does to like capturing data points. But if, for example, your firm produces transaction Bibles and you use like a separate print group, you could implement a process whereby when you're submitting your documents in your Bible request to the print room, you have the lawyer enter in some information about the transaction at that point, there's a precondition to getting the Bible produced. And then you can capture that information from the print room who collect the data and then the lawyer doesn't even know that giving you the data, you're just getting data. 

And the other thing you can do is look at, that's an example of hand off point between different teams and law firms worked really well with things like print rooms and centralized legal services hubs. People are good at following like a defined process, which lawyers generally learn how to do that. The other good thing you can do is look at handoff points between different types of technology. An easy example would be like contract automation tool. If you were filling out a form to populate the first draft of an agreement, could you piggyback off the data points people are entering there and use those as kind of characteristics of the, of the transaction.

And that's obviously brings its own problems because obviously we're not just executing first draft, the document changes after that. But you know, there are things don't change generally, like governing law tends not to change. Look for things like that, you know, that's better insights than having no insights.

Geoff:  It would be interesting to run a study, see how many of the clauses never actually even get read. Because now people, people obviously scroll through documents on a screen.

I think it's a fascinating area, what happened with that data, but, you know, I totally agree it's only as good as the data that you have, and there's no point in collecting it or do anything with it, unless you've got a real incentive, a real purpose to do something with it. Cause otherwise it's work for work’s sake rather than anything that's can be actionable from it.

Jack: And I think, the other point I mentioned here is that sometimes I hear the expectation among some people that like tech can do this for you. Like that somehow we should be able to drag and drop all the valid, you know, entire DMS into an application. And suddenly we're producing a report. Like the one I produced on assignment provisions in loans. That unfortunately is not yet the reality.  

Fundamentally, you need to tell the system what kind of outputs you want from it. You need to build up a structure training sets, so there's no point trying to do an LMA assignment, provisions analysis when half the documents you throw it are share purchase agreements. That's going to produce some pretty difficult outcomes. You've got to, you've got to draw a ring around the training set, but you've also got to be clear on the outcomes that you want.

So, you know, the artificial intelligence, machine learning, can definitely assist these things, but they cannot do it in a vacuum. They need that human input and they need input beyond the mere technology. Most importantly, around the process and how you're capturing the data and, and what you're going to do with data afterwards. So, but that's not to think about those things in a complete silo.

Geoff: Yeah, no, I completely agree. And I think it's going to be interesting to see how all of that transpires. 

I've really enjoyed our conversation today, Jack, it's been really insightful on so many levels, but before we cover the last points is, I came cross your blog, and also your interesting videos and crafty counsel in researching for this interview. And I just thought one of those quotes and I just had to have in this somehow was, “Excel is like getting into a freezing swimming pool. You just have to dive right in”. And I think that's what we've done on so many levels around the adoption of technology across the whole transaction life cycle and what you've done in your transition from a lawyer to a technologist and really taking it in your stride, which is really interesting  to be able to have conversations with you like this.

But, other than probably that moment, what has been the most defining point of your career to date and brought you to where you are today and where it will take you? 

Jack: To be honest with you I kind of always knew. I qualified into the insolvency team at Freshfields and I was sort of almost a bit disappointed in myself that I had, because I always had such a keen interest in technology. So, always wanted to do something in technology.  The ability for me to change into that role was, was undoubtedly one of the most defining things in my career.

But, I'd rather pick something that's a bit more personal, which is kind of midway through the transaction management products I was working in my last role, we decided to bring on board some people with a bit more business analysis experience and product experience to kind of support the project a little bit. To be honest with you, at the time I saw that as a bit of a threat, like these people coming in to tell me a lawyer how to design a system properly. You know, how dare they. But I cannot overstate how much I learned from those guys. And, you know, if they're listening, they'll know who they are. But the moments when they were challenging assumptions I was making in product decisions. When they encouraged us to speak to a wide group of people who potentially were using the product and hearing firsthand my own thoughts being challenged by the very people that were using the product made me see the value of user centricity certainly within product work. And almost a landmark moment for me because I'd come into the role thinking as a lawyer, you're the best person to do these kind of things, but it's actually really made me shift my mindset. And in a way, it's harder if you're a lawyer to be put in charge of legal technology products, because you have to actively work to remove the bias that you have based on the experience you've had before, because you're not designing product just for Jack Shepherd . So, you need to make sure it works for the people actually using it. And it's actually kind of the sentiment I carry through, not just in the product work that I do, but pretty much every single aspect of my entire life.

You're in a difficult meeting, someone saying something challenging to you, why are they saying something challenging to you? Is this, is there a layer of the onion you have to peel back beyond what they're just saying to get to their fundamental need. And that, for me, I think is something that I try to bring to every conversation and every piece of work that I'm involved in.

Geoff:  I think that's something that I will take away from this myself as well. I think I have been learning a lot from my product teams, but, put in that context makes it even more real. Jack, thank you very much. We've covered a lot. We've covered a little bit about you, about how iManage it's still focused on making knowledge work, but in a far more persuasive way than it had done previously, what it was like transitioning out of fee earner world to technology and a change of mindset that was needed to go alongside that. And then finally, really talking about where legaltech might go, particularly around data points and around how that might be used in transaction management, but also in generally the approach to law.

So I think it's been a really thoroughly enjoyable conversation today. Thank you very much, Jack.