“Successful Adoption Depends As Much on People and Processes As It Does on the Tech Itself” — Brian Kennedy

This interview is part of Loio’s series of interviews with legal enthusiasts about the ins and outs of the legal industry.

The following is the interview with Brian Kennedy, a senior lawyer and freelance consultant with three key areas of focus: innovation and legaltech, real estate, and inclusion and diversity. From 2011 to 2019, Brian served as the Senior Associate at Dentons, the world’s largest law firm.

“I have a deep interest in legal innovation, including legaltech, new ways of delivering legal services, and related disciplines, e.g., change management, legal design, and project management. I am especially interested in undertaking innovation-related assignments for legaltech vendors, law firms, ALSPs, and in-house legal teams. I am also an accredited change management specialist,” says Brian.

Let’s dive in!

Thank you for being here, Brian! You have quite a combination of skills and professional interests, with innovation being one of them. Could you please tell me a bit more about your professional journey? Where are you now? Why have you chosen to focus on legaltech? 

I spent the bulk of my career as a transactional real estate lawyer, including a long stint at Dentons. Although I very much enjoyed (and still really enjoy) the practice of real estate law, I’ve always been very interested in innovation in the legal sector, in particular, legaltech. 

“Not just doing the work today, but also reimagining how we could do the work tomorrow, and how we can deliver value for clients through transformation and continuous improvement.” 

There are challenges around giving full flight to that interest in the context of a full-time private practice role… So, after 15 years I took the plunge and transitioned to become a freelance consultant. That’s enabled me to combine two worlds: to specialize both in real estate and innovation, specifically legaltech. 

Why have you decided to take this plunge? Are you satisfied with the results so far? 

Very much so 🙂 At the moment, I’m spending most of my time at Orbital Witness, which is a leading legaltech meets proptech startup. Day to day this involves working with teams of data scientists, software engineers, and product designers to develop AI-powered reasoning and machine learning models to assess risk property transactions. That’s quite different to life as a transactional real estate lawyer and I’m finding it to be very, very stimulating.

I guess I have a strong personal vision as to what the digital conveyancing process of the future might look like. It’s exciting to be a part of the movement for change in the industry and actually be able to bring that vision to life. 

Thank you! Let’s talk a little bit more about legaltech. How do you define the main purpose of legaltech adoption? Why should people do that?

It offers a number of advantages. 

“Fundamentally, legaltech can act as a “force multiplier”, dramatically increasing what is achievable when combined with the right people and processes.  It can change the delivery of legal services and unlock new possibilities. That goes beyond digitising existing services to potentially being able to create new ones.” 

Tech can enable firms to identify new business opportunities and service new markets that wouldn’t have been feasible without the use of technology. Clearly, there’s also a significant efficiency play, allowing lawyers to work smarter and faster, and freeing them up to concentrate on their valuable trusted advisor work. 

Ensuring a better customer experience is a really good point, too. I don’t want to suggest that using legaltech to deliver legal work more quickly and cost-effectively isn’t in itself extremely valuable. But there is a part of me that thinks that, in the minds of clients, it’s almost a given that law firms are striving for continuous efficiency improvements in the delivery of legal work. So, I don’t think efficiency gains alone are going to bowl over clients or massively stimulate their demand for legaltech. 

I think that the more bold and ambitious question is about how legaltech could be used to deliver that improved client experience and add value in other ways. In terms of thinking about adding value to clients, you can look at things like whether the deployment of legal tech will create transparency, will enable lawyers and clients to collaborate more effectively, will help clients to manage risk or will offer insights that otherwise might be lost – particularly with the advent of big data and all the possibilities that holds. It can also enable clients to optimize and improve their own internal processes. 

In my mind, legaltech should be about enhancing and making things better, not just making them more efficient and digitising what we do at the moment.

Thank you very much! Could you please elaborate on the role of legaltech in creating a new legal services delivery model?

I guess this ties into the ever-present “more for less” problem, for which there isn’t a silver bullet. Legaltech, if you deploy it successfully, can be used to deliver more with fewer resources. But it’s not just about legaltech: firms need to look more broadly at how they deliver their services. 

Obviously, there are a host of things we could talk about. But in terms of new legal delivery models, there are two particularly current trends I’d mention. 

One is the advent of law firms and alternative legal services providers offering legal managed services – effectively an outsourced legal function to improve operations and cut expenses. 

Secondly, you have the rise of flexible resourcing models and on-demand lawyers. This allows firms and in-house teams to take a flexible approach to the size and capacity of their legal team in line with fluctuating demand without taking on fixed overhead. That can be particularly useful when faced with peaky workflows or an uncertain economic outlook. Maybe, in the future, the model of a smaller core team of lawyers augmented by this on-demand resource might become the new norm. 

“What’s also interesting is that these new delivery models have the effect of opening new roles like legal technologists and legal engineers and disciplines like legal operations, legal project management, legal process improvement, etc.” 

For me, that’s really exciting, not just because these are exciting roles and we want to encourage diversity within the legal industry and equip it with the expertise needed for the 21st century.

But if you’re serious about delivering transformational or disruptive change, you really need to adopt a multi-disciplinary approach.

You have written a LinkedIn article about the art of achieving a perfect combination of human and legaltech when practicing law. Could you please elaborate on that?

That’s an area I’m really interested in. 

As the practice of law becomes more tech-driven, how do you make sure it still feels human? How do you preserve lawyers’ place at the heart of the client relationship? That’s obviously something lawyers are going to be very sensitive about, as they won’t want to see that eroded through any new technological solutions. 

It’s a difficult question: what blend of human and digital interaction will constitute the optimal outcome from the client’s perspective? The key point, I think, is that it is going to be a combination. As in our everyday lives, clients are not likely to have a binary preference between human and digital experiences. They are going to seek the best of both worlds. 

“I think law firms are going to need to evaluate which aspects of their work provide the most suitable opportunities for technological innovation, and, on the flip side, what aspects of the work are those where the clients will value a more personalized approach.” 

That sort of future visioning can be especially challenging. In particular, because the answer may be different for different clients and in different practice areas.

At the end of the day, what you want to do is to be able to showcase all those human qualities that clients most value in their lawyers. 

Definitely. It’s different for different areas and for different clients. Is there no perfect recipe for success? 

If I knew the perfect recipe, I would go out into the market and sell it. 🙂 

I’m not sure anybody has come up with the perfect solution yet. 

I think the way I would start answering this question is by looking at how we can deliver legal services in a way that emphasises those essential human-lawyer characteristics. You have to think about what those are and how you put those front and center, but without forsaking the efficiencies that tech can facilitate. 

Who can help to decide this in a law firm or in the in-house legal team? Who’s the person to go to? Or is it something that every lawyer should decide for themselves?

I suppose, ultimately, you’ve got to ask yourself what makes clients value one lawyer over another. 

I’m just giving a personal perspective on this. But to my mind, it’s the professional judgment of individual lawyers. It’s their empathy, whether clients feel that support. It’s about whether the lawyer really understands the client’s business, commercial concerns, and drivers. Clients look to lawyers who are great in negotiations, who can read the room, and build bridges when parties sometimes have very different commercial considerations and perspectives. Those are maybe the sort of human attributes that you’d want to put front and center and that it’s hard for technological solutions to replicate. 

Conversely, though, there are qualities clients value in their lawyers which you can build into technological processes. These are things like transparency and being easy to work with. 

I also believe that the legal design movement will increasingly play a role in tech development.  That’s about a lot more than the aesthetics of how things are presented.  It’s about putting the end-user at the heart of the experience, considering how something is going to be used, and how somebody will respond to it: whether that’s a lawyer within a law firm using a piece of technology, or a client who’s going to see their service delivered digitally. When you start looking at things through a design lens, you can then start making technology look and feel more human.

Thank you! My next question is about legal tech adoption and mistakes that law firms and in-house legal teams make when adopting legal technology. What are those? 

Counterintuitive as it may sound, don’t actually start with the technology! 

Technology is a tool, not an end in itself. So, I think you need to have a clear vision as to what you want to achieve, and what the metrics for success will look like. Only then you should explore tech solutions which will facilitate those aims. 

“Remember that successful adoption will depend as much on people and processes as it does on the technology itself.  That’s why you have got to put the end-user first. You have to really understand the requirements of the end-user and stakeholders within the law firm.” 

Don’t make the mistake of assuming that the interests of your stakeholders will automatically be aligned. Take the time to really understand them and think about how you can build a common vision for a particular tech initiative. 

You’ll need to invest some time in really understanding and mapping out existing processes. At the same time, tech adoption shouldn’t be overly influenced by what’s worked in the past. It should go hand in hand with new and improved processes. 

Getting the right team together is also key. You need to get the right blend of experience and include champions, sponsors, and early adopters, who are going to really help drive through the change. There might be some people who seem right on paper for your team, but if they don’t have a real desire to implement change or the bandwidth to be effective participants, then that might need to be carefully managed. 

Speaking about driving through change, I know you’re very interested in change management. Can you explain how this feeds into successful tech adoption?

Some tech initiatives fail because they don’t pay sufficient heed to the change management side of adoption.

You might have the most brilliant tech solution in the world, which is a perfect fit for the law firm, but if you don’t manage the “people side” of change and generate that enthusiasm and buy-in, you won’t succeed. 

Sometimes organizations will communicate very broad and general messages about the need for change, focusing on the requirements of the business and why change is important for the organization. But you’ve got to make it real for individuals. Lawyers need to understand how a particular tech solution is going to benefit them personally for them to fully support it. 

“You also need to recognize that changing over to new systems and new ways of working will require time and effort at an individual level, not just at the organizational level. Don’t just assume that people will adopt something because the management has told them to. You have to think about incentives, rewards, and recognition to boost levels of engagement.” 

Also, I guess you have to be realistic as to the change capacity and change competency within the law firm. You might have a really great initiative but at the wrong time, for example, if you move forward with two pilots simultaneously, when there’s not enough bandwidth. You need to plan for all those factors to support the adoption. 

Do you have any other tips?

Don’t make the mistake of thinking that legaltech adoption is going to be easy. I mean, it’s going to take time, and you might not necessarily immediately get 100% of what you’d hoped for at the outset. You’ll need to take a “test and learn” approach and give the initiative time so that it can be assessed, refined, and improved. 

There should also be an acceptance that sometimes things won’t work. That’s part of the learning process. 

“Don’t be afraid to pivot and change things up, so that at the end of the process what you’re delivering is something that’s going to excite lawyers and clients, and really achieve the commercial aims that you wanted it to.” 

Alright, let’s talk a little bit more about the human side of being a lawyer. What is the most magical part of this profession?

I would probably say it’s coming up with creative and workable solutions to difficulties and issues that unexpectedly arise during the course of a transaction. It’s about being agile and able to generate solutions which reconcile the very different needs of the parties but ultimately leaving them commercially satisfied. 

Because I’m a transactional lawyer, I like to get deals done. That’s always very satisfying, especially if you’ve had to work hard to iron out bumps in the road to get to completion.

The second thing is the relationship-building aspect. Law, like many industries, is all about people and personal relationships. If you can build trust by making the law relevant, really bringing it to life rather than a process that people need to go through or that needs to be signed off, then you can build those deep relationships. 

“When you get there and you become the trusted advisor to a client, I think that’s always pretty magical.” 

If you could have lunch with any prominent legal industry figure, dead or alive, who would it be and why? 

That is a good question. In fact, because I’ve read previous interviews you’ve done I suspected you might ask me this. So I spent last night thinking: “OK. If Jane asks me this question, what on earth am I going to say?” 🙂 

Wow, I’m flattered! 🙂

If I’m allowed to pick one person, dead or alive, I’d like to choose Nelson Mandela. I imagine many people think of him primarily as a statesman. But he was a practicing lawyer who co-founded the first Black African law firm. 

He was looking to serve people who would otherwise have been excluded and who wouldn’t have access to legal representation. He had to do that in a climate that was incredibly challenging. The fortitude, resilience, and commitment to access to justice that he showed are remarkable – among his many, many, many other achievements. 

So I think if I had to choose any lawyer, he’s one of the greatest people of the past 100 years. Inclusion and diversity are something that I feel very passionately about. If I could have lunch with him and talk to him about his life, what could be more amazing than that?!

Richard Susskind would be an amazing person to take out for lunch, too.  It would be fascinating to hear more about his thoughts on the future of the legal industry and legaltech; he is an amazing visionary…

Can I ask you: who would you take out for lunch from the legal industry? 

Oh, I think I’d love to meet all the people I have interviewed since Loio started this interview series. I hope one day we can all have lunch together because it would give us a chance to discuss all of our different perspectives on legaltech, the legal industry, what makes being a lawyer joyful and meaningful, and dozens of other things. 🙂 

That’s a great answer.  And you’re picking up on an important theme — the need to bring a diversity of perspectives to all of our conversations. 

“One of the key things to generate innovation within the law is having that diversity within the industry that perhaps traditionally hasn’t been there.” 

Different people bring different things — increasingly taking a multidisciplinary approach to law, bringing in not just excellent transactional lawyers or litigators, but the data scientists, the digital transformation experts, the technologists, the project managers, the process improvement experts – and ensuring that people from different backgrounds are truly represented, is really powerful.  

“When you have all those people and all of their diverse experiences in the melting pot, that’s when you’re going to get the best solutions – by people working together and contributing their different perspectives.” 

Thank you, Brian! What interview question would you like to be asked, and how would you answer it? 

Given my transition from working full-time in the world’s largest law firm to now spending a lot of time in a startup environment, it might be interesting for me to talk about some of the differences between the two…

It’s very different in terms of the culture and the mindset that you have to adopt. 

Particularly in the tech space, that “test and learn” philosophy we talked about earlier is absolutely critical.  Although you should have a very strong vision and clear strategy when building a tech product, you’re probably going to have to get there incrementally, finding solutions to each unexpected challenge as it arises, exploring, iterating and expanding, and so on. 

This is perhaps very different from the lawyer’s mindset, where the culture might be less “test and learn” but more “get it perfect the first time, or risk being sued!”. Obviously, you can’t treat a live client transaction as a testing exercise or an experiment; you need to do the absolute best job for the client and that necessarily entails some constraints. 

I’m enjoying the change from having everything mapped out in terms of what you have to achieve and exactly how you ought to go about achieving it, to the more creative and iterative building process in the startup environment.

That sounds inspiring! But how do you find the balance between these two mindsets? 

Well, I think when law firms are trialing technology, encouraging lawyers to adopt a different mindset is a good thing. But there are challenges around that, given the various pressures on the delivery of legal work.  

“One approach is to have safe spaces, be that innovation teams, incubators, or slightly separate entities where innovation can be given the space it needs to develop without being killed off by people pointing out all the problems, issues, and limitations from the get-go before people have actually had the chance to solve them.” 

But you also need to be careful to avoid innovation being siloed and having a disconnect between the spaces where innovation is being developed and the lawyers at the coalface. You need to have a certain nexus for the two to be able to feed into each other. 

It’s about creating a kind of a sandbox, right? A safe space where you can try out new tech without influencing real-life outcomes, right?

Exactly. On a client transaction, you can’t fail and learn from it. You have to succeed, and that’s what your clients rightly will expect. As an innovator, you have to not be afraid to fail. That’s an essential part of the learning process. 

Indeed, it is! Thank you so much, Brian!