TRP 325: [Legal] Preparing Lawyers for Technology Transformation with Catherine McGregor

[00:00:10] You're listening to The Rainmaking Podcast, hosted by high-stakes headhunter, author, and professional speaker, Scott Love. You're listening to The Rainmaking Podcast, and my name is Scott Love. Thank you for joining me on the show, friends. I'm excited that you're here. This is part of our Sometimes Tuesdays legal-specific series of the show, where we bring in guests talking about topics that are unique to the legal profession.

[00:00:39] Our topic title today is Preparing Lawyers for Technology Transformation. And our guest is Dr. Catherine McGregor. She and Lloyd Johnson wrote a book called Preparing Lawyers for Technology Transformation. I've read this book, and I will tell you this. If you're a law firm leader, you need to read this book. If you're a C-level executive or director in a law firm, you need to read this book. If you're a practicing attorney anywhere, in-house or in a law firm, you need to read this book.

[00:01:08] Beyond just talking about technology transformation, there are several intellectually satisfying concepts that they present in terms of problem-solving in a vast array of areas, but specifically related to technology transformation. This is going to be a unique topic that we're discussing. I've never had this topic with over 300 episodes on this show before.

[00:01:30] Dr. Catherine McGregor is an executive coach, author, and management consultant, and an expert in leadership and talent development in the age of artificial intelligence. She works with law firms and other organizations, and specifically, I think you're going to find so much tech transformation ideas from our conversation today. As always, this podcast is sponsored by SharePoint Legal Insights, formerly known as Leopard Solutions, turning legal intelligence into opportunity.

[00:01:59] The show is also sponsored by The Rainmaking Magazine. This online publication is created for the intellectually driven and results-focused professionals that want to be the number one professional services provider in their niche. Start your free 30-day subscription today with nearly 40 contributing authors, business development coaches, and consultants providing curated content on business development.

[00:02:25] Visit therainmakingmagazine.com to chart your course to greater rainmaking success. Also, we put all of Catherine's contact information as well as a link where you can order the book on the show notes. So when you're done listening to the show, go to the links that are in the show notes and connect with Catherine directly. And like I said, I'd highly recommend ordering her book. Thanks for listening. And if you've got a minute, if you could give our show a nice five-star review wherever you listen to podcasts.

[00:02:54] And if you listen to this episode and you got some great ideas from it, mention Catherine by name in your testimonial. I appreciate it and I know she will also. Thank you for listening. Hey, this is Scott Love with The Rainmaking Podcast. Our guest today is Catherine McGregor. And we're talking about preparing lawyers for technology transformation. Catherine, thanks for joining me on the show today. Great. Thanks, Scott, for having me. Absolutely.

[00:03:19] And this is also the title of your latest book, Preparing Lawyers for Technology Transformation. So I thought this would be a really good place for us to talk about this and how those listening can really prepare for that. And so let me ask you this, Catherine, in terms of definitions, what exactly does technology transformation mean in the context of your book? How would you define that? Well, it's really all the changes that are coming in and they're coming in super fast.

[00:03:46] I use the term the exponential age a lot in the book. And if folks haven't heard this before, it is a term that's been in use for a few years. But you'll be hearing it a lot more. It's about the increased rapidity of change. And that's being driven by, of course, AI. But it will be other things as well, like blockchain, robotics as they come in.

[00:04:07] But if you just look at it, one of the, you know, in the book, use the statistic that when Google Translate first started, whenever that started, it took about, I think, about five years to get to 20 million users. Chat GPT took just two months to get to 20 million users. So it's like the speed that this technology is coming in and the scope is insane.

[00:04:33] So that technology transformation is what I'm talking about. And we're at this crucial point at the moment where for all industries, but laws included in that, it's coming in. And it's at the point where we still have quite a lot of agency in terms of what we can make of it and how we can use it. Wow. So where do you think people should start? And I know your audience, when you speak, it's to in-house and also to law firms.

[00:04:59] Where do you think are the main points that they should really focus on and being ready for these changes? Well, the question that I always start with, and I do a lot of group coaching, but I also do a lot of individual coaching with both in-house lawyers and law firm lawyers as well,

[00:05:17] is what becomes possible when AI handles what you know, and it actually frees you up to think a lot more broadly and think a lot more about what you see. And actually, rather than thinking about new technologies such as AI, the obvious one, being a threat, what does it actually give you and what are the opportunities there? And it's a fundamental identity shift for every lawyer.

[00:05:45] It's that move away from just doing to actually being much more of a strategist, much more, in many ways, a creative thinker being able to join the dots. And I think the best lawyers, and your podcast is obviously called The Rainmaking Podcast, the best lawyers, whether they're in-house or in private practice, have always been able to do that.

[00:06:08] And I think what AI will do, and technology in general, is hopefully free up more and more lawyers to be able to implement that side of themselves. Yeah. So what have you seen so far? Give me examples of those people that have been able to connect those dots. How have they done that? What have been some observations that you've had recently? Well, I think let's focus predominantly on law firms.

[00:06:31] But I mean, in law firms, it's getting people to realize the breadth of what they see when they, one of the, and so in my book, I talk about, and I also use this in training and coaching, nine exponential age mindset attributes, which just through the practice of coaching myself and my co-author, Lloyd Johnson, realized were fundamental to dealing with technology change and, successfully. And one of the first of those is Zoom Master.

[00:07:01] And that's the ability to be able to, like a camera, be able to see the big picture, but then be able to zoom in on the detail as needed. And the trick there is not being in one state or the other. It's that ability to move in between the two and knowing when it's right to move in between the two. And the negative stereotype of many lawyers, and I see this a lot in my work with in-house where, you know,

[00:07:27] they may have a particular reputation with certain business stakeholders, is lawyers get too stuck up on the detail. And it's important they take care of the detail, but it's also important not to get completely locked in the detail and not see why are we doing, you know, why are we writing this contract? Why are we doing this deal? What actually is, what does success look like for the business? I like this. I think the questions that you brought so far that I think would make a big difference for people listening is,

[00:07:56] how can you use this as an opportunity instead of a threat? I like that a lot. I like the idea of the Zoom Master being able to see the big picture, but also zooming into detail, but also keeping the big picture in mind as well. What are some of the other, what did you call them, exponential mindsets? Is that what you mentioned? Yeah, the exponential age mindset attributes. I often call them E-A-M-A for short, because that's a bit of a mouthful. But there's nine of them.

[00:08:23] I mean, some of the ones that I think are, you know, really, well, they're all pertinent, but I think some that I'd like to highlight, particularly for lawyers, is, you know, joyful tightrope, which is the being able to be okay with uncertainty and being able to realize that things are not always cut and dried. And I think, you know, particularly at the moment, that's becoming very clear in the area of law.

[00:08:50] You know, we've got a lot of technological developments, societal developments, that the law can't actually keep up with because things are being rewritten so fast. So for lawyers, how do you get okay with the fact you may not have all the answers, you may not be able to rely on precedent and legal arguments in quite the same way? You actually have to get creative.

[00:09:15] And again, I go back to the fact that the best lawyers have always been able to do this and have always been able to lean into that. We just have to look at the seminal case of, you know, Brown versus the Board of Education. That was a fundamentally creative piece of legal work that actually lent into quite a lot of uncertainty and got okay with the fact that it wasn't the sure thing. They were taking a bit of a risk, but it changed the world.

[00:09:43] It's almost like the mental and emotional elasticity of attorneys needs to be there for them to be able to flex with these changes, for them to be able to even harness them and use them and leverage them. What do you think about that in terms of your work, Catherine? I think that's absolutely the case. And that's one of the things I do work on a lot with clients. How can you, you know, and the fact I approach this from a coaching mindset,

[00:10:11] what can you do in a small incremental way to start flexing these muscles, to start flexing this elasticity? You know, it can be as simple and this sounds very obvious, but you'd be surprised at what a light bulb moment it is for many attorneys. Say, you know, what about actually talking to a client about everything that's going on with them and not focusing just on your specific piece of work or what you can sell them?

[00:10:40] What about actually just listening to them and listening to their pain points, listening to what's going on for them? And yes, I think the best lawyers do that. I think a lot of lawyers don't do that. And some of the reasons they don't do that is they feel so constrained by the need for, you know, meeting their billable hours, meeting their targets, and they feel that they can't take that time.

[00:11:06] Conversely, when I talk to in-house lawyers about their biggest issues with law firm lawyers, it's the fact that they don't listen to us. They don't understand us. They don't really see our world. It's very transactional and focused. That's interesting. So this can actually be an inflection point in somebody's career, thinking of somebody in a firm where their goal, and I always put it in three different buckets, they've got to be a really good attorney.

[00:11:33] And they have to have good team leadership skills because nobody's going to trust them if they're not a good leader, leading associates, dealing with colleagues, things like that. And they have to be really good at doing business development, building the brand, getting the call, earning the trust. That's a lot. And they've got to meet their billable requirements. Otherwise, things go down and it's a downward spiral. I've seen that up close and personal from the vast number of people I've talked with about that. And I understand and appreciate the pressure that they're under.

[00:12:02] I think this and your book could also, I could see that being a solution for them to take this age of change as an inflection point. Yesterday is done. This is a new day. It's a new era. I want to prepare myself for that technology transformation. So that's what I think about. They could use this as a leverageable concept. I'm going to become good at this. And it's going to change my life and change how I practice

[00:12:32] and change how my clients perceive me and increase my effectiveness in serving them. By really using that. What do you think about that? Oh, I think that's absolutely where this is going. And that runs through whether you're in a law firm or you're in-house. And it could, of course, also be true for areas outside of legal as well. But we are obviously today focused particularly on legal. But I mean, yeah. And one of the exponential age attributes is agile juggler,

[00:12:59] which is the ability to just hold multiple priorities in motion while maintaining consistency, dependable delivery, but also maintaining leadership skills and being able to, you know, a great example would be how we all managed to just pivot so quickly during COVID. Organisations that had said for years,

[00:13:24] we can't do remote work within a few days were able to make it work. And people were, you know, covering for colleagues who were out sick and, you know, having to just make it work. And I think that, you know, as you said, Scott, the different responsibilities of law firm attorneys, particularly as they climb the ladder, you know, agile juggler is exactly what's going on there. Then you throw technology into the mix.

[00:13:50] How can technology help me to be even better at all of these things? You know, can it actually, you know, can I think about ways to bring AI into helping to make sure that I regularly stay in contact with clients? When I coach lawyers around BD, one of the things that, you know, comes up is, you know, oh, I just, you know, I, yeah, I send stuff out to clients, but I'll send the firm's, you know, latest newsletter.

[00:14:19] I'm like, no, you have to have that personal connection. And whatever you need to do, whether you're sticking post-it notes on your computer, you develop an AI agent at the other end of the spectrum to remind you that regular check-in that's really personally driven, that brings the human into it, is the thing that gets you the work. Not frankly, you know, no apologies to people who create law firm newsletters. They're wonderful and they have their place,

[00:14:47] but actually people need that feeling that it's that human outreach, that one-to-one connection. You're absolutely right. I think there's a couple of through lines, what you mentioned that I wanted to kind of bring to you and see what you think about this. When we were talking in the beginning, the first thing I went through about this change was COVID. The entire world changed in a very short, compressed period of time. And bad things happened. We learned, though, that we will be okay. We will survive and we'll thrive.

[00:15:17] And then there were even spikes of opportunities that came out of that. But the one thing that I learned that was interesting from that, the law firms that did the best with pivoting, and we haven't heard that word in six years, with pivoting quickly were those in Louisiana, because they had to make that quick change when Katrina hit. They'd already done that. And so I think our resilience muscles as a society and an industry have strengthened. So now, and I've always said this,

[00:15:45] that the world will change anytime for any reason, because we don't know when the next natural or man-made disaster is going to take place. And we see that a lot. And now we're just kind of rolling with it as a society. So I think as a society, as an industry, I think we are becoming a little bit more elastic in how we respond to things. We've built strength. We can look back at COVID and say, we did that. We did it. We pivoted quickly and we're okay. And here we are. And here's another change we have to deal with. If I was good at that, I can be good at this too.

[00:16:14] Now I think that through line is I can build strength and confidence from this change. And I can not just push it away and try to avoid it. I can embrace it and in fact leverage it. And I think your book is an, that can be like a, a linchpin for people to hang on to, to get ideas so that they can thrive as an attorney. They can take these thought models, so to speak, that you've researched and put together with your colleague as tactical tools.

[00:16:43] And so I like the idea of the Zoom master, the joyful tightrope, the agile jungler. What are a couple of other, like one or two other of the exponential age mindset attributes that you'd like to highlight for us, Catherine? Well, one is biased jujitsu. And this has a particular resonance for me personally, as around the time that I started writing the book, I actually started doing jujitsu for a hobby. So it's kind of like come up with my own journey.

[00:17:13] But if you know anything about jujitsu, it's called the gentle art. And one of the reasons it's called the gentle art in Japanese is the fact that you're essentially leveraging your opponent's strengths against you. Now, obviously, you know, if I fight, you know, I'm a petite woman. If I fight a 300-pound guy, he is going to win. But actually, I can use a certain amount of leverage, even with an opponent that's bigger than me, because I'm using their strengths against them.

[00:17:41] And it's that awareness and sometimes going, that awareness of where the leverage lies and being able to sometimes do things that almost go against what we're trained to do, where the strengths of jujitsu as a martial art lies. Now, what does this mean in terms of law and in terms of technology? Let me get to that next. So it's really biased jujitsu is about the self-awareness to recognize your own cognitive patterns, your own cognitive biases.

[00:18:11] And particularly when you're a lawyer, being aware of those ones shaped by legal training and how to work with them rather than against them, how to leverage those in the right way. It's not about eliminating the way you've been trained altogether, but knowing when it's appropriate and when it's not. And a big one I come up against a lot when I'm coaching and training lawyers is, you know, the classic way that lawyers are trained to deliver information is through the IRAC method. What is it?

[00:18:40] And it's issue, rationale, analysis and conclusion. When you're talking with business stakeholders, you've got to go straight for the bottom line up front. You've got to say, this is what's important. It's what we need to do. Now let me tell you the detail. And where I think a lot of lawyers fall down in their communication is by focusing too much on the detail and the context first when they just need to get to what's really important.

[00:19:08] And that's going to become even more key as we bring technology in because folks are having so much information thrown at them. It's just going to get worse. There's so much, you know, AI, slop, whatever out there. For lawyers to become really great communicators and really focus in on what's key, that's going to be their superpower. That's great. That's good advice, Catherine. What is it that surprised you when you wrote your book and you did the research and you really obviously put a lot of creative thought into this?

[00:19:37] What were some realizations that just surprised you from doing this? Realizations that surprised me and have surprised me through, you know, because the book is really based on practice. So it's based on the work that I, and also the work I've done with Lloyd on training, coaching, both individual coaching and group coaching. The ways, the different ways that people come to a way into this.

[00:20:07] And it's always going to be different. There's no one size fits all. So that's one of the things I would say with the book. You might be reading the book and, you know, obviously, Scott, when I mentioned Zoom Master, that seemed to really resonate with you. Yeah. Someone else might read the book and Zoom Master might not resonate with them, but one of the other attributes might really jump out at them and say, oh, I think that's something I'm kind of doing. Well, how are there more ways you can lean into that? On the same way, if there's something

[00:20:37] that you find really challenging, but you think you might need it, what are ways that you can start to lean into that a bit more? Because is there a reason you're avoiding it? Because it feels uncomfortable. It feels like a stretch. But could it be a stretch that will actually pay huge amounts of dividends for you? It can, I think the interesting point with many law firm lawyers is the place of just doing the technical legal work can feel like a great place of comfort

[00:21:06] for many lawyers. You are going to have to get uncomfortable going forward. What's the bits of discomfort that you can handle and maybe seem a bit easier to work up to the bits of, you know, discomfort that are a harder stretch for you? How does somebody get comfortable in that regard, Catherine? It's really trying it. It's trying, it's like, you know, to use your analogy, you know, about a muscle. It's like, if you start working out,

[00:21:36] you're not going to generally, unless you want very bad health outcomes, you're not going to go straight from starting to run to immediately signing up for a marathon. That's probably going to kill you or come close to killing you. You're going to start by building up to a 5K, then a 10K and then a half marathon and so on and so forth. You're also going to change your mindset probably from, by gradual doing, from being somebody who doesn't run

[00:22:04] and maybe somebody who runs reluctantly to a point where, obviously, if you're training to the level you're going to do a marathon, you're going to be a pretty regular runner and you probably don't even think about running anymore. And I think it's the same thing with a mindset change. It will feel odd at first. It will feel difficult at first. You will have to be intentional about it. You will fail and you may need to have reminders and you may need to, you know,

[00:22:32] work with others like a coach or like colleagues who can help coach you to have that support. You know, hey, that presentation you did wasn't, you know, you weren't leaning into, you know, being a great storyteller there. Next time, maybe you're going to make that better, maybe going to make it more resonant for the audience. So, you know, it will be trial and error, but it's that trying it. Well, Catherine, tell me about, tell me a story of some organization, whether it's an in-house legal department

[00:23:02] or a firm or a group of attorneys, and obviously you don't have to mention names, but what was the arc of them understanding key concepts that you taught them? Maybe it was from your trainings or the book. What were some of the exponential age mindsets that made a difference for them? And what was the result and the changes that they made and how have they grown through that? I think that, you know, some of, a lot of the teams I've worked with, it's what's really been the key point of going in

[00:23:30] is introducing people to the exponential age mindsets in a very human-centric way at first. So people aren't feeling this is about technology and tech, and, you know, there is a lot of fear from a lot of people. And I know you mentioned, you asked me, Scott, about what surprised me. I think seeing firsthand the fear that many people feel

[00:23:57] about what AI will do to their roles and, you know, their purpose, their sense of who they are. Because most lawyers, whether in-house or private practice, they've studied so long. And they, you know, being a lawyer is tied up with who they fundamentally are. So that feeling that I might, it's literally, I might lose my identity if this stuff comes in and starts doing my job. Of introducing them to the attributes

[00:24:26] and really doing it through an exercise around what's your superpower at work? What do you do really well that you don't think anybody else does quite as well? And then linking that to the attributes, but then saying, okay, what's your kryptonite at work? You know, what's the thing that's a bit of an Achilles heel for you? And what might help you? And then getting them to link that to the attributes and start to think,

[00:24:55] okay, how could I bring that in to what I do? And taking it in very small, practical steps, often working with colleagues to really understand that and get that sort of accountability piece working together. Some of the other ways that I've used, which have been really unlocked it with people, is getting everybody to start by thinking of what's one thing in your job

[00:25:23] that is just a real pain, that just really makes your role really difficult. And then trying to figure out what are all the ways that technology could help you with that? And what are, you know, what are brainstorming or the solutions? And one of the other tools that I reference in the book that I've used very successfully, and it actually originates from a book from back 20 years ago called A Beautiful Constraint. And it's called the

[00:25:52] Can-If Problem Solving Framework. But it's not allowing people to say we can't because, it's actually only allowing people to say we can if. So therefore, what that means in terms of showing up as a lawyer is thinking always about what's possible, what success looks like for your client, how you can actually get things therefore to a successful conclusion. And if you're thinking about something within your role

[00:26:21] that is making your role as a lawyer more difficult, maybe it's how you have to bill, maybe it's, you know, the lack of administrative help you have. You know, it could be a lot of quite marginal things. But that, and one of the things I did in the book was work with a neuroscientist around a lot of the neurological aspects of how we deal with change. That's a great way for the brain to be able to cope with change, to be able to think

[00:26:50] what is the happiness that change could give me and how could this heal a hurt that I have in my professional life. And I think sometimes when change is introduced, the instinct, whether it's from a law firm, from a legal department, from a company, is to introduce change in a very overarching way, in a very, this is why, this is great for the entirety of us, but not give people

[00:27:19] the space to be able to find their own relationship with that change and how they can make that change work for them. And I think one of the best pieces of praise I had, and I reference this in the book, because with a couple of legal departments, I've actually done training courses with non-lawyers, with paralegals, legal assistants, who, frankly, most of those people are really scared about what technology is going to do to their role.

[00:27:49] They already can feel a little bit like second-class citizens within the legal profession. So what is technology then going to do? At the beginning of a course, one of the women came up to me in the course and said, I'm really scared about all this change. I just don't know how I'm going to cope with this. I think it might mean the end of my career. At the end of the program, she came up to me and she said, Catherine, I feel, this has been life-changing, I feel like

[00:28:17] I can do this now and I don't feel scared about the change anymore because I know how I'm going to cope with it and what I'm going to do. That's powerful. Yeah. And that, I think, is a huge value, obviously, to people where it's not just what the result is, it's how they grow through that. And I think this is what I see about your book is that that can be, like I mentioned, that can be a linchpin for people, something they can use that they can hang on to and give them

[00:28:46] a construct for managing this change because it is here. And if you don't address it, if you don't face it head on, you might not make it and you'll be left, you'll be left behind, so to speak. But I like the idea that just the tone of your book is exciting and what I want to do now is kind of bring this to three action steps because you shared some fantastic insights that I know are going to make a big difference for people in a meaningful way. If we could summarize this in three action steps

[00:29:16] people can take to get started addressing this change, what would those three action steps be, Catherine? And am I addressing these to law firm partners, law firm lawyers in particular? So I would say number one is really lean into that Zoom master. Have a conversation, a really broad-ranging conversation with maybe three of your biggest clients that isn't focused on legal work, that just hears about what's going on

[00:29:46] for their company, you know, what are the strategic issues coming up for them, you know, if they're in the legal department, what that means for the legal department and resist giving answers, just ask questions and just, you know, see what that gives you when you listen to them and, you know, then you go away and think about it and think about it from that Zoom master perspective. How does that big picture knowledge, how could that really help how you deliver

[00:30:15] legal services for them? Number two, I might, one of the other super, the superlative synthesizer is one of the exponential age mindset attributes and that's really getting to the point. Most of my in-house clients always talk about the way that they have to translate from what the law firm partners or law firm associates give them to their business clients because they have to condense it and get to what's really

[00:30:44] important. Can you as a partner start short-circuiting that process and become the superlative synthesizer because as I've said as there's more and more information out there being able to focus on what's truly important and really get to that point people can always ask for more detail but being able to be comfortable in your knowledge to just get to that nugget of what they really need

[00:31:14] that's a really good one. And I would say the final one would be pointing back again to the bias jujitsu that ability to know when you need to show up with your legal hat on and when you need to lean more into being a trusted advisor and also you know when can you leverage the AI to really help you

[00:31:44] or other technology tools might have. Well Catherine this is fantastic insights that you've shared with us we mentioned your book today tell us about your offerings your services that you have that you'd like our listeners to know about and we're going to put all of your contact info including the link to order your book in the show notes. Great thanks Scott so I offer individual executive coaching for law firm partners also senior associates who may be on partner track want to

[00:32:13] really lean into those leadership skills particularly in this age of technology because leadership is changing I also offer those services as well to in-house lawyers coach number of general counsel and deputy general offering group coaching programs specifically designed for law firms around the ideas in my book so how can you

[00:32:43] really ensure that your lawyers are finding their own way into embracing this technology change and how can they really make sure that they're showing up as a true trusted advisor in the age of AI because that's going to be the way that your firm succeeds and that's frankly what your clients want and what they need going forward well thank you so much for sharing that Catherine thank you for being here a guest on our show and I'd love to

[00:33:13] have you back on the future on the future thank you so much you did a great job today thank you Scott thank you for having me it's been great thank you for listening to the rain making podcast for more information about our recruiting services for international law firms visit our website at attorney search group dot com to inquire about having Scott speak at your next convention conference sales meeting or executive retreat visit the

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