Rethinking the Billable Hour, the Apply All Dilemma, and AI Curiosity with Amy Grubb

Welcome to Studying Law Around the World. I'm Claudio Claus. In each episode, I talk with lawyers, law students, and professors from different parts of the world to talk about legal education, careers, and what the profession looks like in real life. I talk about the hard parts, the surprises, and the decisions that shaped their paths. Whether you're planning to study abroad, thinking about working in another legal system, or just curious about how law works around the world, this podcast is for you. Hello everybody, welcome to another episode of Studying Law Around the World. Today, I have the privilege of hosting Amy Boob. She has an incredible story and career. She is currently redesigning how the legal work gets done with AI in an incredible corporation. She has been into many, many very interesting roles throughout her career as a lawyer, but also as a strategist, as a consultant as well. And I must say, I found someone referring to you in the past as the fairy godmother of lawyers who wants you to go solo. So I was super impressed and found that very, very interesting. Thank you so much for making the time and coming to the podcast today. I really appreciate it. Yeah, thank you so much for having me. I'm excited for this conversation and I haven't heard that fairy godmother in a while. So it's a good memory of kind of where I've been in the past. That's amazing. But to start off the show today, I'd love for you to introduce yourself, tell us a little bit more about your journey from practicing law, working at this fun intersection with innovation, AI, business strategy. Yeah, I did the traditional path. I got a job through the OCI process here in Ontario. I was working at a large firm in Toronto and I eventually moved to Ottawa. So stayed in big law, but just in an Ottawa office. And I was there for many years and it was exciting. It was great. And then after a while it was not so exciting and not so great. So I was kind of looking for something else and I just, I started to get burnt out and I wasn't feeling great. I had young kids. So I took a break from practice. I took a leave and I, I ran into a neighbor. She'd recently moved to Canada and we actually started an online business together and it was unrelated to law and it just opened me up to this world of entrepreneurs and e-commerce and working online. So I actually started my own firm and I was focused on entrepreneurs and it was before the pandemic and all of these lawyers were reaching out to me, especially in big law saying, how did you leave? How did you start your practice? Like all of the questions. And so then I started helping other lawyers launch their solo practices. And from there I eventually joined a company as a business strategist and was helping solo small lawyers and that company was acquired. And I started doing more sales for this company and I was selling products to law firms. And at the time we sold an AI package. So it was for law firms who were interested in AI, but didn't know how to start or what software to get or what was out there. And that's where I learned about Spellbook, their Canadian company. I'm also Canadian and they had this opening for, they didn't even really have a name for the role yet. I reached out to Spellbook. I applied for the role and just through interviewing with them, learned more about this role. And so this is where I am now is I'm at Spellbook. I'm a legal solutions architect and I help support our sales team. So I meet with in-house teams day in and day out, learn how they work. And I help build out playbooks and workflows and different processes for them using Spellbook. Fantastic. I appreciate you explaining to us a little bit more where you've been and what you're being doing these days. And you know, if I could dig into that a little better, you begin your career in large law firms. You're doing business, technology matters as well. What first sparked your interest in legal innovation, in building new ways of delivering legal services? Because it did mention the AI packaging and maybe the time that you got to be an entrepreneur yourself. But was there a few other things that made you really spark into this field? I think I've always been interested in legal tech and testing things out. So when I was in big law, I was always in the small cohort that would test software out before we decided to buy. And I always wanted to see how we can do our work better, how we can work more efficiently. So it was always there. And then I guess it was when I was running my own practice and just learning about the different software because I think it's an amazing time to go solo because there's so many resources and software that are available to solo and small firms that are also affordable. And so I learned a lot about the different software that was available. And it's just kind of snowballed from there. And then it's just, you know, trial and error. So AI, like when chat GPT came out, I was always testing it and trying it out. And so I think it's just curiosity. And maybe also it's like trying to keep up with my kids. I have teenagers. So I want to make sure that I can speak their language as well, which I totally can't, but at least I try. And I think by doing things with AI, it helps me to keep up with younger people, but then also what businesses are doing. And obviously my career didn't exist like five years ago, my role. So it's just being curious and trying different things. I love that. Well, thank you for sharing. Our audience is here in the category of early career professionals or law students. So it's always interesting for those of us who are beginning our careers to know what you can do with a law degree, right? We know a lot about the, so to say, beaten path and how to go through a law firm and basically how that path, and over the last few years, a bit more shared about people have spoken about them a little more. And as you said, new roles have evolved and were created as well. But I'm curious as for yourself, how have these experiences changed the way you look at what a legal career can look like today? You know, Amy graduating law school, do you think that she would have even thought that these were possible? Amy graduating in law school would never have thought she would have done 70% of the things that she has done. So I don't think she would have thought it was possible. I've had a lot of conversations with newer lawyers who've just graduated from law school because I'm really curious, like how popular is legal tech? Is this now a new avenue that law students are looking to explore? And it sounds like it is. And I think that's really exciting because I think when I was in law school, it was basically you go into private practice or maybe government. Those were like the options, maybe in-house if you could get a role. So it's really exciting to have this other opportunity. And I remember when I, so in between big law and starting my own firm, I talked to a lot of people and a lot of people outside of law would tell me, oh, there's so many things you can do with a law degree. You can do anything with a law degree. And I found that actually really frustrating because I would apply to different roles that were not legal. And I usually wouldn't even get an interview because they'd be like, why does this lawyer with 10 years of practice experience want to work in this type of a role? And so I feel like now there's so many more opportunities for lawyers within the tech space and companies just seem very open and understand the value that we can provide outside of providing legal advice to the organization. You do mention the point of law students, law schools, trying to be a little bit more aware of this. As someone who recently graduated from a master's at U of T, we did have access to a few different products as well in student memberships. So it's been interesting to see how legal tech is also connecting with the law schools to provide that experience to students. And on the other hand, once you pass into practice, that has a lot of different layers of complexity, right? In the sense of what firms are doing and you end up being very much tied to the policy of what the company you're working for is planning on using and exploring. And of course, a lot can be done in your spare time. But I wanted to ask you, in this position and with what you've been doing these days, I feel like many lawyers might be curious about AI, but maybe unsure about where to begin. And then if you open LinkedIn, for example, you feel like you missed out the whole boat and it's now too late to get started at all. So from your perspective, are there a few misconceptions or things that lawyers might should have about AI and legal work? Yeah, I totally agree with you. I feel that too when I go on LinkedIn and sometimes I'm like, man, I've totally missed the boat on this. And how am I ever going to catch up? And I think that a lot of people feel that way. And we see people who are vibe coding on weekends and coming out with these amazing things and throwing them up on LinkedIn. And then there are people that I speak with every day who have never even used a platform like Spobo who don't even understand it. So there's a vast, vast range. And I think like it's just all about trying it out and being curious. And I think lawyers are really scared to make mistakes. A personal story, I was texting with my niece and she's 10 and she had made this like beautiful image using Copilot. And I was thinking to myself, it's so cool that she just figured it out and did it. And I wish that more lawyers would just do it. And it's easier said than done because we're all busy. We have so many things going on. But what I've started doing is blocking out every Friday afternoon. I've got an hour in my calendar where I focus on one specific thing that I want to move forward. And it's the compound effect, right? If I do it for one hour a week, it's going to add on and add on. So that would be my suggestion is trying different things. You may feel like you're behind, but you're not because there are some people who have never even done it before. And I also, I, I do have a little bit of concern for lawyers who just are like not willing to try it, who don't want to try it because that's the way it's all going. We're already there. So you might as well, you know, try it out, get used to it. Otherwise you really will be left behind eventually. But I think there's still time to catch up. I find the legal tech community is very welcoming and open. And so don't be afraid to ask people questions. There was one of my colleagues had posted about how she's using AI with LinkedIn. And I just asked her, like, how are you doing that? How are you? She was using Claude, I think. And so she sent me exactly how she does it. And so don't be afraid to ask people how they did it. And I guess my other tip is when you're using Spobook or Claude or ChatGPT, I always, I will often say to it, this is what I want to do. How do, like, give me the prompt so that we can do it. Because they, at Spobook at least, Spobook knows how to use Spobook. And so I will just use the AI to help me come up with the answer rather than the other way around. A few months back, a lot of the focus was on prompt engineering, right? And how to do a better prompt. And then somebody figured out if you ask the AI how to do a better prompt, they'll probably do a really good job. So I appreciate you mentioning that. And I've been finding it's so interesting that it really is kind of bound to our creativity. And there's so many things that we don't even think of doing. But then when somebody shares their use case, they're like, oh, that sounds great. Like I can easily integrate that. That's a great solution. So that's amazing. I love that, how the community is welcoming, how people are always willing to share as well. And I'm not sure if you have a similar experience, but personally, in the last three, four years, I found that the legal community in general seems to be very open to pay it forward in some way in the sense of providing mentorship to young associates and to, you know, go out on coffee chats and tell about their careers. So I feel that very same experience when contacting people who are in tech and who are, you know, in these professions that I think traditionally didn't speak to each other as much, but now we're a lot more aligned. So it's been interesting to see. So Spellbook launched yesterday and I'm going to get the name of it wrong, but it's a legal fellowship for law students or brand new calls who are interested in tech and law. And it's this amazing opportunity. I believe it's $25,000 and you're working with our CRO here at Spellbook. You're working with our product team, getting feedback. So it's a pretty amazing opportunity and I'm, I'm happy to send you the information on it after the call too. That'd be amazing. Absolutely. Absolutely. Well, continuing on here, I'm also wanting to hear a little bit more from you on, on another end of these spectrum, helping firms to move away from the legacy processes and towards a more healthy and modern system. So I wanted to hear a little more on your experience so far. Are there things that separate firms that successfully adapt to change that can integrate those tools and those new ways of doing things? And then are there specific things that separate them from those who might be struggling a little bit more with the change and with, you know, adapting new tools? So I think the, like the elephant in the room with law firms is the billable hour. So if the goal of AI is to increase, increase efficiency, that doesn't work well with the billable hour model. So when I was a business strategist, we worked a lot with small firms who had a bit more flexibility in terms of, I was working with one client who went from the billable hour to flat fee, maybe like in two weeks, maybe even less than that, so small firms can move really quickly and she, you know, saw a lot of value in doing it this way, not only for her clients, but also for her. So it's very different working with a smaller firm than with a larger firm moving away from that billable hour and how they would do that. It takes a lot longer to right the ship. So I think, so that's something that organizations need to consider. And in terms of like what I've actually seen done in terms of systems and processes, I used to work at a company called Lawyerist. So I definitely have to shout out Lawyerist because they have a lot of great resources that are free on their website in terms of how to build systems and processes. And I think a lot of times people are like, that's like the last thing. They know they need to do it, but they've got billable work. They've got personal obligations. But once an organization has laid the foundation for their systems, and so that they're not reinventing the wheel every single time, you see so many gains in efficiency. I think it also helps for retaining staff, for recruiting junior lawyers who want to see firms that are using AI, that are using software, that have systems in place, and especially with the smaller firms as well. So I think there's a lot of opportunity out there, and I definitely still have a small spot in my heart for the small law firms. I do a lot of work now with enterprise large organizations, in-house teams, but I do still have that little place in my heart for small firms because I used to be a solo myself. I feel like your career really shows that there is no one single way to be successful in law. How would you say that that curiosity has played a role in that for your career, you know, helping you to make those career decisions in transitions through your journey when maybe the next step wasn't really clear or outlined, right? Yeah, it's scary for sure. There's this great quote that I'm totally going to butcher, but I believe it, is that everything you want is on the other side of fear. And so going off on leave and not knowing what I was going to do or starting this business with my neighbor, and it totally flopped by the way, like we didn't make any money on it, but it taught me so much and opened up the next door, which once I went through that, it opened up the next door. And so it was really important for me to have strong support at home, to know that my partner like supported me and was okay with making this move. And there was a period of time where I didn't make very much money and we planned for it. We put money away for it, but it's very scary. And I also worried a lot in earlier in my career about what other people thought. And when I started my own law firm, I still remember a woman I know in our neighborhood, our kids were friends. And so she's a partner at a very large law firm. She's very successful. And so she was asking me what I was doing now. And I was, I don't know, I was almost ashamed, not ashamed, but I was a little embarrassed to tell her, well, I'm starting my own firm and I'm working from home. This was before COVID. And I still remember her reaction. She was just like, I wish, I wish I could do that. And I've had so many conversations with people since then. And I kind of want to shake them and be like, you can do that. Like it is a choice that you can make. You can leave a large law firm and go on your own. You can leave your wherever you're working now and work in legal tech. And so earlier in my career to see other people in LinkedIn who are becoming partner and doing these amazing things, I was always in the back of my mind. I was like, Hey, I wonder if that could have been me. But now I am really happy with where I am. And lots of times I tried things and they did not work. Like for example, this business I started totally did not work, but it led me to different things, which eventually led me here. It really takes a lot of courage along with the curiosity as well as planning. So there's a lot of steps to it. It's sometimes from the outside, right? You'd see it as you're so brave or it's amazing that you follow your curiosity, but it's important to acknowledge how much that really so many different things that get involved in making that plan. And I appreciate you sharing this story that is of curiosity, but courage, planning and support. Yeah. Like I think you see people posting these things on LinkedIn about all these amazing things they're doing. They're starting new jobs. They're starting new firms. They're doing TED talks and it's like, wow, that's amazing. But I remember when I first posted about starting my law firm or when I first posted about starting this business with a friend of mine, I was so scared and worried about what other people were going to think before I posted that. So we all know this, like social media is always showing the best of everything and there's a lot going on behind the scenes. It seems to me that you've built a really interesting community and built a community advising lawyers going solo, worked closely with legal professionals at different stages of their careers. Now working with organizations specifically in their AI needs. What challenge do you think that most young lawyers today might be facing that previous generations may not have experienced? And to give a little bit more of context, the more I talk with people in the podcast, the more I see that basically each generation had some kind of crisis or something that has happened in the world that was really outside of their control. That maybe when they were graduating, they thought I'd never get a job or maybe they didn't get rehired because of the economical point that they graduated at and all of that. So I'm curious to hear if you have some thoughts on that as well. Yeah, that's a really interesting point that there always seems to be something with each generation of new lawyers that's coming out. So the thing that I'm really interested in to see how it's going to play out is obviously the impact of AI on new lawyers and their education. Because I came through the traditional model where you work at a large firm, you don't actually talk to clients, you don't see clients for, I don't know, maybe a year or two. You are shadowing a senior associate. You also have a partner on a deal. You're asking those types of questions. I was working in an office where I could just walk down the hall and ask someone a question. So now is a very, very different landscape. And I'm, I don't know the answer and I don't know where it's going, but I'm so curious to see how we are training new lawyers to be confident in the legal advice that they are given. That they are giving to clients rather than just pressing the apply all button when they're reviewing a contract. I just came from a sales call where we were showing a feature in Spellbook where you can take all of the revisions and instead of looking at all of them, you can actually hit apply all. Which personally I like doing because I practice for many years. And so I don't necessarily need to know all the rationale, but I have the experience to know yes, no, yes, no. But a new lawyer would not have that same experience. And so on this call, they were asking if we can turn off that apply all feature. And so I just think I'm very interested in seeing where things are going to land in, in order to help give those new students the confidence and the knowledge and all of the things they need to be successful lawyers. What kind of advice would you give to someone, you know, it could be either a early career professional or really any lawyer who's trying to build a meaningful and sustainable career nowadays? This is probably going to sound cliche because people said it to me when I was a new lawyer and I totally rolled my eyes and I didn't do it. But if I could start over again and if I could give any advice, it's network. Like get to know people you went to law school with the people you're working with, because now I'm 20 years out and all of those people, you know, are heading up big companies. They're managing partners of law firms. They, you know, they're doing really amazing things. And I didn't take the time necessarily back then. And I think it's an amazing community, a super supportive community, and it's hard to do. I found when I was a new lawyer, but just keeping in touch with people, like sending them a quick text or a message on LinkedIn, I think would have gone a long way for me. So because now I'm kind of backtracking, to be honest. So that would be my advice. It's been quite the journey learning so much from lawyers. And I must say that networking is one that I really get often here in the podcast. And it's no wonder that it gets talked about so much. I caught it funny that you said the rolling the eyes, because I do hear lawyers saying, talking about this all the time, how that was the advice they received. They didn't follow through with it. Or on the other hand, they did follow through with it. And they actually recommend, you know, this community, even at times, you know, of uncertainty and at times where maybe there's something going on in your firm that might be an ethical conflict that you just want someone to tell you, Hey, it's time to leave. And having that community really makes a big difference. So thank you for bringing that up. I really appreciate it. Thank you so much for making the time to come to the podcast today to share your thoughts. And thank you all for tuning in to today's episode. And we'll see you on the next one. Thanks, Claudio.