Sarah Cottrell: Hi, and welcome to the Former Lawyer Podcast. I am your host, Sarah Cottrell and on this show, I interview former lawyers to hear their inspiring stories about how they left law behind to find careers and lives that they love. Let's get right to the show.

Sarah Cottrell: Hello everyone, this week on the podcast I'm sharing my conversation with Ivy Grey. As many of you know, legal tech as an industry is just exploding. A couple of months ago I had Alex Sue on to talk about his experience, moving from practicing law to a legal tech company on the sales side. And Ivy also works for a legal tech company called WordRake. And the way that she got there is really interesting so I think this is going to be a very helpful conversation for all of you.

Sarah Cottrell: Before we get to the conversation, I know I never asked this and bad podcaster, bad podcaster, but if you enjoy the podcast and could take a minute to rate and review it wherever it is that you listen to podcasts, I would really appreciate it because that does mean that it gets seen by more people and hopefully discovered by more lawyers who could use the help and the inspiration that it provides. Now let's get to my conversation with Ivy. Hey Ivy, welcome to the Former Lawyer Podcast.

Ivy Grey: Hi Sarah, thanks for having me here. I'm excited to finally get a chance to talk with you.

Sarah Cottrell: Yes. Can you introduce yourself to the listeners?

Ivy Grey: Sure. My name is Ivy Gray, I'm the vice president of strategy and business development for WordRake, which is an add-in for Microsoft Word that helps lawyers edit for clarity and brevity. Before joining the legal tech world I practiced law for 10 years and before that I was in advertising and PR for about a decade and before that I was in IT. So I've had a long and winding path to get to where I am and I'm happy to talk more about it and in fact, that's what I'm here for. So I'm excited to do it.

Sarah Cottrell: Yeah. So did you say before advertising you were in IT?

Ivy Grey: Yes.

Sarah Cottrell: Okay. Interesting. Interesting. Okay. So talk to me, so you were in IT and then you were in advertising and then you were in law. So did you decide to go to law school while you were in advertising? Is that right?

Ivy Grey: Yes. So what happened was that I would complain about my advertising job every single weekend. I would have brunch and the person I was having brunch with would say, "Well, why haven't you left this job yet?" And I would come up with all sorts of excuses. And finally he said to me, "You should consider being a lawyer." And I had never considered being a lawyer before that. In fact, I knew that I never wanted to go to grad school. I never wanted to pick up another textbook. I didn't want any more debt and I'd never met a lawyer so I didn't even really know what lawyers did. So it was kind of a crazy idea for me and went against everything that I thought I knew.

Ivy Grey: So I finally answered the question, why is it that you haven't left this job? What is it that you actually like about what you do? With the following. I said, "I love writing and research. I love meeting client expectations and I love the intensity of project based work that makes a difference." And he thought that that would be perfect for law, which is a great way to use the skills that I already had in a new and different way. And then I use those skills as a lawyer, and I have been applying them in legal tech since then.

Sarah Cottrell: So tell me when you got to law school, did you feel like this was a good choice? This is interesting, I am excited about this career path or did you have a different reaction?

Ivy Grey: I was miserable at least the first semester of law school. I was depressed, I was miserable. I was working incredibly hard and the results just weren't there and I didn't feel like I got it. Everyone else seemed to pick up a lot faster than I did, and there was no amount of work that I could do that seemed to lead to a different result and I wanted to give up. So what I did was I set some benchmarks for myself and got some coaching on how to do the law school game a little bit better. And I said, "If I don't get to top third of my class by the end of the year, I'm going to quit. Because it just doesn't make sense to keep throwing good money after bad." And thankfully it actually worked out and I got the coaching actually from my best friend in law school who was incredibly good at understanding the law school game, but not good at understanding the people game. So we traded those skills.

Sarah Cottrell: Yeah. I was thinking as you were talking about this experience in law school, that it is very much like it's a particular type of game with a particular set of rules. And the law school game is different from the legal practice game, which I think is very surprising to many people, certainly to many non-lawyers. And as you said also, I think too many people who are like, "I'm interested in being a lawyer. I'm going to go to law school." And it is one of those things where you just sort of have to internalize this specific set of rules that in many ways will never apply again in that same way, because law school is such a specific environment.

Ivy Grey: I think you need to trick yourself into playing the game in a way that's going to be useful for you. And at the end of the day, that's what I did. I took the game and then I came up with this basically spin strategy for myself to make it worthwhile and not just this thing that I had to get through. And I was very happy the last two years once I figured that out. So what I told myself was that the grades they matter to a certain extent, but I just had to meet this minimum threshold. And then after that was building a framework to figure things out because ultimately law is project-based work and you aren't going to do the same thing over and over. You have to be able to assess a situation, learn things, and then use what you've learned as fast as possible.

Ivy Grey: And if I took that approach to law school, then I was building skills that were useful rather than just memorizing something for a test. And I spent a lot of time figuring out how I best learned so that I could make those connections and apply them. And it turns out that I am not a linear thinker at all. I have this spoke and wheel approach to things and so I switched to creating diagrams and flow charts. And that diagram, flow chart, hub and spoke approach has actually served me incredibly well in my post-law school career, both as a lawyer and as a legal technologist.

Sarah Cottrell: I think that's such a helpful observation because I think there is this sense in both law school and in the legal profession of like, this is the way that things are done. Like you said, almost like, well, the best way to do it is if you're a linear thinker and like everything else like people can barely even conceptualize that it's a thing. And if they do, it's like, Oh, well, maybe that's a way you could do it, but it's like not the way using air quotes around the and that's actually not true at all.

Sarah Cottrell: And that type of thinking sort of like being conditioned in that kind of environment, I think is what often holds lawyers back from exploring other career options. Because of this whole like but there's the way and anyway, so tell me, you got to law school originally, you were like this is terrible then you sort of figured out how to play the law school game. When you graduated from law school and started practicing law, were you at that point expecting to like practicing law? Were you already thinking, I'm not sure this is going to be for me forever. Where was your head at that time?

Ivy Grey: When I graduated, I loved the idea of practicing law. I was excited about the firm that I was going to. I had accepted an offer at a large law firm called Davis Wright Tremaine in Portland. And I was certain that was going to be my life. And I was excited about the type of law that I was hoping to practice, which was bankruptcy law. People told me that I wouldn't really get to practice bankruptcy law because the economy hadn't yet crashed and everything was so good.

Sarah Cottrell: I was going to say when was this? I graduated law school in 2008 so...

Ivy Grey: Same. Same.

Sarah Cottrell: Okay. Yeah. Just wait.

Ivy Grey: Which is what I said. I kept telling people, "Just wait, it's coming. Just wait, it's coming." And people thought I was this horrible pessimist and then the bottom fell out and I know that you're not supposed to cheer, but I definitely did. And I got great work and great opportunities and I really loved practicing law. And for three years it was just wonderful. Maybe this is just a big sales cycle for joining Davis Wright Tremaine because it was an awesome experience. And I think that if I had never moved on from there I'd probably still would've loved practicing law and be doing it today.

Ivy Grey: They had a flexible problem solving approach that was very aligned with their clients. And for me, that's fulfilling and there's a lot of room in that to do a lot of different things. But I got greedy like young associates who get good opportunities do, and I dreamt of moving to New York and I wanted to work on those big cases that you saw in the Wall Street Journal and so I did. I quit, I moved to New York, I got my LLM. I got the job that everybody in my LLM program wanted. And then I was billing insane amounts and working past midnight, seven days a week and I was then miserable. And I started looking for other things to do, because I figured there just had to be more to life than that.

Sarah Cottrell: Yeah. When you said that, you know my experience like I remember during my summer, my two L summer I did a rotation with the bankruptcy group and I just remember this was in Chicago, but I remember getting the impression that like, they worked a lot like a lot, a lot. So I imagine that in New York it was just that plus even more. And I think it's interesting because you say like, it sounds to me like what you're describing is something that so many lawyers experience, which is this idea of like, well, this like X, whatever X is, is like the thing I should be aiming for. So like in your case, as a young bankruptcy associate like I should be aiming for the most high profile bankruptcy cases. And that means going to New York and getting this type of job and doing this type of thing. But not necessarily spending a lot of time thinking about like, okay, what is my life going to look like when I am doing that thing?

Sarah Cottrell: And that can be any number of things for lawyers that can be like, if I were a partner at this firm, if I went to a different type of firm, if I went to a different type of job, if I tried to get this prestigious fill in the blank. I find that a lot of people sort of have that experience of aiming for and getting the thing that they thought that they were supposed to want. And then, like you said, realizing like, Oh, this actually makes me miserable.

Ivy Grey: Definitely.

Sarah Cottrell: When you realize like, Oh, this makes me miserable. Did you have a plan as to what your next step was? Was it just like, wow, this makes me miserable and I have no idea what I want to do next? What happened?

Ivy Grey: So I cataloged my skills, cataloged what I liked about what I was doing, which should sound familiar and I said, I always know where to start. I'm never stuck. I've got a flexible mindset, I can manage huge quantities of information, I can learn things really quickly. What can I do with that? And I had not thought about actually joining the legal technology world. I assumed that I would go into something like bankruptcy claims management instead. And then the legal tech world fell in my lap via a hobby and that changed everything.

Ivy Grey: But I couldn't have said yes if I hadn't started building my plan to get out. And I started building my plan to get out of practice about a year before I switched from full-time to part-time. And then I was in this part-time world for a couple of years before getting out of law entirely.

Sarah Cottrell: And tell me a little bit more about what it looked like for you to build your plan?

Ivy Grey: So participating more on social media, reading more about the industry cross-training and other industries, because if all that you know is law, then you see everything through a law lens and you don't do a great job of actually hearing what your clients are saying. Instead you're filtering everything through this legal filter, and it doesn't help your clients because your client doesn't say to you, I have this legal problem. Your client has a problem.

Ivy Grey: So I went about learning to recognize these other problems, to see where they fit in the world, to understand business more, and to build myself up so that I could be a better partner to clients and to the companies that I wanted to work with. So I learned about the broader world so that I could actually be ready to do something other than think only like a lawyer. And I also saved money because I knew that it could take a while to make the change that I wanted to. And I would be sucked right back into the sort of thing that I didn't want to do if I didn't have that financial cushion.

Ivy Grey: So those are really the two big things that I did, and then the small thing was just building up my network and letting people know what I did. They didn't really know before, because I had been head down just producing the work for so many years. I had to reintroduce myself as professional to my friends.

Sarah Cottrell: So what did you end up doing next?

Ivy Grey: So from there, I joined a company called PerfectIt and I helped PerfectIt create the legal specific version of its software that does proofreading and editing, and Bluebook citation for formatting for lawyers. And I got there through my hobby, which is swing dance. The founder of PerfectIt had been one of my dance buddies for several years and he convinced me to try the product. I didn't love it and in response I gave him pages and pages and pages of feedback. And instead of saying I'm not listening to you, what do you know? He said, "Why don't you join me and build this tool that you're imagining?" And that's how I got into the legal tech world.

Sarah Cottrell: And is PerfectIt specifically... Because you mentioned something about like a specific version that's for legal. So was it sort of like a more generic tool and then there was a specific application for legal or how did that work?

Ivy Grey: Correct. So it was a more generic application that mostly editors and professional proofreaders and book publishers were using. All of the people who care deeply about words and want to make sure that they're right, just like lawyers do, but somehow lawyers weren't looking at this software. It didn't have legal in the title and so they didn't care. And my friend wanted to fix that, and in response, I created American Legal Style for PerfectIt, which is the legal specific version.

Sarah Cottrell: Got it. And that was something that you did once you had come onto that team?

Ivy Grey: Yes. So in 2015 I stopped practicing law full-time and I started splitting my time working with a firm of friends. I helped found the firm, which gave me a lot of flexibility. And I also joined another friend and that's Daniel in his startup called PerfectIt, which I just been talking about. So I was at the ground floor in two organizations at the same time, which gave me the flexibility to really juggle those two things together in a way that I wouldn't have been able to do if I had entered at any other point in time or in the organization.

Sarah Cottrell: And when you started with the firm that your friends were starting, was your thought always eventually I'm going to transition to this other thing, to legal tech full-time or did you start it thinking I'm going to try to do both of these and then eventually decided that wasn't going to be the best fit?

Ivy Grey: I thought that I was going to do both. And I was fortunate that at the very beginning I said to my friends, "I will join you, but these are all of my conditions. I need to work whatever hours I want. I need to work only on the high level cases that I find intellectually stimulating and I need to do them on the timelines that I need to do them. And I'm not going to do any of this route work it's not worth my time. I'm only going to do this high level stuff." And surprisingly they said, yes. They still wanted me to join the team, even with all of those stipulations. And that made it both rewarding to do the work and actually possible to do the work around my startup life.

Sarah Cottrell: So tell me, at what point did you decide to make the transition fully just to PerfectIt and talk to me a little bit more about that process of marketing to legal professionals. And the reason I say that is because I think things are definitely changing, but sort of traditionally I think legal practice was rightly viewed as very resistant to any sort of like new technology. And so I'd love to know some about that experience as well.

Ivy Grey: Those questions really need to be answered separately. So I actually never worked for PerfectIt full-time. My entire life with PerfectIt was part-time lawyer, part-time legal technologist. And well, it was supposed to be part-time I was really working 80 hours a week. I had 2 full-time jobs.

Sarah Cottrell: I was going to say two part-time jobs also known as two full-time jobs.

Ivy Grey: Exactly. And I didn't leave the practice of law until I joined WordRake and WordRake made me an offer that I just couldn't refuse. How I got to WordRake is actually kind of a fun story. WordRake had been in the legal market for several years before PerfectIt entered the legal market. And they were our guiding light for what we wanted to do, how we would set ourselves up, how we would market. And PerfectIt, we kept reaching out to WordRake saying, "Will you mentor us? Will you mentor us? Will you help us? We want to learn from you we admire you."

Ivy Grey: And eventually after enough hounding, their CEO actually said yes and started mentoring us. And over time our roles reversed and the CEO of WordRake started to say, "We need an Ivy." Instead of PerfectIt saying we need advice from WordRake. And in November, 2018 I joined WordRake full-time and that's when I actually stopped practicing law.

Sarah Cottrell: Got it. So that I'm trying to think 2018 so a little over two years ago?

Ivy Grey: Correct. Correct. So for legal marketing, did you want me to do that now or do that in a follow up?

Sarah Cottrell: Yeah. No, let's talk about marketing, marketing technology to lawyers.

Ivy Grey: So with marketing technology to lawyers you can't take the approach that lawyers are these Luddite idiots, which I think a lot of people who decide that they're going to go into legal technology think that that's a good sales approach. And I'm here to tell you today that it is not. Insulting the people that you would like to buy your things is just not a good plan.

Ivy Grey: So a lot of times there's this educational component of marketing that people don't want to do and don't think is important. But for the people who are in the weeds, practicing law every day they're just trying to get through projects. They're not asking the question about how this project can be done better. They are not looking for solutions to a problem that they don't know they have. So you need to show lawyers that there is another way, you need to show lawyers that the way that they're doing things now is problematic and that they do need a solution to that problem that they didn't recognize until they spoke to you.

Ivy Grey: So that's a lot to think about if you've only ever practiced law, because you are probably not seeing that there's anything wrong with how you do things. You just know that it's too tiring and that it doesn't feel right. So I suggest going to conferences, speaking with lots of people and learning about what they do and how they position their products so that you can start to embrace that way of thinking. If you only apply your legal brain to your legal technologist job I think that you will not get very far.

Ivy Grey: So cultivate a marketing mindset and figure out where your customers are and meet them where they are, and then build them up from there. So you show them that there's this problem and then you actually start marketing to this problem that they now recognize. And that answer or the marketing solution can be different for a lot of different types of lawyers and a lot of different segments.

Ivy Grey: So again, you have to get out there and network so that you understand each of those people who might be buying and where they're coming from. A solo is going to end, or a small firm is going to care a lot more about efficiency, if they have a high volume practice than a large white-shoe firm that has a cadre of 50 document professionals just waiting to do your work overnight. Those people will never care about efficiently creating a document and they'll probably never learn how to use styles, et cetera.

Ivy Grey: But the solo lawyer is going to care about those sorts of things, because they don't have that pool of staff just waiting to do the stuff that they don't want to do. They have to do it, and they have to do it efficiently so that they can do the more thoughtful work. So you have to learn to recognize the segments and then actually segment your pitch. But you can't do that if you don't talk to lots of other people.

Sarah Cottrell: This episode of the Former Lawyer Podcast is sponsored by the Former Lawyer Collaborative, my program that helps lawyers figure out how to transition out of legal practice. In the Collaborative, you'll find a proven framework to follow, a confidential community and real time advice and support that helps you figure out what you want your career and life to look like. What specific careers align with what you truly want, how to pursue and land jobs in those fields, how to make a plan financial and otherwise to put you on a path towards a new career and much more.

Sarah Cottrell: When you join the Collaborative you get access to the monthly group calls and workshops, as well as the program content and the community for as long as the program is offered. Find out why lawyers like you are calling the Collaborative invaluable, and life-changing. For more information about the Collaborative go to formerlawyer.com/collab. That's formerlawyer.com/C-O-L-L-A-B. Now, back to the conversation.

Sarah Cottrell: So tell me more about WordRake, the product itself? You mentioned sort of going to WordRake and asking for mentorship when you were at this other company so I'm assuming, and I do know some about it, it's a similar type of thing. So can you just talk a little bit more about that for people who haven't heard of WordRake before?

Ivy Grey: Sure. So WordRake and PerfectIt are both add-ins for Microsoft Word, which means that you can run them seamlessly within Word and they run right from your ribbon, just like you would run Spellcheck or any other built-in Microsoft function. The two programs are complementary. One does proofreading, that's PerfectIt. The other one does editing, that's WordRake. WordRake specifically edits for clarity and brevity, and is based on a series of algorithms that our founder, Gary Kinder created. He discovered them after teaching about a thousand courses on legal writing. He found that people were making the same mistakes and that certain words led to lots of other words.

Ivy Grey: And from there, he worked with some engineers to create the algorithms that are the basis for WordRake. So what WordRake does is just like an editor with a red pen or that partner that was an English major that really knows how to give great feedback, WordRake ripples through your document, marking up in the familiar track changes form making suggestions for how your writing can be clearer and more concise. And then you can accept or reject those changes based on your own style, whether you think it makes sense, whether you think it works and improves the sentence, just like you would accept anything from an editor in track changes.

Ivy Grey: It's super fast. You can check a hundred pages in a minute and I've been really impressed with it. And I used it for... I mean I still use it every day. But in practice I would run PerfectIt and WordRake on every single document that I created. And I did that for five years before coming to legal tech full-time.

Sarah Cottrell: Tell me a little bit more about what you specifically do for WordRake? Because you mentioned, I think you said that it got to the point where WordRake, the company was saying like, we need an Ivy here. What role do you play or what specific things are you doing? Like what does a typical week look like for you in your role at WordRake?

Ivy Grey: There is no typical week for me. I wear an unusually large number of hats. And that is because I have an unusually winding background and a lot of people would look at my background and say, "Wow, you need to commit to something. That's terrible." But WordRake instead looked at my background and said, "That's perfect. That's exactly what we need." Because I write for the blog, I write in-depth white papers, I will do the marketing and the pitching. I write our brochures. I design our brochures, I've redesigned our website. I write new editing suggestions into the product and I actually do the legal specific tweaking now.

Ivy Grey: I work on the operating budget and I manage a lot of people in the company. And then I also check out the watch for the legal industry trends and guide us according to those trends. And I think so obviously social media, and then the final thing is that lately I've been doing the UI for all of our new features. Which is a skill that I didn't realize I had and it's turned out incredibly well and it's been really fun. So that's a lot of stuff.

Sarah Cottrell: That is, that is, I was going to say just a few things. And I was going to say for different people who maybe are not super up on the tech lingo, can you just tell them what UI is and sort of like how that differs from some of the other like backend stuff you're talking about?

Ivy Grey: So UI is the user interface, and that is for instance, if you go to Microsoft Word and you see all of the buttons on the ribbon and they launch some sort of function, that is what the UI is. It's what button do you click? Does that button make sense? What happens when you click that button? And do you have confidence that that button is going to do what you expect it to do when you click it? And that's the sort of stuff that I plan for, for each new feature.

Sarah Cottrell: You said you started out in IT back in the day, so when you were doing that and then advertising and then went to law school, did you have an interest in legal tech at that point or was it truly just something that you came across naturally as you were developing that hobby once you were like into your legal career?

Ivy Grey: So I didn't think about legal tech at all when I was in law school. And I didn't think about it as a separate thing while I was practicing. I just thought of the tools that you need to get the job done. I didn't think, Oh, there's technology and then there's this non-technology thing. They were all just how do I get to where I need to go? And I think that's probably a more useful way to do things and keeps you from developing these mental blocks, where you give yourself some sort of self-talk about what you can't do and what you don't know. Just think of it as the tools that you need to get the job done.

Ivy Grey: So with that all said, I am the child of a secretary. And that means that there's always been a lot of simple technology in my household and the expectations for using it well, we're super high. I type fast, I use Word well, I cared about PowerPoint and Excel for longer than most people have, at least in most people my age. And it didn't occur to me that those things were legal tech until I actually got into the legal tech world.

Ivy Grey: So I didn't go about trying to find some sort of legal tech skill, I didn't think that I was building legal tech skills. I was just doing what I needed to, to get my work done. And in law school, I guess I was doing more of that because I had to use some sort of technology to draw my diagrams and to create all of the interlinking things that I would use. And I did that by kind of bastardizing Word and PowerPoint to draw more than most people would usually draw. But I developed those skills from when I would work over the summers with my mom in biotechnology, illustrating patent applications. But those were like skills that I developed when I was 15 and I didn't go to law school until I was in my late 20's. It's kind of weird how those things came back and became useful and now I use them all the time.

Sarah Cottrell: Yeah. I was going to say, I think that's such an important insight because often when I talk with people who are thinking about leaving the law and people who like when they first come into the collaborative, there is often very much this like, okay, well, what skills do I have? And that's what I should be using to figure out what's next. And they're looking kind of myopically at just the thing that they've been doing in their job as a lawyer that they think of as lawyer skills, if that makes sense.

Sarah Cottrell: And the reality is that figuring out what's next is so much more about figuring out what it is that you want to be doing and having a more whole holistic view of yourself. And like you were saying you didn't necessarily start out on the front-end saying like, well, this is clearly where the ultimate trajectory of my career should go. But as you look back there is that thread. And I think sometimes lawyers look at someone's experience like that and they think almost like, Oh, well you must have known on the front-end because it all has this thread, right?

Ivy Grey: Yeah. But that's the story you tell yourself, you get to write that story in hindsight.

Sarah Cottrell: Exactly. Yes, totally. Totally. And the reality is that like it's really just about learning to understand yourself better. Which I think sometimes does not sound as exciting as just like figuring out that perfect next job that will like match every single thing. But the reality is that like the more you understand yourself and the things that you enjoy and the things that you're good at, like you said, the things that you just assumed were a part of it, but in fact, you had like some unique and specific things that you were particularly excellent at because of your upbringing and because of just like your natural strengths. And so I think it's so important for people to realize.

Ivy Grey: I want to inject or interject there with my upbringing. I have a far more humble background than a lot of people in law. And I think a lot of people think of that as a disadvantage. And I actually think it's an advantage because I ask how can something be different? And I see the struggles that my family has gone through and I don't assume that there's always a legal solution. I understand opportunity costs because those costs were really high when you didn't really have a lot of choices and your back was always against the wall. And I understand how to just jump in and learn something when somebody doesn't want to hold your hand, or when there isn't an immediate reward for that.

Ivy Grey: That was the life that my mom always lived and I'm really glad that I got to develop that perspective, even though it's not as glamorous as what a lot of lawyers prefer. Most of the time you hear these stories about these people who they went to Harvard and their dad went to Harvard and their dad's dad went to Harvard and they've got all this pedigree and they think that they need to have all this pedigree. But then the only thing they know how to do is think of something as a legal problem and think of, well, my secretary should do this better. They never stopped to think that it could be them that could do it better, that it could be a social problem, that it could be a business problem, that it could be solved in some other way. That pedigree can actually narrow your thinking, disadvantage you.

Ivy Grey: So if there's only one thing that people take away from this conversation is don't be embarrassed about your background, don't write it off as useless or something that's going to hold you back. Your background is a unique superpower that makes you you, and that makes you able to do something that other people can't. And you should embrace that.

Sarah Cottrell: Yes. And the legal profession, at least pockets of it may be obsessed with prestige, but prestige is actually not a particularly good guiding light to rely upon in making your career and life decisions. In fact, it is one of the things that tends to result in a great deal of unhappiness, which I think is also a common pitfall that people, that lawyers fall into when they're thinking about of these issues.

Ivy Grey: I think that you're more likely to fall into that mindset if you have always been successful. So, if you went to a very prestigious undergrad and only got A's, and then you went to a prestigious law school and only got A's, and then you went to a prestigious law firm. Then you expect that you're going to get the equivalent of only A's and it destroys your picture of yourself if you aren't immediately successful and it's very hard to recover from that. And I think that it hinders you in terms of feeling okay about yourself and also in terms of pivoting. People who have some struggles or they teeter, and then they come back, I think are better prepared to find the next right thing and to ultimately find happiness.

Sarah Cottrell: Yes, I agree 100%. Okay. So tell me more about what you're doing with WordRake right now, and some of the things that you're involved with related to that?

Ivy Grey: Sure. So with WordRake, we understand that drafting is incredibly important part of legal practice and automation is not going to solve everything or forms aren't going to solve everything. And while we know that, a lot of people don't take that next step to actually improve their writing. And with WordRake I'm always trying to refine the product so that we do improve your writing. We are, at some point early this year, we are going to release a new version that includes a set of edits called Simplify, which actually will help you meet the plain language requirements from the Plain Language Act of 2010.

Ivy Grey: So that's on the horizon, I'm super excited. And then the other thing that I've been putting a lot of time into is this new thing called the Effectiveness Project, which is a collaboration with LTC4 and several other legal industry representatives from academia and vendors to law firms, et cetera. And we are trying to prompt people to actually ask the question, can this be done better? And to say, this is hard but should it be this hard? And then give people the answers.

Ivy Grey: On the flip side, we are hoping that we can train clients and judges and other people who actually pay the bills to evaluate legal bills and say, yes, this is a bespoke project. Yes. The work that you're doing is valuable, but no, it shouldn't take you this long. You are not using the tools at your disposal, and I need you to fix that. So we are trying to give some power to the duty of technology competence that hasn't been given before. And I hope that instead of waiting another 10 years to see technology competence take off, that we'll see some movement in one to five years and hopefully it will be on the back of this project.

Sarah Cottrell: And my understanding of what you're saying is like in really practical terms would be like, hey, maybe you should not be billing for endlessly tweaking the fonts and the super... I don't want to say basic, but like [crosstalk 00:40:53]

Ivy Grey: The super technical things?

Sarah Cottrell: Yes, yes. As opposed to sort of the higher level legal thinking and actual like drafting.

Ivy Grey: Yes. So we're definitely trying to improve that part, but if you are doing it right, those basic things are part and parcel of your drafting process. For example, if you're writing an asset purchase agreement and it has internal cross-references, then you should be inserting those cross-references using Microsoft's built-in tools while you're drafting. Because you're referring to the provision that you're referencing. It makes no sense to leave that to some other time. And even if you do leave it to some other time you should not be updating those by hand. You can update them with one click and you should know that you can update them with one click, but a lot of lawyers don't and a lot of clients don't, especially if they come from those white-shoe firms.

Ivy Grey: So if you see a bill that says update cross-references six hours and you're just like, "Okay, well, that makes sense. It's a 60 page asset purchase agreements, very detailed work." You should actually freak out because the first time that you do the work, it should be part of the drafting. And then the second time that you do the work and update it, it should be merely seconds, seconds, not even something that should appear on the bill, because it should be seconds, one click. And hopefully we will actually train people to think about that.

Sarah Cottrell: Yeah, it's interesting because there I think it's a lot of functionality in Microsoft Word that, and this isn't just lawyers, there are just people in general, I think don't necessarily have an awareness that it even exists.

Ivy Grey: Yes.

Sarah Cottrell: That's definitely something I've observed.

Ivy Grey: So we've got this white paper that is out for comment right now. And then the next step is to split it apart into modules and checklists from different perspectives. So that if a lawyer is drafting, a lawyer can say, I'm in this part of the drafting process, let me download this checklist that's short, just one page. And I can see whether I'm using the tools at my disposal, I can see whether I'm over-billing because there will be time and value metrics in there so we will be able to say updating cross-references should take seconds and is not considered billable, even though it is a necessary and important task. And Bluebooking should take you less time if you're using an add-in that does that et cetera.

Ivy Grey: So hopefully with those checklists, you actually might prompt yourself to do a better job or to consider learning. And hopefully clients will use it when reviewing their bills. So with that, I think we'll be pushing and pulling from all the directions and maybe see some change.

Sarah Cottrell: So Ivy, if there are people who are listening to this, and it sounds interesting to them and sort of your experience in the work that you're doing sounds interesting and they're thinking like legal tech as a field seems like something that I could be interested in. What advice do you have for those lawyers in terms of next steps?

Ivy Grey: Catalog your skills and figure out what you are willing and excited to build on. If you are good at something, but you hate doing it, don't build on that one. It's probably the shortest advice that I have.

Sarah Cottrell: Yeah, no, that's so good. I was just having a conversation with someone about that yesterday. Like one of the things that I talk about, one of my big sort of realizations, which seems so ridiculously simple, but in leaving big law was like, just because I can do something doesn't mean I should. And I think there are a lot of lawyers who get in this mindset of like, well, I can do this, so I should do this or like here are my skills and I'm thinking about them in a very narrow way. And they fit in a very narrow set of possibilities, but like that's and don't give a lot of thought to, hey, do I actually want to do the thing that I'm thinking is? Is that thing my skills point towards?

Sarah Cottrell: I think it's really important and it's definitely overlooked, which is why we talk about it on the podcast a lot. Yeah. So Ivy, as we're getting to the end of our conversation, is there anything else that you'd like to share that we haven't talked about yet?

Ivy Grey: I think that a problem solving mindset will take you to wherever it is that you need and want to go, even if you decide to stay in practicing law. Learning to understand those problems and come up with creative approaches to solving them that aren't necessarily legal. That's not to say illegal, just not about [crosstalk 00:45:50] law from a textbook. So if you think creatively about those problems then you might find happiness in law. And even if you don't find happiness in law, I think that you will start to reevaluate your skills and see where else you can be successful and happy. So creative problem solving work on it.

Sarah Cottrell: I think that's really good advice. Ivy, where can people find you and WordRake online?

Ivy Grey: WordRake is at www.wordrake.com. That's rake like rake a leaf. And I am Ivy G as in color Grey, @wordrake.com. You can find me there and my Twitter handle is IvyBGrey and it's also the same on LinkedIn.

Sarah Cottrell: Awesome. And I will link to all of those things in the show notes so people can always head there. Thank you so much, Ivy for joining me today and sharing your story. I really appreciate it.

Ivy Grey: Thanks so much, Sarah. It's been a pleasure talking to you, and I hope that people get a little inspiration and direction from this.

Sarah Cottrell: Thanks so much for listening, I absolutely love getting to share this podcast with you. If you haven't yet, I invite you to download my free guide, First Steps To Leaving The Law at formerlawyer.com/first. Until next time, have a great week.