“Transition to Tech” with Ivy Grey 238
Categories: Podcast

In today’s episode we joined Ivy Grey, Vice President of Strategy and Business Development for WordRake, the creator of American Legal Style for PerfectIt, and an advisor to Intelligent Editing Ltd. 

Ivy practiced corporate bankruptcy law for ten years before making her transition to full-time legal tech in November 2018. During her decade of legal practice, Ivy was named a Rising Star in the New York Metro Area for five consecutive years, and her significant representations included In re AMR Corp. (American Airlines) and In re Filmed Entertainment Inc. (Columbia House). 

5:50 what are add-ins
11:24 word add-in you should know about
14:25 Wordrake
16:00 marketing a product vs practicing law
16:40 efficiency seems threatening because or the way lawyers bill
23:00 flat fee vs billable hours
26:02 tech for solos from the beginning27:45 calendaring and automations

Jim’s Hack: From the I Love Marketing podcast by Dean and Joe: a way to clarify things when you’re doing video, when you’re getting ready to make a point use one of two words – Look or Listen – and then pause. This grabs the listeners attention. 

Tyson’s Tip: Our friend John Fisher shared his intake binder in the Facebook group – go take a look!

Ivy’s Tip: Book – Thanks for the Feedback: The Science and Art of Receiving Feedback Well by Douglas Stone and Sheila Heen. This helps with changing your behavior to actually be successful

If you enjoyed the show, we’d appreciate a 5-Star review!

To keep on maximizing your firm, stay connected!





Transcript: “Transition to Tech” with Ivy Grey

Jim: Welcome back to The Maximum Lawyer Podcast. I’m Jim Hacking.

Tyson: And I’m Tyson Mutrux. What’s up, Jimmy?

Jim: Oh, Tyson, if we were recording this 15 minutes ago, we would’ve had to stop and restart. Our electricity went out for about two minutes because there was a big lightning strike and it’s just been pouring today. I got drenched getting into USCIS today.

Tyson: Well, it might still happen to me because it is going crazy around me right now. There’s a lot of thunder so we’ll see. The electricity has never gone out in this office. Knock on wood. I should be good.

We do have a guest today. Do you want to introduce our guest?

Jim: Yeah, so her name is Ivy Grey. I’ve been following her for a long time on Twitter. I told her that before we got started and she said, “Well, you guys must have high standards.” And I was like, “Well, we let Mike Whelan on here.” I know you and Mike are good friends so. 

Ivy is the Vice President of strategy and business development for WordRake. I can’t wait to ask her about WordRake because I honestly sort of don’t understand what it is. I’m glad we’re going to talk about that. She had her own bankruptcy firm for 10 years. She’s been listed as one of the 2020 Influential Women in Legal Tech.

Ivy, welcome to the show.

Ivy: Thanks so much for having me, Jim. It’s a pleasure to be here. Now, I absolutely feel pressured because Mike is a lot funnier than I will ever be.

Tyson: Don’t give Mike too much credit. Come on, don’t do that.

Well, Ivy, before we get into WordRake and what you’re doing nowadays, give us a little bit of information about your background and kind of how you got to where you are now.

Ivy: Sure. So, I had a winding path that took me to law and then, from law, to technology. I started off as a journalist and I moved into public relations and damage control and worked in advertising for nearly 10 years before shifting gears and going to law school. 

When I decided to go to law school, I catalogued my skills. I did not have this great desire to be a lawyer. I didn’t grow up wanting to be Atticus Finch or anything. Instead, I said, “What am I good at and what can I do with those skills?” Somebody suggested becoming a lawyer, so I did. After 10 years of practice, I somehow fell into technology. And then, that took over my life. That’s the shortest version I can give you.

Jim: So, Ivy, when you were a bankruptcy lawyer, did you work on your own or were you with other people? And then, sort of, how did that progress?

Ivy: Sure. I started at a large law firm that’s actually known for innovation, Davis Wright Tremaine. I was in the Portland office. I was working on huge cases, mostly on the creditor side. And then, like any young associate, I got hungry and stupid and decided that I would move to New York to try to work on the big cases. That’s when I got my LLM and I joined a bankruptcy boutique and I was working on huge cases that you’ve probably heard about in the Wall Street Journal, everything from American Airlines, and Kodak to Dewey & LeBoeuf which is the largest law firm failure in history. Working on Dewey really got me thinking about what law firms are doing wrong, and the culture and the incentives that lead us to where we are.

Tyson: Ivy, it looks like you’re really, really involved in tech, right. And so, like, why the legal route and why not the tech route from the beginning?

Ivy: I thought that technology was just something that I did for fun. And I thought it was something that was simply a part of life. When you grew up in the Silicon Valley, that is what it is to you. It’s just a thing that you do or, at least, I didn’t really consider that it would be a career. And all throughout law practice, I was always the most technical person in the firm. And it still didn’t occur to me that it could be a career.

It wasn’t until a friend who had an add-in, his name is Daniel and he is the founder of Perfectit, challenged me to using his product and actually testing it against myself that I thought about joining the technology world. 

The short version of that story is that I was writing my LLM dissertation and I thought, “I don’t need any tools for this. I’m perfect. There’s no way that your proofreading program is going to be better than what I can do. I had two executive board positions on my journal. Hmm hmm hmm.” You know, standard lawyer ego, right. Then, I tried PerfectIt and I used it on my dissertation, and it found errors. So, I lost the bet and instead of simply buying my friend a bottle of scotch, that I owed him for losing the bet, I came back to him with about five pages of changes that I thought he should make to the program to make it more effective for lawyers. He thought lawyers should just run out and buy it no matter what. And with that, he said, “Really, why don’t you join me and build the program you envision?” And that’s how I tumbled into technology.

Jim: And so, what did that look like as you began that process and how have things progressed?

Ivy: So, I had to figure out the world of add-ins. Now, I’m all in on add-institution but, at the time, I’d never heard of what an add-in was. I thought that Microsoft had this functionality and I didn’t really think beyond that. So, while working with Daniel, of PerfectIt, I learned really what add-ins did – regex which are regular expressions, C#, etc. and figured out how the program worked from the front end all the way to the back end.

After figuring that out, I was able to see where I could add value, where I could use existing technology and bring in the aspect that lawyers would need. I backed into where I am, but that’s kind of how I do everything. You figure out what your solution is, what do you need, and then you develop the solution from there rather than having a solution, search problem.

So, that’s how I how I ended up getting into it, and learning things, and really just figuring it out and trained myself.

Tyson: All right. You’ve got to remember, Ivy, that we are not these high-tech guru people, so what the hell’s an add-in or add-on? Break it down for us. Make it simple.

Ivy: All right. So, Microsoft add-ins are these little features that you can add to existing Microsoft programs. They are created to run within the programs, to harness the structure of Microsoft Word, or Excel, or Outlook, etc., and to function within that world so that you don’t have to leave Microsoft Word to do what you want to do and then enhance the existing functionality.

I love them because it’s familiar. You have the ribbon. You have your drop-down menus. Everything looks the same. And it’s a low barrier to entry.

Essentially, an add-in is, if you move where the button is, it will feel to you just like using something that existed in Microsoft Word. So just like you would use Spellcheck. Spellcheck could have been an add-in if Microsoft didn’t already create it. An add-in will do that same sort of thing. You click a button. It runs. It runs within that world. It doesn’t make you change or do anything different. It’s seamless integration and automation.

Tyson: Is this like a commonly known thing? It’s like I’ve never heard of an add-in. Google Docs, like they have– like, I don’t know what they’re called, but I’ll call them an add-in. But like, I didn’t know you could do the same thing for Microsoft Word. So, is this like a commonly known thing?

Ivy: It is becoming more common. In 2017, when Microsoft changed its platform and started creating a marketplace for add-ins, it became more common. Before that, it was a lot harder, you had to know so much more and there were a bunch of restrictions. I think only the most obsessed people actually heard about it. And now it’s much more common.

If you look to other industries, where writing and editing are super important, you’ll see a higher adoption. So, for instance, editors and professional proofreaders, they’ve been using add-ins for a decade and it’s just now coming to law. Those people, they get paid by the word, rather than by the hour, so they’re constantly looking for ways to efficiently edit and do their jobs. So, their careers and the way that they’re compensated, makes them go out and look for a solution.

Lawyers are the opposite. We get paid by the hour. And the slower we are, the more money we make. So, we’re discouraged from looking for ways to be efficient. Luckily, with the new technology competence rule, things are pushing back with that.

Jim: Let’s talk about that model rule for technological competence. How does that come into play for lawyers? I bet a lot of our listeners don’t know about that.

Ivy: Sure. So, in 2012, the ABA issued an adjustment to a rule. Model rule 1.1 tells learners that they must be competent in all things. Historically, we’ve thought of that rule as meaning that we must be competent only in how we practice law and how we analyze law. And we’ve ignored all other business aspects.

In 2012, that changed. Comment eight to model rule 1.1 was modified to specifically include technology and to require lawyers to be technologically competent in every single thing that they do. The first people who started talking about it went way off and they started talking about blockchain, and AI, and all sorts of things that are scary and often irrelevant, especially for solo and small-firm lawyers. You know, who really cares about blockchain?

When I started writing about it, I said, “You know, why aren’t people talking about how this actually impacts daily practice?” And I thought, “Microsoft Word, how many lawyers don’t know that they can add things to their dictionary? How many lawyers don’t know how to mark citations and use the built-in table of authorities feature? How many lawyers don’t know how to do something simple like format bullet points or properly change line spacing to comply with court requirements?”

Realizing that people really didn’t know that, but most commentary was about this other inaccessible stuff, I started writing about technology competence and thinking about how it mattered practically.

Tyson: So, I’m going to ask you something fun. Tell me this. What is like one cool add-in that most people don’t know, or one cool tool – not add-in, one cool tool that most people don’t know about with Word that you think most people should know about.

Tyson: Oh my gosh, I love Word, so the list could be so long.

No, I think that the easiest one for people to begin using right away is the navigation pane. When you use Microsoft Word styles and all of the headings, Microsoft will automatically create outline based on those headings and put them into navigation pane. So, if you look to the left of your screen, you will see everything that you’ve created in an outline form. That outline actually helps you stay on point and stay focused.

For me, once I started using the navigation pane and drafting with that outline next to me, my briefs got so much better. They were so much more persuasive. I felt less tempted to throw in every argument simply because I could or to throw in arguments that were irrelevant or otherwise weak. Seeing that outline, as I drafted, made me constantly question whether this argument or this sentence actually advanced what I needed to do for my clients. My drafting became so much better. So, it’s a simple thing, Ctrl-F, expand, you will see the navigation pane on the left side and it is life changing.


Thanks to our sponsor, Smith AI. Smith AI is a superior receptionist service for law firms, trusted by many Maximum Lawyers, including me.

At my immigration practice, the Hacking Law Practice, Smith’s friendly US-based receptionists respond to potential clients in English or Spanish, screen and schedule new leads, and even take payment for our consults. The best part is that they don’t just handle these conversations via phone. They also have live agents and chatbots capturing leads on our website through their chat widget. They serve as our friendly gatekeepers while my team and I work uninterrupted. We get new clients and we get work done. How awesome is that? If you’re in a solo or small firm, I know you’ll appreciate this. 

Plans start at just $70 a month for calls and $100 a month for chats. They even offer a totally free chatbot so there’s no excuse. Try Smith AI today and see for yourself why attorneys like me say, “Smith AI receptionists are the secret to business growth.”

Smith AI offers a free trial and Maximum Lawyer listeners get an extra $100-dollar discount with promo code MAXLAW100. That’s M-A-X-L-A-W-1-0-0. Sign up and learn more at

Trust me when I say don’t let another day go by, try Smith AI.


Jim: All right, great.

Well, we’re talking about model rules and formatting on Word sort of some of the things that really need to be talked about but sometimes aren’t. I want to shift gears a little bit and talk to us about WordRake. What is WordRake and how can it help people who are practicing law and dealing with briefs and things?

Ivy: Sure.

So, WordRake is, as we started talking, an add-in for Microsoft Word. It helps lawyers and other professionals seamlessly edit for clarity and brevity in Microsoft Word and Outlook. It presents its changes in the familiar Track Changes style. So, if you like something, you can just click and accept. I really hope that Track Changes are familiar to everybody.

WordRake will help you edit for plain language and reduce legal jargon and legalese, cut throat-clearing introductory phases such as clearly and furthermore – things that really don’t add to your writing. It will remove unnecessary descriptive words, modifiers, correct nominalizations and wordy adjective phrases. Those are all of the things like make a decision to all those words that end in -ion, remove redundancies and correct usage errors, correct high-level grammar errors and punctuation mistakes, and edit conversational language to be more professional. And it will do that all in one click. It would take you hours to go through and look for those sorts of things and you become rather blind to your own writing and own habit, but the software doesn’t become blind and it never gets tired. So, WordRake will catch all of those things for you and it can edit 15 to 35 pages in under a minute.

Tyson: All right, so I’m going to ask you something not about the product itself but actually– like, what’s it like marketing a product like this? I mean, it’s so different from practicing law. I mean, what is it like marketing this? Is it more difficult to practicing law? Is it easier? I mean, tell me the differences.

Ivy: So, I would actually say that it’s harder than practicing law. When you’re practicing law, people have a– they have a pain that they recognize and you don’t need to convince them that they have a pain and that it should be fixed. With software, that makes you more efficient, you must educate people that there is another way, that this pain actually can be fixed, and that the thing that I have is the solution you want. And then, you have to convince people that being more efficient is actually a good thing.

I know that most people would say, “Oh, no. Lawyers are ethical. They’d never choose to work slower.” But the fact of the matter is that lawyers do choose to work slower. Efficiency is threatening and it is scary. And when we look at our billing records, and we see that lawyers are billing two to three hours a day, even though they’re working 10, the notion of scraping off six minutes here, 15 minutes there, 30 minutes here is just terrifying. So, educating people and helping them see that they can be more efficient, that they will deliver a better work product to their client, and that they will actually continue to bill the same amount. It’s just that their efforts will be spent on useful things, things that clients want to pay for.

Yes, a client doesn’t want any typo’s in their documents, and they don’t want any errors or long-winded winding sentences, but they don’t want to pay for those things. They want to pay for your analysis. And if you can shift your effort from hunting for commas and capitalization issues to actually analyzing something better, then your clients will be happy.

Jim: Do you think that it’s easier to convince lawyers who are paid on contingency fee or who operate on a flat fee than it is to convince lawyers who operate on a billable hour?

Ivy: Yes. If you’re working on a flat fee or a billable hour-basis, then like the editors I was speaking about before, then your interest’s already aligned with your client and the faster you get something done, the better it is. 

One of the key people who has been vocal about their work on flat fee and contingency work is Patrick Lamb, who’s now with Elevate. He’s a WordRake user. He was talking about how it helped with efficiency all these years ago. I think that, at least to me, that shows me how much it matters and what a difference it makes to have your interests aligned with your clients.

Tyson: So, Ivy, with WordRake, do you have plans of expanding into things like Google Docs or any other sort of softwares or word processing systems?

Ivy: Not at this moment. However, we do keep track of the requests that people make. We work in Microsoft Word now. We also work in Microsoft Outlook. And we are improving our functionality and the things that we check in those realms. However, if people, came and said, you know, buy 500 million licenses, if only you worked in Google Docs, we’d probably listen to that.

Jim: So, what has the response been? What are your struggles in trying to get greater adoption of WordRake? And are there competitors? 

Ivy: So, there are competitors. Most of the time, when people first start to understand what WordRake is, they think, “Aha, I’ve heard of this. Grammarly.” Grammarly is out there and they do a good job, but it is not aimed at sophisticated writers. It is aimed at a lot of people who could not write a grammatically correct English sentence if they spent an hour on it. Grammarly will help those people, so that’s great. But what about people who are already smart, people who can already write well? That’s when you need a more advanced tool and that’s really where WordRake comes in.

The other thing that just general consumer off-the-shelf products will do, that a lot of lawyers don’t think about, is that they will collect and track your usage data. So, anything that you are writing or editing with Grammarly is recorded in Grammarly‘s database. Every document that you see, every keystroke that you type – all of that is recorded. The only way to get rid of it is to delete your Grammarly account. Even then, your documents will remain on their server until they do whatever purge and you don’t know when, where, or if that is going to happen.

Tyson: I think your explanation of the differentiation between you and Grammarly is so spot on because I mean, I’m looking at how WordRake looks. I mean, it is way different. I mean, like you’re talking about like in line. It is really cool. It’s really, really impressive.

Ivy: Thank you.

Tyson: It’s really, really neat.

Like, how long did this take? I mean, it seems like it would be so hard to do. I mean, like, how did you know to set up the systems, and the processes, and all that? I mean, like this is really impressive. Like, how did you do all that?

Ivy: So, I am not the founder of WordRake. Our founder is Gary Kinder. He is an expert legal writer and has taught thousands of lawyers and thousands of writing courses to teach, basically, what you see here in WordRake. So, it was his idea. And he worked with some engineers to develop the algorithms that we use to deliver our suggested edits.

I am now in this world and, as part of my work in strategy and business development, I get to come up with new things. And because I’m familiar with the process of looking at a program and then reverse engineering it and figuring out what’s missing, and what else I can add, I have this unique thing that I bring to the table. I cannot even begin to explain how I wound up there. It was a surprise to me too.

Jim: Tyson and I met because I was teaching a class on Law Practice Management at SLU. In fact, tonight, we’re talking to the successor of that class. So, we’re going to be meeting with law students. I wanted to raise two things. One, there’s a guy named Dennis Kennedy, who I’m sure you’re familiar with who came–

Ivy: Love him. He’s a friend.

Jim: A real good guy. He came to talk to that class and he told this really funny story that I liked. It gets to one of the points that you raised earlier. And that is that Dennis was an estate planning lawyer. He told Tyson and the rest of the class that, in the old days, it took him 20 hours to draft a will and a trust and everything for somebody. And that he was like an early adopter of word processing – so even before computers, word processing which I saw on TV the other day. I don’t remember what show it was. Anyway, he figured out that he was able to get the work time that it took to do a standard will and trust from 20 hours to three hours, and he billed by the hour.

So, what do you say to lawyers who really are having that struggle with flat fee versus billable hour? I mean, I think the billable hour should be cut up. It should be killed off. I don’t think clients like it. I don’t think lawyers like it. Really, the only people that advocate for it, I think, for the most part, are big firms and that’s because they have such big overhead. So, I like your software to the extent that it’s going to help kill off the billable hour, I think, but I’d love to hear your thoughts on that.

And then, I have another question.

Ivy: You know, I’d love to kill off the billable hour, but I doubt that it’s going anywhere. People have been talking about it being dead or its imminent demise for years and it doesn’t seem to be going anywhere. So what I, instead, think about is, “What else could you be doing that would benefit you or benefit your clients if you weren’t wasting the time on those low-value tasks that you can automate?” So, yes, a will might have been a 20-hour project and now it’s three.

Initially you think, well, I’ve lost all of that to bill, if you were billing by the hour, but instead now you can spend more time with your client and say, “What assets are you’re trying to protect? What eventualities are you worried about? Do you have a family medical history that we should consider? What about creating a package of documents that are going to serve your family better?” So maybe you don’t just need a will for your ultimate demise. Maybe you need a living will. Maybe you need to trust it to protect some exotic animal that’s going to outlive you or, perhaps, you need advanced directives because somebody is sick and they might become incapacitated. I mean, in this COVID era, the idea of advanced directives has become all the more important. And if you are not just focusing on getting the document out and doing the bare minimum, then you can actually move to consulting with your clients and solving problems that they weren’t sure they had but, now that you’ve mentioned it, they are so relieved that you saw and you could help them with those very real world problems.

Jim: All right, that’s perfect.

And then, as a follow up to that, tonight, Tyson and I are speaking to third year law students who may or may not go out on their own and, when it comes to technology, I’m wondering what advice you would have for us to share with them tonight when we meet with them.

Ivy: So, if you’re striking out on your own, you need to develop sound technology practices from the very beginning. It’s hard to reorganize and retrofit a dysfunctional process after you’ve already been doing it for a year. So, I would spend some time figuring out what your file naming protocols will be, how you will manage your documents, setting up calendaring, getting your Quick Parts together.

So, say you are licensed to in a state that has a great bank of precedent documents and they show you the templates for, say, collecting a judgment. And those documents are, for the most part, the same. You can use Quick Parts in Microsoft Word and create a template of those documents yourself. You’ll be a lot more effective. You won’t have to worry about forgetting something and committing malpractice. If you do that on the front end, then you can really serve your clients once you get started.

A lot of people jump right in and they try to bring in business as fast as possible when they don’t yet have the resources to serve those clients’ needs effectively. I would say focus on getting those resources together so that you so that you do it right.

The other thing that I would say is calendaring. As much as I’ve just talked about Microsoft Word, calendaring is the number one reason for ethics complaints and malpractice so set it up so that anytime you get an email, from Pacer, it automatically leads to a calendar item on your Outlook calendar. Set it up so that every time that you finish a phone call and you say “log the time for it”, you automatically enter a time on your calendar to follow up with that person.

Get all of those things in place and then go out and get the clients. That way you are doing your best and you’re not committing malpractice.

Tyson: Very good stuff, Ivy. 

All right, we do need to wrap things up. Before I do. I want to remind everyone to go to the Facebook group, get involved there. Actually, my tip’s going to be related to something in the Facebook group that John Fisher shared. And then, if you don’t mind, taking a couple seconds just going and giving us a five-star review, it helps us show the love. We would really, really appreciate it.

Jimmy, what’s your hack of the week?

Jim: I was listening to a recent episode of I Love Marketing as I’m wont to do and they still get together, Dean and Joe, every now and then. One of the guests that they had on was talking about a way to clarify things when you’re giving a talk on YouTube, when you’re making your videos. He came up with this really interesting phrase that I really liked. It’s that when you when you are getting ready to make your point, you use one or two words, “look” or “listen”. 

So, as you’re giving your talk on your YouTube video, you can pause for a second and say, “look”, and that gets the person to pay closer attention to the next thing you’re going to say. So put the important points you want to do there. You do with the word and the pause. So, “look, listen” and then go right into it.

I think one person who does this really well in our group is Joey Vitale. He’s really good at sort of refocusing your attention. I think, thinking about those two phrases, I’m going to try to start using them in my YouTube videos, so I thought I’d pass that along.

Tyson: Yeah, listen, Ivy has a really good tip for us. And so, Ivy, what’s your tip?

Ivy: My tip is to get the book, Thanks for the Feedback: The Science and Art of Receiving Feedback Well. It’s by Sheila Heen and Douglas Stone. For me. I love this because one of the most difficult things, as a young lawyer especially, is listening to feedback and actually changing your behavior so that you can be successful. This book will help with that. I think everyone needs to read it.

Tyson: That’s really, really good.

I actually can’t wait to read that book. You mentioned it before the show started and I’m really interested in that.

Hey, Jimmy, look, I’ve got a tip for you, okay. It’s from our buddy, John Fisher. He shared his intake binder. Now, he shares all of this stuff. He’s like just an open book. I don’t think he calls it an intake binder, but he basically explains to the client what to expect with everything. It’s 100 and like 90 pages or something like that. He shared the PDF in the group.

So, go and take a look at it, if you’re listening to this. And if you’re not in the Facebook group, join the Facebook group because he just– I mean, no one asked him to do it. He just did it and it was awesome. It’s really, really cool. It’s branded. You may have to ask him, you know, who branded it for him. It’s got all of these logos and everything on it. It’s really, really neat.

So, if you haven’t seen it, go and check it out. And you can probably steal some ideas, especially if you do personal injury, you can steal some of his ideas and put them into your own marketing.

So, Ivy, thank you so much for coming on. I got a lot out of it. A lot of technical stuff. A lot of great takeaways in this episode. Thank you so much.

Ivy: Thank you. It’s been an absolute pleasure. I’m so excited that I got to be here. 

Jim: Hey, sis.

Tyson: Awesome.

Ivy: Thanks.

Tyson: Thanks, Ivy. We’ll see ya.


Thanks for listening to The Maximum Lawyer Podcast.

To stay in contact with your hosts and to access more content, go to

Have a great week and catch you next time.

Subscribe for Email Updates