Ivy Grey is an experienced bankruptcy and distressed transactions attorney as well as an entrepreneurial legal tech innovator. She worked on numerous complex major bankruptcy matters prior to her entering the world of legal technology. Ivy created American Legal Style for PerfectIt, which is a proofreading and editing MS Word add-in for lawyers. 

What piqued your interest in legal tech?

My route to legal tech was indirect. Legal tech was not a goal or an interest. Though I now create legal tech, I still practice law and my focus has been on being the best lawyer I can be. That means being effective, efficient, and accurate. And when I moved from a large law firm to a bankruptcy boutique with limited resources—but with bigger cases—it became clear that I would need to find new ways to be a good lawyer. So every time I encountered a new problem or recognized that certain work would be tedious, repetitive, or ripe for human error, I would look for a way to address the problem long term. I felt that if we were going to tout experience, then we needed to be able to draw on it using technology. With limited resources, and with this being my own personal approach, I did not have the option to buy new technology. I had to hack what I had to do the work that I wanted. That meant using the MS Office Suite to its fullest extent, and in creative and unexpected ways. Having grown up in Silicon Valley, and having worked in IT in college, I was pretty good with MS Office Suite, but I needed to be better. And I needed to use my tools for legal-specific functions. So this was my mindset when a friend approached me and asked me to try his proofreading add-in for MS Word. I tried it, I liked it, but I could see that it could be modified to be a better fit for lawyers. That friend was Daniel Heuman, the founder of PerfectIt. When I gave this feedback, Daniel asked me to join him and build the solution that I envisioned.

What is the biggest misconception you think lawyers have about legal tech?

Lawyers seem to believe that legal tech must be expensive, disruptive, and look like something they have yet to imagine. In the tech startup industry, shouting that something is “disruptive” is positive, but, in law, disruption is negative. Lawyers want certainty, predictability, and smooth transitions. Not upheaval. So unsurprisingly, adoption is slower than most law futurists or people in legal tech would like. When that is the outlook, legal tech seems like a huge investment that requires a lot of soul searching before a decision can be made. With these misconceptions, legal tech seems risky and unappealing. It also makes legal tech seem like something that only BigLaw can have. Now that I have been in legal tech for nearly three years, I have seen options that cover the spectrum in terms of cost, disruption, and uniqueness. I’ve found that there are plenty of inexpensive, small legal tech options for boutique firms like mine. I can buy an affordable license of a plug-and-play option that integrates seamlessly with the technology that I’m already using. And when the licenses are under $150, I can buy several options that meet my needs. With SaaS subscriptions, I can also change my technology choices easily, and without major financial loss.

Tell me a little about your role at PerfectIt.

I am director for the legal sector and the creator of American Legal Style for PerfectIt, which is a proofreading and editing MS Word add-in for lawyers. (I spend at least half of my time working on PerfectIt and the other half of my time practicing law.) By creating American Legal Style, I adapted an existing program to work better in the legal context. I began by learning to understand how PerfectIt works and to use its functionality to meet my goals. I also learned to manipulate its rules to increase functionality without requiring new development. Then I scoured the leading legal writing and style guides and dictionaries to determine what went into American Legal Style. At first, I wanted to include every potential rule and error. It was exciting to make these decisions! But Daniel warned me against doing too much. I needed to create something that would be more beneficial but less annoying than a sticky note on my computer monitor and that would allow lawyers to write in their own way. This approach had made PerfectIt popular with thousands of editors all over the world and I needed to stick to it. So I weighed the value of each correction and insight, the level of certainty that we were helpfully flagging a real error, and the user experience. I trimmed down the corrections and we did extensive testing to tighten it up. When we launched in 2015, we had 5,000 legal-specific corrections. In 2016, I added 8,000 corrections bringing it to 13,000. And now I’m working on an update that will add thousands of corrections based upon my continued work experience and feedback from our users. In the three years that I’ve been working on PerfectIt, my role has expanded. I’m no longer focused on just American Legal Style; we’re upgrading and expanding, and I’m playing a role in moving the general use program forward and spec’ing out future versions. I’m also responsible for developing all of our legal-specific content and strategy and working to collect and integrate feedback from our legal users.

How can folks learn more about legal tech?

If you’re looking to have sustained involvement in legal tech, then I recommend Twitter. Twitter is an incredible resource for learning about legal tech. It’s free, it’s timely, and the community is active and knowledgeable. Some great discussions happen on Twitter that likely wouldn’t happen were you listening to a speech since speeches are one directional and Twitter is multi-directional. Twitter also gives knowledgeable people a voice who may otherwise get ignored. Via Twitter, I hear from lawyers using legal tech products in their law practice, judges, professors, staff, students, creators, and futurists. Better still, I hear from more women, minorities, and other diverse under-represented groups than I would at a conference. And if you follow a broad swath of people tweeting about legal tech, you’re likely to see your way through the hype. Besides Twitter, I would suggest subscribing to three or four blogs (like LawSites by Bob Ambrogi) and one or two podcasts (like New Solo by Adriana Linares). The blogs and podcasts will expose you to new technology, topics, and ideas. Finally, I would pick one conference to attend where you can demo a lot of products and hear from many people. I think it’s important to attend a conference where you will get to discover and try things on your own—your entire experience should not be solely digesting things that other people recommended to you. If you’re looking to spend a single day investigating legal tech, but not immersing yourself in the community, I would look for long-form content like white papers, buyer’s guides, and industry analysis.

What has been the most important lesson that you have learned in your legal tech journey thus far?

Just like in law, trust is everything. Trust is difficult to earn but easy to lose. This is a community so it’s important to hold yourself to high standards to earn and maintain your place in it. Part of that means admitting mistakes or weakness and asking for help. It also means being willing to give help to those who need it and praise to those who deserve it. We must both care and contribute like this is a community. Pettiness and hubris will break down trust and impede progress. We’re all in this together trying to make law and its delivery better—so we must act like it.