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Show Notes

Debbie talks with legal tech trailblazer Stephanie Wilkins as she shares her insights on the transformative impact of artificial intelligence in the legal landscape. From navigating challenges to embracing innovation, they delve into the intricacies of legal technology, emphasizing the vital role of trust, collaboration, and overcoming imposter syndrome in fostering a dynamic and resilient legal profession. Join us as they unveil a compelling vision of the future, where innovation and human expertise converge to shape the next frontier of legal practice.

Links from the episode:  

Legal Tech News  

Find Stephanie on LinkedIn 

Powerful Leaders, No Apologies Podcast Merch

[08:27] The Growing Importance of Legal Tech

[17:23] Legal Week and Future Plans

[25:14] Leadership Superpower: Trust

  • Transcript

    Debbie Foster (00:03): 

    Welcome to the Powerful Leaders. No apologies podcast, a show about women who are ready to own their power and change the world. My name is Debbie Foster. 


    Beth Thompson (00:12): 

    And I’m Beth Thompson. Our guests are fierce and fabulous women who are making a difference in their personal and professional communities. Are you ready to be inspired? If so, stay tuned and also check out our website at affinityconsulting.com slash powerful leaders. Here’s the show. 


    Debbie Foster (00:34): 

    Welcome to another episode of Powerful Leaders. No apologies. I am flying solo today because Beth Thompson is out and I really miss her because I love having a co-host to banter with. But I’m super excited about our guest today. I have Stephanie Wilkins with me today, and I met Stephanie the first time at the Carrot Legal Conference in San Diego a few months ago. She did a keynote presentation there. I’m also a little bit of a follower stalker of the legal journalists round table that happens every Friday at three o’clock. We’re going to talk a little bit more about that, and I’ve loved hearing Stephanie’s voice on that round table. And Stephanie’s got an interesting journey in how she got to being the editor in chief of Legal Tech News for a LM. And Stephanie, welcome. I’m super excited to have you here today. 


    Stephanie Wilkins (01:32): 

    Thanks for having me. I’m excited to be here. 


    Debbie Foster (01:34): 

    I would love for you to tell us a little bit about your story. You’re our first journalist. I’m pretty sure you’re our first journalist. I hope I’m not saying that wrong, so I apologize if there was a journalist already on, but I’d love to hear a little bit about your story about how you got to a LM. 


    Stephanie Wilkins (01:49): 

    Sure. It’s probably not your typical journalist story, so if you have another, it will be different. I went to law school. I was a practicing lawyer for about eight to 10 years. I always liked the writing part of it, but this part is a common story. I just got burned out. I didn’t really have the passion for it. It wasn’t for me and I didn’t want to go the partnership route and be in it for the rest of my life. So I quit and I got into freelance writing and photography. At the time, I thought I was going to have nothing to do with legal. I just needed a break. I thought I would never be back in it. But sure enough, over time I did, because when you’re a freelancer, you don’t really have the luxury of turning down a lot of work. And I still knew a ton of people in legal, so they started offering me writing jobs. 



    I took them, a lot of it was with Above the Law. I’ve known those people for a very long time before any of us were at Above the law. And then from there, that connected me with different legal marketers and different legal tech companies who I started writing for directly. I was still doing the photography, but then during Covid when everyone was locked down at home, there wasn’t a lot of photography going on. So I doubled down on all the writing, a lot of it in the legal tech space and place right time, a LM. The job opened up at Legal Tech News and I applied for it. At first, I actually wasn’t really sure about applying for it because I technically had never been a quote journalist before, even though I’d been writing tons of content for publications, a lot of it, not in my own name, but I did have the legal background and the legal tech background, which is very specific in there, even though there are a lot of people out there that have that not really in the journalism writing space as much. And I applied and it went pretty quickly. And here we are. That was 15 months ago. 


    Debbie Foster (03:35): 

    Tell me a little bit about a LM and the role that they play in the legal industry and kind of your piece of that with Legal tech news. Tell me about how that works. 


    Stephanie Wilkins (03:47): 

    Sure. A LM is probably most known for the American lawyer. That’s their flagship publication. May I remember getting it in my inbox when I was at Big Law, and they have a number of different publications that try to touch on most aspects of the legal ecosystem. There’s an in-house publication and there’s different regional publications. We are the legal tech focused publication, legal tech news, I guess it used to be called Law Technology News, legal Tech News. So we focus on everything that touches on tech. Of course, there is some crossover in stories, so the different publications will pick up each other’s stories. So if we’re writing a legal tech story that’s focused on big law, the American lawyer will probably pick it up. Or if it’s focused on the in-house, corporate counsel will pick it up and vice versa. If they write a story that touches on legal tech, and obviously we try to coordinate so we’re not writing the same stories, which usually is not a problem. But now that AI is so popular, more people are interested in our space, I would say, than they have been in the past. But we all work together pretty well, and we all communicate on a regular basis about what we’re writing. So that keeps things going pretty smoothly. 


    Debbie Foster (04:55): 

    And tell me about the technology. Were you just always really interested in technology as a lawyer? How did that part of it get woven in? 


    Stephanie Wilkins (05:05): 

    Yeah, that’s funny. I mean, I always sort of make this joke that I didn’t realize I was particularly tech savvy because it’s not hard to be the most tech savvy in big law. But I did true thinking back, even as a kid though, I was mean, my dad was a CIO somewhere, so we had a computer really early. Just things like that that just in retrospect, I guess I was always fairly into technology. And as I worked at the big firm, primarily a lot of legal tech then mostly consisted of legal research or e-discovery. And then when I went to a smaller office before I ultimately quit, I, our ID department was one person and she would take me to meetings with vendors and things, which at the time was like, this is a little odd, but I guess I understood it. And I mean, that makes a lot of sense. And so when above the law just needed someone to write Migo Tech product reviews and things like that, they basically just offered it as like, oh, give it a shot. And I just really took to it and obviously they must’ve thought I could do it. Sure, yeah. But it was then, it was over a decade, I sort of became a specialist in the area without even realizing it. I looked back suddenly and was like, oh, I am a legal tech expert of the sort. 


    Debbie Foster (06:20): 

    I love that. I love that. And I had some serious FOMO this week, watching all of you at TLTF. Tell me about it. How was it? I’d love to hear your three minute recap. 


    Stephanie Wilkins (06:34): 

    Yeah, it was great. I need to be working on writing that recap right now. 



    We’ll get to that next week. It’s been a busy week, but no, the TLTF summit is great. Last year was the first year I wasn’t at it, so I can’t compare. I’m told this one was probably twice the size of last year, but it’s 500 people. It’s a very curated list of investors in the space in-house counsel, some people from law firms who are looking to implement technology themselves. And then just a bunch of providers, a lot of them very small, still looking for funding, which is, I mean, that’s the idea of the conference is to connect people who need money with people who have money to spend. But it’s done in a very non salesy or marketing way. Everybody there was a CIO or a CEO. Nobody was there from sales or marketing or whatever. So there was sort of a pitch competition where people just explained what their tools do, but there weren’t marketing pitches. 



    There were no vendor booths, there was nothing like that. It was just a lot of really good conversations. And then a handful of panels, which were some really great speakers. I thought I was sort of past learning new things at panels, and I’m wrong, which is good. It’s good to have different voices and different conversations. I’m glad to see the conversation, especially around AI is shifting and evolving. So yeah, it was just a really good day. They planned. It was very well organized. And yeah, I would go again. It’s definitely, there’s a lot of interest in it. It’s sort of the new hot new conference. 


    Debbie Foster (08:08): 

    It really is. And I mean, I was so jealous with all of my connections that were there, and I just live in West Palm Beach, so I could have been there except I really needed a week at my desk doing work. I don’t get to do that very often. I’m sure you understand that. But yeah, no, it looked really cool. And I think that just in the last five years, the amount of investment money that is getting poured into legal tech companies is, for me, it’s just mind blowing. So I love that there’s a conference that’s focused on connecting new technology and existing technology with people who are ready to invest in it and just make it better. Because as you said at the beginning, it’s not hard to be the most tech savvy person in a big law firm. And I remember before AI even was this household name probably three years ago, someone asked me on a panel if I thought AI was going to change how people practice law. 



    And I might even still have the same answer today, but I was like, I don’t know, maybe, but I think probably not. And the person who asked me that said, what do you think is going to revolutionize how the practice of law works? And I said, when Lawyers learn how to use Microsoft Word and Outlook in their PDF program, that would revolutionize how law is practiced in a law firm if Lawyers really doubled down on learning the technology that they use every single day. And I still think that that’s true. And I think there’s so much information out there, and there’s so many publications and websites and above the law and attorney at work and Lawyers, which is one of our companies that are really trying to educate Lawyers on the tech that is available to help them better serve their clients, that it’s just really overwhelming. 


    Stephanie Wilkins (10:00): 

    It really is. And education and training is key here. And I do feel like, I wrote an article about this recently about how legal seems to be an education mode more so than they have been in a long time. And I mean, that is driven by ai and there’s a sense of collaboration going on. People who are usually competitors are getting in a room and talking about how we’re going to succeed with this. Of course, that needs to trickle down, like you were saying to the average users. It’s really interesting to me because one of the big impacts of this gen AI boom that I don’t think people are talking about as much is that it’s raised interest in other technology too. I mean things that people are probably behind on for a while. I mean, it became, oh, how do we put AI on this? And sometimes you don’t even need AI on this. You had this tool all along, you just didn’t bother to learn it or nobody told you about it. And so now it’s just sort of retroactively getting this tech renaissance that is, in my opinion, long overdue. 


    Debbie Foster (10:59): 

    That’s such a great point. I heard on a podcast that I was listening to the other day, actually, I was driving, I drove down and had dinner with some people who were at the conference on Wednesday, and I heard something on a podcast that the guy said, if you’re standing still every day, you’re getting behind every day. And I thought that was so applicable to where we are right now. And I think your point about the tool isn’t always ai, the tool might be something that you already own. So such a great point. So Stephanie, tell me this. Who is inspiring you? How do you stay motivated? Who are your go-to podcasts, authors, whatever that looks like? 


    Stephanie Wilkins (11:40): 

    It’s funny. In the podcast realm, I tend to do things completely opposite of what I’m doing. Just more turn my brain off. I’m very much a true crime junkie, I will admit it. But think honestly, and this is part of why I love the conference this week so much, is that who really inspires me are these startups that are coming up with these amazing ideas, things that, and again, they don’t have to be the flashiest or the biggest or the first, just people looking to solve a real problem. And whenever I see a tool that would’ve made my life so drastically different when I was practicing, that’s what I love on LTN, I started a startup spotlight, which profiles different startups. They fill out a form and we talk to them. And just because I love shedding light on that part of the industry, it’s not always the biggest players, which we know obviously still write about and they matter and they’re going to have a lot of influence. 



    But it’s these little companies that I love them, and a lot of them, more and more of them are women led too. And I just love that there’s a lot of, both legal and tech have long had issues with diversity. That’s no secret When you combine the two of them, it doesn’t necessarily make it better, it just compounds it. But there are a lot of fresh diverse voices out there and just meeting them and trying to give them some of the spotlight, I love that. That’s what really, those are the people that really inspire me particularly to do my job, but also to just try to put good things out into the world. 


    Debbie Foster (13:11): 

    Yeah, that’s one of the people that I saw that was leading a panel discussion at TLTF is Gabby Ur. She was one of the founders of ITimeKeep, and she was always someone who was such an inspiration to me. And so when I saw the picture of her on the stage, I was like, Gabby was there too. Added to my fomo. I love the women in tech and the cool ideas that are being generated just across the board at these tools that can just, they’re not revolutionary, but they are at the same time because they take something that is time consuming or is just a rote task that can just be made so much simpler. 


    Stephanie Wilkins (13:58): 

    And I don’t think revolutionary needs to be big. I think people equate it with this drastic seed change. It can be one small part of that drastic seed change. I mean, we saw it a lot as AI blew up. We saw it a lot in the pr and there’s good PR people we’ve worked with for a long time. And then suddenly there were all these new PR people, some of it, half of it written by Chatt BT, where it would always just be this is the first, this is the biggest, this is the whatever. I’m like, I mean, you don’t even need to be first sometimes first is bad, but just tell me what you do and what you’re solving. And it’s these little things and I think it’s great. And they all add up to be that change that I think is going to improve the legal profession. And they had a nice women’s lunch. It was before the conference officially kicked off. It was that first afternoon, morning, afternoon. And it was just great to see a bunch of women in the same room talking. They did this book exchange thing where people could write down a book they found inspiring, and then they wrapped them all up and put them at tables randomly, and they put a sticker of who had suggested it so you could talk to people. And it was a lot of interesting books and it was just great conversations to have. 


    Debbie Foster (15:09): 

    I love that book exchange. That’s such a great idea. I love that. So in your journey through being a lawyer and being a journalist and applying for a job that you were like, I don’t know, maybe, and now where you’ve landed, I’m sure you face some obstacles and challenges along the way. And one of the things that we are really passionate about with this podcast is hearing people’s stories about how they got where they got and how they overcame some of the obstacles that were presented. So I’d love to hear anything that you would like to share about that. 


    Stephanie Wilkins (15:46): 

    Yeah, I think when you do sort of the weird journey I did to get here where you start a bunch of different freelance jobs and keep trying new things, and this, technically it was my first journalism job and I came in as editor in chief. I mean, there’s definitely imposter syndrome that pops up along the way. I think being a lawyer is good for teaching you how to fake it till you make it. Hopefully I wasn’t faking it too much, but there are definitely times you just have to trust yourself, even if you’re questioning, am I doing this right at all? And just going ahead and asking for help too, which I mean, thankfully my editor, Gina Paella is so willing to answer any questions I have. She’s so supportive. And everyone at a LM has been super supportive, so that makes it a lot easier. So you don’t feel stupid asking that question. But I mean, I think it comes up a lot in conversations, the imposter syndrome thing. I think that would be it. That would be the biggest. And then always, especially in the freelance world, just feeling uncertain. You’re always just like, is the next paycheck going to come in? What if this steady client disappears? 


    Debbie Foster (16:54): 

    Right. So tell me about what you’ll be doing January 29th to February 1st, 2024, and what will your week look like during legal week? 


    Stephanie Wilkins (17:07): 

    Yeah, it’s a little chaotic. So last year was my first legal week in this role, and I came in midstream at least this year. I’ve had the whole year of planning. And there are definitely some lessons I learned about how I managed my time last year that I will not be doing the same again. But it’s an incredibly busy week for us. My whole team, the whole legal tech news team comes in. We do a lot of coverage of it, but pretty much starting from Monday, Monday night is the awards, the legal tech leaders in law. I know how to say that 



    The awards we give out at Legal Week are Monday night. And so I host that whole show. So that’s a big lift from the very beginning. And then there’s just lots of panels, lots of meetings. I actually won’t even know until probably a week or two before Legal week exactly which panels I get slotted into because I mean, I know I’ll be on the future state of the industry. I did that last year, and I know I am on one about tech competence. I’m actually very excited about that one. But there might be other ones where there’s a moderator slot, they need to fill me in, and then otherwise, it’s just meeting so many people who reach out and want to meet with us. And I think that was where I sort of failed myself last year with overbooking and allowing too many people to slot in because I didn’t give myself any breaks. And it’s a long exhausting, it’s a marathon. You have to stick with it. I mean, I do enjoy meeting people, but even with that, there were people I didn’t even have a chance to see, and I didn’t go to any panels that I wasn’t on, and everyone was at parties, but I’m like, I need sleep. I have to be on stage in the morning. And so it’s fun. It’s great. I love seeing my team too, but it is, I won’t lie. It is a lot of work 


    Debbie Foster (18:50): 

    And it’s a great event. I mean, I’ve been going to Legal Week, formerly known as Legal Tech, New York. Well, I’ve been going to Legal Tech for so long that at the very beginning we went to Legal Tech West out in California and back in the day when there were many, and now there’s one, and it’s a big deal. And I don’t know that New York Hilton feels a little bit like home. Every time I walk in, I’m like, oh yeah, I love this place. I’ve been here a million times. So it’s a great event. And for anyone who is looking for an opportunity to just see everything that’s going on in legal Tech, this is the place to be. And speaking of everything that’s going on, most of everything that’s going on is going to be all around ai. Oh 


    Stephanie Wilkins (19:39): 



    Debbie Foster (19:39): 

    What’s your take? What’s your take on ai? We talked about it a little bit, but as you think about preparing for this big week where there’s going to be what feels like a million vendors and a million attendees, and everybody wants to know what’s next, what’s the future? What’s your take on ai? 


    Stephanie Wilkins (19:57): 

    Yeah, I mean, it is the future. I think it maybe not in every way it was initially hyped. It takes a lot of thought and careful implementation and strategic use cases for it. And I think that’s the point we’re at now where people are really focusing on what are the actual use cases here? Great. I just don’t want to hear it’s magic, just tell me what it actually does. But yeah, so I mean, last year we had an AI workshop on the first day, because I think Legal Week was really the first big conference that happened after AI hit the scene so quickly put together a workshop, and it was standing room only. People were literally almost fighting to get into the room. They had to expand it into a second room. And that was more of still at the intro stage. So this year we are going to have a workshop again, but it won’t be the AI 1 0 1. 



    It’ll be a lot more practical. And we of course added some tracks, but then there are sponsored tracks, and they could pretty much talk about whatever they want to. And almost everyone’s talking about ai, and I mean, it is the future, but I do think eventually, I don’t know if it’ll be legal week 2025 or where it won’t be so much the topic. It will just be so ingrained in everything that it’s just table stakes at that point. People will have figured out how to use it. I mean, the prices will come down a little bit. I think it’ll be less about, oh, we’re using AI because people will be expected to use ai. So I’m curious to see how that shift happens. But it’s here. It’s not going away. It really is. People need to get on board and not everyone needs to actually be building their own tools or anything. I’m certainly not doing that, but it’s here. I mean, there’s no avoiding it. Anyone who’s splitting their head in the sand and refusing to innovate, it’s going to catch up with them. This is evolving so much more quickly than other technologies in the past. So I understand maybe not wanting to be the first mover, but there’s going to be a very short window between the first mover and the last mover, and you don’t want to be that. 


    Debbie Foster (21:55): 

    I agree. And I think that we could probably predict that just like we used to have to say cloud when it was cloud and not say cloud when it wasn’t cloud. And now you don’t have to say cloud at all because it better be cloud kind of thing. It’s going to be something similar to that. Right? Of course. Of course. It’s using ai. Why wouldn’t it use ai? Right? 


    Stephanie Wilkins (22:18): 

    Yeah, yeah, that’s a great analogy. Yeah. 


    Debbie Foster (22:21): 

    Yeah, super interesting 


    Stephanie Wilkins (22:23): 

    Because already AI in things and people never even really thought about it. Like you were saying earlier, you were talking about ai. I found an article I wrote for somebody, I think it was 2016, I totally forgot I had written this article, but it was like, can AI be used in legal and what can it be used for? And it was exactly the same sort of areas we’re talking about. Now. AI was not the powerhouse we have now. It was the earlier iteration of it. But there’s plenty of ai, and it doesn’t have to be the generative ai. There’s AI in almost everything we do in our lives to some degree already. So people who say they’re not using it, you might not even know you’re using it. 


    Debbie Foster (23:00): 

    Well, I mean, I remember one of the first examples at an AI thing that I went to, I don’t even, this feels like it was five years ago, was people who watched this also watched that Netflix suggestions. And when Alexa first came out, and some of what Amazon is doing, it really has been a part of our lives for a long time. But it’s just nothing like the splash that chat GPT made and the awareness around how smart generative AI can be, I think took a lot of people by surprise. 


    Stephanie Wilkins (23:40): 

    Yeah. Well, because it’s producing content now, before it was just always quietly in the background and we just took it for granted. And now it’s, I guess noisy if that’s the opposite of quietly in the background. It’s creating text, it’s creating art, it’s creating music, and it’s everywhere. And you really can’t avoid it. And it does. I mean, everyone, myself included was blown away by chat GPT because it did feel like magic. It felt sentient in a way it hadn’t before. So for sure, the power is there and there are a lot of incredibly intelligent people figuring out how to harness it. And I am excited to see what comes. 


    Debbie Foster (24:17): 

    Yeah, I am too. Okay. So we are at the place where we ask this question of all of our guests on our podcast. What is your leadership superpower? 


    Stephanie Wilkins (24:29): 

    I thought a lot about this actually. I did. I think it’s trust actually. I have great reporters whenever, if I had great associates for me or whatever, if they have proven themselves and they’re good. And right now my team is fantastic. So really I just pretty much trust them. I trust them to do good work. I trust them to check in with me when they have questions and feel safe doing it. And it allows them to experiment and enjoy their job more. So I’m definitely not a micromanager. I am there to look everything over. I’m there to help as much as I can and work together and collaborate. But I pretty much just trust them to be the really intelligent adults, reporters that they are. I don’t need to be babysitting anybody. And I think they appreciate that. And a lot of that is when you work. I think it’s a reflection of leaders I had in the past where there’s tons of micromanaging in big law. There’s tons of, I’m like, I am an adult with a law degree. How do you not trust me to just do this without checking in on me every five seconds or just rewriting it for the sake of rewriting it? And that drove me crazy. So I think I just evolved into the very opposite kind of leader. 


    Debbie Foster (25:40): 

    I love that. And trust is one of my favorite things to talk about when I’m talking to a law firm about solving problems. I always start with, do you trust each other? We’re about to enter into a really hard conversation. Do you all trust each other? Do you have each other’s backs? Can you talk about hard things? Can you trust that everyone has the best interest of the firm? First and foremost, I think trust is such an important thing for a leader, trusting your team and being trustworthy, which is part of how that really all starts is when our teams can count on us and we can count on them, the magic really happens. 


    Stephanie Wilkins (26:19): 

    No, I totally agree. I mean, you should be able to work with your team. It shouldn’t just be a formality. You should actually be that well-oiled machine, and you can’t do that without trust. 


    Debbie Foster (26:31): 

    And when you struggle with it, it’s what are the trust building activities and what are the trust busting activities? And you start to talk about how do we build trust? It’s relationships. It’s talking about how things are going. It’s asking me for help when you have a problem. Those are the kinds of things that really build that trust. And it goes a long way. 


    Stephanie Wilkins (26:54): 

    And being honest and upfront about expectations too. I don’t want fake deadlines. I don’t want any of that. This is what the job is. This is what we expect you to do. This is the level we expect and this is what you should hold me accountable for as your leader. 


    Debbie Foster (27:09): 

    Yeah. So Stephanie, as we wrap this up, tell us what should people be subscribing to when it comes to the work that you’re doing? How do they read your work? They can follow you on LinkedIn and we’ll have all your contact info in the show notes, but what should they be subscribing to? 


    Stephanie Wilkins (27:28): 

    Yeah, it’s Legal Tech News. So it’s law.com/legal tech news. It’s an email registration. It’s not a paywall, so everyone that’s a common misperception. So you just have to give an email registration to be able to access it. But we don’t spam you with emails unless you sign up for newsletters or a lot of them. People do like getting them, but no one forces you to get them. But yeah, we are just trying to stay on top of everything. Legal tech, it is a lot of ai, but it’s not only ai, it’s we so many good stories coming in, people coming to us with their product announcements and fundraisings and just, we do bigger enterprise pieces too, looking at, that’s why I like going to conferences like the one this week where I get the big questions people are asking, and then we try to dig into that with sources. So subscribe to Legal Tech News. There’s a way to contact us through that. We always love ideas too, like good and bad. We like feedback of what are you seeing out there? Why is nobody writing about this or that? And we’ll try to write about it. 


    Debbie Foster (28:27): 

    Excellent. So we will include that in the show notes. We’ll also include the website for Legal Week New York. If you’re looking for something to do January 29th through February 1st, we would love to see you there. And thank you so much for being our guest. 


    Stephanie Wilkins (28:40): 

    Yeah, thank you for having me. 


    Beth Thompson (28:44): 

    And that’s a wrap. Thanks for listening to Powerful Leaders. No apologies. Be sure and subscribe to our show and help us spread the word by sharing our show with your network. 


    Debbie Foster (28:55): 

    And check out our show notes at affinityconsulting.com slash powerful leaders for resources and ways to connect with us. See you next time.