On this week’s episode of Lawline's Lawyers Who Lead podcast, Sigalle interviews Keith Lee, Founder of LawyersSmack and Chief Marketing Officer at Case Status. Keith discusses how he focuses on Edge Knowledge and how this informs how he approaches fulfilling the legal industry's needs around community and case management. Listen to the full interview or read highlights of the interview below! Transcribed answers were edited for readability.
Interview with Keith Lee
On a Piece of Gratitude
An Aligned Executive Team Meeting
If I'm gonna say I was grateful for something that happened today, our executive team met, our executive team weekly meetings happen on Thursday mornings, but, um, we're just in a good groove and everybody was having, you know, you've been an executive obviously at Lawline for a long time. And sometimes you have good exec team meetings and sometimes you have bad exec team meetings. And when you have a good one and everyone's like on the same page and on the same wavelength and business is doing good, it's just a good feeling. Everybody's pointed in the same direction. And I had one of those meetings today. So that's what I'm probably grateful for so far.
On Running a Successful Team Meeting
Patience, Assume Good Intentions, and Always Ask Yourself “Why Am I Talking?”
Certainly patience is the number one thing. I always try to give everyone the benefit of the doubt and I think we have that really well on our team. Like assume good intentions. Even if you're butting heads on an issue, like pause. Be patient. Always like the acronym, wait, like W-A-I-T, which is, why am I talking? So I use that a lot. I'm like, wait, why am I talking? I always feel that serves me really well. Maybe that's going back into being a lawyer and like thinking about being in a depo and you get trained really well to ask questions and people answer, and then you just wait and let it be awkward because people tend to fill the silence. So even in a team environment, being mindful of, you know, let this other person talk. Let them keep talking, let them talk it out. And that can usually lead to a lot of things. Because hopefully they'll get to the core issue of what they're about. And then you can make progress.
On the Catalyst for His Legal Blog Associate's Mind
Reading Other Bloggers, Inspired by Ari Kaplan and His Book, and a lot of Consistent Writing
I think there's probably a couple things. One, you know, when I was graduating law school, which now seems like an awkwardly long time ago. Mentally, it feels like yesterday, but when I say it aloud to people and you're around like new lawyers, they're like, Ooh, that was a while ago. I was like, wait a minute, what? Um, but when I did, you know, blogs were very much still like really big in a way that they've sort of been eaten by social media in a way. And it's not that there aren't blogs around, but they've had their heyday and it's in the past. And so I was in law school and I was looking online. And I was like, oh man, there's all these really cool lawyers out there. And they've got all these websites and they're talking about their practices and what they do.
It was really exciting. I was like, wow. And I started trying to engage as a law student and that can be good or bad as a law student trying to engage with lawyers, you just gotta be very carefully navigated. But I did, I started doing it. And that finally inspired me to start my own website. Also at the same time, I'd be remiss to not give credit. I also read, you know, Ari Kaplan.
Ari's so great. At the same time, Ari had a book just out called The Opportunity Maker and it was all about don't wait for opportunities. Make opportunities happen in your life. And I remember being in law school, looking at blogs, having read Ari's book, and now Ari's like a friend and I was like, man, I just should just do this.
Like I should just, so I started Associate's Mind, which is my blog that I started like a dozen years ago. And I was probably in the right place, the right time. I think I was consistent. There were a lot of people who started stuff back then, but they all did it for a few months, then stopped. And I just kept plugging away and, yeah, that desire to, to join that there was a burgeoning, pre-LawTwitter, social media, everything else, the original sort of core social media for lawyers was this network of legal bloggers. That was my initial foray into that for the legal industry.
On the Theme of Associate’s Mind
Japanese Shoshin, Experience Transitioning from Student to Lawyer, and Being Vulnerable About the Journey
So Associate's Mind is a play on the Japanese Shoshin beginner's mind, right? And that's the whole phrase of that is you should have a beginner's mind for your whole life because in an expert's mind, the ways forward are small. But as a beginner, because you don't know better, you think there's lots of ways forward. So, it's a play on that to be like, oh, as an associate, I need to have a mind that's open to new ideas and trying new things.
And so a lot of the blogs back then you get people who were criminal defense lawyers writing about criminal defense or an IP lawyer writing about trademark stuff. I was in law school. I couldn't write about a practice area that would've been so fake that everyone would've read through it. So I really focused on, hey, I'll just be transparent and authentic. I'm a new lawyer. I'm trying to figure this out. What does it mean to be a good lawyer? What does it mean to build relationships? What does it mean to be a better writer? What does it mean to be a better communicator?
And it was really all the process of like, how do I want to grow into this role as an attorney? I've never been an attorney in my life. I'm going through this period to get me ready for it, which we all know going to law school actually doesn't get you ready to be a lawyer. That's the biggest lie. And yeah, so I was just like, here I am warts and all. Here's what I got and I'm trying to figure this out and I think that's what resonated with people. That's why the ABA came to me and asked me to write the book for them about transitioning from law school to being a lawyer. Cause I wasn't pulling punches. I was like, wow, this is crazy. I don't know what I'm doing. And I'm just trying to figure it out, which you know, we all are. I just, I was more, forthright about it, I guess, than most people.
On Being a Lawyer and Being Vulnerable Online
You Have to Be Okay With Not Being Everyone’s Cup of Tea
Yeah, there's a fine line to walk there about what's too much cause yeah, certainly being a lawyer, being confident is a big part of the job. The clients need to believe that you can do what you can do. They wanna hire people who are competent in their jobs. And so, you know, there's concern. If you're too vulnerable, too open, you're exposing yourself in a way that clients and other lawyers might be like, eh, I don't, I don't know about that. You know, that's too much.
There's no magical answer. It's the typical law school answer. It depends. It was very situational. I'm inclined to just be a very open person. I'm just very take it or leave it. I was fortunate through a variety of experiences in my life that I discovered pretty early on it's exhausting to constantly like to shift and be.
We all wear masks in our life. There's a mask you put on for your family. There's a mask you put on at work. There's a mask you put on with old friends, there's a mask you put on with new friends. Maybe who you are underneath stays the same, but you show different parts of yourself to different groups of people. That's very situational. Look, you're never getting away from that, but I tried to be me as much as I can in all situations, just because frankly it's easier.
You know, and maybe it does alienate some people, you know, I'm not everybody's cup of tea. I'm not gonna please everybody. I'm probably a little rough around the edges for some folks, but c'est la vie. And there's plenty of people in the world to be friends with. So I'm good on that front.
On Meeting, Connecting, and Interacting with Others
Assess Whether He Gets Energy, Maintains Energy, or Loses Energy
Hmm, well, in my experience, when I interact with people, after I leave them, I fall into three categories. Either I feel like a higher energy, like, oh, engaging with that person left me with a better feeling than I actually even started, which is pretty rare. But you know, you get it. Then more often than not there's a neutral, which is fine. You interact with people and that's day to day.
And then there's a like, oh, being around that person was a lot of effort for me to interact with that person. And, um, I wanna be in that number one category. So if I'm engaging with people, I always wanna try and leave that sort of like positive energy impression because I know I find that invigorating. So that's probably part one. Part two is I'm a big believer, and there's a lot of different terms for it, the one I've just landed on is trust equity. Just like you buy a house, you build up equity in the home, and eventually you can take some of the money out to use different things. I believe in relationships there's such a thing as trust equity. Particularly when you meet someone new and it's a kind of early stages of relationship, you've really gotta invest in that trust equity. You've gotta give, give, give, give it's the Vaynerchuk, jab, jab, jab hook type of situation. It's like, you've got to invest first. You've gotta show that you are going to be a good actor in the relationship. Hey, I'm gonna give a lot as I interact with you. And not because I'm like, Ooh, I know later I'm gonna take something out of it, but it's just like, Hey, I'm here to give. I'm not that category three person who's gonna suck energy away from you. I wanna be a category one energy giving person to other people.
On the Journey to Creating LawyerSmack
Missed the Camaraderie of Other Lawyers
Yeah, so, I was practicing at a couple different firms, one right out the gate where I did insurance defense. Love those guys that I'd worked with, don't care for the practice area. It's not great. Mostly just the billing practices and insurance companies. It's such a nightmare. It was rough. Then, uh, my own practice with a couple guys I went to law school with. Like I mentioned, I wrote a book for the ABA during that time. Started writing for Above the Law back when David and Ellie were still there. And I was doing that for a while.
And then I stopped writing for Above the Law, and blogs had faded and receded into the background and social was this thing. And I started doing some consulting work actually to legal tech companies on how to market to the industry.
So I was practicing law, doing some consulting work, but one thing I realized is, you know, social media was maybe not the authenticity level of vulnerability you're talking about, which is a pretty recent thing. So we're talking about four or five years ago. And I think LawyerSmack might be four or five years old.
I'd missed that camaraderie from the earlier blogs era had not actually translated well to social media. Because a lot of people on social media present very farcical, curated versions of themselves, or they're just anonymous, you know? And they're like, I'm LawDude420 and let me tell you about rules of civil procedure and it's like LawDude420. I have no idea who you actually are like, not if he's actually an attorney or, or even if he is an attorney, he might be some transactional guy and he might not know a damn thing about the rules of civil procedure.
So I kind of looked around and, uh, there was this new thing called Slack, which was new and everyone was like, man, this thing Slack is gonna take over the world. I looked at it for a little bit, then I just kind of decided. I was like, you know what, all right, I'm gonna start a community. I knew what I wanted. I was looking for a place for lawyers to come that was private, not public. That's again, another problem with social media. It's like here, everybody can see all our conversations. And lawyers want to have private conversations with other lawyers because they wanna talk shop on some level and they're never gonna do that publicly. They're never gonna do that publicly.
So creating a space for that and putting people into, you know, real name, real picture, gotta prove you're a lawyer. There were all these requirements and, uh, and initially it was free, but then eventually it became a paid community, just like any other bar association. And it's like the more barriers I put in the way, the better the community got. Right? Filtering out the people who weren't willing to commit to, you know, being who they really were. Put some skin in the game, some nominal fee realistically, but put some skin in the game. That, all right, I'm gonna make a commitment to this. That was kind of just this weird kind of slow journey into something that does 10, 15,000 messages a week. There's hundreds of lawyers there. It has its own life. I could go away tomorrow and it would just keep on trucking.
On What Compelled Him to Build His Own Community vs. Join a Bar Association
Saw a Gap in the Market and Decided to Build It
Not hating on bar associations. I actually think bar associations are really valuable to members and particularly local, like the more local the bar association, probably the more valuable it is. The ABA is like this thing in Chicago, somewhere that most people never even interact with. But they serve their own role and my like, Ooh, incredible insight is that like this social media thing, networking on internet, that could be a thing. And bar associations just aren't equipped to do that.
So it just became apparent that the only way this was gonna happen is if I do it or somebody else does it. And so I had the time and inclination. So I just, I made it happen and, and I think maybe bars issues will come around one day. But, um, it might take a while.
On His Journey to Becoming Chief Marketing Officer at Case Status
Consulting Client Turned Employer
Case Status was a consulting client that I was working with for a while. And uh, eventually we kind of got to a spot right before the pandemic actually like weird timing of the world that they said, Hey, we'd really like you to become a permanent member of the team. You're a lawyer who understands getting lawyers' attention and is good at communicating with attorneys.
We'd really like for you to come in and be the chief marketing officer. I thought about it a lot cause I'd never actually come inside a company before to do this type of work. And the product is great. I mean, Case Status solves a real problem for law firms. And it was something that I felt like I could really get behind and speak about, again with real authenticity, that Hey, this is not just another case management system. At the ABA tech show they're already a half dozen really well-entrenched strong players in the case management system. Every year, a dozen more pop up. And I'm like, this is a solved problem and Case Status has done that. So, um, that attracted me there. And yeah, so things are going good.
On What it Means to Be a Lawyer Who Leads
Authenticity, Transparency, and Inspiration
Authenticity, transparency, and inspiration, and I feel like I've talked a fair bit already about being authentic and transparent to people cause I very much believe in that. You know, the last one is inspiration. It's not something I feel like I consciously do or even seek to do, like I'm gonna go out and inspire people. That's weird. I don't, I don't like that. People will sometimes be like, oh, Keith, you're such a thought leader. And I'm like, I'm not comfortable leading my own thoughts, let alone other people's like time out on that. Like I'm not, I'm not here for that. But as a leader, even as a maybe sometimes a bit of a reluctant leader in that regard, you know, inspiration is just people believing in what you're doing.
And again, if you're authentic and transparent and recognize you're not everyone's cup of tea and being okay with that, saying, look, here's who I am. This is what I'm about. This is what I'm not about. I don't like any of that stuff. There are so many people who are like, so puffed up and again, present this farcical nature of who they are.
One of my favorite comics is from like 10, 15 years ago. It's like two, and there's like you on Facebook. And it's like a guy on a skateboard doing an ollie with like a guitar. And like, he's just awesome. And then it's like you in real life. And he is like eating Cheetos on the sofa, you know? And I think still to this day, a lot of people present themselves to be this one thing in a way.
I just, man, I really don't like that. I'd rather just people be who they are. Like it's cool. Just don't be, don't be scared about that.
And there's particularly in any industry, but you know, there's advisor, coach, guru, you know, there's all kinds of industry of people that are not actually what they say they are and it's like, I don't have time for that.
I see people who are in leadership roles, in different areas, lawyers or not, and when they conduct themselves with real authenticity and transparency about who they are, that's inspiring. It's like, yeah, look at that person in this important role and they're not scared of who they are.
I mean, the LawyerSmack community is that way in a big way. There's lawyers and they're at all types of firms - small, big, corporations, little, Fortune 500, and they all are very transparent with who they are and lead very different lives and do different things, I find that inspiring. I mean, I find the community inspiring.
On One Thing He Could Improve About The Legal Industry
Rethink Law School from the Ground Up
Oh, wow. I have a laundry list of things. Um, I think if I was gonna have one thing to change, gonna have the largest systemic foundational impact is I would radically change a law school. Law school is stuck in the 1950s still. And even everything they say about, oh, we're getting more modern, this, that, and whatever. It's mostly lip service. I mean, it really is. And you know, there's a real incentive alignment problem there. Like the schools are incentivized to just get warm bodies in the door. Cause law schools are profit centers for colleges. They don't have labs. They don't need tons of, you know, computers. They don't need lots of space. It's like you need a library, some professors, students, and laptops and you're off to the races. And you can charge people a hundred thousand dollars a year around that to go to law school for three years. Great money. So the schools love it and professors get paid really well, but they're incentivized to produce research, not actually equip their students to be successful attorneys.
And so there's all like misalignment. And the third year of law school is largely BS, frankly, and it's like, oh, you. The law and the world of Harry Potter or something. And it's no offense to Harry Potter. I've read the books. They're fun. But like, you know, the third year of law school should be articling, like they do it in Canada or it should be, uh, you have to do clinics for a half the year, you know, and walk across campus, there's a place called the business school and they know how businesses work.
Law professors don't need to reinvent the wheel. No, send the students over to the business school, make them take a couple semesters of accounting and stuff like that. And they'll be way more equipped to come out and interface with clients in the business world, the business of running a law firm. So for me, I, I would change legal education. I would nuke it and probably restart. And really rethink it from the ground up, which is never gonna happen. But I think that's, we gotta start there.
If we don't start really changing how future lawyers are educated, then we're just gonna be stuck in the same cycle again and again and again.
On Something People Misunderstand About the Work He Does
Marketing for a Business Requires Immense Understanding of All Aspects of a Business
You tell lawyers like, I'm an executive, I'm a Chief Marketing Officer for a legal tech software platform. And they're like, oh God, that must be so easy. You must just post on social media all day. And it's like, again, that shows me how little you actually know how businesses function. You get so entrenched in like being a lawyer and doing the legal work that you don't understand the vast array of things, the multitude of projects, you know, managing budgets, strategic development of campaigns, working with other departments, supporting other, I mean, it's like, it's a lot of work. And so I'd say that's probably the biggest misconception is that lawyers are a little stuck in their own world. And don't recognize how things work at times.
On A Piece Of Practical Advice To Leaders And Future Leaders In The Law
Focus on Edge Knowledge and Edge Work, Areas That People Are Trying to Still Figure Out
I would say to constantly be pushing for what is the edge of knowledge or the edge of what is being done or worked on because things at the edge by definition, people are still trying to figure out what that is and what does that mean and how to do it? There's no course you can take on it, right? If there's a piece of work or something that you do that can be commoditized and trained and taught, well, then eventually, it is gonna be commoditized, trained, and taught and that's can get put into a box and people go to school for it and eventually computers are gonna be doing it.
The more you can be comfortable with seeking out edge knowledge and edge work that is sort of frontier level work. Where you sort of have to figure it out. Like there is no here's the playbook for starting, you know, one of the largest online legal communities for lawyers. Well, no, none existed. The willingness to engage on the edge of knowledge and work, I think will always return high dividends if you're willing to do it.
On His Favorite Self-Care Practice
As a High Functioning Introvert, He Builds in Alone Time to Decompress
I need alone time. I am an only child. So I grew up with a lot of alone time and everyone assumes, oh, you're such an extrovert. You're so out there with people and whatever. Man, I'm a high functioning introvert, right?
After the last week of the tech show, I got home late Saturday. My wife and son know me well enough now, like Sunday, I was like, cool, no, I can't talk to anybody. I need to be by myself and not interact with anybody for a while. I need the time to decompress in a big way. Obviously not that I didn't also immediately go spend plenty of time with my family, but I really need just time by myself.
I need to be able to read a book, exercise, my Peloton's like right on the other side of the computer, do something that I can be alone with my thoughts.
Lawyers Who Lead is a weekly podcast that celebrates lawyers who are making powerful changes through extraordinary leadership. Each week, Lawline’s Chief Storyteller, Sigalle Barness, interviews a lawyer who is driving meaningful change in the legal industry. Guests represent a diverse and exciting range of experiences but with one common thread, the pursuit of bettering the legal profession.
Each episode explores the guest’s journey to leadership, the underlying principles that helped them make an impact, and devises ways listeners can apply these concepts in their own lives.