Transcript

Brittany Leonard 00:00:00

People say, I mean, it used to be money. It used to be the next position. I tied success to my work life, and now I tie it to what brings me joy.

Candice Reed 00:00:11

This is Leveraging Latitude: Cultivating a Full Life in the Law, and we are your hosts, Candice Reed-

Tim Haley 00:00:18

And Tim Haley.

Candice Reed 00:00:20

Please join us on our journey as we discover how to leverage the hard work of becoming a lawyer, to achieving success, and leading a rich and fulfilling life in the law.

Candice Reed 00:00:35

Welcome to the Leveraging Latitude podcast, everyone. We’re happy you’re here with us today.

Tim Haley 00:00:40

Yep. It’s going to be fun. I hear we have another legal influencer on deck.

Candice Reed 00:00:45

That’s right. Today is the second in our Legal Influencer series. We are going to be talking with Brittany Leonard. She is the General Counsel of Civix, and she will tell you a little more about what that company does. But basically, it is a multinational company in the aviation and technology space, and Brittany has served as its general counsel since 2020, and she also has a really large LinkedIn following where she engages the legal community with pieces of advice. Then has a lot of people comment on the advice that she gives, and then also adds their advice. So, she’s one of those legal leaders who has built an online community that informs and entertains a lot of us from our desktops and phones.

Tim Haley 00:01:43

We talked to Alex Su in our first Legal Influencers podcast a little bit ago, but we’re using this term legal influencer. What do you mean by legal influencer? What does that mean to you, I guess? Maybe it means something different to me, which-

Candice Reed 00:01:56

Yeah, that’s a good point. So, at a very simple level, I feel like the people who are regularly showing up in my LinkedIn feed are influencers. I mean, they’re the ones who are posting regularly, who are putting out a lot of content that both informs, educates, guides, directs other legal professionals. Also, they’re initiating these conversations where, like we talked about with Alex, and I think the same is true with Brittany, they’re developing these online communities.

Candice Reed 00:02:33

I think a lot of the development or a lot of their influencing started in the midst of the pandemic, when many of us were not able to gather together in places like conferences or even more locally in our local watering holes or diners or lunch spots. So, they’re the folks who are starting conversations that for whatever reason, a lot of people are jumping in on. So that’s where I feel like they are our Sherpas in a way.

Tim Haley 00:03:06

Sure.

Candice Reed 00:03:06

Leading us into community and conversation around certain legal topics.

Tim Haley 00:03:10

I guess when I first started thinking about influencers generally, and I guess it would be true for legal influencers, I was thinking in terms of market disruptors or people who are just shaking things up. I guess content-wise, that’s totally true. I mean, most of the content generated online is attention-grabbing and you’re trying to shake up what everyone’s normally seeing in a way to get attention. But once you have it, then yeah, where do you go from there? I guess that’s something that is probably different for everybody.

Candice Reed 00:03:41

I think there’s an element of humor with most of the legal influencers. I think they have-

Tim Haley 00:03:49

Well, being a lawyer is funny. I mean, it can be.

Candice Reed 00:03:53

It can be. A lot of us are not funny, but I’m not including myself in that, among those people. I think I’m hilarious.

Tim Haley 00:04:02

You are hilarious. It’s good. Yeah.

Candice Reed 00:04:04

I have my moments. But I guess what I’m saying is the people who I consider legal influencers especially, they don’t take themselves too seriously in that they are willing to put something out there that the rest of us might have been afraid to.

Candice Reed 00:04:22

So going back to what you said about being a disruptor of sorts, I feel like to some extent just having a conversation, just being willing to say something online without fear of being mocked or ridiculed, or the whole idea of “This could be Exhibit A,” and you’re on trial or something, that in a way, that is disruptive or that is something that is different within the legal industry. Because a lot of us are relatively buttoned-up and we don’t comment at the speed that is required on social media.

Tim Haley 00:05:01

Totally true, right.

Candice Reed 00:05:03

So, you have these people who are just commenting on things that are timely and relevant, and I’m like, “Oh, wow.” I see it, and I’m thinking to myself, “Yeah, I would’ve probably mulled over that for at least a couple of weeks before I put anything out there.”

Tim Haley 00:05:15

Well, and I mean, there’s so many stories too of social media gone wrong out there, and lawyers are risk-averse to begin with.

Candice Reed 00:05:22

I do think that particularly with Alex and Brittany and some of the other folks that we will be talking to in this series, they’ve got the smarts and the expertise to back up what they’re saying. So, they’re just not good at getting attention.

Candice Reed 00:05:36

I think they’re getting attention because what they’re putting out there resonates with other people, either because of a commonality that folks share, or again, because they’re observing or recognizing something that maybe the rest of us overlooked in our busyness.

Tim Haley 00:05:54

Or just took for granted. I think I’d add two other things to that list. One is authenticity.

Candice Reed 00:06:00

Absolutely.

Tim Haley 00:06:01

And belief in self. Then the other would be the relationships. So, nobody’s perfect, but if you know somebody well enough, usually when you make a mistake, you’ll find grace, especially if you give grace in return.

Candice Reed 00:06:13

Yeah, I hadn’t thought about that. That’s a great point. I mean, I know that I marvel at these communities that have sprung up from a simple series of LinkedIn conversations. I mean, now we’re attending conferences and we may actually be meeting some folks that we’ve only ever communicated with online, and that’s fun and exciting. But you feel like you know someone. I mean, if you are reading what they post and then you’re responding, there is some level of familiarity that comes with that. I know-

Tim Haley 00:06:51

It is relationship building, for sure. Yeah.

Candice Reed 00:06:54

Yeah, and it’s not a replacement for person-to-person conversation or getting with people in-person, but there’s a lot of power in what they’re doing online. I’m here for it. I love to hear their observations and their thoughts about what’s coming down the pike. Brittany has some interesting observations on again, technology is always a hot topic that folks are discussing online.

Candice Reed 00:07:21

She also has a really unique and interesting personal story about how she made it to the GC spot in her company. So, I’m anxious for people to hear that and know that not every climb to the top spot or the GC position is the same, that there are a lot of different routes that lead to that job. Also, how your satisfaction with your practice of law and your career really can change based upon the job or the work that you’re doing. So even if you might be feeling discouraged in the job that you have right now, or in the work that you’re doing right now, don’t lose heart. There are other ways to practice law than whatever it is that you’re doing right now. So, I’m anxious for folks to hear from Brittany and we can wrap up on the other end of the interview.

Tim Haley 00:08:17

Well, let’s do it. I’m excited. Let’s hear what Brittany’s got to tell us.

Candice Reed 00:08:21

Okay, here we are. Let’s go. Brittany Leonard, General Counsel of Civix.

Candice Reed 00:08:30

So, today I am thrilled to be with Brittany Leonard. Brittany is the general counsel for the multinational company Civix, a software and technology company with both public and private sector clients in the election space and the aviation space. She oversees the legal department and focuses on managing intellectual property, compliance and global human resources situations for risk management, data privacy, negotiations, M&A transactions, sounds like a little bit of all of it, as-

Brittany Leonard 00:09:06

Yeah, all the things. I don’t even need to give an introduction.

Candice Reed 00:09:06

All the things.

Brittany Leonard 00:09:09

I think you did it perfectly.

Candice Reed 00:09:11

Okay. There we go. Well, Brittany, let’s just pull you into the conversation. You do a lot. One of the things that you do in addition to practicing law is to share a lot of your hard-earned wisdom, I’m sure, and just observations on the legal profession to a pretty wide social media following. So, we’re happy to have you here talking to our Leveraging Latitude audience as part of our Legal Influencer series. So, thank you so much for joining me today.

Brittany Leonard 00:09:41

Thank you for having me. I appreciate it.

Candice Reed 00:09:43

So, let’s start from the beginning and tell everyone why did you decide to go to law school?

Brittany Leonard 00:09:50

I think it was always instilled in me. Both my parents have a background in law enforcement, and they were like, “You’re not going to be in law enforcement. You’re going to be an attorney.” Of course, as I got older, they’re like, “Do whatever you want to do. We’ll support you no matter what.” When I graduated, it was the economic downturn era, and there just wasn’t a lot out there. I was like, “Okay, I’m not 100% sure about this whole law school thing, but I do know right now, job market’s not looking good. At least let me get this degree to have it behind my name, even if I don’t use it.” So that’s how it started, then obviously fast-forward 10 years, and here we are.

Candice Reed 00:10:33

Yeah, at least my assumption is that you are probably one of the younger general counsel currently serving in that position. Certainly, that is the end goal for a lot of people, is to reach that position. Did you think you would be here when you first started law school? Was this the goal for you, and did you follow a pretty thoughtfully charted career path, or were there some pivots along the way?

Brittany Leonard 00:11:04

Yeah, yeah. So, for me, like I said, when I first started law school, I only really knew about state prosecution because my parents were in law enforcement. That’s what I thought I was going to do. It turns out towards the end, that’s when I learned about in-house. Now I was told, “Hey, you can’t go in-house until maybe 10, 15 years down your career.” It’s like-

Candice Reed 00:11:25

Sounds familiar.

Brittany Leonard 00:11:26

Towards the end, you need the experience, whatever. So, I was like, all right, let me jump into a firm, and my goal was let me get different experiences at different firms so I can be a generalist, be well-rounded, and I’m not siloed into one practice area. So, I did that, and I have said it, and I’ll be very frank, I did not like law school, I didn’t like the stress, I didn’t like the rigamarole.

Brittany Leonard 00:11:52

College was very easy for me. Then I get to law school, and it’s just like you have to compete against everyone and everyone’s your enemy. It was very rigid. I was like, “Phew, I’m out of that. It’s done.” It’s probably me. I put so much stress on myself to always be top of the class every semester. I was like, “Finally, I’m done with school. Let me live my life as an adult in a career.” Fast-forward a year and a half, two years into the law firm experience, and I felt the same level of stressful environment, toxic environment. I just couldn’t be me.

Brittany Leonard 00:12:31

So, I got to a point, and I want to say I knew what I was doing, but I did it in a very roundabout way. So about two years after being in a firm, I said, “I hate this. I will give up my law license. I will go work at Starbucks. I do not care. I’m done.” So, I had experienced social media marketing, and marketing in general from college during when I was transitioning, waiting for my Bar license to be approved. So, I said, “You know what? Let me apply to some marketing positions.” I did. Then the next day, this was my first in-house counsel position. The CEO called me and said, “Why are you applying to this position? It’s a marketing position.” I said, “Listen, I can’t stand the law. I don’t want to be here. I have marketing experience.” He said, “It’s very odd because obviously your resume is this,” but he goes, “I’ll give you the job. But I do have in-house attorneys, will you help them on the side every once in a while?”

Brittany Leonard 00:13:31

I think I cheekily said, “If I’m up to it, if I feel like it. I can’t stand it, but if it’s something I want to do,” he said, “Okay, that’s fine.” About a month and a half into it, I realized that I am not someone that’s great at marketing, back in the day, especially when I first started out. But I loved the in-house work. I loved working with attorneys, and because I had that goal to have different areas of practice, the other in-house attorneys there only had specific real estate, specific employment. I had the IP experience, all that kind of stuff. So, I just took it and ran with it, loved it immensely. I remember the first CEO that I had called me a year into it and said, “When you told me that you hated the law,” he goes, “I don’t think you hate the law. I think you hated the environment that you were in.” That’s always stuck with me, because it’s true.

Brittany Leonard 00:14:27

So, fast-forward, I was there for four years, and then I transitioned over to being general counsel for Civix. Yeah, like you said, I believe because of that backdoor marketing into that company, I do believe… For a while, I don’t think anymore, I’m old now, but I think at the time, I was the youngest in-house general counsel in Florida.

Candice Reed 00:14:48

People all over the country who are listening to this conversation are now applying for all the marketing positions, thinking that’s going to be some backdoor approach to an in-house position. It is one that is pretty unusual. I’ve not heard that, but I really appreciate what you’re saying about not loving the environment that you were in. One thing that I will often tell candidates who talk to me about making a change, who some might say, “I want to get out of law altogether,” but often it is just that particular job or that environment, maybe it’s the practice area, maybe it is the culture of a particular place that is a problem and or maybe not even a problem, but just not a good fit.

Brittany Leonard 00:15:34

Yeah, I was speaking to a girl from this in-house too last night, and it was funny because we were talking about how we graduated around the same time from law school, how the opportunity that is out there now with legal ops being such a prevalent thing and the jobs that have been created, like I said, 10 years ago when I was graduating, it was work for the government, be a firm attorney, or maybe some type of pro bono nonprofit situation. That’s really all that was out there.

Brittany Leonard 00:16:01

Now, there’s so many things that you can do with a law degree. You don’t even have to take the bar. I mean, I know so many founders of companies, I know so many people that have just done things that have that background but don’t necessarily even practice.

Candice Reed 00:16:15

Right. There really are a lot of things that you can do with that education, with that degree. Even once you practice, I mean, this is the space where I sit every day, but people don’t want to practice the same way. That’s okay. I mean, those three buckets of opportunities that you just mentioned, law firm, public interest, or government, there are other buckets now, and you don’t even have to-

Brittany Leonard 00:16:43

People used to tell me when I graduated, “Oh, there’s so many things you can do with a law degree.” I would literally laugh. So, if anybody’s listening now and they’re like, “What is there? You’re saying that.”

Candice Reed 00:16:51

Yeah, we mean it this time.

Brittany Leonard 00:16:54

I know.

Candice Reed 00:16:54

We’re telling you the truth.

Brittany Leonard 00:16:57

I’m not just saying that to say that. If someone’s says to me, “You’re saying there’s other jobs I can do, but I don’t have…” My big thing back when I was applying was, “You don’t have the experience.” You don’t need experience for legal ops. You don’t need experience for certain things nowadays. So, there’s so many things that you can do. I’m not just saying that to say it. There are things out there and by all means, I’m proof of applying to some random odd job and then back-dooring my way into what I really wanted to do.

Candice Reed 00:17:30

So, I imagine that there are also people listening to this conversation saying, “Yeah, that worked for you, but there’s no way that would work for me.” So where did your confidence come from? Because it takes quite a bit of confidence to tell a CEO, “Yeah, I may dabble in the in-house work if it suits me.” So, where did that come from?

Brittany Leonard 00:17:52

I’ve always been, and I can’t remember who called me this, a good friend of mine years ago called me a firecracker. I think it’s so funny saying that. I am. I never showed that, that’s where obviously we’ll get into that down the line in the podcast, but I’ve always had this nitty-gritty firecracker attitude. I never showed it for so long because I felt like I had to be boxed in and siloed and all that stuff, but when it really came down to needing to use it to make a change for myself, I did it. That’s where I’m really proud.

Brittany Leonard 00:18:30

A lot of people will tell me, and I think the biggest thing about me that’s different from anybody else, not to say other people don’t do this, but when I say I’m going to do something, it doesn’t matter what it is, I’m going to get it done some way or another. I knew I wanted this, so I was going to do any way that I needed to do to get it done.

Candice Reed 00:18:46

Talk to me about imposter syndrome. I know that phrase gets thrown around quite a bit and I know that you’ve posted on this before. So, how do you define it and how do you combat it?

Brittany Leonard 00:19:02

I’m glad you brought it up, because I need to start posting a little bit more about it because I used to post a lot about it, and then I felt like it was getting saturated. So, I backed off, and I actually wrote… I found it, and I don’t know if we can attach things, but I found the article I wrote last year for ACC and I said, “What is imposter syndrome?” This is where I have the angst with people saying, “Here’s how there’s so many articles in the world and this is how my article’s different. This is how you get over imposter syndrome.” I’m like, “Hi, I have followers,” and whatever you want to call me, legal influencer, I think that’s funny. That’s why I laugh. But I have all this stuff behind me now. I still have imposter syndrome to this day.

Brittany Leonard 00:19:42

So, I don’t think you ever get over imposter syndrome. I think that there’s ways to combat it. What I talk about in my article is you can use your experience and the experiences you had, the jobs that you’ve had, the opportunities that you’ve created for yourself, if you sit back for five minutes and say, “I’ve done this, I’ve done this, I’ve done this,” whatever is bothering you about you feeling like you can’t do that next step for your journey, look at everything that you’ve done in the past to be able to propel you into that next step.

Candice Reed 00:20:14

It sounds like your approach is a very lawyer-like approach. Because what you’re doing is looking for evidence, identifying the issue, looking for evidence to support either your position or the contrary position in this case, right?

Brittany Leonard 00:20:29

Because words to me, words are sweet, but words to me, as much as I love them, they are fluffs. I need to see actual action. If I can’t see that, then that’s where I get stuck. So, I need to be able to tell myself, “You have done this, you have done this, you can do this.”

Candice Reed 00:20:47

Do you have any easy go-tos? What are some of the things that you have done in your career that you’re particularly proud of and that you get encouragement or confidence from?

Brittany Leonard 00:20:58

This makes me feel awkward when I talk about myself, but I started college in high school, a year earlier. I basically never went my senior year. I was first in my class every single semester in law school. It’s different from just being valedictorian. I literally never gave up that ranking. I wanted to go in-house so badly that I backdoored my way into it. Now obviously that was up until my point of doing when I started on LinkedIn, that’s how I looked at things, like I accomplished this, I accomplished this.

Brittany Leonard 00:21:30

Now I can say my life, and we can get into it, but my life has completely changed in the last three years. Things that I never in my life thought I would do, talk at, be at, anything. I’m like, “Oh my God, I’m there, and I’m doing it.” It’s like, it’s almost I’m starstruck that I’m the one that people listen to.

Candice Reed 00:21:52

Love that.

Brittany Leonard 00:21:53

I’m like, “Oh my God, you want to listen to me? Thank you.”

Candice Reed 00:21:55

“Look at me, look at what I’m doing!”

Brittany Leonard 00:21:55

I know.

Candice Reed 00:22:00

Let’s go there. Let’s talk about it. What are you doing? I know what you’re talking about, and I suspect most of the people listening do, but for those five that may not know, what are you doing on LinkedIn and in other venues as well?

Brittany Leonard 00:22:14

So, I started about three years ago. Obviously, it was mid-pandemic and well, we’ve shared in the past, I felt so siloed. I felt so alone. I was in a toxic environment. It wasn’t healthy. You always heard, “This is how it’s always been.” As a newer attorney, I don’t say younger. As a newer attorney, you have to do the grind. You have to be treated this way; you have to do that. I’m like, “No, there’s a difference between who I am as a person at home with friends and family versus this work person.” I’m like, “No, I want them to combine. I have all these things to say, and I want to change our industry. I want to disrupt the legal industry because it’s not healthy.”

Brittany Leonard 00:22:57

So, I first started commenting on people’s posts and stuff when I found LinkedIn. Then about six or seven months after I gained that confidence to be like, “Hey, I know this person. I talked to this person,” blah, blah, blah. Someone reached out to me and said, “Why don’t you post? I was like, “Oh, what would I be able to add?” They’re like, “You are you, you yourself are a unique story.” I just did it, and there’s been no plan of action. People say, “Oh, I have my posts a week in advance, and they’re scheduled on…” whatever. I write mine sometimes five minutes before I post. There’s no rhyme. It’s just literally, naturally me, and what’s on my mind.

Candice Reed 00:23:43

So, you’re very prolific. I mean, you post if not every day, just about every day.

Brittany Leonard 00:23:48

I try every day.

Candice Reed 00:23:48

Correct?

Brittany Leonard 00:23:49

Mm-hmm.

Candice Reed 00:23:50

So, where did the ideas come from? How do you decide what question or topic you’re going to tackle on a given day?

Brittany Leonard 00:23:59

When I first started out, a lot was based on my experience, the unhealthy environments, what a lawyer should be, and how do you get in-house, things that I just knew from so much experience. Now my posts really come obviously from my day-to-day things I interact with, things I do. But just the inspiration of I guess when you get to a certain level of… It’s so funny, oh my God, someone that is in legal ops, she commented on a post last week and I admire her greatly. She said, “A lot of what posting is about as being creative.”

Brittany Leonard 00:24:37

I was like, “You know what?” I said, “I never thought of myself as a creative person, but now that I think about it, I think I’m getting into that because the inspiration just comes.” I don’t know how to describe it. When I first started, I was like, “What the heck am I going to say?” I had that experience to fall back on, just to share with others how I wanted the industry to be, how you should if you’re in a toxic environment, get a plan of action. If you want to just leave, leave. But if you don’t have the means to, get a plan of action. But now I have so much more experience and wealth from learning from others that I’m like, “Here, here’s my take on this XYZ thing.”

Candice Reed 00:25:18

It’s interesting to hear you say that. It reminds me of how I’ve heard book authors talk about the writing process, which just fascinates me, how someone can create a story that’s never been told or maybe a version of a story that has been told before, a new version of a story that’s been told before. I remember a former coworker, who wrote books in her free time. I mean, I shouldn’t say that. She was very intentional about it. Her name is Tish Mosley. Last I knew, she had written a trilogy that I’m sure is available out there wherever you buy your books.

Brittany Leonard 00:25:59

Shout out to…

Candice Reed 00:25:59

Yeah, shout out to Tish, but it was always interesting for me to listen to her talk about the writing process, how it came together. It was almost like she didn’t know what a character was going to do until she started writing it. Then the characters would start to reveal themselves.

Brittany Leonard 00:26:17

It just flows.

Candice Reed 00:26:19

I mean, in some ways, it sounds like what you’re saying.

Brittany Leonard 00:26:22

It does. If I really have a hard time, I think and I’m like, “I don’t know. I’ve said everything I could say.” First of all, every day is a journey. So, I would sit there and be like, okay, if I really feel like I have nothing to say tomorrow, I would write down things that happened during my day and figure out how to take those things, and transition it into a post about a learning experience.

Candice Reed 00:26:46

Interesting. What’s some of the best advice you think you’ve given in some of your posts?

Brittany Leonard 00:26:52

The best advice I can give, I think I give a lot of advice just in general, how to be a better attorney. Like, don’t fight. I think what kills me to this day, and I can say this because it bothers me to this day, is when opposing counsels or outside counsel or anything, anybody in our industry that fight with each other or even… Actually, I’ll give you an insight. I’m going to make an open letter next week about this. Even legal ops vendors that fight amongst themselves, we’re all in this industry together. Let’s get along, because it’s the biggest thing I can say is you’re going to need that person possibly down the road. So just because you’re at one company now or you have one client now, this is what I tell the outside counsel, just because you have that one client now and you’re trying to advocate, yes, be a zealous advocate, I’m all for that, but don’t be a jerk. Because that client’s not going to be there for you two, three years later, but your reputation will be.

Candice Reed 00:27:48

Yes, yes. Were you the person who all your friends always asked for advice?

Brittany Leonard 00:27:53

Yes!

Candice Reed 00:27:54

I mean, is this something that you feel like was in there all along, and it’s just that during the pandemic, you tapped into the part of you that shared it on LinkedIn? But I mean, have you always been comfortable sharing your experiences with others so that they can learn from some of the lessons that you’ve experienced personally?

Brittany Leonard 00:28:13

Yeah. Before the whole LinkedIn thing, I was a lot more private and I still am very private, but I do feel like it’s… I don’t want to say duty, but I feel like I have the need to not let others experience the bad things in the toxic environments and things. If they’re in it, obviously that’s one thing, but I want to be that, “Here’s some light, I got out of it, and here’s how I can help you get out of it too.”

Candice Reed 00:28:40

Yeah. You mentioned that you want to be a disruptor or that you want to disrupt the legal industry. So, what are you disrupting in your opinion? What needs disrupting or what needs changing? What’s the end goal?

Brittany Leonard 00:28:55

This sounds so hippie and I’m the farthest from the hippie type of person. I’m very military background, whatever, from my parents. Happiness. The happiness level of so many in the legal industry, from the firms to in-house, everything, I think being in-house is great. I’m very happy, but I know in-house attorneys that aren’t. So, getting that happiness, and what does that happiness come from? If you really step back and take an approach, how do you get to that happiness? It’s like, what do you value as an individual? Do you value the environment? Do you value money? What makes you tick?

Brittany Leonard 00:29:34

For me, that’s freedom to have an opinion, that’s supportive bosses, what have you. That’s being able to be who I am and express my thoughts without being told, “No, you can’t do that. No, sit on the sidelines.” That’s where I’m like, this needs to change, because this whole, “You’re a new attorney. You only bill, you only do XYZ until I tell you otherwise, I don’t want your opinion,” it’s just such an unhealthy… not only unhealthy for someone’s growth, but just unhealthy in their self-esteem.

Candice Reed 00:30:13

Yeah. I shared with you earlier that I’m often the lurker on social media where I’m reading you and others, the content that you’re putting out there. But I may not comment. I may like it, but I may not comment or jump into the conversation out of… I think it’s probably fear, if we’re being honest.

Brittany Leonard 00:30:39

Yeah, no, and I know that-

Candice Reed 00:30:40

Fear of saying the wrong thing, of being-

Brittany Leonard 00:30:44

Judged?

Candice Reed 00:30:45

… judged, yeah. Saying something that someone might think is stupid or irrelevant or worse, hurtful. So, I keep those opinions to myself. Now, if my husband is listening to this conversation, he’s like-

Brittany Leonard 00:31:02

He gets all your opinions.

Candice Reed 00:31:03

… when in the world have you ever kept your opinions to yourself? Who is this person? But on social media, I think there is something about being a lawyer in particular that you have been taught, or we have been taught that there is a right and a wrong thing to say.

Brittany Leonard 00:31:21

Correct. Yeah.

Candice Reed 00:31:21

And that everything that you say, what was the whole… I remember as a younger lawyer, “pretend like every email that you write might be put up on a large screen as Exhibit A at trial.” So, I feel like it keeps us from having some necessary conversations. I’m wondering if you have any advice for how to break through that, or maybe even what we’re missing by not engaging with each other where we are, whether that’s social media or across the table from each other?

Brittany Leonard 00:31:53

I think the biggest thing I can say is people, and I learned this a long time ago, people aren’t as interested in you as you think they are. I don’t know if I’m allowed to cuss, but they have their own crap that they’re worried about, they’re not as worried about you as you think they are. If they are consumed with you, then it’s about them and their own internal struggles and a reflection of who they are versus a reflection of you. I think that’s the biggest piece of advice that I can give anyone. If someone’s mean to you, it’s not because you’re in the wrong, it’s because they’re severely dealing with something and they’re inherently sad.

Candice Reed 00:32:33

Did you struggle with that, or was that a challenge for you at all when you first started?

Brittany Leonard 00:32:37

For people being…

Candice Reed 00:32:39

Like, were you censoring yourself? Or do you do it now? I mean, do you-

Brittany Leonard 00:32:43

I don’t censor myself still. Maybe I should.

Candice Reed 00:32:46

I thought that might be your answer, but I wanted to give you the opportunity to say something different.

Brittany Leonard 00:32:52

Yeah, I mean, when I first started out, I probably was a little more buttoned-up, if you will. There’s still people out there that post very buttoned-up and all that kind of stuff. It works for them. That’s great for them. I’m just very me. It’s funny, someone commented a couple days ago on one of my posts and said, “The higher her following count gets, the more savage she gets, and I love it.” I remember screenshotting it to my boss, because we have a really great relationship. I was like, “Should I tell them this is my natural personality on a day-to-day basis? Or should I just let them keep finding this shit out?” He started laughing because it’s so true. I am this very bubbly but very stern, sarcastic… I’m a Gemini, so I don’t know if that goes into anybody’s – having multiple personalities, but I am very much like I don’t take crap from people, but I love equally as hard.

Brittany Leonard 00:33:54

At the end of the day, and I think this is for me and my journey, I’ve come this far, so I don’t censor myself. I have that freedom to – because I know if someone doesn’t appreciate it, someone doesn’t like it, that’s not the environment I need to be in anyway, so I’m going to remove myself. But I do see, and I do completely understand someone starting out wanting to censor themselves because they don’t feel comfortable, they don’t have that backing to be… They don’t have the safety net I have, and I understand that.

Candice Reed 00:34:23

Did you have a conversation with your employer, your CEO, whomever, someone at work before you started to do this, or at any point as your popularity has increased, have you had a conversation about your social media presence?

Brittany Leonard 00:34:41

So, the first part of the question, did I have a conversation about starting? No. Drives me nuts when friends of mine are like, “Hey, my company wants me to start posting.” I’m like, “If you don’t want to post, don’t post.” Post for yourself. I will never post for a company. If someone tells me to do something, never had a conversation about it. I think, no, I was probably already working here when I first started. I don’t really recall, but I just did it because it’s just who I am. Now, fast-forward to today, I think I don’t want to say lurker. There’s a more endearing term for people that watch what you do, but-

Candice Reed 00:35:18

Thank you.

Brittany Leonard 00:35:18

Yeah, I think my boss is my biggest lurker, my biggest fan. He 100% loves what I do. Thinks the funny posts are hilarious. He thinks the serious posts are right-on, spot-on. So, I do have a very supportive background behind me, which I really appreciate.

Brittany Leonard 00:35:35

But yeah, no, when I first started, it was just, “This is what I’m going to say.” I think I hit a wall. We’re all in that pandemic era and I was feeling tight and boxed in and I was like, “If I can’t breathe and let this out, it’s not going to be good. I can’t spend another 20 years in this industry where everyone feels like this is how it’s always been done, so this is how we have to do it.”

Candice Reed 00:36:00

That’s interesting that for you, the posting and your social media content is a way for you to express who you are. On this podcast previously, we’ve had a running conversation about showing up as your authentic self in the practice of law and recognizing that while that’s great advice and the goal and probably the desire that we all hope for, that it’s far more difficult for some people to do that than others, particularly people who may not fit the traditional profile of what we assign to being a lawyer. So, what are some other ways that people can show up as their authentic self in the practice of law?

Brittany Leonard 00:36:58

I think that it’s so personality based. So, you’re going to get someone, and I had referenced this, who very much wants to post about topics that they know about, and they just want to teach you. That’s lovely and that’s great. I love those posts because I’ve learned so much from them. But then there’s people like me who are going to do that and teach you things but also are going to be very real with you and tell you the down low, like, “This is not okay.” So, I think you really have to figure out what your journey, if you want to post, if you want to do this, what makes you happy and what makes you feel secure. If you don’t feel comfortable talking about something because you don’t want to be frowned upon by your boss or what have you, then you go, “Okay, I don’t feel comfortable.” So, you either decide, do you want to stay where you are and not post or does posting mean more to you than what your current situation is? How-

Candice Reed 00:37:57

Posting could be anything, right?

Brittany Leonard 00:37:59

Correct.

Candice Reed 00:37:59

I mean, you could substitute the word posting with fill in the blank, whether it’s how you dress or where you work in the office versus from home, or the schedule that you keep, or-

Brittany Leonard 00:38:12

At the end of the day, what makes you tick, what makes it worthwhile to you. Are you okay where you are, or do you want to do something, and it’s… I hate to say killing you so much that you can’t do that, so you need to remove yourself? I got to the point where I was like, “I have to say things and I want to say things to disrupt our industry. If I don’t say it, I’m going to be that 25-year-old grumpy partner that hates life.”

Candice Reed 00:38:36

Yeah. Yeah. Not that any of us know that 25-year-old grumpy partner.

Brittany Leonard 00:38:42

No, we don’t know them.

Candice Reed 00:38:43

I never encountered that person, but I’m assuming that surely, there’s one of them out there somewhere. So, I would imagine that you have to stay abreast of what’s going on in the legal industry, the trends that are coming down the pike or that you see on the horizon, because people are looking to you for that information a lot of the time. So, give us some insight as to some of the topics that are generating a lot of buzz right now.

Brittany Leonard 00:39:15

I guess two really huge ones. I’ll say three, because that third one is how I really feel is… So, one is AI.

Candice Reed 00:39:24

Sure.

Brittany Leonard 00:39:25

AI’s been around, but with ChatGPT, it’s just exploded. I was at Harvard Law two weeks ago and we had a classroom professor and oh my God, it was so good. He was explaining how AI works, what’s the risk, what’s not the risk. It was a phenomenal class. So, AI and specifically, obviously, ChatGPT is a huge thing.

Brittany Leonard 00:39:46

Legal operations, that has exploded in the last three or four years. It was never a thing. I met someone the other day, he’s like, “I’ve been doing legal ops since 2002.” I’m like, “Maybe something titled something differently, but no.” Because legal ops, it’s very new and it’s needed. I wish I would’ve thought about it 10 years out of law school, when I didn’t know what I was wanting to do, because it is so helpful for our industry.

Brittany Leonard 00:40:12

Then thirdly, I don’t want to say this in a hippie way, ESG, because everyone thinks ESG, like climate change, being green. No, I’m thinking in the government side, I guess it would fall under the social governance side of making our work environment in our industry healthier. It’s getting there slowly because people are being called out. I don’t want to name any posts, but when people get named out on posts and it goes viral, people lose their jobs and everyone knows what I’m talking about, like what happened a couple months ago, it’s doing the changes that are necessary to make our environment better, to make our environment healthy. It’s needed. Unfortunately to me, and I’m sure you see this, there’s still not a lot of firm attorneys on LinkedIn. I think it’s slowly getting there, and firms getting on LinkedIn. But until everyone sees the collective force that we’re creating to say, “Hey, none of us are happy, or the majority of us aren’t happy doing this how it’s always been. We want to show up as our authentic self.” That means a healthy environment. That means doing things for retention. That means not making someone feel small in a workplace. That means giving credit where credit’s due. So many things that aren’t done that need to be done.

Candice Reed 00:41:32

You just mentioned some things that may not be done that need to be done. Are there other things that you feel like are just blinking with big, flashing lights, things that need to be done that we should be focused on as top priorities for creating that better, healthier work/professional environment?

Brittany Leonard 00:41:55

I say this sarcastically. I love when people put down on paper, “Oh, we’re a really healthy work environment. We’re so great. We won Top 20,” whatever. First of all, half these awards are bought. I hate to be that person to tell you this, but if you sponsor them, you get an award. Let’s not go down that route. But that’s the thing, is I think we talked about this earlier, and I don’t know if we’re recording, there’s a difference between words and there’s a difference between actions. So, if you say you believe in a healthy work environment, don’t be calling somebody at 9:00 and demanding that they get you XYZ unless it’s an absolute emergency, obviously. But don’t have a consistent routine where you’re always questioning somebody, or looking over someone’s shoulder, or questioning “Why you weren’t here? Your calendar says this.”

Brittany Leonard 00:42:45

Everyone knows this. I blocked mine; no one sees my calendar. It’s not a healthy thing to sit there, and like… People are like, “Oh, well, I like to see people’s environment,” the flack I get when I post about it is like, “Oh, so I know where to schedule.” I’m like, “If you’re going to schedule me and put me on a calendar without even asking me first, that’s the number one problem. Ask me if I’m available, because I may not have something posted on a calendar that I need to get done personally or XYZ.” So, I think that’s my first thing, is not trying to say one thing on paper, but not actually living by those standards.

Candice Reed 00:43:23

We often talk about how the client drives a lot of change or improvements in the practice of law and then the law firms follow because the clients are demanding it. Are there things that you feel like you can do as in-house counsel or as the client to maybe push firms in this direction?

Brittany Leonard 00:43:47

My good friend, I’m sure a lot of people know, Matt Margolis talked about this. He had posted about it, putting our money where we speak. So, if we’re not satisfied with XYZ outside counsel and we bring it up and it still continues to be a problem, we can easily take the purse strings and bring it somewhere else.

Candice Reed 00:44:08

So basically, I mean, again, it goes to what you just said about actions-

Brittany Leonard 00:44:14

Speak louder than words.

Candice Reed 00:44:15

Yeah, actions supporting your words. If you’re going to say, “This is important to us…”

Brittany Leonard 00:44:20

Do something about it.

Candice Reed 00:44:21

Yeah. Well, I have been following you for quite some time on LinkedIn and I know that you like to post questions to your community and seek their feedback. Again, I’ll admit I’ve not been a participating answerer of those questions, but I was wanting to turn the tables on you a little bit here and ask some of those same questions back to you, if you’re game? Is that-

Brittany Leonard 00:44:48

Yeah, let’s do it.

Candice Reed 00:44:48

Okay, let’s do it. So, you recently said or posted that it’s sometimes better to leave things unsaid.

Brittany Leonard 00:44:58

Yes.

Candice Reed 00:44:58

Which most of us lawyers have a really hard time doing. So can you give us an example of a time when you found – I think the word you used was magic – when you found magic in remaining silent?

Brittany Leonard 00:45:12

So obviously not naming situations/names. The biggest one I could say is gossip. I was told one story when I knew the facts of the situation was completely different, but the way the story was told was that person has a deep-rooted sense of wanting to feel like they belong, like this hero concept almost. So, they spun the story to make themselves the one that did what was happening. I knew all along I was the one with someone else working on that situation for that person, that person wouldn’t have gotten that situation if it wasn’t for what was going on in the background. But it’s funny how obviously, we’re on a podcast and people can’t see how I moved my chair just now to emphasize my point, but-

Candice Reed 00:46:03

Yeah, there’s lots of hand gestures going on with this story.

Brittany Leonard 00:46:08

Basically, they said one thing and said that this happened for them, on accord. There was a lot of moving parts in the background for that thing to happen. But I knew that person needed that, needed that energy, needed to feel good.

Candice Reed 00:46:23

Needed that recognition of being the-

Brittany Leonard 00:46:25

Instead of being the downpourer on their parade, I was just like, “Oh, that’s awesome. Congratulations, great for you.” As much as it pained me, because I felt like the other person that helped that person needed the credit, I wanted that person to feel recognized too. So, it wasn’t my battle to fight, so I just stayed silent.

Candice Reed 00:46:42

Yeah, thank you. Thank you for that. I’m thinking of other examples. I mean, this is what you do so well. You pose these questions that then start a conversation, it’s really hard to just answer them succinctly. I think that’s the point with these online communities, and it’s a way that we can start a conversation that goes from one seemingly simple question to a bigger conversation.

Brittany Leonard 00:47:07

I think it’s because I’m sure in your mind, I’m seeing your face, you have that internal battle of you want this person to feel good about themselves, but at the other end of the spectrum, you care and you see the other person that helped that person and you want to protect the person that you care about. So, it’s like you want the truth to be told because you care about that situation, but you care about the other situation too. So you’re at a middle of the ground, like what situation do I care more about? So, that’s when I just take the approach of not my battle, it’s okay.

Candice Reed 00:47:39

Yeah, I think that’s it. What I was thinking is the whole idea of giving credit where credit is due, and where sometimes, particularly in an environment where you or the person who first had the idea is an outlier. By that, I mean you may not look like everyone else in the room. So maybe you’re the woman in a room full of men, or a person of color in a room full of white people, and it was your idea and then someone’s taking credit for it. I know we’ve had conversations about how particularly as someone who may be in an executive role, or in a position of some power to be able to say, “Actually, I think that was so-and-so’s idea,” to allow them the space and the room to get the recognition. But what I hear you say is that in other situations, it’s just as meaningful and powerful to let someone else have the recognition for wholly different reasons.

Brittany Leonard 00:48:44

Yes, yes.

Candice Reed 00:48:45

Hey, we’re lawyers, we’re smart. We should be able to discern when one situation calls for one type of action and when another situation calls for another type. I think especially now that we are more dispersed in our working spaces than we might have been a few years ago, that type of social intelligence and bringing that with us to work every day is really, really important, just the awareness.

Brittany Leonard 00:49:11

The key question is in 24 hours, in 48 hours, is it really going to matter? What you have to say, is it really going to change the outcome anyway, or is it just going to hurt someone’s feelings? If it’s just going to hurt someone’s feelings, don’t do it.

Candice Reed 00:49:24

Yeah. Great advice. Okay, here’s the next one. If there’s one thing, again, this is your question. If there’s one thing you wish you knew back then — and you choose the timeframe — that you know now, what would it be and why?

Brittany Leonard 00:49:38

People don’t care what you’re doing. People aren’t worried about you. I think I said this earlier, I was so consumed with being a perfectionist, wanting to make everything perfect before I said something, stated something, because I didn’t want to be judged. I didn’t want people’s opinions. I was worried about that. There comes a point when – whether it’s my confidence has grown so much, or I’ve just had the experience – but people just don’t care like you think they do, and I wish I would’ve known that back then.

Candice Reed 00:50:13

They don’t care about you as much as you care about you, isn’t that what you said earlier?

Brittany Leonard 00:50:18

I wish I would’ve known that back then and made more decisions for myself instead of decisions that I thought other people wanted me to make.

Candice Reed 00:50:27

Yeah. Again, that makes me think of a lot of other questions. Just the whole idea of not acting or performing within someone else’s framework.

Brittany Leonard 00:50:38

Yeah. I mean, I can give a great example. Now that I’m older, I have a lot closer relationship with my parents. I always thought they wanted me to be the best student. They wanted me to excel in everything, blah, blah, blah. Now, years later, we can have these conversations and they’re like, “We never cared if you got straight As, as long as you were doing decently well.”

Brittany Leonard 00:50:58

I wish I wouldn’t have put that much pressure on myself to do so well, so I could’ve networked, and I was bad at networking back then. I mean, I had talked about it immensely. I didn’t like it. I was terrified of it. But I wish I would’ve had someone come up to me when I was studying 12 hours in library and said, “Hey, you want to go grab a coffee?” I wish instead of saying, “Oh, no, I’m studying,” I wish I’d have said, “No, let’s do that.” I wish I would’ve done that back then.

Candice Reed 00:51:25

Yeah. You observed recently that we’re all going to be working hard at something to make the point that you might as well do something that you love as opposed to something that just brings the paycheck.

Brittany Leonard 00:51:38

It’s so funny, I forget my posts and then you bring them up, and I’m like, “Oh, yeah, that sounds so smart. I said that.”

Candice Reed 00:51:45

I know, this is all Brittany, there’s no Candice in any of these questions here, but why do you work? Why do you work now? What do you get out of it?

Brittany Leonard 00:51:54

I think for me, I can’t even believe I’m mentioning it. I think it’s so funny. So, the other day I was watching something and North West, everyone knows is Kim Kardashian’s daughter, she was pulled on stage by Katy Perry, and Katy Perry asked her, “What do you want to be when you grow up?” Literally she goes, looks at Katy and goes, “Everything.”

Candice Reed 00:52:12

Oh, I love it.

Brittany Leonard 00:52:14

That to me has still resonated. I work because there’s so many adventures that I want to do, so many things I still want to do. So many things that I never thought possible three years ago because I thought, “I’m just going to go on this path of being in-house and move my way up and that’s going to be my life.” Now I have just opened doors to things that I never thought possible, and there’s so many things I want to do, run a business, do this, do that. It’s overflowing with ideas.

Candice Reed 00:52:43

Now this is my question. What’s next for you? Do you know? I mean, maybe not what else, not instead of what you’re doing now, but what in addition are you contemplating?

Brittany Leonard 00:52:56

Yeah, so I’ve alluded to it. Not really ever stated it, it’s going to happen in… I would say in the next month or two, but I do want to open a consulting business. Very exciting, I-

Candice Reed 00:53:10

This is exclusive first.

Brittany Leonard 00:53:13

Yeah. Yeah, I’m super, super excited. The website’s almost done. I’ve been wanting to do it for a very long time, probably last year, year and a half. There’s been a lot of outreach for it. I think it’s just going to be super exciting. Just my journey to LinkedIn, how I don’t really know how it started, it just did, I don’t know where I’m going to go with it. This goes back to being a perfectionist, I don’t really have a plan for it. I keep not announcing it because I’m like, “Oh, this, this, this.” But the other night I was just like, you know what? You just started this journey and you had no idea. So, just let it rip. Let it ride.

Candice Reed 00:53:52

Yeah, it’s out there now. So, you’ve already started.

Brittany Leonard 00:53:55

I know, I know.

Candice Reed 00:53:56

Whether you were wanting to start or not, it’s out there now. What type of consulting will you be doing?

Brittany Leonard 00:54:02

So, I actually have a TED Talk scheduled with ACC. It’s a partnership, it’s an ACC TED Talk on it, that’s where I officially said, “Okay, we’re going to go do this.” The title of that one is “Fear to Joy: The Pursuit of Career Happiness Through Personal Branding”.

Brittany Leonard 00:54:22

So, that’s a mix of me wanting to reach out to firms to say, “Hey, you need for you, let’s make your retention better, the environment’s not healthy. Let me come in and deep dive with you to better your environment, better the career happiness for your employees,” that sort of thing. To me, that looks like also helping people. I get tons of inquiries that I just can’t do. Helping people show how to build a personal brand for themselves, whether you’re in legal, whether in legal ops, whatever you are, a banker, whatever you are, this is what you need to do to build your own self.

Brittany Leonard 00:54:58

I think a little bit of it comes into – I have colleagues of mine, friends of mine that are starting their own businesses that are like, “Hey, I need your help from that standpoint.” So, I’m like, “Okay, I can help you review contracts, review documents, that sort of thing.” That’s going to be a little snippet of it, but the main thing obviously is going to be the branding and the pursuit of career happiness and disrupting our legal industry.

Candice Reed 00:55:23

Oh, I wish you so much luck with that. I think that sounds like a wonderful next step for you. I hope that you’ll come back at some point in the future and tell us how it’s going, because I imagine that it will be very successful, and you’ll help a lot of people in the process. So-

Brittany Leonard 00:55:40

I think-

Candice Reed 00:55:40

… best of luck.

Brittany Leonard 00:55:41

Thank you. Thank you. I think that’s where it means so much to me, because this is the first time where it’s like, I really want this too, and it really means something to me. It’s not just a job. It’s not just something I need to do for a paycheck. This is what I feel deep within my soul.

Candice Reed 00:56:00

Oh, that’s powerful.

Brittany Leonard 00:56:03

Thank you.

Candice Reed 00:56:03

That’s powerful. So, one last question, Brittany. Again, this one’s yours, but I think it’s a good one for us to end on. So, you’ve said that you want to believe that people are inherently good, and so I’m wondering if you believe that, do you believe that people are inherently good? How does that belief influence your practice of law and your future consulting?

Brittany Leonard 00:56:29

So, I think people, there’s different personalities for everybody. There’s going to be people with different backgrounds, the way they were raised, whether they were raised in a healthy environment, that sort of thing. I always want to give someone the benefit of the doubt to say that you’re inherently good. Now, obviously if you show another side, that’s a different story, but I think we’ve alluded to this earlier, people that are mean, opposing counsels that yell, or colleagues that yell at you. I hope that they’re not inherently wannabe mean people. They have a lot of internal struggles and I’m sure at night when they sit with themselves, they probably think, “I shouldn’t have done that. I shouldn’t have done this.” Hopefully, you never know.

Brittany Leonard 00:57:16

I read an article and it said if people inherently think mean things all the time, that they may have psychotic tendencies. You never know. Yeah, basically the article was saying if you can’t see right from wrong, but people even if people, wrong, if they inherently see that, that is something that can be helped, that can be fixed. But don’t think that people are mean to you or inherently bad, just because they take something out on you. You never know people’s struggles and what they’re going through.

Candice Reed 00:57:51

Yeah, absolutely. I heard someone say once to always assume positive intent.

Brittany Leonard 00:57:58

Yes.

Candice Reed 00:57:59

So, as you’re describing the example of an opposing counsel that may be acting like a jerk, that it’s not you. Maybe that’s the example they had of a zealous advocate and they’re trying to do their job, or not that that makes it okay-

Brittany Leonard 00:58:17

It really-

Candice Reed 00:58:17

… but that it’s definitely not about you in that situation.

Brittany Leonard 00:58:22

I hate to say it like this, or they really need that client because they really need the money, and the client’s awful to them, and they’re just taking their frustration out on you.

Candice Reed 00:58:32

Yeah, I said that was the last question, but I have one more. What is your piece of advice for attorneys specifically on how to be a happy, healthy, well lawyer?

Brittany Leonard 00:58:49

That’s really digging deep and seeing at the end of the day, what makes you happy. When you think about things during your day-to-day, what made you smile throughout your day-to-day? Was it traveling? Was it your family? What makes you tick? Then converting that into something that you enjoy doing. So, do you like chatting with others? Do you like having conversations? Do you like being by yourself and working by yourself? What makes you happy? How can you turn that into your career? Because at the end of the day, you’re going to spend so much time in your career, don’t do something that you’re not happy in.

Candice Reed 00:59:32

I agree. Well, thank you, Brittany Leonard. That’s I think great advice to end on. I appreciate so much that you share your wisdom and your thoughts, and that you hold those of us who aren’t quite where you are yet with grace and patience, and invite us to participate in the conversation, even if we’re just listening. So, thank you.

Brittany Leonard 00:59:57

No, thank you. Like I said, this is probably one of the most exciting podcasts I’ve been on just because like I said, the research that you did, and I really appreciate sharing my story and like I said, I want to help others, so I’m happy to be here.

Candice Reed 01:00:08

You’re doing that. You’re definitely doing that. Thank you so much.

Brittany Leonard 01:00:12

Thank you.

Tim Haley 01:00:19

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