The Importance Of Leading By Listening

On this week’s episode of Lawline's Lawyers Who Lead podcast, Sigalle Barness chats with our very own Angelica Cesario, Lawline’s Director of Attorney Education & Development. Angelica shares her journey to finding a career that combines her love of education and the law as well as the importance of listening in leadership. Listen to the full interview or read the highlights of Angelica’s interview below! Transcribed answers were edited for readability.

Interview with Angelica Cesario

On Moving to an Alternative Legal Career

“I wanted something outside the billable hours … while staying challenged and connected to what brought me to law school.”

Before joining Lawline, I was a labor and employment attorney representing labor unions and individual employees at a labor law firm in New York City. I was looking for a change. I knew I was going to be starting a family soon, and I wanted something that was a little bit outside the hustle of billable hours and make a lifestyle change, but I still wanted to be close to the law. I wanted to still be learning every day and be challenged and stay connected to what I love and what brought me to law school. 

I came across this posting on LinkedIn. It was a Program Attorney. I liked the job description. I submitted my resume, had a phone call with you. Um, and it went really well. I was like, okay, cool. Like, she was really nice, really easy to talk to. This seems like a place where I could see myself.

Then, you know, we had the interview and through the process, I met more and more people and everyone that I liked, I just really enjoyed speaking with. And then when I learned more about what Lawline does and like, okay, wow this is an organization, you know, it's not just about CLE, but they actually really care about educating attorneys and I've always had a background in education too, and an interest in that. So it kind of was just the best of both worlds. I started over five years ago, and from there it's really only been up and I continue to learn every day, which is something I really love about being here.

On Her Love for Education

“I see what it's done for me and how it's really helped open doors.” 

When I was in middle school, I joined an organization called the Teak Fellowship. It's over 20 years old at this point, now dating myself a little bit. I was in the first class. And so that was an organization really designed to help low-income students in New York City go to some of the best schools in the city, best colleges and it really helped me in my journey and it really started my interest in education.

For a while, in college, I thought that I wanted to be a teacher. I was like, oh, I love education. I see what it's done for me and how it's really helped open doors. I was the first in my family to go to college, graduate from college, first to go to graduate school. I consider myself really lucky to have gone to really good schools too, and worked really hard for that. I was like, I want to give back and I want to be a teacher too. 

In college for a summer I did a program called summer bridge, which has student teachers and so um, I'm from New York City, but I spent a summer in California teaching middle schoolers in a similar program to help them sort of achieve and get to some of the top schools in San Francisco. I really loved it. 

On Finding a Career in Legal Education

“It’s Full Circle”: Marrying the Love of Law with the Love of Education

I was also really involved in social justice issues and advocacy as well. So ultimately, I chose law school as a path instead, which I think is just another vehicle for change. There are different ways to do that and law school, I saw it as a way of going and making policy changes, but I never lost my passion for education. And so it's something I like to continue to always be involved with. Eventually I joined the board of the Teak fellowship and I was the first alum of the program to join the board, which is really, really exciting.

I was sort of able to pass that on, and there's now other alums on the board of the Teak fellowship as well. I'm still involved in that because education has done so much for me. So this is like a full circle. It's the best of both worlds that I get to be involved in the law, which I love, but also marry that with education too.

On the Importance of Mentorship 

“Don't just achieve and keep going….look back and make sure you're keeping those doors open.”

[The mentorship work was] helping students with mock interviews for high school and for college, practicing handshakes with students, how to make eye contact, giving them tips on what to wear to a formal interview, helping with the admissions process, helping translate for parents who are only Spanish speakers. 

I served as a mentor for the Teak fellowship as well, which is a five to six year commitment where you mentor an incoming junior high school student and then you stay with them as they enter high school and apply for college. Which was just so amazing and such an honor to be able to be a mentor to a young student and really just see them thrive. And, you know, every year she would invite me to her dance concerts at school, and I got to meet her mom and grandmother. She's now in college, I'm just so proud of what she's accomplished over the time. 

I mean, honestly, I feel it’s the least I can do. The program has done so much for me. And you know, I've always been taught and really believe in giving back and doing the same for others. You don't just achieve and then keep going. You always have to look back and make sure you're keeping those doors open.

On How Joining Lawline Aligns With Her Values

“We have a critical role to play in educating attorneys so that they can then take what they learned to help their clients.”

At Lawline we serve attorneys and we serve the legal profession. We have a really critical role to play in educating attorneys so that they can then take what they learned to help their clients, right? Every attorney, regardless of whether they're at a small nonprofit organization or a big law firm, they all have a common goal.

They want to achieve something for their client and help their client to succeed. And we play a really big part in that. The courses and the content that we create really helps attorneys in that journey and that's really how I see our role. We are serving the legal profession and hopefully making it better along the way too. You know, with some of the content we're creating, like our diversity, equity, and inclusion content, our attorney wellbeing content that not just serves an attorney's education, but also like who they are as people. 

If someone watches a course and they take one thing away and then they go back to their firm or nonprofit or government agency, or a lawyer friend that they know, and then teach that person, then they teach that person and so, you know, we have that power to make an impact.

On How She Creates Content for Thousands of Lawyers

Listening to Lawyers, Examining Trends in the Industry, Considering Real World Context, and Having a Great Team  

I can't take credit for it because I have an amazing team that I'm so fortunate to work with every day. But essentially what we do is we take a holistic look every year and on an ongoing basis at how attorneys are consuming our content. I think that's the place to start. You know, what are attorneys watching the most, what are they telling us they want more of? What types of organizations do they work with? What's happening in the world around us, right? Of course we have continuing legal education requirements but none of this is happening in a vacuum.

We're all learning in the real world in the context of what's happening around us. So really we're gathering all of those insights, right? Attorney behavior, requests from our customers. You know, if nothing else that's one of the most important, we want to make sure we're hearing our attorneys and providing them the content that they need and want every day on an ongoing basis.

Then we're also trying to anticipate trends in the industry too. And we always want to be ahead of the curve. We want to be staying up-to-date and anticipating. So we have conversations with our faculty, to our faculty or the attorneys who teach our courses. We are lucky enough to have a faculty roster of over 1,500 attorneys.

And they're the people on the ground day-to-day who are practicing and we're having conversations with them too where they're telling us, you know, okay that idea sounds good but last week this happened or last week I had a conversation with so-and-so and they're like, okay, wow, that's really insightful. If you're telling us this, other people are experiencing this as well. 

So we use all of that to create our strategy and determine what programming we're going to create in the coming months and coming year. I think one thing that distinguishes Lawline too, is all of our Program Attorneys, the people creating our programs are attorneys. So they have experience practicing law. They understand the experience, the benefits of being an attorney and all that brings, but also the challenges that attorneys face too. And so they're bringing their real world experience with them every day as well.

On Managing a Permanently Remote Team

Treat Everyone with Empathy, Support, and Understanding

Managing remotely brings a lot of challenges because you're not physically with a person. You're not able to always connect in the same way and get those nonverbal cues that you would get in the room with somebody. Having said that, during this time, I think I also deepened my relationships with the people that I work with and manage.

I think really it comes down to recognizing that we're all people first. At the beginning of the day and the end of the day, we're all people, we're all waking up and we're just doing the best that we can. And I think it's really just understanding that. 

When the pandemic hit, I was facing my own struggles, right? And so I think a lot of that is being empathetic and understanding that people have a lot going on in their lives. As a manager, it's my job to support the people who I work with and the people on my team, and really try to make their lives easier. People work harder and they're more committed to the work that they do when they realize that the people that they're working with care about them and understand that they're people with real challenges, um, and everyone wants to succeed. 

Everyone wants to do their best work and they just need the opportunity to be able to do that. So, if someone can't work a nine to five, and you know, and they need a break in their day or they need a mental health day. Sure. Of course. Right? Like they need support to be able to have successful lives. And with that comes a successful work life where they care about what they do and really put their all in. 

On Being a Supportive Leader While Also Meeting Business Goals

Communication, Clarity on Accountabilities, and Really Listening

It comes down to communication and clarity. So for everyone on my team, and Lawline is really good at setting up the structure, everyone has a weekly coaching session, myself included. Everyone is very clear on what their accountabilities and responsibilities are at the outset. So there's no question, like what am I doing today? What's my priority? 

In the weekly coaching sessions, we're really talking about progress towards those goals and working on talking through any obstacles that people are facing towards achieving those challenges.

And that's really my role, is listening very carefully and seeing where I can help someone break through some of those challenges that they're facing. So I think it's really listening, like active listening, hearing what someone is saying, and also not just providing the answer to someone, but empowering them and talking through with them, how they can face their own challenges. And so once you have that clarity on what someone's expectations are and what they're expected to achieve, then that makes everything so much easier. Once we have that all laid out, it's really about results and not micromanaging.

I don't need to know what someone's doing every minute of every day. That's not what it's about, but are they achieving the results that we hope to see? And in every instance, yes, it is, because we're meeting regularly. We're having conversations, talking through stuff, talking to each other as people with mutual respect.

And so, you know, going back to those examples, if someone needs a flexible work schedule, or they couldn't get childcare on a certain day or whatever the situation is, that's fine. Like we're all people and it's about the results that they're able to achieve at the end of the day. 

On Helping Those Who Struggle to Achieve Accountabilities

Regular Meeting Rhythms and Continuous Reflection of  Whether Goals Are Achievable

Because we're meeting regularly and having conversations, nothing is a surprise, right? You're never like, oh my God, how did this happen? Like, you know, because you're engaging regularly and so you're able to course correct before things really get off track. Or at a certain point, you know, maybe the expectations also need to be adjusted. Like maybe this benchmark we set needs to change and that's okay too. 

We know what our goals are as a company, we know where we want to get, but plans are also made to be revised sometimes and, you know, as you start executing a plan, you realize, okay, this I can do, this is achievable, maybe this benchmark was a little bit too high and we adjust over time. But because you're having those regular weekly coaching sessions, you always know what's happening.

And I work really hard to create an environment where we can have open conversations, where if someone is having a challenge, they can just say this is something I'm really stuck on, I can't figure this out, or this really didn't go well for me. And that's okay. We all have those challenges and we all have failures too, but it's, you know, if you're clear on what your expectations are and what you're supposed to achieve, then you're also able to know, okay, this isn't quite going the way I want it to. And then you can alter things as needed. 

On How She Creates Safe Environments for Her Team

Demonstrating Genuine Interest and Creating An Environment Devoid of Blame and Reprimand

One, it's demonstrating interest in someone as an individual. Like asking someone without wanting anything from them or asking them to do something. Demonstrating, you know, that you really care about people as individuals, you know, how so-and-so, how's your son or your daughter doing? Listening, right? Remembering what they tell you and then next week. Oh, how was that performance that they had at school and you build trust over time. 

I think when you have conversations and coaching, it's also making it clear, like these sessions are, they're not about someone ever getting in trouble or reprimanded or anything like that. It's really about working together towards a common goal, right? If someone on my team succeeds, we all succeed. I am here to help my team members succeed. Then I succeed, the company succeeds, and that's really what it's about. 

I will say that all the time, like how can I help you? What do you need to be able to get this done? But I think it's about building that relationship and putting in time, building trust, and having that place where anyone can understand, like, this is a safe space and that this time, this is me time, like this is about me and helping me. This is like my hour to shine and get the most out of what I do every day. 

I think about what I would want. You know, it kinda goes back to the golden rule, like treat people how you want to be treated. Like, I know I want to be treated with respect, right? And I want to know that my supervisor cares about me and who I am and yes, of course, it's still a work environment. But we can work together in a way that supports each other and helps us achieve our common goals. 

On Debunking a Common Myth About Legal Education

It’s Not Boring Or a Chore if You Find The Right Content Creators

You know, I think probably one of the most common things is that it's boring. It's not interesting. I know before I learned about Lawline, when I was practicing law [I would think] oh, here we go. My CLE requirements are coming up and like, I dreaded it, right? Like it wasn't something I wanted to do. It was gonna take time out of my busy schedule. Like, I have calls with clients, I have a pleading I need to write, like, I've got to draft this complaint. Like, I don't have time for this. Why do I even need to do this? I'm practicing law every day, I went to law school, you know, I imagine that's how many of my attorney colleagues still feel. And we really try to get away from that. 

One, we create programming that attorneys need to know. So it's not the, you know, oh my God, this is something I have to like to get through somehow in the next 60 minutes. But it's like, this is something you would want to watch anyway. Even if it wasn't required for CLE, because it's so important to what you need to know. And so that's really the myth that I want to debunk. 

On the Biggest Piece of Advice to Other Leaders in Law

Actively Listen to Your Clients, Your Partners, and Your Team

I would say listen to the people around you actively and hear what their needs are and struggles are. That has really helped me with listening to our Lawline customers to understand what they need, but also understanding the needs of the people who teach our courses and the people who I work with and manage and coach on a regular basis. It's one of the most important things I have learned. To be humble and always be open to learning because there's just always room for improvement and doing better every day.

On What Leadership in the Law Means

We’re All Part of a Shared Community and We Have a Role to Play in Doing Better Every Day

Leadership means innovation. Constantly working to do better and improve. And learning. There's always room for learning. And I think if you're not learning anymore, you're probably doing something wrong. You probably want to reconsider that. 

And also making an impact on whatever it is that you're doing for the better, always for the better on those around you. And as an attorney, in society at large, like that's what being a lawyer is about at the end of the day, is achieving, and I know it sounds cliche, but it's all about achieving justice and that's why we all went to law school. And I think it's remembering that we're all part of a shared community and we all have a role to play and in doing better every day.

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.

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