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Lida Jennings Of Teach For America Los Angeles: 5 Ways Empathy Will Affect Your Leadership

An Interview With Cynthia Corsetti

Builds trust: I’ve spoken to this quite a bit, so I’ll be brief. Trust is always evolving and it’s something that needs constant care. Empathy is a way of building and caring for that trust and when done properly can strengthen relationships and promote honest and open communication.

Empathy, the ability to understand and share the feelings of another, is increasingly recognized as a pivotal leadership trait. In an ever-evolving business landscape, leaders who exhibit genuine empathy are better equipped to connect, inspire, and drive their teams towards success. But how exactly does empathy shape leadership dynamics? How can it be harnessed to foster stronger relationships, improved decision-making, and a more inclusive work environment? As part of this series, we had the pleasure of interviewing Lida Jennings.

Lida Jennings joined Teach For America (TFA) in 2010 and is now in her eleventh year as Executive Director of the Metro Los Angeles region. She is a passionate advocate of educational equity and an aspiring anti-racist leader. Lida has over 30 years of experience in the higher education, corporate retail, and non-profit sectors. Prior to joining TFA, Lida served as assistant dean at the RAND Corporation, following nine years as the director of the full-time MBA Program at the University of Southern California Marshall School of Business. At TFA, Lida has held multiple roles on the leadership team, including Managing Director of Strategy, Talent, and Operations, and Managing Director of District and School Partnerships. Lida earned her BA in psychology from Smith College, MBA from USC Marshall School of Business, and Doctorate in Education from the UCLA Graduate School of Education and Information Studies. Lida currently serves as a board member at Camino Nuevo Charter Academy, ExED, STEM To The Future, the LMU School of Education Board of Visitors, and as board chair for Da Vinci RISE High School.

Thank you so much for joining us in this interview series. Before we dive into our discussion about empathy, our readers would love to “get to know you” a bit better. Can you share with us the backstory about what brought you to your specific career path?

I’ve also always been obsessed with access. I had very easy access to opportunity growing up, in particular as a white cisgender woman. I did nothing to deserve that. Access is fundamental to success and it begins with education. Before joining Teach For America Los Angeles (TFA LA) I had extensive experience in the private sector and higher education. I was on a charter school board at the time and found myself surrounded by TFA alum leaders. They were everywhere — board members, school founders, advocates, educators, politicians — you name it. They were all brilliant, extremely committed to their students, and very focused on the well-being of their students’ families and the surrounding communities. After much encouragement, I applied for a role, joined the TFA LA team, and found my people, purpose, and space.

Can you share the most interesting story that happened to you since you started your career?

I experienced harassment at a former workplace and left the organization after many years as a result. Given the nature of the particular situation, it put my career at stake — my network, my job, my financial stability, my self-confidence — all of it. I knew I needed to get out of a very damaging situation, but beyond that, there was no plan. Through this experience, I found myself thinking a lot about access and how people in more vulnerable positions, because of their identity, financial situation, or other factors, are constrained with limited choice. It took all of my energy to keep my head above water, and all the while I knew I was much better off than so many others simply because of my race, gender, and background. It was a defining experience that gave me a glimpse of what it’s like to have my resources and my access severely threatened.

What do you think makes your company stand out? Can you share a story?

What makes Teach For America stand out is the talent we attract — the people who apply to join the corps and teach in communities and go on to lead across many sectors, and the people who apply to work here — they are extraordinary. They are the strongest learners and smartest people I’ve ever worked with, and the most kind and generous, as well. I’ve never worked anywhere where feedback was a normal part of conversations, and I learned quickly how to give and receive it. One of my UCLA classmates and colleagues at TFA with whom I shared my self-doubt told me feedback is a form of love. That really changed my orientation.

When the pandemic hit in March 2020, we had a ton of corps members — these are our first- and second-year teachers–who were admitted to the program and preparing to start teaching in the fall. No one knew what was ahead, and many of our Los Angeles school partners were experiencing record-high teacher attrition. We were concerned we would not have the number of new teachers we initially committed to. For our new corps of teachers, there was uncertainty about everything, including whether they’d be teaching virtually or in-person. I remember being on a call with these teachers, most of them who grew up in the communities where they would ultimately teach, and they were FIRED UP. The extreme challenge of the moment was nothing compared to their passion and dedication. They were truly doubling down on their commitment. They understood what the unfolding circumstances would lead to in historically marginalized communities and became even more activated, committed, and open to navigating the uncertainty. It was remarkable and truly inspiring. And that speaks to the leaders that we attract and the environment we create with and for them.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

Inclusion: Amazing people make an amazing team — the smarter, more talented, creative and diverse, the better. It’s important to be proactive in hiring and working with people who are different from you — and way smarter than you! People who have many skills and experience you don’t have. If you follow that philosophy and you’re genuinely open to the perspectives of others, then inclusion becomes the foundation for the work. It’s about decentering yourself while also still owning your responsibilities as a team and business leader. I try to be as inclusive as possible for as long as possible when leading up to a decision that I may ultimately have to make, and when we can make the decision as a team, we do. Making high stakes decisions completely on your own is power-hoarding and erodes trust. I’ve learned that the hard way! These days, I make very few final decisions on my own — and many of those processes are led by members of my team regardless of role or band, given their talent and experiences.

Curiosity. My growth and learning as a white, female leader in this work never ends. I got a lot of coaching and support early on in my time with Teach For America. I wanted to immediately offer people my support and try to problem-solve for them, even before I knew the extent of the issue or concern. I learned quickly that this was not a successful strategy from exceptional and generous BIPOC colleagues. It’s terrible that the burden fell on them to teach me that lesson, and I’ll never forget their feedback and advice. I learned to let my curiosity lead and come into conversations with an orientation to listening versus trying to solve things. Harnessing that curiosity is a learning strategy and makes a significant difference in how a team member experiences you and your leadership.

Relationship-building: At 25, I was put in charge of a team of 120 people. I was terrified and overwhelmed, but also proud and excited. I realized very quickly that one of the best ways to support this team, have great outcomes, and create a strong culture was to get to know as many individuals as possible. The big move to build those relationships and open lines of communication was to have all the small conversations about their work, weekend plans, families and friends, new movies, etc. Those conversations built familiarity and trust that translated into an improved culture and bigger impact. The best part is that I get a tremendous amount of joy from knowing people. When I moved to the executive director role, I had never raised money and was very nervous. Luckily my relationship-building skills are applicable in that work, too! I believe that most of the work we do is more about the relationships than anything else. My goal is to continue building relationships with the people I work with, who I love and care about, and also leverage this skill in new and different ways to have an even greater impact in Los Angeles.

Leadership often entails making difficult decisions or hard choices between two apparently good paths. Can you share a story with us about a hard decision or choice you had to make as a leader? I’m curious to understand how these challenges have shaped your leadership.

Across my career, role eliminations are by far the worst experiences I’ve ever had. In some cases over the years, there were decisions I had to make. In some cases, there were decisions that were made for me. Regardless, being a team leader, I was the front person for what happened and I needed to own that as a leader. It would not have been appropriate to throw my organization or individuals under the bus. It’s my responsibility to own the work. There are many micro stories in there, but across the board that has been the single hardest thing that I’ve had to do. Honestly, I don’t think that will get easier.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. Let’s begin with a basic definition so that all of us are on the same page. How do you define empathy in a leadership context, and why do you believe it’s a vital trait for leaders to possess in today’s work environment?

I believe empathy is intrinsically tied to connectedness. An empathetic leader is defined by their ability to be accessible and open, and to lead with compassion. Some connections happen quickly while others are gradual, building over a long period of time. In either case, leading with empathy is the top priority. It allows us to open the door to trust-building, have the necessary conversations, and take care of each other while doing hard work together. In my opinion, it’s impossible to reach your goals without it. And if at some point goals need to be adjusted or changed, your connectedness and empathy becomes even more important — you must include as many of the affected people as possible in that process.

Connecting and empowering women, in particular women of color, is a huge part of this work. If I consider myself an empathetic leader, I must continuously support, elevate, and connect women peers, team members, and mentees with one another and opportunities.

More specifically at TFA, we support teachers who are building connections with students and their families. What we model and how we support them matters. These connections are paramount to student academic and social-emotional success. But it takes a village. Public education needs the necessary funding, talent, partnerships, and teacher support systems in order for children to thrive.

Can you share a personal experience where showing empathy as a leader significantly impacted a situation or relationship in your organization?

I worked with an incredible corps member many years ago who was in a financial crisis. Los Angeles is expensive, life is challenging, and teacher wages are far too low. They found themselves in a very dire situation, and I knew it had taken them a lot of courage to share their story with me. They were extremely close to leaving teaching, even though they were a brilliant, effective educator and very passionate about the work. I do not share the same gender, race, or background with this person, and for several reasons was unable to directly relate to the situation. But it was my job to show up and be as helpful and empathetic as possible, just as they did for their students every day. I remember my focus on being present, listening, and playing back what I was hearing to create conditions as best I could for them to continue sharing. Making sure they knew I was there for them, would help them access support, and navigate next steps with our partners were my priorities. Ultimately, we were able to provide financial assistance and ensure they had more support from a partner, as well.

How do empathetic leaders strike a balance between understanding their team’s feelings and making tough decisions that might not be universally popular?

I think it all comes back to relationships. I am very open with my team, dig into the work with them, and learn as much as I can from and with them to improve our practice and impact. I think my proximity and openness have built trust, and that my team members believe I will include them in important decisions whenever possible, even when it might be a bit risky for me. It takes time and intention, it furthers my growth, and it brings me joy! I am successful only if my team trusts that while I ultimately might have to make a difficult decision, I do so with their perspectives in mind. Additionally, if I make a mistake, I name it, own it, and apologize. Many years ago I withheld details and decision-making from my team during a crisis, thinking I was protecting them. Not the case. If anything, I needed them in the mix and I was holding them back.

I think transparency and inclusion are especially important in education. We must invest in leaders who can create positive, impactful culture and change. There is a trickle-down impact of investing in and connecting the right people: When our leaders have the right access and support to succeed, they pass that along to those they support, like our teachers leading in classrooms. In turn, their students benefit, which is the most important outcome. Surrounding our students with passionate and thoughtful role models is paramount, and that’s only possible if we model inclusivity and connectedness in our decision-making behind-the-scenes.

How would you differentiate between empathy and sympathy in leadership? Why is it important for leaders to distinguish between the two?

Given my identity as a white, female leader, there are times when I can identify and empathize and other times when I can’t. Sympathizing can be very tricky. When talking with someone, it’s extremely important to step back for even a brief moment in your mind to understand what a situation calls you to be and do. What are they sharing with you? What do they really need from you? For example, I can’t identify with the experiences of the students we serve, but I can show up for them and support them through the work we do. Sympathy at times can lead to pity, and pitying discredits the strength and capabilities of others.

What are some practical strategies or exercises that leaders can employ to cultivate and enhance their empathetic skills?

Learning to be an active listener. I am a talker and an extrovert, so listening did not always come naturally to me. I’m also a very excitable person, especially when people are talking about really interesting things! It’s been a journey for me learning when to step forward and when to step back. Practicing active listening means not forming my response while someone is talking, not getting distracted by my thoughts or technology, and not participating in side conversations. I’m susceptible to all of these! You have to indicate to people that you are tracking with them. That could be by engaging with them, asking relevant questions, sharing how much something they told you meant, or providing them feedback to help them grow. It’s so easy to make assumptions or guess someone’s feelings based on one thing they say. But if you are listening to someone holistically, you’ll find there is nuance in their perspective.

How can empathy help leaders navigate the complexities of leading diverse teams and ensure inclusivity?

If we are successful in building a diverse and excellent pipeline of leaders for our nation’s students, they will see themselves and their experiences reflected in their teachers. Teachers must be role models and mirrors. This means we must prioritize recruitment, support, and retention of leaders of color. We must also provide opportunities for our students to learn about different experiences and opportunities that may further their own journeys. Students thrive when they can look through windows to find new points of views and gain access to what they might otherwise never know. Their teachers, regardless of background, have chartered a path through college and into their career, for example, which is something that may be very hard to imagine for some students and families.

TFA LA practices what its leaders preach — our staff is comprised of 80% people of color. This representation ensures that the people leading TFA’s programming and support systems feel genuinely connected to the communities where we work, understand the importance of diversity and inclusion, and in many cases, the lived experiences of our students.

Based on your experience and research, can you please share “5 Ways Empathy Will Affect Your Leadership”?

  1. Builds trust: I’ve spoken to this quite a bit, so I’ll be brief. Trust is always evolving and it’s something that needs constant care. Empathy is a way of building and caring for that trust and when done properly can strengthen relationships and promote honest and open communication.
  2. Strengthens connections: Empathy is a key ingredient to any functioning relationship whether it’s personal or professional. By strengthening connections between yourself and those you work alongside you model the importance of relationships. Whether I’m meeting with a donor, school principal, corps member, or a partner, understanding their circumstances through listening and through conversation strengthens our connection. The more you understand about someone’s situation, charge, work environment, objectives and goals, the more you’ll be able to accomplish together.
  3. Safety: Creating a safe environment across lines of difference is very difficult to do and something I cannot and will not attempt to do by myself. I don’t know what people who do not share my background, or even those who do, need to feel safe. So, I ask. I ask my team what they need to feel safe and able to bring themselves to work each day, then we use their answers to guide our cultural norms and the way we work and engage with one another.
  4. Inclusivity: I’ve highlighted inclusivity many times throughout this conversation because it is fundamental to being a successful leader, human, and member of society. This work requires multiple perspectives and experiences — not just those of a few, in particular a few people who have positional power and/or don’t share the background of those who are directly connected to our communities. So even when I already have very strong opinions, including others and taking the time to listen enables me to have a deeper understanding of the people involved and the opportunities ahead. Understanding and celebrating the different aspects of folks’ identities as best you can is critical to planning, decision-making, relationships, and so much more.
  5. Proximity: I find proximity always furthers empathy, inclusion, and outcomes. The closer you are to your peers and the work as a leader, the better. For me, one example is going to schools with our Coaches who work directly with corps members on their instruction and leadership development. I could do these visits on my own, but going with Coaches means I’m able to learn from them and from the teachers they support, and see things from their perspectives which are different from mine. This exposure in turn means I’m not only a better leader, but also a better advocate.

Are there potential pitfalls or challenges associated with being an empathetic leader? How can these be addressed?

We often talk about compassion fatigue in teaching — the concept of taking too much home with you and burning out. In a field like education, that can be hard to avoid. We work with real students and families who face real challenges. It’s a sign of trust when students and family members choose to open up to a teacher, and our educators often have it in their DNA to go above and beyond. And we only have so much energy — we are only human. When our teachers can directly relate to a student’s circumstances, they will feel empathy and at times, re-experience trauma which can take an ever greater toll. It is paramount that we consider how to meet people where they are with support and empathy — not where we think they should be. In my field, it’s providing wraparound resources for our teachers, those who choose a profession that revolves around supporting others, which will enable them to do the same for their students. Alongside our many partners, we need to model and support work life boundaries, provide mental health resources, financial support, and more.

Off-topic, but I’m curious. As someone steering the ship, what thoughts or concerns often keep you awake at night? How do those thoughts influence your daily decision-making process?

I worry our public education system will continue to let students and families down and perpetuate inequitable systems. We will be processing the trauma that has come from the pandemic, racial reckonings, and global and national unrest for many years. Our young people need all hands on deck social-emotionally and academically. I also worry about accessing the funding needed to take our teacher support and programming to the next level. But while these thoughts may keep me awake, they also get me out of bed each morning because I know the importance of our work and leaders on a day-to-day basis and in the greater scheme of things.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

I likely wouldn’t stray too far from our vision and mission at TFA because I really believe in what we do! We strive for the day that all children have access to an excellent and equitable education. And we’re still a long way away from that day. U.S. students are subject to one of our world’s worst public education systems and that’s unacceptable! And the schools and communities that have been and continue to be marginalized bear the brunt of it. That’s not a path to equity and excellence. And it’s certainly not the path to a strong and sustainable state or national economy. So I’d start a parallel movement to drive as much public and private funding as possible to historically marginalized public schools. Numbers-wise, that’s where most of our kids are — it’s undeniable — and they are the future leaders of our country and world. Productive society relies on young people having ambitious and achievable pathways to their careers of choice. This movement would include a diverse range of partners, advocates, and practitioners, to ensure the necessary funds made it all the way to schools, classrooms, and kids. We’d have to create or elevate the necessary conditions, develop and nurture programs, and create proof points to learn from. I’m not sure who would manage or distribute the money but I don’t trust the current systems so we’d figure it out!

How can our readers further follow you online?

You can find me on LinkedIn here!

Thank you for the time you spent sharing these fantastic insights. We wish you only continued success in your great work!

About the Interviewer: Cynthia Corsetti is an esteemed executive coach with over two decades in corporate leadership and 11 years in executive coaching. Author of the upcoming book, “Dark Drivers,” she guides high-performing professionals and Fortune 500 firms to recognize and manage underlying influences affecting their leadership. Beyond individual coaching, Cynthia offers a 6-month executive transition program and partners with organizations to nurture the next wave of leadership excellence.

Lida Jennings Of Teach For America Los Angeles: 5 Ways Empathy Will Affect Your Leadership was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.