This interview is the twenty-fifth in our series, Black & Bold: Perspectives on Leadership.
Lucecita (Lucy) Castillo, Chief Governance and Equity Officer, Charter Board Partners
Freedom. Energy. Evolution.
What are some of your career highlights?
I would certainly say teaching. Being in the classroom was super impactful for students and for me. I taught in Washington Heights in Upper Manhattan and kids and families were amazing! They trusted me so much. The experience was impactful, due to relationships I was able to build, and instructive in how inequity was built into and playing out in the system. The school, however, was tracked and the administration didn’t encourage building relationships with students and families. It was eye opening in terms of education. I grew up in a community of color with working class parents. I often describe it as an “after school special” of sorts; it was very communal; all the adults took care of all of the children. (Lucy Castillo pictured at right.)
After completing my Master’s, I joined Teach For America (TFA), which feels like 500 million years ago. I got to see the reality of an organization up close and behind the curtain, which showed me what a group aligned to a common cause or mission could accomplish. This was at a time when Wendy (Kopp, co-founder and CEO) didn’t have any children. We were so young, so green. Seeing young people make it happen and make it work demonstrated the level of clarity and drive for results and what could be accomplished. Those two experiences continue to give me understanding and context for my work.
I also worked for the Metropolitan Transportation Authority (MTA), the body responsible for managing public transportation in New York and some parts of Connecticut. That was the longest stint I had since being in the classroom. My role focused on organizational development and training. I wasn’t going back to school, but got a degree at the MTA. The work opened me up to things I loved: training and coaching, helping adults be better at work -- happier and more satisfied at work so they can be more impactful. It was a huge political bureaucracy and I had to figure stuff out. The intuition and trusting my instincts were super important. I would take on insane projects from scratch. We needed a performance management system. I was like, “I’m gonna create that.” We needed succession planning, manager training, and I was able to develop it all. The MTA was an amazing place to create stuff, stuff that lasted.
Those three experiences together – teaching, working at TFA, and the MTA –gave me insight into how organizations run and clarity around what I could contribute. I didn’t always see some of my skills as skills. I figured “this is Lucy” because of personality, or because of gender, or because of my Caribbean background. When other folks leveraged my talents, I realized those were indeed skills. I figured out that what I did and how I did it was of value to people and organizations.
If there was a headline for your leadership journey throughout your career, what would it be?
Journey to self. I think that has reinforced how who I am is the best way to lead and be. On Friday, I facilitated a training with 30 people ages 30-60, and one woman thanked me for leading it so authentically. That is the biggest compliment for someone to give me. When I became an executive director, I asked a friend to help me figure out who Lucy, “the executive director” was. He said, “Lucy the executive director is Lucy.” I didn’t need to play a role or put on something that wasn’t me.
In each situation I determine what’s important to me, what I value, why I am here, and how the best of me can show up and contribute to what this team or organization is doing. It requires getting past any muck and being okay with me in the professional space. All of that is stuff you have to work through. At the end of day, I’ve only wanted to – over the last 10 years – be in spaces where all of me can show up. Accepting my flaws and all has been a journey. All of that has reinforced me into understanding that I am uniquely positioned and have expertise that will give me whatever I need.
What are your favorite types of challenges?
I like cynical, slightly curmudgeonly people. I have often been the person implementing something new or different. At the MTA rolling out the performance management system, I had someone who had been with the organization for 20 years. She said, “Lucy, you know how many times people have come here and tried to do this?” Here I was an energetic whippersnapper Pollyanna chick. I don’t mind if you show up and are cynical, but show up. I will work to convince and convert you.
When I was in the classroom, there was that one student who was the toughest nut to crack, but if I could just get to him. A people challenge is always my thing. Working with boards, sometimes there are folks who question what I am going to teach them. I build the relationship, do the people work, figure out what their point of entry is, and what’s important to them. When someone is not convinced something will be beneficial, I still engage and allow them to have that doubt while partnering to get it done.
Another is speaking reality to power. Everyone’s truth is their truth. I have an uncanny ability to tell people in power what others are thinking but not saying. Sometimes it’s a compulsion that I can’t stop.
What is one book that was meaningful or influential in your development as a leader?
I get annoyed that sometimes books become bibles of the education reform world. I skew away from leadership-type books and tend to value books about people and culture more.
Black Pearls: Daily Meditations, Affirmations, and Inspirations for African-Americans by Eric V. Copage talks about stepping up and being engaged as a person of color. There are short, relevant affirmations. I have had this book since college and got another version of it after TFA. I will literally pull it out and use it in training. Anything that shows me how peoples’ values enable them to stand up for a cause are the most impactful for me. I don’t see my work as separate and apart from anything else I do. I can pull from Leadership on the Line, though I’m most inspired by reading about another person who has overcome or achieved success in their field. I am always asking, “what does that mean for my work in life, not just my 9-5 job?”
I’m reading The Conscious Parent: Transforming Ourselves, Empowering Our Children by Dr. Shefali Tsabary, and what’s so fascinating is it’s about parenting. It has nothing to do with leadership and emphasizes that parents need to be conscious and get out of their own way. My child is a full and complete person. He is clear about who he is. The book is about acceptance and enabling my child in a good way. I accept exactly who he is and how he shows up and create space for him to thrive and flourish. Most adults haven’t experienced that kind of acceptance. How am I creating that space for colleagues at work to feel validated and accepted? I’m looking at you first and giving you that space, so we can work together and it will be off the charts. By offering that acceptance, they are willing to share and put in the extra effort.
Work in the social sector can be very personal and linked to one’s values. Can you think of a time when your values were in tension during your career and how you reconciled that tension or not?
One of my values – and I’m not sure if it’s because I’m the youngest or an Aries – is that I like balance and peace in my life. I’ve experienced moments where I might like the work or the people, but the situation doesn’t work for my energy or my peace. Even when I was leaving the classroom, I knew I didn’t want to be a middle school classroom teacher, but I loved my students. I didn’t want to feel like I was abandoning them.
A few years ago, I was happy at the organization, but concluded that the role wasn’t for me. I knew I couldn’t offer my best work being in a place I didn’t exactly fit. Those moments when I’m in conflict or torn between being my best and feeling commitment or obligation to the work are the hardest thing. I only put myself in spaces where I can do work I believe in. It’s about self-preservation; personal peace wins out.
Summer 2017, Democratic Representative Maxine Waters coined the phrase, “reclaiming my time,” as she thwarted Treasury Secretary Steven Mnuchin’s attempts to waste her time with nonsense. Can you share an experience in the workplace where you have had to reclaim your time? What was the context? How did you navigate it? What was the outcome?
I do it on the regular. I reclaim my time by choosing when I will and will not engage people about their oppressive behavior. I have said if I was going to call out every micro aggression, I wouldn’t be doing anything else. Do I have the additional physical, mental, and spiritual capacity to do this? Is the person on a journey where if I take this time, the person will do something with it? I have a child, a career, and not a lot of extra time for those moments with adults whose behavior should align with their words and verbal commitments.
In the last year, I have chosen to not have some of those conversations. I’m preserving my mental state. I come in contact with a lot of folks who are choosing when to engage and when not, especially in my work more recently in last couple of years. If you are of a certain age and doing mission- driven work in a social justice space, you should have a working understanding of how that (privilege, dominance, oppression) manifests. In your waking hours, you should be aware of what you are doing and how that impacts others. If I get evidence that you are really interrogating your habits, experiences, and behaviors then maybe I will jump in with you. I am not trying to convince anyone to get on the path when you say you’re on the path. Ain’t nobody got time for that!
What’s your approach to self-care? Are there any rituals you use to survive and thrive?
No one will ever have to say to me, “Lucy, you really need to take time for yourself.” I do little things to create space that is just for me. I get my nails done regularly and find myself in the company of people I can be intimate and free with. My sister friends are dope; they are my recharge. I love a massage, but some days it might just be a brownie and quiet time. I have to sit in it – I have a five-year-old, and there’s not a lot of alone time with a five-year-old. I find time for small moments – meditation, prayer with or without friends – everyday. Whether it’s a walk, reading The Atlantic or National Geographic, watching mindless reality television, I build it in every day. I take time to decompress and be with people who uplift me, encourage me, or sit in silence with me.
What advice would you offer other Black women trying to develop or amplify their voice and become self-advocates?
Listen to yourself and do that work. It’s a journey. Some of the benefit is you going through it and learning. So, while I want to offer advice, the journey matters. Trust ourselves and don’t denigrate or feel bad about intuition. It’s an amazing thing: I believe women of color, of the diaspora, have a spiritual connection in some way to all things. Honor that, be open to it and share it. Trust that who you are is enough and your gifts are things people and situations need. Who you are -- perfectly imperfect -- is the best you. The sooner you get to you, so much will make sense and you will have clarity navigating any path or space.
Have an amen corner – folks who are able to tell you the truth, especially as you rise up in leadership. Cultivate strong, honest relationships; they are super-duper critical. Know self and trust that. Have people who can support you whether they look like you or not.
I wish I would have told me this: Create stuff and stick with it. So many of us have ideas, whether it’s a women’s circle or a podcast. Bring them to life.