Growth Mindset & Humility: I’ve shared my commitment to life-long learning and feedback throughout my responses to these questions. I receive feedback almost daily from folks across the organization. I view it as a gift. The day I stop receiving this feedback, and/or stop approaching it with humility and care, is the day my leadership is no longer viable.

We are living in the Renaissance of Work. Just like great artists know that an empty canvas can become anything, great leaders know that an entire organization — and the people inside it — can become anything, too. Master Artists and Mastering the Art of Leadership draw from the same source: creation. In this series, we’ll meet masters who are creating the future of work and painting a portrait of lasting leadership. As part of this series, we had the pleasure of interviewing Heather Jenkins.

Heather Jenkins is the Chief Executive Officer. Prior to joining The Literacy Lab, she was the Chief People & Equity Officer at uAspire where she was responsible for ensuring that uAspire’s people, equity and organizational culture work is done with a people-first mindset to drive retention, inclusivity and sustainability. Heather has two decades of experience working for equity and access in education including: teacher and administrator at the K-12 level; non-profit leader; diversity and equity consultant for secondary and postsecondary institutions; public and private school college readiness education consultant; and a mentor to students of color and economically marginalized youth. She has a BA in psychology, an MS in education, and a Ph.D. in sociology of education. She is the proud mother of two young women, one in college and one in graduate school.

Thank you for joining us. Our readers would enjoy discovering something interesting about you. What are you in the middle of right now that you’re excited about personally or professionally?

Personally: My oldest daughter, who is a 3rd grade teacher, is getting married to a thoroughly wonderful man this summer. I am so grateful to be able to share this experience with them and the rest of our family. And, I am one step closer to having grandbabies to love and spoil, which makes me very happy.

Professionally: We have launched our first ever strategic plan as an organization this year at The Literacy Lab. The first step in the process is an internal gap analysis and an external market analysis. We are starting to review the data with our consultant and I’m incredibly excited about how this learning will shape the future of our work and deepen our impact for those we serve.

We all get by with a little help from our friends. Who is the leader that has influenced you the most, and how?

I would say Bob Giannino, who was my boss at uAspire. As CEO Bob really dug into understanding his identities and worked to lift up other leaders. As his Chief of Staff, I learned a great deal, primarily because he trusted me to use my prior knowledge, lived experience, and best judgment to own and drive the bodies of work for which I was responsible. I learned a lot about infrastructure, human resources, operations and general leadership in this role. It is really Bob’s faith in me that led me to believe in myself in a way I did not prior to working with him.

Sometimes our biggest mistakes lead to our biggest discoveries. What’s the biggest mistake you’ve made as a leader, and what did you discover as a result?

Things that have not gone as planned or truly failed in some way have been the most important places for growth and discovery throughout my career. One that is top of mind came with my first professional role, starting in 2001. I was overseeing a diversity, equity, and inclusion program at a predominantly white, affluent private school, while serving as a liaison for families of color at the school. When I started, I was young and found myself in a room of much older white men, including the head of the school and some board members, who gave me a list of resources and activities that were effective at other similar schools and directed me to start implementing them. I remember having a feeling that this may not be the best way to launch this work. But, I deferred to them. The first two years, despite making important connections with students, were a disaster. There was significant backlash from white students and parents and a lack of buy-in from the majority faculty, with our emphasis on racial awareness and equity. And, students of color, namely black students, stopped wanting to participate in the school-wide activities, and likely lost some faith and trust in me. During this time I was immersing myself in workshops and conferences to gain important content knowledge. A theme emerged — assessing the culture of the school or organization systematically and using the data to build a roadmap for DEI work. At the end of my second year, I convinced my boss to allow me to spend year three collecting and analyzing data rather than doing more activities. Sharing this data with the full community, gathering their thoughts and perspectives, and then using this to define what we did and how we did it in years 4 and 5 was a game-changer. I learned the importance of data and evaluation and the importance of building the context and the foundation for any work, particularly work that brings about significant change. I learned the importance of involving people in building out the plan to generate buy-in, investment and ownership (and to be truly equitable and inclusive). And, I started to listen to my inner voice and trust her more. These are all things I strive to keep top of mind every day in my leadership role at The Literacy Lab.

How has your definition of leadership changed or evolved over time? What does it mean to be a leader now?

I think my core tenets of leadership are quite similar to very early in my career, with some important revisions as I’ve worked in different spaces. Starting as a teacher, my leadership has always been very people-first and leading with an ethic of care. Middle schoolers require you to be your authentic self and show value for who they are in order for you to develop a teaching and learning relationship. When I started working more with adults, I saw this as highly transferable — who doesn’t want this? As mentioned earlier, data and evaluation and DEI have also been core tenets of how I think and behave. What these tenets mean and how I enact them has changed with different roles I’ve taken on — being people-first as a teacher, as a program director and as a CEO look different because my immediate stakeholder groups are different and the scope of my work is different. How I enact these has also changed with the feedback I’ve received over time. I collect a lot of feedback on my performance and the outcomes of my work. I make a concerted effort to course correct or completely change what I’m doing or how I’m doing it based on thematic feedback on my areas for growth.

A few learnings on what it means to be a leader now, particularly in my role:

  1. Embrace a both/and mindset. I must show care for people, remain humble, and be open and proximate and I must set clear expectations and accountability measures for myself and my team. I must be focused on driving our impact and investing in our programming work on the front end and focused on our infrastructure and the systems that drive The Literacy Lab’s work on the back end. I must be strong and present internally and externally. I must invest resources back into the organization and maintain financial sustainability. I think earlier in my career a lot of these were painted as mutually exclusive. I now know them to be complementary and interconnected.
  2. Embrace change and uncertainty. If the world has taught us anything over the past three years it is that we will not know what is coming our way in the next 12 months, even the next 6. We need to have plans, of course, but they must be adaptive and we must be flexible.
  3. Never waiver on your values. It is very easy to lose sight of our values in the face of uncertainty, turmoil, crises, pressure and challenges. This is the time when we need to hold our values closer and tighter.

Success is as often as much about what we stop as what we start. What is one legacy leadership behavior you stopped because you discovered it was no longer valuable or relevant?

While I am just as data informed as ever, I no longer feel an artificial need to have a certain, arbitrary amount of information before taking action. I used to spend a lot more time looking for one more piece of information that I likely believed would reduce the uncertainty of a given outcome. That wasn’t true and I wasted a lot of time in the process, and annoyed people who were looking to for clarity and decisiveness. I remember seeking feedback, analyzing it, checking it with folks, and then going back for more feedback, rinse and repeat. I do not feel the need to do that anymore as I learned that it did not make any decision any better. What actually proved to be true is that one of the best ways to improve decision-making is to approach data and input with an equity lens on the front end, make a decision and then pulse check the effectiveness of that decision, rinse and repeat.

What is one lasting leadership behavior you started or are cultivating because you believe it is valuable or relevant?

Honestly, the first thing that comes to mind here is believing in and trusting myself. As a woman of color who has not had a linear path to the CEO role, my career has been filled with moments, or episodes, where I did not fully believe in my strength and capabilities and did not fully trust in what I believed or knew. Age and experience have helped me to really lean into my knowledge, expertise, and lived experience to lead. I check things with folks who are my thought partners, of course. But I stand in my leadership now in a way I never have before. I have learned to embrace my most courageous self. It is rather liberating.

What advice would you offer to other leaders who are stuck in past playbooks and patterns and may be having a hard time letting go of what made them successful in the past?

This is such a great question. Lean into your most adaptive, life-longing learning self. Each time we face something new or different, we have to ask what we need to let go of and what we need to adopt to meet the moment. We need to put our egos aside and really lean into what we do not know with curiosity. In my mind, there is simply no other way to continue growing as a leader. And, if we do not grow, our organizations will be stale and stagnant. It is not about us, it is about the work and the stakeholders who depend on the work, whether, in our case, that is staff, Tutors, Fellows or students. We also need to continually ask if we are doing the very best on behalf of the internal and external people connected to the organization, and be ready for the answer to be no. We must maintain an ethical commitment to meet that “no” with openness, humility, and creativity.

Many of our readers can relate to the challenge of leading people for the first time. What advice would you offer to new and emerging leaders?

Find a great coach or mentor and make sure you have the leadership team required to do the work that is needed. You cannot lean into all of the things I’ve mentioned without having both of these in place. I did not have a mentor or coach (at least formally, consistently) in the first two years of my tenure. It hurt me, my leadership, and my leadership team. I am so proud of all that we accomplished, and we accomplished a lot, but there would have been less bumps and bruises with strong, consistent guidance for me as CEO.

Based on your experience or research, what are the top five traits effective leaders exemplify now? Please share a story or an example for each.

I like to think of these in complementary pairs — this has served me well over time.

  1. Empathy & Equity: Whether we are in a for profit or a nonprofit, the people are the work. If we do not show authentic, consistent value for who they are and what is important to them, we will not succeed. Further, we must ensure that those most impacted by whatever we are working on have their voices and perspectives centered in decision-making. The Literacy Lab has nothing to offer our students, schools and communities without taking care of our staff, Tutors and Fellows. This is why we are making investments in things like pay equity and improving our benefits, all of which are based on feedback and data.
  2. Growth Mindset & Humility: I’ve shared my commitment to life-long learning and feedback throughout my responses to these questions. I receive feedback almost daily from folks across the organization. I view it as a gift. The day I stop receiving this feedback, and/or stop approaching it with humility and care, is the day my leadership is no longer viable.
  3. Adaptivity & Accountability: I spoke earlier about embracing uncertainty. This is simply a must. To do this we need to lean into adaptive thinking and problem solving. This is not easy, and, as such we must ensure we have strong accountability measures for how we think, behave and decide. It is very easy to slip into more tactical, either/or thinking and behaving, unless we are holding ourselves accountable and pushing through the discomfort that often comes with being adaptive. The reality is, this must start with senior most leaders. We must talk openly about this, model this for the organization, and have honest conversation when we fall short.
  4. Stability & Security: With the world being uncertain and unpredictable, my team needs to feel stability and security in how I lead. I can only breed commitment to trying new things and letting go of “the way we’ve always done things”, or ask people to step way outside of their comfort zones if I provide a safe, secure, stable work culture and structure. Of course, some of this is about ensuring that we are financially sustainable and that we have strong results in our work. It is also about how I show up, day after day, the way I live our values, and the support I provide others leaders who also must do this consistently. At the end of the day, it is faith and trust in leadership that foster and maintain stability and security more than anything else.
  5. Courage & Creativity: I believe that doing all of these well, consistently, requires a significant amount of courage and creativity. Leading has never been easy or straight forward, and it has become less so over time. We are often called upon to act without all the information or clarity we would like (and others would like for us) to have. We are often asked to take bold steps without knowing whether or not they are going to work. We are asked to approach our mistakes with humility and curiosity. This is the reality of leadership. It is the courage and creativity to lean into these other four mindsets that will set us and our organizations up for success.

American Basketball Coach John Wooden said, “Make each day your masterpiece.” How do you embody that quote? We welcome a story or example.

My team hears me say this just about every day… I am excited to be here doing this work. I wake up each morning looking forward to whatever the day brings, whether that is good news or bad, success or setbacks. Everything that happens is part of the process of our growth and development as an organization, and part of making me a better leader. I start each day with the belief that I will learn at least one new thing and the goal of having a positive impact on at least one person. I will never control most of what happens, but I can certainly control my mindset and my approach.

What is the legacy you aspire to leave as a leader?

Well, I plan to have this role at The Literacy Lab be my last before I retire. I have big dreams for this amazing organization. I certainly hope part of my legacy is seeing transformational, positive, systemic change in the communities we work with, and for the Tutors and Fellows, staff and anyone else who works with our students, schools, and communities in the future of the organization. In order for this to be true, I need to leave a legacy of caring, compassionate, courageous, connected leadership. People connected to the organization in different ways will say I know her, like really know her, and she really knows me. People will cite examples of how I’ve shown care for who they are and what they bring. People will talk about all of the pilots and experiments we tried and how I approached those with courage and humility. People will cite examples of how I worked to live my values and our values, and how I responded with gratitude when I received feedback that I fell short. If I am able to do these things, among others, I will consider my tenure at The Literacy Lab successful and will feel proud of the ways in which I lead with and through our team.

How can our readers connect with you to continue the conversation?

It is certainly my hope that my stories and perspectives resonate with readers. Anyone looking to connect can reach me via email at [email protected].

Thank you for giving us the opportunity to experience a leadership master at work. We wish you continued success and good health!