Interview with Monica Roberts, Executive Director of City Year Greater Boston

Posted September 5, 2023

We spoke with Monica Roberts, Senior Vice President and Executive Director of City Year Greater Boston. She explains how she found her role at City Year, her commitment to educational equity, and leadership lessons she’s learned along the way.

Monica Roberts: City Year’s mission is to advance educational equity by supporting students furthest from opportunity and to develop diverse leaders through national service who can work across lines of difference.

We do this work by recruiting young adults to serve in schools – ages 18 to 24 – and they work full time to help students stay on track for graduation and fully engage in their learning.

They are providing one-on-one and small group academic tutoring in E.L.A. and mathematics, providing social/emotional support and tutoring, peer mentorship, and then lastly, providing support around attendance, because if our young people are not in seats, they are not learning.

What brought you to City Year?

Monica: I have been in public education for probably 15 years or so, or education-related fields. I did not start off as an educator in a classroom. I started off in what we call central office, so working as part of the support structure that supports schools.

November 2021, I was approached about City Year, and one of the things that I did in my last role was I was responsible for partnerships in the school system and thinking about how do we equitably bring them in, but also having to make sure that they were having impact and measuring that impact on young people.

So, City Year I was very familiar with both as a Bostonian who came up through the Boston Public Schools and having experienced them in our community, but then as a district administrator and executive, being able to see the impact that City Year has had in our schools and on our young people – it was an easy sell for me.

What are the biggest challenges in public education right now?

Monica: If you think about what’s happening in public education, this is probably one of the most challenging and devastating periods in public education in recent history where students were out of school for a long time.

We know that black and brown students, students who have historically – been historically marginalized experienced less of academic growth. The opportunity and access gap has widened during that period.

School districts, educators everyone who’s working in public education is working incredibly hard. They are looking to solve for a number of challenges and support students who have experienced a lot of challenges that are outside of what we would typically want for public education, right?

I think our schools have become the place where we expect everything to be provided. That’s why they need programs like City Year, because there is work that needs to happen alongside, because they can’t be all things to all people.

And then the second piece for me is for us to remember that a lot of the challenges that our school systems face are reflective of the structures, the history, the policies in our society that reinforce inequities, right?

And so a school system alone cannot make changes, that part of what we have to be doing collectively is addressing the root causes that give way to that, to the inequities that we see and that we’re trying to solve for.

What leadership lessons have you learned in your career?

Monica: There are a few leadership lessons I learned in working just with some really strong leaders in public education.

One is to lead with transparency and honesty. I myself am not an ivory tower leader, so my entire staff down to the corps members who are in classrooms have access to me.

It’s important to me that that my leadership team is not, you know – we might, we have hierarchies for a reason, but that we’re accessible and approachable. It allows folks to understand who I am, it allows us to establish trust, but it also allows me to more easily galvanize folks and build ownership and move folks in a direction that we’re trying to move. So that’s one.

The second thing is most leaders, I have found, come in saying “I need to get rid of the team that’s there.” And that’s often because you want to come with your own people who you trust, you want your team. And what I’ve found is you need to take the time to understand how people got to where they are and to ask a different question. Not “we’re here, this is an awful place, we’re not where I think we should be as an organization.” But to pause and ask the question: “how and why did we get to where we are?” You understand what I’m saying?

And then to be able to do the additional work of listening to folks, because very often there are reasons for some of the challenges and gaps that you might see as a new leader coming in. That allows you to assess what you need to do, but also to assess the folks that are there and determine whether they can remain on as the team that you lead or whether you need to make shifts to your team.

And I think that’s really critical because when you come in, you don’t really know everything and you need those people to help ground you and help you understand the organization.