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From 5th Grade Teacher to CEO

By Meital Caplan
June 19, 2019

When OneGoal CEO Melissa Connelly reunited with her former student and OneGoal Alumna Diamond Delay, it initially felt like no time had passed as they settled into the mentor-mentee relationship developed long ago. They first met in 2007 when Melissa taught Diamond’s fifth-grade class at Bronzeville Lighthouse Elementary School in Chicago and have stayed in touch since. In the intimate interview they recently conducted, they recalled the life experiences that led them to today. The conversation has been cut down for length.

Diamond: I remember you never wanted me to say “I can’t do it.” And when I cried, it didn’t phase you. A lot of teachers in Bronzeville would see me cry and say “ok, just leave her alone in the corner.” But you? You said, “We’re going to sit here. We’re going to go over this.” I’m glad that you did that though.

Melissa: Why do you think that I did that?

Diamond: Because I feel like you believed in me when no one else did. You didn’t let me blame my IEP [Individualized Education Program, a tool for special education] as the reason that I didn’t like to learn. You didn’t let me do that. You saw something in me that I didn’t see in fifth grade.

Melissa: You know what’s so crazy about that, Diamond? I had a teacher, her name was Mrs. Jeter, who changed my life, and whenever people ask about her I say that exact sentence. She saw something in me that I didn’t see in me.

Diamond: Yes! Now that you’re CEO of a national nonprofit, how did your experiences in the Bronzeville classroom impact this new role you’re going to take on?

Melissa: I mean the reality is my experience as a teacher has changed every part of who I am. I became a teacher because I was a sociology major in college and was learning about racial inequity and gender inequity and the ways in which our system fails people who look like you and me. And I realized that I could do something about that by being in schools and by doing exactly what you just said: helping people see the brilliance that they have in themselves — their natural gifts, their natural intelligence and never letting them hear any other message than, “It’s possible for you.” And I will say, teaching was one of the hardest things I’ve ever done. And I’m at a place now where I actually have the ability to support 13,000 students across the country and ensure that every student has some sort of experience like we had.

Diamond: Yeah, this world is going to change.

Melissa: I remember one of my favorite days. I was being really hard on everyone, and I remember one of the students being like, “Mrs. Connelly, why are you being so hard on us?”

Diamond: I remember that; you cried because we didn’t really understand …

Melissa: I said, “I think it’s unfair that you’re so brilliant, with so much potential, and there’s a real risk that it’ll go underutilized if we don’t get this right as a community and as a school.” And I talked about inequity and what it’s like to experience inequity as Black students on the South Side of Chicago. And I remember one student raised their hand and said, “But I thought racism ended in the ‘50s.” That moment was really beautiful because I realized two things. First, I needed to have more conversations with my students about why I lead the way I do. And I needed for you to know that I was going to be strict, and I was going to be tough, and I was going to introduce you to really hard material all the time, but it was really from a place of love. And then the other important lesson that I needed to realize then was that at the end of the day, you all were still kids, right? And that was more important than anything else.

Diamond: Oh gosh, yeah.

Melissa: More important than your grades or test scores was that you actually felt cared for and that became a part of my job. Honestly, as I think about now becoming CEO and leading an organization of 170+ people, I will feel like I’ve done my job well when the people here feel really cared for because that’s what’s going to allow them to show up for others.

Diamond: You’re a good listener so I feel like you’re not going to have any issues with that. I feel like you’ve helped me become the soon-to-be Purdue graduate I am today. How would you say you’ve impacted my life?

Melissa: Goodness, I feel like I should ask you that question. That’s hard for me to answer.

Diamond: You want me to answer it?

Melissa: Yes, why don’t you take a shot and then I’ll share my version.

Diamond: You never gave up on me. Today I had to write a paper about the person who impacted me the most, and it was you. No one else ever took the time to understand why I didn’t like school or try to understand my life outside of school. Everyone else just saw my IEP. And I feel like you didn’t judge me, you know?

Melissa: You know, it’s funny, I’ll never forget how we were doing small group reading and you were a beautiful reader. You didn’t believe that you were, but you were. And we had this moment where you had read three paragraphs and then stopped, and I asked you to tell me what happened and you were able to articulate a level of depth and understanding of the text that most kids in our class wouldn’t have. You really internalized it. And I remember in that moment seeing your strengths more than anything else and figuring out, “Ok, if we can figure out how to leverage this strength, then that’s going to unlock everything for you, including your belief in yourself.”

Diamond: Definitely.

Melissa: It impacted me too, though. Because I think it’s way too easy as not just as a teacher but honestly as a human to sort of categorize people as “pretty/ugly,” “smart/dumb,” “right/wrong,”, right? Very black and white. And I think it takes real curiosity and effort and belief in others to seek out the brilliance in everyone. Because it’s there, it’s always there, but you have to actually look. And you actually have to do the work. Thankfully, you made that fairly easy.

Diamond: While taking on this new role as CEO, what is one big goal or mindset that you have in place?

Melissa: I think there are two words that come to mind for me, and they are core values of our organization. They are “People” and “Impact,” and I think they’re interconnected. When I was deciding whether to take this job, I realized that I would be basically accepting this job for the remainder of my children’s childhood. So if you imagine that I’m in this job for the next 10 years, by the end Ashland will be 21 and Addae will be 19. And so I had to really reflect on why would it be worth it to miss so much of their childhood, to give so much of my life to this work, and this mission.

Melissa: I realized it was because I actually think at OneGoal we have the opportunity to influence what the postsecondary planning process looks like from start to finish in all high schools across the country. When I look at how we are innovating and taking some of the best practices that we’ve learned over the last 10 years, I think we can have a very real impact, especially for students who are the least likely to get that kind of support: students of color, students from low-income urban and rural areas, etc. So I think about impact, and at the end of the day that’s what drives me, that’s what motivates me. I mean you know me, I was probably one of the most goal-driven people I’m sure you’ve ever met.

Diamond: Yes.

Melissa: But I also have just learned, that none of that matters if people aren’t fully engaged in their work, if people feel like this work is being done to them. I mean, you know, a big part of what made us successful in the classroom was that it wasn’t my success, it was our success. Right? I really have learned that it takes a community of people coming together and feeling a shared sense of belonging, a shared sense of direction, to accomplish major goals. I think I have a responsibility in this position to do that and do it well.

Diamond: Yeah, and not everybody cares about what they do. I feel like people enter careers just for the money and not for the passion.

Melissa: As someone who wants to be a social worker and who is currently interning at a prison, you’ve found, it sounds like, a career or path for you that is much more about passion.

Diamond: Yeah. I really like talking to people and connecting with them. Every time I talk to a prisoner, they want to know, “you’re young, so why are you telling me what to do?” and I have to tell them, “It’s because I see myself. I could have been like you, but I’m not.” And a lot of people told me, “You can’t connect with them on a personal level because they’re going to think you’re friends.” And I’m like, “Some people need friends. Some people need that person to talk to.” Building that trust helps them stay out of trouble. They don’t want to come back and see you again explaining the same story. They want to see you out in the street and say, “I knew you and you did this for me.” Like how I see you.

Melissa: It’s so good that you’re entering that profession with that mindset because I truly believe that for people who are in professions that are mission-driven or about helping others, I think they learn the hard way that if you don’t actually express real care and interest in who that person is and what they want for themselves, it doesn’t matter how smart you are, it doesn’t matter how good you are at your job, they’re not going to want the help or support from you.

Diamond: Exactly. I feel like your background also matters so you can figure out how you connect.

Melissa: I will say it’s been really humbling and beautiful to see how many of my former students and how many current OneGoal students are just excited to see a Black woman as a CEO of a major organization.

Diamond: When I saw the news, I was like “I know her! This is not happening right now!” Because being CEO is so big Mrs. Connelly, it’s so so big. And to see your name on that shows you’re doing good things.

Melissa: Well, you can and will, too. There’s nothing about me that is different or special. It’s been about my passion, and my commitment, and doing what I love. And that’s something anybody can do if they make the right choices and keep good people around you.

Diamond: That’s true. Now that you’re in this position, what is one or more things you wish you could change about educational programs being offered in schools?

Melissa: There are a lot of things I would change. I mean for one, I would love for us to much more holistically think about what it means for a student to be successful. I would love to see us actually define success of a school year as yes, academic achievement, but also, how do your students feel about themselves? Are they dreaming bigger?

Melissa: I also think there should be better training for teachers, specifically on working in a way that’s developmentally appropriate for students but also culturally relevant. Because if people are missing the beauty and the differences between each student, then they’re not going to feel seen. And I think the last thing is we have to redesign different pathways to career. I think we have to actually take into account that when you are 17 or 18 years old and sent off into this world, the system that is receiving you, typically on the higher education side, is not prepared to support you adequately. And so I think we have to do better on the secondary and postsecondary side to make sure there are actually very clear, with hopefully significantly less barriers, pathways to get you to where you want to be. Because otherwise we’re making empty promises.

Melissa: So as I move to try to deliver on these promises as CEO of OneGoal, do you have any advice for me?

Diamond: Stay the same. Remain a down-to-earth and caring person. Because I know some things, like being CEO, can change you, and it’s like you forget who you are. Just be yourself.

Melissa: Thank you, that’s really good advice. I will take it.

Diamond: What advice do you have for me?

Melissa: Don’t ever question what you’re capable of. And start to think less about proving other people wrong and instead doing right by you. Set your own goals and crush them because they’re what you care about most, not because somebody else said you couldn’t do it. And recognize that you can’t carry other people’s baggage. A lot of people’s doubts in you are coming from their own shortcomings and society’s shortcomings, not yours. And you owe it to yourself to not carry that burden.

Diamond: Thank you.

Melissa: You’re too smart for that. Your future is too bright.