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A City Education: Mentoring Is Key to Student Success

Developing meaningful relationships with students helps improve their grades and their confidence.


In our A City Education series, City Year corps members share their experiences working as tutors and mentors in schools in hopes of closing the opportunity gap and ending the dropout crisis.

Growing up, I was constantly surrounded by adults who would take the time to encourage me either through their words, their actions, or a combination of the two. At the time, I truly didn't know how blessed I was to have individuals recognize my potential and most importantly, make efforts so that I could recognize it too. However long those people were involved in my life, each served as a mentor.


It wasn't until last year during my first year of service with City Year Chicago that I was able to understand how important mentors are in a young person’s development and how fortunate I am to have had so many. In understanding my purpose last year as a “near-peer mentor”, I valued my role and would do everything I could to develop meaningful relationships with my students.

One student who I was able to develop such a relationship with is Kevin Perez who I met while serving at Kelvyn Park High School in Chicago's Hermosa community.

I worked closely with an English teacher at the school and in the beginning of the year, Kevin was a source of disruption during last period. He was the class clown who took pride in getting his classmates off task, which also caused him to get below average grades. One of City Year’s strategies to transform distracting behavior into positive behavior is to meet with students during lunch on leadership development. When it was time to decide which students would join me during my leadership lunches, I knew I wanted to invite Kevin.

When I first started having my leadership lunches, Kevin was the student who had something funny to say in response to any discussion question asked. He refused to seriously participate. However, I didn’t give up. I continued to have conversations with Kevin in the classroom, in the halls, and during our leadership lunches. I continued to work with Kevin not only on his leadership development but also on his grades as well.

Slowly but surely, Kevin began to make a change.

Now instead of me having to remind him when we were meeting for leadership lunches, he would see me during Morning Greeting and would say, "You’re picking us up during lunch today, right?"

Kevin became my biggest cheerleader when it came to motivating the other guys in our leadership lunches. Similarly, Kevin’s performance in the classroom began to improve. He would raise his hand, volunteer to assist in the classroom, and would even help other students who didn’t understand what was going on in class. This change in behavior also encouraged Kevin to focus on raising his grades.

On the last day of school, I held it together all day. However, when Kevin thanked me for pushing him throughout the year and gave me a hug I lost it—I cried.

To this day, I still keep in contact with Kevin.

Due to the relationship we developed last year, Kevin and I were asked to speak about our experience at City Year Chicago’s Women’s Leadership Breakfast hosted by Deloitte in December. The annual event is an opportunity for influential women to get together over food and learn more about City Year Chicago.

Kevin was still extremely nervous the day of the event. As I had done the previous year when Kevin was anxious about how he would perform on a test or quiz, I tried to refocus him on being confident in his ability instead, which in turn caused me to completely forget that I too was nervous.

I was the first to speak and confidently delivered a speech about my experience with City Year Chicago and more specifically my relationship with Kevin. As soon as Kevin reached the microphone, his confidence began to shine as he delivered a humorous and heart-felt speech that completely won over his audience. Tickled by his wit yet touched by his authenticity, Kevin received nothing but praise for his speech.

Understanding how far Kevin has come and witnessing him in action that day made me extremely proud and honored to know that I was able to play a part in helping him discover his potential. He is now a sophomore and getting good grades.

Serving with City Year has allowed me to work with amazing students like Kevin who need that extra push and need to know that there's someone in their corner who won't let them give up.

Photo of Deb DeHaas, Vice Chairman, Central Region Managing Partner and Chief Inclusion Officer for Deloitte, Kevin Perez, and Meghann Estrada courtesy of City Year Chicago


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