Meet Colorado’s ‘Oscars of Teaching’ winner

A man with short dark hair and wearing a blue t-shirt, waves his arms in the air while celebrating in a school gym with the bleachers full of people in the background.
Caleb Flores, a teacher at Greeley West High School, won the prestigious Milken Educator Award in December 2023. (Image Courtesy of Milken Family Foundation)
How do teachers captivate their students? Here, in a feature we call How I Teach, we ask great educators how they approach their jobs.

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Teacher Caleb Flores knew a top-secret assembly was planned at his northern Colorado high school. The principal wanted the building to look flawless and for students to be on their best behavior. Flores wondered if an important government official was visiting on that December day.

Turns out that the visiting dignitaries, speeches, and gym full of cheering students were for him. Flores, who teaches English language development and language arts at Greeley West High School, had won a Milken Educator Award — also known as the” Oscars of Teaching.” The award, which is for early and mid-career teachers, comes with a $25,000 cash prize.

“I was speechless,” said Flores, who was the only Colorado teacher to win the award this year. “The entire day was phenomenal and something that I will always treasure.”

Flores, who was raised in Greeley and attended college there, talked to Chalkbeat about how coaching youth football changed his career path, why he began incorporating music into his lessons, and how a student’s request for a letter of reference humbled him.

This interview has been lightly edited for length and clarity.

Was there a moment when you decided to become a teacher?

As a college student, I was a business marketing major at the University of Northern Colorado. Throughout my sophomore and junior years, I was a little league football coach with my college roommate. We had a blast getting to know the kids that we coached, and coaching was always the highlight of my week. I made the decision in my junior year to switch my major to English to pursue a career in teaching.

The moment that made me decide to pursue culturally and linguistically diverse teaching was after college. Since I switched majors as a junior, I could not graduate with a teaching license. I began my career in Greeley-Evans District 6 working as a migrant advocate. My job involved supporting migrant families and students, most of them English learners, to make it to graduation. I fell in love with the role and saw that population as the subject area that I wanted to teach. I then applied to be an English language development teacher at Greeley West and enrolled in an alternative licensure program to receive my teaching license while working my first year.

How did your own experience in school influence your approach to teaching?

My parents had me and my siblings when they were young, so they did not have the opportunity to pursue a college education until we were older. My dad received his degree when I was in high school, and my mom and I graduated college on the same day. My parents always told us that they expected us to attend college right after high school, so I took school very seriously growing up.

I was always a talkative student in class, but I was fortunate enough to have teachers who were patient with me and held me to a high standard. These high expectations were crucial to me as a student to be able to perform well enough to be able to receive a scholarship to attend college. My parents and teachers were able to change the trajectory of my and my siblings’ education. (Both of my siblings also graduated from college.) This is something that I know firsthand can influence my students. I hold my students to a high standard and communicate with their families often to encourage them to perform well enough in high school to, hopefully, have the chance to pursue post-secondary education.

Tell us about a favorite lesson to teach. Where did the idea come from?

As an English 9 teacher, we incorporate students’ culture within our lessons so that students can see themselves within our classroom and our instruction. The idea for my favorite lesson came from a 9th grade student curriculum advisory committee. They wanted to incorporate music within our poetry unit — specifically, music that represented them.

One of my favorite poems that we annotate is a Spanish song called “Corrido de Juanito” by Calibre 50. The song is a first-person narrative describing the perspective of an immigrant to the United States named Juanito. The song is entirely in Spanish (we don’t provide a translation at first), so it makes my Spanish-speaking students the experts for the lesson. After annotating the song, students dispersed into small groups to discuss what they interpreted from the song and the themes it presented. After discussions, students do a comparative analysis project based on a song of their own choice and the themes that it presents. We’ve had amazing conversations and projects that students created from this unit.

What are your go-to strategies for connecting with new students, whether they’re new to your building or new to the country?

When they enroll in my class, we begin with an enrollment meeting with the student and family. This is such a crucial step because it helps ease the family’s apprehensions about enrolling in a school in the U.S. We make sure that the students understand their schedule, provide them with any school supplies that they need, and give them and their families a tour of the school.

When students arrive in my language development class, I always introduce them and involve them in the collaborative classroom activity for the day to encourage them to get to know their new classmates. Allowing this time for students to cooperate has been so crucial to building a sense of community within my class.

As a mentor to new teachers, what advice do you share?

Teaching is not meant to be done in isolation; get to know the staff and community of your school and learn from the experts who have found success. That definitely helped me learn and grow when I first started.

I would also encourage new teachers to embrace the diverse student populations. For me, it was teaching language learners. They may not be the easiest students to educate. They come with gaps in their learning, emotional traumas, and many responsibilities outside of school. However, they are some of the most thoughtful, inspirational, and fulfilling students that I have had the pleasure of teaching. Learning how to properly educate language learners made me a better teacher.

Caleb Flores, a teacher at Greeley West High School and a recent recipient of the Milken Educator Award, center in the black robe, poses for a photo with students at their graduation. (Image Courtesy of Caleb Flores)

Tell us about a memorable time — good or bad — when contact with a student’s family changed your perspective or approach.

One of the most memorable moments came from a student who was a part of my Language Development class. He had asked me if I would be willing to write a character reference letter for him. After calling his uncle, his legal guardian, I found out that the letter was to be presented to a judge because the student was facing an order for deportation. I knew that this was a pivotal moment for the student and his family, so we went and contacted several of his teachers to get letters of recommendation on his behalf. My wife and I attended court with him and saw firsthand the legal battles and additional barriers that my students face just to receive an education. My student was allowed to stay. It was a great moment. He is a junior now and is on track for graduation.

I was humbled that my student and his family trusted me to share what was going on, and it reminded me how important it is to be accessible to my students.

What was the biggest misconception that you brought to teaching?

My biggest misconception was about classroom management. I went into teaching thinking that one had to be stern, tough, and unkind to run an effective classroom. I came to find out that the opposite was true; most students did not respond to teachers who yelled. My style of classroom management is more around building relationships. I still hold students accountable and have high expectations for them, but when students misbehave or distract others, I can address it without embarrassing or disrespecting them.

What are you reading for enjoyment?

I just finished the book “Brown Enough” by Christopher Rivas. It’s a personal memoir and a social commentary about being brown in the U.S. and how to find one’s identity, sense of belonging, and place within it.

Ann Schimke is a senior reporter at Chalkbeat, covering early childhood issues. Contact Ann at

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