Some of the biggest challenges in teaching math aren’t about the numbers and operations themselves, but students’ attitudes toward them.
Getting students to think deeply about problems, persevere through difficult questions, and simply feel confident in math class can be tall hurdles in a subject that many children say makes them anxious.
Education Week spoke with three award-winning math teachers about how they try to lower these roadblocks in the math classroom.
All three—Jenna Stewart, Ashley Davis, and Charday Wilson—are recipients of the 2024-25 Milken Educator Award, a $25,000 cash prize for early- to mid-career teachers, principals, and other educators who have embraced innovative teaching practices and advanced student learning. The contest has run since 1987; Davis is the 3,000th awardee.
Read on to learn how these teachers build students’ conceptual understanding, navigate wide ranges of student ability, and work with colleagues to replicate promising practices.
Jenna Stewart
5th grade teacher, Longbranch Elementary School, Boone County schools, Ky.
When Jenna Stewart was a math student, she was a “kind of a nervous Nellie,” she said, worried about getting questions wrong.
Now, in the math classes she teaches, Stewart encourages her 5th graders to see mistakes not as evidence of failure, but as an opportunity to learn. It’s part of her broader goal to encourage deep thinking in her classroom.
Often, Stewart will pose one question to the class, asking students to work out the answer on a white board. When everyone finishes, students hold up their white boards to compare answers. There are always students who hesitate to share, she said, and immediately want to erase wrong answers. But Stewart stops them.
She has explained to her students: It’s better to know that you gave it “110 percent,” said you were confused and asked for help, and got the answer wrong, than to not try at all. After drilling that message again and again, Stewart said, “I usually see a mindset shift.”
Even when students have mastered the steps to complete a problem correctly, she pushes them to dive deeper into the concepts and relationships that underpin math. With her more advanced students, she offers enrichment activities that aim to develop further conceptual understanding—for example, asking students to write an explanation of how they solved a problem, using mathematical vocabulary.
Sometimes, she challenges them with logic puzzles that require abstract thinking, an activity that can initially cause some high-performers to “crumble,” Stewart said.
She wants them to push past that discomfort, so that when answers don’t come easily to them, they know what to do.
Ashley Davis
4th grade teacher, Central Intermediate School, Central Community school district, La.
Ashley Davis knows that 4th grade is a transition point for some big ideas in math.
It’s around this time that many of her students are learning how to represent core concepts of addition and subtraction in more abstract ways—instead of using counters or pictures, they’re mastering the skills involved in using the standard algorithms, like regrouping.
Still, not everyone is ready. Davis co-teaches in an inclusion classroom with a special education teacher. About half of their students have individualized education programs, or IEPs. Many of Davis’s special education students need additional practice with more concrete representation of operations. Throughout the day in small groups, “we go back to the basics,” she said.
In whole class time, though, Davis and her co-teacher have worked to develop methods that support their general education and special education students alike.
“Within the classroom setting, what I try to do is I teach the lesson as it’s intended to be taught,” she said. “But there’s no harm in also showing the concrete and pictorial methods, even when we’re trying to move to the abstract.”
In practice, this might mean having the whole class practice the same concept, but in different ways. One group might work on a subtraction problem with four-digit numbers, using the standard algorithm, while another might gradually work up to that point—first starting with two-digit numbers represented by blocks or counters.
Davis hopes all of her students feel that they’re on a level playing field, she said. “My goal is, if a visitor were to walk in, for them not to be able to tell which one is the special education teacher.”
Charday Wilson
Master teacher, Logansport High School, DeSoto Parish schools, La.
Charday Wilson wants math teachers to be able to learn from each other.
“If we stay in the classroom that we’re in, then we have the perspective from one classroom in the building,” she said.
At Logansport High School, which serves grades K-12 in Louisiana’s DeSoto Parish, Wilson facilitates educator observations between classrooms and professional learning communities so that teachers can try out practices that have worked well for their colleagues.
Through these conversations, educators at the school have discovered that they share a lot of the same challenges, Wilson said. One big issue that crosses upper elementary, middle, and high school grades is stamina—helping students develop the ability to persevere through multi-step word problems, for instance.
Another is showing their work. Many students think that being “smart” means having the ability to do math quickly, in their heads, Wilson said. But when students don’t show their thinking, it’s harder for teachers to address any misconceptions that can lead to wrong answers.
To address this, teachers have shared strategies for encouraging “visible thinking.” And schoolwide, teachers are promoting a new idea: that being “smart” isn’t just about getting the right answer, but being able to show all of the steps taken to get there.
Making that shift, Wilson said, “has been a game changer for us.”
