Several decades before she was a Washington Post 2025 Teacher of the Year, J. Lupton Simpson educator Kimberly Poole was a marketing major with dreams of a corporate career. But even then, she felt tugged toward a different calling.
“I was always teaching,” said Poole, a Simpson alumna herself. “I taught Sunday school, I taught swim lessons, I coached swim team—everything I did was about working with kids. But I kept saying, ‘I want to wear heels and carry a briefcase.’”
The real turning point came in the mid-1990s, during a conversation with a marketing executive. “He said, ‘How important is family to you?’ I told him, ‘God first, then family, and everything else will fall into place.’ He said, ‘Then I don’t think this is your best option.’”
That conversation helped clarify what she truly wanted. “I am a teacher at heart,” she said. “I love kids, I love relationships. Most teachers aren’t just teachers. They’re investors and relationship-builders, especially in middle school.
“When you're choosing to be a teacher, an educator, you're choosing to invest in students, not simply to share knowledge of a subject matter,” she continued. “And I think that is so important, the teachers that stick with kids. If I think back to who impacted us as we went through school, the teachers who impacted us the most were the ones that chose to invest in us, as opposed to simply sharing a lesson.”
Now in her third decade at Simpson in Leesburg, Poole is still investing in kids everyday and watching that investment pay off as her students go on to college, to jobs, and to having children of their own. It’s also earned accolades among her peers in the school system: before receiving her 2025 Washington Post Teacher of the Year honor, Poole was named Loudoun County Public Schools’ 2024 Teacher of the Year.
Even after 30 years in the classroom and having raised her own two kids, too, she still feels energized at the school. “I’m not tired of teaching,” she said. “The paperwork is the part that feels like work. The students? They’re a joy.”
The Middle School Moment
“Even elementary and high school teachers will go, ‘You chose middle school?’” she said, laughing. “But I’m like, ‘Yes, it’s the greatest place on earth.’ These kids are in between, and they need people who are positive.”
Her guiding philosophy has a straightforward starting point: kids want to be loved. “They want to feel joy,” she said. “They want that sense of peace when they’re at school. They need people to be patient with them. They want to show kindness and be good kids. And where they get all of that is through teachers who are giving them that gentleness, that grace, to be themselves, to learn to make mistakes, and have that compassionate redirection. You have to start by thinking, ‘What do these kids need? And how are we as teachers bringing that solution?'”
That kind of relationship-building starts small. “It can be as simple as remembering a kid had a soccer game and asking about it on Monday,” Poole explained.
It also means taking responsibility for one’s own actions, even as you hold students accountable for theirs. “I’ve had times where I handled a situation and thought, ‘Great job.’ And I’ve had others where I thought, ‘Kimberly, you need to circle back,’” she said. “Being willing to say, ‘Hey, I think we both could’ve handled that better’—that’s important.”
Investing in Students
That consistency, accountability, and a willingness to show them she values their perspectives form the foundation of trust—something Poole says has helped her earn students’ attention and respect.
“We have substitute teachers who’ve told me, ‘This is why they listen to you,’” she said. “It’s because they know my heart is theirs. From day one, they know I care.”
It also helps to address behavior with warmth rather than cold authority. “It can be connecting with a student who is struggling with their behavior, and instead of feeling frustrated with them, pausing, having that quiet conversation with them, and trying to understand what’s going on with them,” Poole said. “Sometimes they can't share exactly what it is, but you can have conversations around it, right? I try to respond with the knowledge that that behavior is coming from somewhere. How I choose to respond to a behavior that's not appropriate or that is disrespectful or that is pushing limits in some way says a lot about me.”
Even meting out consequences for bad behavior can become an opportunity for connection rather than only punishment. Poole points to a recent example where taking a less authoritative stance toward a student paid off. “A student had a problem in class, and I told her, ‘We’re going to eat lunch together tomorrow.’ Not detention—just the two of us, talking,” Poole said. “We figured out what happened, what we can do differently, and what I can do for her next time.”
Spending that kind of time, energy, and attention is vital to creating an environment that helps students mature, Poole feels.
“That’s my calling: to build those relationships,” she added. “I love walking the halls, calling kids by name, standing outside my door when it's time for them to come to class and greeting them. I think the teachers with the best relationships are the teachers who are focused on the kids and giving them attention.”
Preparing for the Leap
The transition to middle school is a “big leap” for both students and their parents, says Poole. Her first piece of advice: “Everybody take a deep breath. The more nervous parents get, the more it transfers to their kids.”
Luckily, schools are there to help. “Look for your school’s communication plan,” Poole advised. “Most schools have a newsletter or a website where a lot of information is pulled together. At Simpson, it’s the Mustang Messenger. It answers 875 million questions! Our principal, Dr. Tripp Di Nicola, is meticulous. Everything he can think of ends up in that newsletter.
Parents also can join kids at special events designed to familiarize them with a new school’s surroundings, the teachers, and staff. “Take advantage of summer intro programs,” Poole said. “Our ‘Stampede into Simpson’ gives rising sixth-graders a chance to see the building, meet teachers, and connect with kids from other schools. We also have a load-your-locker day. Normally, there's a little orientation, or a time when you get to come in and load your locker and walk to school, walk your schedule, you know, just kind of have that vibe, see friends, catch up on things. Those are all great opportunities to just kind of have that I'm ready. Here's the prep. Let's get excited. And the more excited for middle school that parents are, the more excited for middle school the students will be.”
"They know my heart is theirs. From day one, they know I care," says J. Lupton Simpson Middle School's sixth-grade teacher Kimberly Poole.
Four Ways to Ease the Middle School Transition
You can help your child thrive during the shift to middle school by staying calm, staying informed, and embracing the experience.
- Take a deep breath—your attitude sets the tone.
- Read the school’s newsletter or website for key info.
- Attend orientation programs and walk-through days.
- Encourage excitement about new friends and new routines.
These simple steps help both students and parents approach middle school with confidence and curiosity.