20 Conversations, 20 Lessons — What I’ve Learned from School Leaders on The Little Wins Podcast
Team Letter | October 20, 2025
Happy Monday, Alpaca Team!
WOW — what a fun milestone today — our 20th Little Wins Podcast episode is live!
We started this podcast as an experiment, with a goal of connecting to more school and district leaders across the country, building a community of culture-focused educators, and getting the positive narrative of education out into the world. I’m going to be honest here — I wasn’t sure if it would work, if we’d be good at it, or if it was the right move for us as a company. After all, I thought, “it’s not our core business.”
Well, as it turns out — listening to teachers IS our core business.
From Alpaca Pulse to our resource library, to the celebrations we design for schools, it all starts with listening to educators to understand how they’re doing, what’s going well, and what they need.
What I’ve found from every single interview for the podcast is that I learn something new, build new datapoints, understand the role of principal or superintendent more closely, and see new ways to connect the dots.
So! I put together a list of my top lessons from the first 20 episodes. Ready!? Here we go:
Here are twenty lessons these incredible leaders have reminded me.
1. Culture is every choice.
“In a small school, culture isn’t a side project—it’s part of how we do everything.”
— Sarah Harless: Joy is Contagious
Culture isn’t something we manage on Fridays or as part of the Sunshine Committee—it’s woven into every hallway conversation, every smile, every morning greeting.
2. Relationships are the real work
“Our school is a place where people want to be.”
— Jeff Dock, The Win is in the Relationship
Ah! I love this. Imagine what happens when students, staff, and families want to be in your building each and every day. Belonging isn’t a by-product; it’s the heartbeat of a healthy school.
3. Lead with purpose, not position
“So long as I am working in service to other people, I am exactly where I need to be.”
— Gus Carter: Culture isn’t a poster on the wall
The best leaders don’t chase titles—they center themselves in service. I love Gus’s focus on working in service to his teams. It came through in absolutely every part of the interview.
4. Every day is a chance to win with kids
“I look to win the day with kids. It’s more of a mindset than a checklist.”
— Evan Hecker: “Passion shapes the team”
Little celebrations compound. Joy is the most renewable energy source in education.
5. Build trust before systems
“We started what we called Wing Pals… that’s how we built connection again.”
— Alison Canter: Culture that outlasts the leader
People commit to each other before they commit to initiatives. I loved Alison’s example of how she used a simple program to build connection among her staff.
6. Invite families into the story
“We want parents to feel like they can come in and have real conversations with us.”
— Jennifer Rosenbloom: Leading with Purpose and Positivity
Families don’t just visit strong schools—they help build them. Jennifer’s approach to building her new school involves families every step of the way. I can’t wait to see how her school emerges.
7. Recognition rituals fuel joy
“We have a crystal apple the staff selects weekly. It’s our way of saying, ‘We see you.’”
— Samantha Sebestik: Little things make a big difference
A few heartfelt words of recognition can move a whole team forward, and a little ritual goes a long way! I love to hear each of the rituals and traditions our guests have in their buildings.
8. Wellbeing starts with honesty
“We don’t realize how much emotional labor we’re carrying until we stop long enough to breathe.”
— Dr. Luke Beall: Give Teams the Opportunity to Flourish
Sometimes, guests will say things that just floor me! Naming the hard things gives educators permission to rest, reset, and utlimately… stay.
9. Community connection multiplies impact
“The doors are open. We love coming to school—and that makes parents love coming too.”
— Alison Canter: Culture that outlasts the leader
When schools feel like homes, families become partners in culture.
10. Never lose sight of what it means to be a learner.
“I took the Africa geography quiz with students. I went to class, I learned the material, and I took it seriously.”
— Troy Hopkins: “Is there a better way?”
When purpose is clear, the noise quiets.
11. Positivity is contagious
“We have a lot of positive people. It’s kind of contagious.”
— Sheila Taylor: “We Built a Family, Not Just a School”
Positivity isn’t naïve—it’s strategic. Gratitude multiplies the momentum of that positivity!
12. Student voice matters
“Phones away, bell to bell. Once we embraced it, our students started embracing it. Now, we’re seeing the benefits as a school community.”
— Dr. Jessica Sonntag: “Calm, Safe, Enthusiastic.”
I have LOVED hearing the ways that schools and districts engage their students in the work of building their culture. Countless examples — and each of them a repeatable little win. When students help create the environment, they protect it fiercely.
13. Stay connected to why you lead
“I’m coming back to teaching [from being a principal] because I truly believe in what we’re building here. I moved across the country for it.”
— Lindsay Pietrzak: Joy is the strategy
Sustaining culture takes belief—not just in students, but in the mission and the leader. Hearing Lindsay’s story about returning to the classroom was one of my favorite days — and when I got to meet Lindsay’s new principal a couple of weeks later, I GOT IT — great leaders and great cultures can make all the difference.
14. Go to the teams you don’t know!
“My tendency is to hang out with the science department because I love them—but leadership means showing up for everyone.”
— Jeff Dock, The Win is in the Relationship
Jeff illuminated for me a great lesson in going beyond your comfort zone to know and meet the people on your team that you might not have as much in common with.
15. Clear is Kind
“I think Brene Brown said it best: Clear is Kind.”
— Dr. Jeffrey Collier: “We call it Saginawesome.”
Clarity is everything when it comes to feedback, culture, and team dynamics. Jeffrey reminded me how much I love this concept, and SO many other leaders echoed their favorite leadership tips from their favorite books, podcast, and mentors. I have a running list of the books they’re reading, and I’m working my way through it.
16. Communities of leaders creates strength in numbers
“Principals need circles too. You can’t hold all that weight alone—it will crush you.”
— Amber Henderson: You Can’t Pour from an Empty Cup
We all need the communities and circles that build us up. Amber’s lessons on taking care of your self and each other resonated with me deeply.
17. Anchor culture in inclusion
“In our first year, we tried to embed multicultural books in every classroom.”
— Samantha Sebestik: Little things make a big difference
Simple ideas to change culture — it’s what this thing is all about. Representation tells every student, you belong here.
18. Leadership takes curiosity
“One of the things you learn as a building leader is to ask more questions than you answer.”
— Jordan Stuhan: Connection is the Curriculum
YES!! Curiosity opens doors that authority alone never could.
19. Mindset > Checklists
“I look to win the day with kids. It’s more of a mindset than a checklist.”
— Evan Hecker: “Passion shapes the team”
I love the way our guests think less about WHAT they should do and more about HOW they should work. Mindsets over checklists, every day.
20. Love you all.
“I end every email, every announcement, and every chance I get to speak to our school with three words: Love you all. I used to get a lot of pushback for it. But it’s how I feel and I think that matters.”
— Gus Carter: Culture isn’t a poster on the wall
This was the first (and not last) moment in a Little Wins interview when I cried! I loved this story so much, and I think about it every day.
That’s the full list! Please take an opportunity to listen to these amazing leaders — I promise you will learn so much.
I went in to this podcast experiment hoping to better understand our customers. The unexpected result is that I think it’s changing me — in ALL the best ways — as a leader.
LET’S KEEP GOING!