Redefining the Ladder: From Corporate Climb to Classroom Change – with Helen Chang

**Mike Montoya: (00:00:00)**
Welcome to The Stronger Podcast. Each week we have honest conversations with education and social impact leaders about their leadership and career journeys. We talk about their origins, inflection points, and the work that they're doing today. The conversations are honest, human, and practical. If you're here for real stories and real takeaways, you're in the right place. Let's jump in and let's get stronger together.

**Mike Montoya: (00:00:43)**
Today I'm with Helen Chan, the VP of Talent at the KIPP Foundation. She went from being an immigrant kid in Queens to corporate HR consulting and then hit a quarter-life reset to teach kindergarten. We talk about why joy and excellence can live together, how to hire leaders who reflect the kids they serve, and why measuring fewer, better things helps everyone win. Helen creates teams that make schools feel warm, safe, and alive. In our conversation, she connects her path from Teach For America to systems-level leadership to three big ideas: stay close to students, take care of the adults, and use data that serves people—not the other way around.

**Mike Montoya: (00:01:14)**
Before we dive into today's conversation, I want to give a quick shout out to podcastmatter.com. Their mission is to help impact-driven voices get the visibility they deserve. If you want to share your message with the world, check out their website in the show notes.

**Mike Montoya: (00:01:21)**
Well, I mean, let's just kind of jump into that a little bit. I've heard some of your story from my history with you, but in a couple of sentences, how did you end up in the ed space—and what are one or two anchors that have guided your work over many years?

**Helen Chan: (00:01:46)**
Yeah. I think we all started in that space because we were all students first, right? So the question is: how did I circle back to it?

I always tell everybody I had a quarter-life crisis, because in my 20s my first career wasn’t in education. Well—actually my very first job out of college was in education. Oh my goodness, I’m thinking so long ago.

My first job out of Brown University was for a small nonprofit called World Links.

**Mike Montoya: (00:02:22)**
Okay.

**Helen Chan: (00:02:23)**
It was a program that spun off from the World Bank at the time. They worked on international communications and technologies in developing countries, and I was their first business development associate. I was there for almost two years.

I was attracted to it because I’m an immigrant. I came to this country and always grew up thinking I wanted an international career.

**Mike Montoya: (00:02:49)**
Got it.

**Helen Chan: (00:02:50)**
We were helping schools in places like Macedonia, China, and Ghana figure out how to use the internet more productively in pedagogy. But what was actually happening was people would take the same lesson plans they’d put on a blackboard and instead put them on a PowerPoint and call it ICT—Information and Communications Technology—which wasn’t using the potential at all.

**Helen Chan: (00:03:26)**
There was also this big question: “How do we generate revenue? We’re going to spin off from the World Bank; we can’t rely on their funding. How do we keep doing this?” It felt cool—being a 20-something working with ministries of education in places like Jordan and China.

But I became disenchanted quickly. I realized I was working with a lot of U.S. aid agents in Gucci suits making plans about poor children in different countries. I thought I would be making the world a better place, but I was pushing papers.

I moved into corporate consulting two years later because a friend of a friend said it was a great way to use a liberal arts degree and make good money. I was a poor kid. My parents had mortgages I had to help pay, and I had student loans. I thought, “Maybe I should focus on making money.”

**Mike Montoya: (00:04:46)**
To earn an income. Make a living, right? Yeah.

**Helen Chan: (00:04:47)**
Yeah. I fell into human resources work—HR consulting—and after two to three years I realized I was climbing a ladder toward something I didn’t care about. That’s where the quarter-life crisis came in. What am I doing all this for?

**Helen Chan: (00:05:13)**
I wanted education because access to quality education changed my family’s trajectory. My mom was one of nine kids—super poor. She brought us over in 1987. I was the kid in NYC public schools who didn’t know up from down—no English, zero social capital. It sucked to feel lost.

**Helen Chan: (00:06:03)**
But I ended up at a magnet school, and then Brown University. Everything I have today is because of access to quality education—access my mom didn’t have. She didn’t even go to high school, yet she’s one of the smartest women I know. School taught me how to learn, to think critically. It gave me networks and social capital to reach what my parents couldn’t even imagine.

**Mike Montoya: (00:06:40)**
Yeah. They couldn’t picture that future because they never played in that space. That’s how I see my own story, too.

**Helen Chan: (00:07:07)**
Exactly. I remember as a kid someone asked, “What do you want to be when you grow up?” I said, “I think I want to be a secretary,” because my parents worked in factories. To me, going into an office with a white-collar shirt—that was making it.

**Mike Montoya: (00:07:37)**
Yeah.

**Helen Chan: (00:07:38)**
My bar was low because I didn’t know what was out there. Then I ended up in schools that revealed a bigger world. Education was a door opener. I could have done hunger relief or worked at the Red Cross, but I chose education because learning how to learn opened doors I never could have accessed otherwise.

**Helen Chan: (00:08:40)**
When I was 25 or 26, working 100-hour weeks, I had a moment of crisis. I quit my job and tried on a bunch of “outfits.” I took the GRE, taught Chinese lessons, became a photography intern, worked at the American History Museum, freelanced as a photographer—everything under the sun, including applying to Teach For America.

**Mike Montoya: (00:09:22)**
Yeah.

**Helen Chan: (00:09:23)**
That’s how I became a 28-year-old Teach For America **corps** member teaching kindergarten and first grade.

**Mike Montoya: (00:09:34)**
So you’d already been working four to six years, and then TFA jumped in front of you?

**Helen Chan: (00:09:44)**
I tell people I transitioned from consulting chief HR officers on recruiting and leadership development to working with five- and six-year-olds at a charter school in Los Angeles—and both clients don’t like to listen to you. A lot of skills transferred!

**Mike Montoya: (00:10:06)**
Kids are like, “Whatever.”

**Helen Chan: (00:10:06)**
Right. But that really started everything. I changed careers multiple times in my 20s, and once I became a TFA **corps** member in 2010, I haven’t worked outside education since.

**Mike Montoya: (00:10:25)**
So ~15 years, right?

**Helen Chan: (00:10:30)**
Yeah. And because of my HR/consulting background, Teach For America said, “Maybe you can help us recruit **corps** members—find other lost souls who realize they don’t want to work outside education.” I spent several years convincing people in the corporate sector to teach instead.

**Mike Montoya: (00:11:03)**
Got it.

**Helen Chan: (00:11:04)**
I fell into the talent space in the education sector.

**Mike Montoya: (00:11:09)**
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**Mike Montoya: (00:11:51)**
When you were recruiting folks, did you share your personal story? Was that part of your toolkit?

**Helen Chan: (00:12:05)**
I did. You share something about yourself to build a bridge. If people say yes to you as a recruiter, they’re already open and thinking.

**Mike Montoya: (00:12:09)**
Yeah.

**Helen Chan: (00:12:10)**
I appreciated having been born in Hong Kong, living in New York, teaching in LA, consulting in DC—being an immigrant, growing up poor, becoming a fluent English speaker. There are many ways to build a bridge: “This is how we’re similar, and why it’s helpful to talk.”

**Mike Montoya: (00:13:06)**
Yep.

**Helen Chan: (00:13:07)**
Recruiting is like sales, except I’m not selling coffee pots. I’m selling opportunities and dreams—the dream you already want.

**Mike Montoya: (00:13:34)**
I always think recruiting is like grabbing the little paper thread on a Hershey’s Kiss and unwrapping together—finding that hook and exploring it. People come with openness and potential, and we discover it together.

**Helen Chan: (00:14:30)**
Totally. The key is asking the right questions: What matters to you? Why now? I often opened with, “I had a quarter-life crisis.” I gave up a $90k consulting salary to become a K-1 teacher making ~$40k, and it was worth it. I had no business telling school leaders what to do without working in a school.

**Mike Montoya: (00:15:02)**
Yeah.

**Helen Chan: (00:15:03)**
People are motivated by different things—parents, upbringing, school as the only safe place. For me, school was sometimes safe and sometimes not.

**Mike Montoya: (00:15:43)**
Sure. Were you a misplaced child in a huge elementary school? What city?

**Helen Chan: (00:16:05)**
PS 107 in Queens, New York City. First day, they didn’t know I didn’t speak English. I remember bawling at the end of the day. They found the only person in the school who spoke my dialect, and she asked—in broken Chinese—what was wrong. I didn’t know anything. It was scary. I had my scariest moments in school and my best moments there.

**Helen Chan: (00:17:10)**
Teach For America gave me language for things I hadn’t named—racial inequity, oppression, DEI. I didn’t learn those in K–12 or even in my specific university courses. You realize access is inequitable, and even with access it may not be safe.

**Mike Montoya: (00:17:41)**
Right. Kids can get lost—even when we’re trying to create safety—especially without language. Isolation follows. That’s scary.

**Helen Chan: (00:18:16)**
It was. But school was also where I discovered books. I felt lucky—right place, right time, right people. What if you could systematize that luck? Codify practices so kids don’t depend on chance? There are still kids floundering.

**Mike Montoya: (00:19:15)**
Sure.

**Helen Chan: (00:19:16)**
I worked at Teach For America for almost 10 years before coming to the KIPP Foundation about five years ago. I had no reason to leave—TFA was education equity work. The reason I picked up the recruiter’s call was KIPP updated its mission to include the word “joy.” Children can have academic excellence and joy; they’re not mutually exclusive.

**Helen Chan: (00:19:47)**
I didn’t have consistent joy. I was driven by fear and the desire to make it better. I wanted to help build a system that didn’t instill more fear.

**Mike Montoya: (00:20:25)**
Yeah.

**Helen Chan: (00:20:26)**
That’s been my biggest shift in the last five years. You can be a whole human and learn and be excellent without making kids feel high stakes all the time. Early charter movement vibes were intense—if you didn’t have all kids passing, it felt punitive. When you’re working with children, you don’t want them constantly feeling the high stakes.

**Mike Montoya: (00:21:28)**
Right. Otherwise kids who aren’t A+ feel inadequate and spiral into comparison.

**Helen Chan: (00:22:36)**
There’s still a lot of that. Seeing KIPP’s mission centering joy made me want to be part of it—even if we stumble.

**Mike Montoya: (00:22:54)**
You can feel it in a school—the warmth—versus the sterile, overly perfected, march-in-lines vibe.

**Mike Montoya: (00:23:55)**
Kids need different things. I gravitate toward environments where you feel loved and safe, encouraged, and clear on the bar. You don’t feel alone.

**Helen Chan: (00:24:25)**
Some of our original schools were designed for safety—but only for certain children. To live into KIPP’s mission, you have to make it safe for everyone. That’s hard. I get impatient because it takes time.

**Mike Montoya: (00:24:55)**
What are one or two things you’re working on now that keep joy centered—especially since many of the people you recruit aren’t in schools day-to-day?

**Helen Chan: (00:25:31)**
I joined the KIPP Foundation to help set up Talent Acquisition. Since then, my scope has evolved—supporting teacher recruitment and helping define strong, data-driven decisions across the talent lifecycle. At the end of the day, the work is about people.

**Helen Chan: (00:26:42)**
People make program decisions that affect leaders and teachers. We want student-driven decisions, 100%. But you also have to take care of the adults who care for children. It’s the airplane oxygen mask: if adults can’t breathe, they can’t help kids.

**Helen Chan: (00:27:46)**
I’ve burned out a lot over the years. When you’re burned out, you make fearful decisions that make things harder for adults—and then for students. It sounds right to demand “90% proficiency,” but every classroom is different—undiagnosed learning disabilities, students multiple grade levels behind, co-teaching or not. Demanding the same thing everywhere can hurt adults and students, even with good intentions.

**Mike Montoya: (00:29:21)**
Sure.

**Helen Chan: (00:29:22)**
My job is to help talent thrive. If I can recruit people who understand the diversity of our students’ experiences—recognizing there’s no monolith—those people will make different decisions.

**Helen Chan: (00:30:17)**
Helping people thrive means hiring the right, diverse people and creating ecosystems where they belong. Clear goals, resources, and support. It’s not that different from what a teacher does.

**Mike Montoya: (00:30:52)**
Of course—similar work at different levels.

**Helen Chan: (00:30:57)**
In my kindergarten class, I ran small reading groups. You shouldn’t teach the same reading lesson to all 25 students when they’re at different levels. We sometimes do that in classrooms—and at work. We give blanket training and expect everyone to “get it” on the same timeline.

If you do talent right, you help recruit and support school leaders who model love—love begets more love.

**Mike Montoya: (00:31:40)**
Yeah.

**Helen Chan: (00:31:42)**
We’re becoming more data-driven at KIPP. You have to measure what matters. If you’re not measuring it, you can’t fix it. There’s power there—but also danger if you measure the wrong things.

**Mike Montoya: (00:32:20)**
Right—focus on fewer things more carefully so people aren’t overwhelmed.

**Helen Chan: (00:33:30)**
I like the direction KIPP is moving—being data-driven, defining what to measure, and holding ourselves accountable. It’s important and potentially high stakes.

**Mike Montoya: (00:33:57)**
Well-intentioned, diligent people—especially with diverse thought—can get close to the target.

**Helen Chan: (00:34:25)**
Our student population is 95%+ Black and Brown. No workforce I’ve seen mirrors that. And yet I already work in one of the most diverse organizations I’ve been in.

**Mike Montoya: (00:34:50)**
There’s still a big gap between leaders/teachers and kids—everywhere, not just at KIPP.

**Helen Chan: (00:35:10)**
Yes. I want people who understand my kids’ upbringing making decisions that affect them. Our diversity targets help. So does having a clear definition of what it means to thrive—progress toward goals, flourishing, leveraging strengths.

**Helen Chan: (00:35:54)**
I used to manage like “everyone needs to get excellent at everything.” Today I manage more like a conductor.

**Mike Montoya: (00:36:20)**
Your symphony.

**Helen Chan: (00:36:23)**
Exactly. You’re great at data analysis. You’re great at office politics. You’re great at relationships. You’re great at curriculum design. Everyone’s willing to learn, but the hardest thing to learn is being a good teammate.

**Helen Chan: (00:37:25)**
Build projects with the right mix so people’s strengths are optimized. Know each other well enough to ask for help. Be responsive and give constructive feedback. You don’t need A+ in every aspect—just A+ in your lane and be an excellent teammate. The best learning environments do that. Doing it at scale is hard, which is why KIPP’s charge takes coordination and strong team-building muscles.

**Mike Montoya: (00:38:26)**
That’s the work of leaders and managers—build cultures where teams cooperate and co-contribute across teams.

**Mike Montoya: (00:39:00)**
We have a thing called “unified ownership.” We’re in the same boat, rowing together—the coxswain steering and coaching. We’ve been practicing that.

**Mike Montoya: (00:39:41)**
It’s a massive skill to help people develop cooperative, co-contributing habits so it feels normal—and they learn from each other.

**Helen Chan: (00:39:56)**
It will take collective power to drive change. Education is fascinating: at the most fundamental level it’s classroom learning, but it’s also part of government and subject to state policy.

**Mike Montoya: (00:40:31)**
Policy decisions steer resources, for sure.

**Helen Chan: (00:40:37)**
If you go in wanting to run the best single school, you won’t move the needle systemically. KIPP has a growth/advocacy team tracking what’s happening in DC. Our schools are funded by enrollment and tax dollars—that’s about policy, not just need. You can be the best teacher and still not move systems without policy shifts.

**Helen Chan: (00:41:27)**
When I was a 28-year-old TFA **corps** member, I thought I’d become the best teacher in the world. That was…naive.

**Mike Montoya: (00:41:45)**
Youthful!

**Helen Chan: (00:41:49)**
There are many ways to leverage your strengths—frontline teaching, research, politics. So many entry points to contribute.

**Helen Chan: (00:42:27)**
That’s how I recruited for years: “There are so many things you can do.”

**Mike Montoya: (00:42:33)**
Exactly—some people think systemically and at scale; others are tactical and deeply engaging with kids. Both matter in the ecosystem.

**Mike Montoya: (00:43:24)**
We’re mostly trying to go in the same direction, though sometimes forces work against us—different orientations about outcomes and the “right” way to raise a kid.

**Mike Montoya: (00:43:55)**
The U.S. is diverse—leaders, experiences, immigrant stories. That’s a benefit and a challenge for schooling.

**Helen Chan: (00:44:48)**
My take: you need proximity. You can’t design for the margins if you’ve never been at the margins or don’t know anyone there. Otherwise people design for the middle.

**Mike Montoya: (00:45:24)**
Yeah.

**Helen Chan: (00:45:26)**
How you get proximity is your choice. I became a teacher. Others join City Year. Others volunteer. There’s no right way. But I’ve noticed proximity often determines whether you’re still in the work 10 years later or gone after three to four.

**Mike Montoya: (00:46:20)**
When you get close to kids and their experience, you find that thread and apply it more broadly.

**Helen Chan: (00:46:56)**
Yes—and now you’re making me want chocolate.

**Mike Montoya: (00:46:59)**
Let’s step out and help listeners experience you as a human. What matters to you personally? What books are you reading—fun, interesting, different?

**Helen Chan: (00:47:40)**
Unfortunately for my wallet, I am a reader. My reading is eclectic—are you sure you want to ask?

**Mike Montoya:**
You can share as much as you want.

**Helen Chan: (00:48:11)**
This summer I read three great books. One was a Murakami novel, *After Dark*. Are you familiar with him?

**Mike Montoya: (00:48:19)**
I’m not. Tell me.

**Helen Chan: (00:48:21)**
Have you seen a Dalí painting? Imagine that, but as a novel—surrealism, creative, disconnected from reality in interesting ways. I also read *Lexicon* by Max Barry.

**Mike Montoya: (00:49:03)**
Okay.

**Helen Chan: (00:49:04)**
It’s about using words as persuasion to convince people to do things. It’s fiction—someone dies in the first chapter and you don’t know why. A mix of sci-fi and a bit academic with the history of words. A thriller—total page turner.

**Mike Montoya: (00:49:43)**
Sounds fun—intellectually stimulating fiction with creative thinking.

**Helen Chan: (00:50:04)**
Yes—both fiction. I went through a non-fiction phase—Gladwell, Adam Grant, all of it—but right now I appreciate good fiction. As a kid, school was sometimes escapism, but it also brought me books.

**Helen Chan: (00:50:50)**
Once my English was strong enough to read quickly, I realized everyone else could go on exotic summer vacations, but I could go anywhere through books.

**Helen Chan: (00:51:15)**
Fiction transports you into realities created by someone else.

**Mike Montoya: (00:51:29)**
Quick pause to talk about Books That Matter. Every entrepreneur or leader needs a book that elevates their business, builds credibility, and makes an impact. If you’ve got more money than time, a ghostwriter can help. If you’ve got more time than money, a great book coach can guide you. If you’ve already written a draft, they can shepherd you through publishing. Head to booksthatmatter.org for custom support on your book idea or manuscript.

**Mike Montoya: (00:52:33)**
Fiction can create whole universes. I like historical fiction—anchored in reality at a time I didn’t live through.

**Helen Chan: (00:52:50)**
Have you read *Homegoing*?

**Mike Montoya: (00:52:55)**
I haven’t.

**Helen Chan: (00:52:59)**
It’s an intergenerational story of two African families that diverge—historical fiction, rich history, strong character development. It’s a tearjerker, though. I’m leaning into joy right now.

**Mike Montoya: (00:53:23)**
Okay.

**Helen Chan: (00:53:27)**
That’s a theme. I joined KIPP because they focused on creating joy. I grew up being hard on myself—and around people who were hard on themselves.

**Mike Montoya: (00:53:51)**
High demand.

**Helen Chan: (00:53:54)**
Yes. I hope my kids—and our students—can be great and feel whole and joyful without needing to escape into a book to find it.

**Mike Montoya: (00:54:20)**
Be more present. And since your work can be heavy and high-stakes, reading can also rest the brain.

**Helen Chan: (00:55:20)**
And creative outlets help. I do a lot of that.

**Mike Montoya: (00:55:25)**
I think I saw you painting—maybe with your family?

**Helen Chan: (00:55:36)**
This one here—I painted it as a portrait. Can you see it?

**Mike Montoya: (00:55:42)**
Yes. It’s beautiful.

**Helen Chan: (00:55:46)**
I had a few art classes as a kid, then my mom couldn’t afford more. Drawing is something anyone can do. I picked it up again recently. I’m very pro-internet, pro-YouTube—you can learn so much.

**Mike Montoya: (00:56:32)**
I knew you’d say YouTube!

**Helen Chan: (00:56:44)**
Totally. I learned how acrylic behaves vs. oil vs. watercolor. There’s a science to portraiture, and I can get lost for hours. It helps with the heaviness of the work.

**Helen Chan: (00:57:16)**
This is the stuff getting defunded in schools. I love literacy and understand the importance of math, and some of our schools still prioritize arts and sports, but those are often first to go.

**Mike Montoya: (00:57:43)**
They get pushed aside for longer math and reading blocks to catch kids up.

**Helen Chan: (00:57:55)**
Or we say we need “more learning time,” but every moment is learning time. I’m learning talking to you. How you define and measure things matters. It pains me that I didn’t get many creative opportunities growing up, so I’m giving myself license now.

**Mike Montoya: (00:58:40)**
You’re returning to something you had to pause for financial reasons—and survival.

**Helen Chan: (00:58:53)**
Also, creativity helps people make better decisions. If you stay in one lane too long, you get stuck.

**Mike Montoya: (00:59:08)**
Left brain and right brain need to cross. When schools focus only on STEM, we forget arts and embodiment. Those intersections help decision-making.

**Mike Montoya: (00:59:45)**
There’s data about exercise and cognition—move your body or your brain gets crunchy.

**Helen Chan: (01:00:46)**
Exactly. Some kids can sit still; many can’t. The world is more interdisciplinary now. Everyone’s using AI. Technical skills that mattered 10–15 years ago may be obsolete. We need people who think critically. AI can produce things that look good but feel hollow without human design and empathy.

**Mike Montoya: (01:01:40)**
Right—the margins and empathy aren’t baked in.

**Helen Chan: (01:01:54)**
I heard on a podcast that art degrees may be more in demand. My husband learned basic coding in an hour and made a site—but it looked horrible. Wrong visuals in the wrong places. We don’t know the future, but the ability to learn well and think critically is evergreen.

**Mike Montoya: (01:03:13)**
We hope! If AI has come this far in a few years, imagine 10 or 20.

**Mike Montoya: (01:03:42)**
Helen, I want to be respectful of your time. One last question: if you could tell your younger self something—any age—what would you say?

**Helen Chan: (01:04:15)**
It’s okay to go for it. There are so many chances to reinvent yourself.

**Mike Montoya: (01:04:31)**
Okay. We’ll end there.

**Mike Montoya: (01:04:39)**
Helen’s reminder lands clearly: great schools start with great adults. Put the oxygen mask on the team and then on the kids. Hire for lived experience. Measure what matters. Design for the margins so everyone rises.

Thanks to Helen for her commitment and care.

Thanks for joining us today. To find out about other podcasts that matter, visit podcastthatmatter.org.

Thanks for listening to The Stronger Podcast.

If this conversation inspired you, follow the show and share it with someone on a journey to become a happier, healthier version of themselves. Links and resources are in the show notes. See you next Thursday, 9:00 a.m. Eastern time. Have a great day and stay strong.