Colin Darling

My “How Might We” Question:
How might we help alumni discover ways to give back that align with their financial capacity while helping them see how their contributions directly support the transformative experiences that shaped their HTS education?

Introduction

When I started this Cohort 21 journey, I knew our school had untapped potential in our alumni community. But potential without a clear pathway to action is just hope. My challenge was to create multiple entry points for alumni to reconnect with HTS and understand that their support—at any level—directly fuels the transformative education we provide. This wasn’t about asking for big donations. It was about educating our community, shifting mindsets around legacy-building, and making it easy for alumni to say yes.

What We Did & The Impact

This year, my department launched three interconnected initiatives, each designed to meet alumni where they are:

The Giving Catalogue was our flagship project. We identified specific giving amounts within our Student Financial Assistance fund, ranging from something as tangible as a school store gift card or a monthly bus pass, all the way up to a full year’s tuition. This simple shift—moving from “please donate” to “your $50 funds a bus pass that helps a student get to school”—transforms giving from abstract to concrete. We’re still in the communications rollout phase, but the framework is in place and ready to scale.

The Alumni Journeys Wall became an unexpected community hub. Every two weeks, we update a campus screen to showcase what’s happening in our broader HTS community and why giving back matters. The response has been remarkable—people stop to read it, take photos, and reconnect with why HTS shaped them. It’s become a quiet but powerful reminder of our mission.

The Class Legacy Gift has been our biggest win. We asked Grade 12 students to contribute $20.26towardaclassgoalof$1,200. Not only did we surpass that goal—over 50% of the graduating class participated. This wasn’t just about fundraising. It was a cultural shift. These students are learning that education has a cost, that their school depends on community support, and that they can be part of that legacy. That’s transformative.

The evidence is clear: our alumni community is more engaged than ever. More alumni are attending events, reconnecting with their HTS roots, and—most importantly—beginning to see themselves as stakeholders in the school’s future.

What I Learned

This year taught me something crucial: it’s one thing to present giving opportunities; it’s another to be targeted, thoughtful, and consistent in how you meet people in their actual lives.

I was also surprised by who stepped up through the Class Legacy gift. Some students I thought might hesitate jumped in with both feet—a reminder that a school’s impact runs deeper than what we see on the surface. A student might not be the loudest voice in the hallway, but HTS shaped them profoundly. And that insight translates directly to alumni giving: it won’t just be the “keeners” from their student days who want to stay connected. Impact is personal and often invisible.

The biggest challenge was prioritizing this work within an already relentless events and programming cycle. But my colleagues supported every initiative with grace and answered countless questions about fund structures, budget codes, and the difference between restricted and unrestricted accounts. Coming into this role without formal fundraising training was initially daunting, but I learned that asking for help and building on existing systems creates win-win scenarios for everyone.

Resources to Share

While our Giving Catalogue was inspired by Crescent School’s original model (since removed from their website), everything else was built from the ground up for HTS’ unique community. I’m happy to share:

• Alumni Journeys screen content – the messaging and visuals we use to keep our community informed
• Grade 12 Class Legacy appeal – how we framed the ask to students
• Giving Catalogue framework – the categories, amounts, and thinking behind our tiered giving structure

If you’re working on similar initiatives, reach out—I’d love to share these resources and learn from your work too.

My Big Takeaway

Here’s what this year has taught me: Start small, but throw weight and effort behind that tiny snowball, because once it starts rolling, it can get super big.

The Alumni Journeys wall didn’t need to be elaborate. The Class Legacy gift didn’t need to be a massive ask. But because we showed up consistently, communicated thoughtfully, and believed in what we were building, they became catalysts for real change in how our community thinks about giving back and legacy-building.

My work has always been about education—educating our community, keeping them informed, and shifting their mindset around what it means to support an independent school. This year proved that easy wins, when executed with intention and consistency, create momentum that compounds over time.

Questions Still Unfolding

As I look ahead, I’m curious about how the concept of legacy-building lands differently across our alumni segments—young alumni navigating early careers, alumni in established professional lives, and retired alumni with different capacities and motivations. Understanding these nuances will help us be more targeted in our communications and outreach.

The next big step is developing a comprehensive alumni donor funnel with clear standard operating procedures that help us capture interest, assess capacity, and ultimately convert engagement into sustained giving. This isn’t about being transactional; it’s about building a system that honors each person’s unique relationship with HTS.

Reflections on Cohort 21

This Cohort experience has reinforced something I already believed: that meaningful change doesn’t require grand gestures. It requires clarity of purpose, consistency of effort, and faith that small actions, when aligned with community values, can reshape how people think and act.

As we continue to build HTS’s culture of giving and legacy-building, I’m carrying forward the lesson that our alumni—like our students—are shaped by HTS in ways both visible and invisible. Our job is to create the conditions for them to recognize that impact and choose to sustain it. That’s the real transformation.

The Eisenhower Matrix has a way of revealing uncomfortable truths. As I sorted my work into urgent versus important quadrants, a pattern emerged that I suspect many of us recognize: my urgent work rarely appears in my actual job description, while my most important work—the legacy-building, culture-shifting work—gets swept under the rug.

But here’s what surprised me most: the work that keeps calling to me isn’t just professional development. It’s personal completion.

The Gap That Demands Attention

At HTS, there’s a disconnect that’s been nagging at me. On one side, we have families and alumni who have “seen the light”—they understand the transformative power of an HTS education while they’re experiencing it. On the other side, we have those who never fully grasp the blessing they’ve received, or worse, never come to understand it at all.

The result? Families paying tuition without understanding where their investment goes. People who love HTS deeply but don’t know how to channel that love into lasting legacy.

What’s missing is education—not just about our status as a registered charity, but about the profound impact their contributions make. We’re missing the stories that make the invisible visible.

My Thread: Digital Storytelling for Cultural Transformation

Among all the interconnected pieces of this challenge, one thread pulls at me most strongly: creating digital storytelling that educates, empowers, and motivates donors to see themselves as change makers in the HTS community.

I envision a series of video testimonials—relatable, candid, and raw—that live both on our school’s social media and on the new donor wall we’re installing in the new year. These won’t be polished marketing pieces, but authentic conversations with current parents and alumni who can speak their unfiltered minds about why they give and how it helps our school grow.

Picture this: someone walking past our donor wall and suddenly hearing a real person’s authentic story about their journey from loving HTS to understanding how to channel that love into action. That moment of connection between digital story and physical space—that’s where transformation happens.

My Declaration of Intent

This work feels like the legacy I want to leave at HTS as an alum who acknowledges how much this school did for me. I want HTS to be a place where people don’t just think about the future of educational environments—they do something about it.

My commitment for this year is clear: I will build our capacity for digital storytelling that transforms culture. This month, I’ve started by identifying current parents that are alumni who volunteer and donate—those who are living the story right now, watching their own children benefit while actively contributing to that future.

This isn’t just about donor education. This is about completing my own circle of gratitude by helping others discover theirs. It’s about becoming the bridge between people’s love for HTS and their understanding of how to channel that love into lasting impact.

The urgent work will always be there, demanding attention. But the important work—the work that builds legacy and transforms culture—that’s where I’m choosing to focus my creative energy this year.

Because when someone watches one of these stories and thinks, “I want to be part of this legacy,” that moment of connection will honour everything HTS gave me by helping others discover everything they can give back.

That’s my thread. That’s my commitment. That’s how I’m choosing to make change this year.

UPDATE:

Heading into our second Cohort Session, the power that this kind of curated, visual content holds has never been more apparent to me. Recently, I stood up in front of our grade 12s and talked to them about legacy, something I’ve done every year when asking them to consider what kind of HTS alum they hope to be.

And in that presentation, we layered in a video from a graduate of last year’s class who was a recipient of financial aid. He was the type of kind, put together, model student who everyone gravitated towards and he agreed to speak candidly about not only what financial aid gave him at HTS, but also what he might have lost without it.

Now this video wasn’t edited, no name key graphic, no music. Nothing but a selfie video of a community member who was more than keen to, in his words, “do anything [we] need[ed]” of him to give back to the community he grew up in.

This doesn’t change my declaration of intent or the kind of output I hope to produce, but it might change some of the language around my “how might we” question. I think now it needs to acknowledge that everyone has a story, a connection, a thread to contribute to the cause. All you have to do is ask those that have a pulse on the community, those that have trust.

Because trust is everything in independent schools. Trust that we care and see each and every student for who they are and who they’re becoming. Trust that we are caretakers of all those that came before us (students, staff, parents) and the history they wrote. And most importantly in my case, trust that the time, treasure and talent our community decides to pour back into our community will be stewarded and invested back into the school in ways that maximize value for all involved.