In a previous piece on why schools must practice radical hospitality, I discussed why schools must intentionally create cultures of welcome and belonging.

I shared the alarming statistics about student loneliness and made the case that our schools should greet students with at least the same warmth as our favorite coffee shops.

But here's the truth: hospitality is just the beginning.

A warm welcome at the door matters immensely. Remembering a student's name, asking about their weekend, celebrating their birthday—these practices are essential.

But if we're honest, they're also relatively easy. They cost us little beyond a few moments of attention and genuine care.

The harder work—and the work that ultimately transforms student experience—is moving beyond initial hospitality to creating the kind of deep, lasting connections that sustain students through difficulty, failure, and struggle.

Here's what I've noticed: some of the schools that excel at hospitality still struggle with retention, engagement, and student wellbeing.

Students feel welcomed on day one but disconnected by day ninety.

Why? Because hospitality without depth becomes performance.

It's the difference between a hotel concierge who greets you warmly at check-in and a friend who sits with you when life gets hard.

Students don't just need to feel welcome.

They need to feel known.

They need relationships that persist beyond the good days, beyond their best performances, beyond their ability to meet our expectations.

Creating lasting connection requires a fundamentally different approach than practicing hospitality.

It demands we move from transactional interactions to transformational relationships.

Hospitality asks: How can I make you feel comfortable here?

Lasting connection asks: How can I understand who you really are?

This shift shows up in concrete ways.

Instead of just asking how the soccer game went, we remember that this student is struggling with a new coach and follow up weeks later about whether things improved.

Instead of celebrating the A on the test, we notice when a typically engaged student seems withdrawn and create space for them to share what's happening.

Lasting connection means we're paying attention not just to what students achieve but to who they're becoming.

It means we notice patterns, remember stories, and invest in understanding the full human in front of us.

Through years of working with schools, I've identified three essential pillars that move us beyond hospitality into genuine, sustaining connection.

Hospitality is often episodic—we show up warmly at designated moments.

Lasting connection requires showing up consistently across all seasons of a student's experience.

This means being present not just during the victories but during the valleys. When a student fails the exam they studied hard for. When they don't make the team. When their parents are divorcing. When they're struggling with depression or anxiety.

One of my favorite teachers, the Head of Academics at his school, is best known not for his brilliant erudition, but for his willingness to sit crosslegged on the ground listening to a student sharing the deep burdens of their life

Presence through difficulty communicates something hospitality alone cannot:

"I'm not here because you're performing well. I'm here because you matter, period."

Schools that create lasting connection build systems that ensure no student can fall through the cracks unnoticed.

Advisory programs, mentorship initiatives, and intentional check-in protocols all serve this purpose (you can see how we do this through daily mentoring at Odyssey Leadership Academy here).

But systems alone aren't enough—we need adults who genuinely show up, week after week, semester after semester.

Hospitality tends to be one-directional. The host gives; the guest receives. But lasting connection requires reciprocity—a willingness to be known even as we seek to know our students.

This doesn't mean oversharing or making students our therapists. It means appropriate vulnerability that humanizes us as educators. When we share our own struggles with learning, our failures, our questions, we create permission for students to show up authentically too.

I've watched classrooms transform when teachers admit they don't have all the answers, when they model learning from mistakes, when they acknowledge their own growth edges. Students stop performing and start being real.

I’ve often said, the most dangerous and vulnerable thing a teacher can say to a student is “I don’t know”…then follow it up with “so let’s find out together”

Connection deepens when students see us as whole people—not just authority figures or content experts, but fellow humans navigating complexity.

Perhaps counterintuitively, lasting connection requires us to actively work ourselves out of the center of students' lives. Hospitality can sometimes create dependency—students who rely on our affirmation, our direction, our validation.

True connection builds student agency. It equips young people with the tools, confidence, and self-understanding to navigate life without us. It means we're asking not "How can I solve this for you?" but "What do you need to solve this yourself? How can I support that?"

Schools that create lasting connection invest heavily in student voice and choice. They create structures where students lead, make decisions, experience consequences, and develop their own sense of competence and capability. (See how we do this through our Mastery Program at OLA).

When students know we believe in their capacity to handle difficulty, to make good choices, to recover from failure—that's when connection becomes transformational.

Moving beyond hospitality to lasting connection might look like:

The teacher who doesn't just celebrate when a struggling student finally passes but calls home to celebrate the effort they put in even when they fail. Who sees persistence, not just performance.

The administrator who builds into their schedule weekly lunch conversations with students—not the high achievers or the struggling students, but random students, learning their stories without agenda.

The counselor who doesn't just help students solve immediate problems but teaches them frameworks for decision-making, emotional regulation, and self-advocacy they'll use long after graduation.

The coach who has individual conversations with team members about what they're learning about themselves through sport, not just about athletic performance.

The school that creates structures where seniors mentor freshmen, where student councils have genuine authority over school culture decisions, where student feedback directly shapes policies and practices.

Moving beyond hospitality to lasting connection requires a fundamental culture shift in how schools operate.

It means we have to rethink:

How we measure success. If we only celebrate test scores and college acceptances, we signal that performance matters more than people. What if we also tracked how many meaningful adult-student relationships exist in our building? How many students report having an adult advocate they trust?

How we structure time. Lasting connection can't happen in five-minute passing periods. We need sustained time with students—whether through advisory, long-term projects, or redesigned schedules that prioritize relationship building.

How we hire and train. Are we selecting and developing educators who excel not just at content delivery but at genuine human connection? Are we giving teachers tools for having hard conversations, for understanding adolescent development, for building trust across difference?

How we define our work. If teachers see their job as covering curriculum rather than knowing students, connection will always be secondary. We need institutional clarity that relationship is not a "nice addition" to learning—it's the foundation.

This kind of connection is costly.

It requires more emotional energy than hospitality. And far more than passing out worksheets or giving a lecture

But my guess is, many of us are in education precisely because an educator connected with us, saw us, reached out to us, believed in us, made us feel seen and valued

While individual relationships matter immensely, lasting connection ultimately requires collective effort.

A student might have one great teacher, but if the rest of their experience feels disconnected and impersonal, that single relationship can't carry the full weight.

We need schools where connection is the norm, not the exception.

Where every adult takes responsibility for knowing students. Where the culture itself communicates belonging.

Students don’t need to be made to feel seen, heard, and valued in Algebra and then invisible in History class or shamed in P.E.

This means breaking down silos between departments, between grade levels, between curricular and extracurricular. It means cross-functional teams who know the same students and collaborate on supporting them.

It means whole-staff commitments to practices that prioritize relationship.

The work of fostering deep, meaning connections must be the central focus of what schools mean by education

Radical hospitality opened the door to reimagining how we welcome students.

Now the invitation is to go deeper—to build the kinds of relationships that sustain students not just through a school day but through the complexity of becoming human.

This work is harder than learning students' names or standing at the door with a smile.

It requires us to examine our own capacity for relationship, our biases about which students are "worth" investing in, our willingness to show up even when it's uncomfortable.

But I'm convinced it's the most important work we can do.

Because at the end of the day, students won't remember most of the content we taught.

They'll remember how we made them feel. They'll remember whether we saw them. Whether we stayed. Whether we believed in them even when they didn't believe in themselves.

That's the difference between hospitality and connection.

Hospitality says "You're welcome here." Connection says "You belong here, and I'm committed to walking with you while you figure out who you're becoming."

Our students deserve both. And they desperately need the latter.

The 2026 Flourishing School Leaders Cohort is gathering and this is the exact kind of thing we work out together

Whether you are a seasoned vet needing support navigating the coming technological changes to education, a brand new administrator still learning the ropes, or just feeling the weight and burn of leading a school…this community is for you!

Our first session meets on January 30th where we will discuss what it means to future proof education through meaning and mattering

Come join us!