As we head into a new school year, this is exactly the kind of episode I want school leaders to hear early. I sat in on Jason Craige Harris’s session at the LeadTeam Summit, where he broke down what it actually takes to build a strategy for culture that works, and I left that room energized in a way that stuck with me.

So when he joined us on the podcast, I wanted to go even deeper. Jason is a strategist, mediator, and mindfulness teacher who spends his time helping leaders navigate conflict and uncertainty without losing themselves in the process. We talk about what resilience actually requires, the difference between reacting to a moment and being ready for one, and how the small, consistent practices we build in private show up in how we lead in public.

In This Episode, We Discuss:

• Why “powering through” isn’t real resilience, and what actually builds it
• The balcony metaphor Jason uses to get perspective in the middle of conflict
• How naming an emotion can measurably calm your nervous system
• The two types of practices, routines and in-the-moment resets, that keep leaders grounded
• Why schools tend to swing between all transaction and all relational, and what the middle looks like
• The pre-action and post-action reviews Jason recommends before big decisions
• What separates teams that bounce back from teams that just survive

Every spring, schools pour weeks of staff time and thousands of dollars into a gala or auction because that’s what has always been done, even as the return on all that effort keeps shrinking. Barbara Barron joins us in this conversation to talk about why that model is running out of road and what a school might do instead if it actually let it go.

We also get into how many separate asks a family absorbs in a single school year before the annual fund even launches, why alumni giving looks so different for day schools than it does for boarding schools, and what it actually means to bring mindfulness into a fundraising conversation instead of running through a script.

In This Episode, We Discuss:

• The approach Barbara uses to get marketing, development, and admissions rowing in the same direction
• Why galas and auctions have some of the lowest ROI in school fundraising, and where she recommends looking instead
• How alumni giving realistically differs between day schools and boarding schools, and why that changes the strategy
• Why the months leading up to the annual fund can quietly work against it
• What actually gets a school’s email opened when families are drowning in their inbox
• Why being a little imperfect in donor communication builds more trust than a polished message
• How reframing interruptions as “the work” changes what a fundraising conversation feels like

Andrea Gribble manages social media for around 85 schools across the country, so she’s usually the first person to notice when something is shifting for school communicators. In this conversation, we get into the real tension a lot of schools are sitting with right now, how to protect students from deepfakes and misuse without disappearing from social media altogether, and how to keep posting consistently without leaning on AI so much that everything starts to look the same.

We also get into the pressure to make every post perfect before it goes out, and why that instinct is often the thing holding school marketers back the most. Andrea shares what has actually worked in her own small district, from a photo that was never supposed to perform well to a reel strategy that took almost no equipment and reached more people than her page’s follower count would suggest.

In This Episode, I Discuss:

• Why treating student photo permission as strictly in or out is easier to manage than a mix of exceptions
• The small details, like identifying names or labeled desks, that can quietly turn a simple photo into a privacy risk
• What is fueling parent concern about AI-generated content, and why an AI-made flyer can cost a school its branding
• Where AI can genuinely help with social media strategy, beyond just writing captions
• Why an imperfect, in-the-moment photo can outperform a planned, polished post
• The mindset shift behind “posted is better than perfect and unpublished”
• Why reels do not require a professional camera, a large following, or a complicated plan to get started