Opening Narrative
Most conversations about AI in the nonprofit sector are really about time.
How to save it. How to protect it. How to not fall behind.
That's worth talking about. But there's a more interesting question that rarely surfaces: When the administrative layer lightens — when the data entry, the reports, the routine communications get easier — what does your week actually look like? What does your team's week look like?
AI can absorb a significant portion of the transactional work. What it cannot do is decide what your culture stands for. It cannot navigate the tension between two strong-willed staff members. It cannot help a team member find meaning in work that has changed around them. It cannot hold a relationship.
Those are leadership tasks. They always were. AI doesn't eliminate them — it surfaces them. And for leaders who haven't had time to attend to that work, the opening is both a gift and a challenge.
Louis Diez has worked alongside more than 400 nonprofit teams navigating this shift. He doesn't approach this as a technologist. He approaches it as someone who has watched the sector grapple with what it actually means to bring AI into mission-driven work.
Join Louis and Gary for a conversation that goes beyond tool recommendations into the territory that matters most — what changes in how you lead people when the work around them changes.
"You can't disrupt a relationship. You can't move a conversation forward with just money and confidence. Relationships have to be lived."
— Louis Diez
Gary's Note
Leading through the shift.
Every conversation in this series has circled the same underlying question: What does it mean to lead well when the conditions around you are changing faster than your frameworks can keep up?
Christophe Kempkes (April) helped us think about holding coherence when systems fragment. Mary Ann Allison (May) helped us name the deep currents beneath the turbulence. Now Louis brings a question that is both immediate and consequential: When AI absorbs the transactional layer of your team's work, what gets revealed?
Louis holds the technology question and the leadership question at the same time. That's rarer than it should be. I think this conversation will leave you with something you can actually use.
— In gratitude, Gary
Who Belongs in This Room
You'll recognize yourself here.
- You lead a nonprofit team and you're somewhere between "experimenting with AI" and "not sure where to start"
- You're ready to think about what AI means for how your team works together, beyond personal productivity
- You care about organizational culture and how AI reshapes the human work around it
- You want a practitioner’s perspective—not vendor enthusiasm or technophobia
Session Format
A 75-minute facilitated conversation, not a presentation. Gary and Louis will offer a brief framing, and then the room takes over. Gary facilitates. Questions guide. Participants think together.
Live only. Not recorded for distribution. Limited to approximately 20 participants so everyone has a chance to actually speak.
The Connection
These conversations are expressions of the same conviction: that the most important leadership work happens between people, in conditions of trust. If this resonates, learn more about The Flourishing Framework →
