1I: Adaptive Solutions, Technical Moves: How Check-Ins Address Complex Leadership Challenges

The University of Chicago’s Network for College Success has partnered with 14–18 Chicago high schools for over a decade, helping principals and leadership teams strengthen collaboration to support student success. Recently, the network introduced adaptive 1:1 check-ins between principals and their direct reports. This routine clarifies roles, reduces work duplication, strengthens accountability, and creates consistent opportunities for reciprocal feedback. As principals adopt this approach, schools will see clearer roles, improved initiative follow-through, stronger staff engagement, and healthier learning cultures that advance student outcomes. In this interactive workshop, participants will examine case studies from two large Chicago high schools, explore research, and practice tools such as a “Buckets of Work” mapping protocol, leaving with strategies to apply adaptive check-ins in their own leadership contexts. Note: This Summit session also invites attendees from the Deeper Learning Conference to participate. At Deeper Learning 2026 (DL26), a global community of educators, visionaries, and change-makers unites to reimagine what's possible in education. The Deeper Learning Conference features immersive and transformative learning experiences that inspire participants to design and lead with purpose, creativity, and joy. In 2026, we're bringing together the powerful Deeper Learning and Improvement communities through select crossover sessions, culminating in a joint closing keynote. You are invited to dive deeper and make new connections at Summit 2026. Check out our Summit and DL26 comparison to learn more.