SHOW NOTES
GUEST INFO
Episode Guest:
Missy Couch, Founder & CEO of CheckBox Pro
Website:
EPISODE SUMMARY
On Episode #59 of The Charter School Insider Podcast, host Daniel Casselli sits down with Missy Couch, Founder & CEO of Checkbox Pro LLC, to discuss one of the most pressing challenges in charter school leadership: time.
Missy shares how Checkbox Pro helps school leaders reclaim their schedules, avoid burnout, and refocus on the work that truly moves their schools forward. From practical tips on delegation and boundaries to maximizing technology without letting it take over your life, this episode is packed with strategies to help executives lead effectively and sustainably.
Whether you're a founding school leader juggling it all or part of a growing network managing multiple campuses, this episode will show you what’s possible when you gain back control of your time—and your sanity.
EPISODE TAKEAWAYS
The cost of being busy: How endless meetings and admin tasks drain leaders’ energy and impact school culture, academics, and fundraising efforts.
Delegation strategies that work: Practical advice to help leaders prioritize what truly matters and let go of tasks that don’t.
Time-blocking and boundaries: Why scheduling think time, using calendar tools, and creating no-email zones are essential for long-term success.
Technology as a double-edged sword: Tips on using tools like G Suite, AI, and project management software without letting tech run your day.
Sustainable leadership practices: How leaders can prevent burnout, empower their teams, and model a healthy work-life balance
RESOURCES
Checkbox Pro Series Podcast - interviews experts in the field of education to offer tools, tips, and insights to make the life of a charter school leader even more sustainable.
CHAPTERS
00:00 Background and Overview of Prospect Schools
04:18 Enrollment Culture and Challenges
09:20 Identifying Systemic Issues in Enrollment
13:48 Operationalizing Enrollment Strategies
20:50 Engaging Stakeholders for Buy-In
27:16 Navigating Challenges in Change Management
32:24 Key Takeaways for Future Leaders
ABOUT OUR GUEST
Missy Couch is the Founder & CEO of CheckBoxPro. With over a decade of experience in school operations and administration, Missy has seen the tension school leaders face every day. It's the question, "how can I do the work that will make a lasting impact when I spend all day putting out fires?" That's why she founded CheckBox Pro. Missy uses her gifts of organization and prioritization to help school leaders reign in their workloads and re-focus on what matters most, impacting students. She lives in Austin, Texas, with her husband and two daughters.
ABOUT OUR HOST
Daniel Casselli is a life-long learner whose passion for education has driven his professional endeavors. He is a former classroom teacher and youth ministry director whose entrepreneurial spirit landed him in the world of education technology. At EVERFI Inc., Daniel helped run the business development efforts for EVERFI’s Financial Education Program and the company was eventually sold to Blackbaud for $750M in 2021. Shortly before EVERFI’s acquisition, Daniel joined Class Technologies as one of the earliest sales hires and went on to lead K12 Enterprise Sales and helped the company land its first 100+ K12 customers across public, charter, and private schools. Daniel brings his unique experiences to BuyQ where he is focused on growth, operational excellence, business strategy, and client satisfaction. He is a graduate of Grove City College where he studied Religion and History.
You can listen to Charter School Insider: Lessons from the Nation's Top Charter School Operators on your favorite podcasting platform...