CheckBox Pro Series

Missy Couch
  • 5.0 (9)
  • EDUCATION

CheckBox Pro founder, Missy Couch, 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.

  1. 51: Where Education Meets Healthcare

    4D AGO

    51: Where Education Meets Healthcare

    In this episode of the CheckBox Pro Series, Missy sits down with Kristy Beam, Founder of the Academy for Innovation in Medicine (AIM), for an honest and energizing conversation about the realities of building a school from the ground up. Kristy shares her unexpected journey into education, from a young mom searching for a stable career to a longtime teacher and district leader who ultimately felt called to build something different. After years of seeing the same challenges persist in traditional systems, she began asking a bold question. What if we designed a new system instead?  That question led to AIM, a 6–12 career immersion school focused on healthcare pathways. Kristy explains how the model blends early college, STEM, and real-world work experiences to give students earlier exposure to careers and clearer postsecondary options. With a growing healthcare shortage and increasing expectations for hands-on experience, AIM is designed to help students graduate with both direction and opportunity.  The conversation also dives into the realities of planning year. Kristy shares what it feels like to move from instructional leader to "everything else," navigating facilities, finance, hiring, and recruiting families while selling a vision that, at times, exists only on paper. She speaks candidly about the pressure, the ambiguity, and the challenge of building something new while learning as you go.  What sustains her is a clear sense of purpose and a strong community. Kristy reflects on the power of a mission-aligned team, the importance of being unapologetically clear about who the school is for, and the joy of seeing families choose a vision they believe in. She also shares a simple but powerful leadership practice, her "meeting with herself," which helps her stay grounded, organized, and focused during an intense season.  This episode is an honest look at the complexity of founding a school and a reminder that even in the hardest seasons, clarity of purpose and strong systems can carry leaders forward.  Key Takeaways: Why some leaders choose to build new systems instead of trying to fix existing ones. How early career exposure can change student outcomes and postsecondary paths. The hidden complexity of planning year, from facilities to finance to enrollment. The importance of being clear about who your school is and is not for. How a simple weekly planning practice can bring clarity and sustainability to leadership. Connect with Kristy: Learn more about AIM: https://aimgeorgia.org Connect with Kristy Beam on LinkedIn https://www.linkedin.com/in/kristy-beam-78aa6b12/ About CheckBox Pro: CheckBox Pro helps school leaders create sustainability through added capacity, taking repetitive tasks off their plates so they can focus on what matters most. https://www.checkboxpro.com/ Licensed music ID: ILRNI9DIEHE4JTVQ Music: Energizer by Chris Phaze licensed through Premium Beat by Shutterstock ID: ILRNI9DIEHE4JTVQ

    41 min
  2. 50: The Power of Words

    MAY 4

    50: The Power of Words

    In this episode of the CheckBox Pro Series, Missy sits down with James Mosley, Superintendent of Yellowstone Schools, for a thoughtful and practical conversation on leadership, communication, and building systems that sustain both people and results. James shares his unexpected path into education, from initially pursuing law to discovering a deep passion for teaching and leadership. Now serving a unique pre-K through high school model in Houston's Third Ward community, he reflects on the responsibility and purpose that comes with leading a school designed to serve students and families with both excellence and care.  The conversation dives into one of the most overlooked but critical leadership challenges: communication. James explains why clarity across stakeholders, from board members to staff to families, is essential for alignment and execution. He shares how even the most complex problems can be simplified through clear expectations, strong systems, and consistent messaging.  James also offers a window into the systems that help him stay grounded in the work. From using OKRs to track priorities, to structuring meetings around real-time challenges, to intentionally separating "office days" and "coaching days," his approach is rooted in focus, visibility, and follow-through. He emphasizes that leadership is not about doing everything yourself, but about building strong teams and creating systems that allow others to execute well.  Throughout the conversation, James returns to a central theme: sustainability. Whether it is being present in classrooms, showing up for his team, or making time for his family, he shares how intentional structure and discipline make it possible to lead well without losing yourself in the process. This episode is a practical and encouraging listen for leaders navigating complexity, offering a clear reminder that when systems, people, and purpose align, meaningful change becomes possible.  Key Takeaways: Why communication with clarity is one of the hardest and most important leadership skills. How simplifying complex problems leads to stronger execution. The role of systems like OKRs in keeping teams focused and aligned. Why leaders must build strong teams to get results through others. How structuring your time can support both leadership effectiveness and personal sustainability.  Connect with James: Connect with Dr. James Mosley on LinkedIn https://www.linkedin.com/in/james-mosley-ed-d-62a0a060/ Learn more about Yellowstone Schools https://yellowstoneschools.org/ About CheckBox Pro: CheckBox Pro helps school leaders create sustainability through added capacity, taking repetitive tasks off their plates so they can focus on what matters most. https://www.checkboxpro.com/ Licensed music ID: ILRNI9DIEHE4JTVQ  Music: Energizer by Chris Phaze licensed through Premium Beat by Shutterstock ID: ILRNI9DIEHE4JTVQ

    50 min
  3. 49: Choosing Purpose Over Timeline

    APR 20

    49: Choosing Purpose Over Timeline

    In this episode of the CheckBox Pro Series, Missy sits down with Tiana Stephenson, Founder and CEO of The Wright Community School, for a powerful conversation about purpose, persistence, and building a school with—and for—community. Tiana shares her journey into education, shaped by personal loss, a deep search for purpose, and a commitment to ensuring students feel seen, heard, and valued. That purpose now lives in The Wright Community School, a 6–12 charter school designed to help students explore who they are and what they love through early college access, community partnerships, and a strong focus on restorative culture. The conversation offers an honest look at the challenges of planning and founding a school, especially when navigating setbacks outside of your control—like facilities delays that have pushed back opening timelines. Tiana shares how staying grounded in non-negotiables and community voice has guided every decision, even when it means waiting longer to get it right. She also reflects on what she's most proud of: a deeply committed community that has stood alongside her through multiple application cycles and continues to believe in the vision. Tiana names her leadership superpower as the ability to figure things out and create solutions when they don't exist, and she shares a practical planning system she built to help manage the complexity of leadership while giving herself grace along the way. This episode is an encouraging and honest reminder that founding is not a straight path—and that staying rooted in purpose and community can carry you through the hardest seasons.  Key Takeaways: Why building a school with community leads to stronger alignment and ownership. The realities of founding, including delays and decisions outside your control. The importance of holding non-negotiables, even when timelines shift. How to create systems that support both productivity and grace. Why community support can make the founder journey feel less lonely.  Connect with Tiana: Learn more about The Wright Community School https://www.thewrightcommunityschool.org/ Connect with Tiana Stephenson on LinkedIn https://www.thewrightcommunityschool.org/ About CheckBox Pro: CheckBox Pro helps school leaders create sustainability through added capacity—taking repetitive tasks off their plates so they can focus on what matters most. https://www.checkboxpro.com/ Licensed music ID: ILRNI9DIEHE4JTVQ Music: Energizer by Chris Phaze licensed through Premium Beat by Shutterstock ID: ILRNI9DIEHE4JTVQ

    28 min
  4. 48: What's Saving My Life: Winter 2026

    APR 6

    48: What's Saving My Life: Winter 2026

    In this quarterly What's Saving My Life episode, Missy reflects on the small (and surprisingly impactful) things helping her navigate the busy winter season—January through March. From systems that reduce mental load to simple routines that bring joy, this episode is a reminder that what sustains us doesn't have to be big or complicated. Sometimes, it's as simple as a shared calendar, a family show, or finally getting your kids to do their own chores. If you're in a full season (and let's be honest—who isn't?), this episode offers practical ideas and gentle encouragement to pause and notice what's working in your life right now. \Key Takeaways: Small systems can create big relief. Tools like a shared digital calendar or a planning spreadsheet can significantly reduce daily friction. Kids can—and want to—contribute. Creating clear expectations around chores builds independence and reduces parental load. Shared experiences matter. Whether it's a family TV show, the Olympics, or an Oscars watch party, having something to enjoy together builds connection. Look for ways to "stack" your time. Pairing connection with productivity (like folding laundry while catching up with friends) can be both efficient and life-giving. Lower the bar to make things sustainable. Simplifying holiday decor or meal routines makes it easier to maintain traditions without overwhelm. Future planning can be energizing. Booking trips or mapping out summer childcare provides something to look forward to—and reduces future stress.  Resources Mentioned: Skylight Digital Frame (for shared calendars, chores, and lists) Kendra Adachi's (The Lazy Genius) Homemade Granola Recipe https://www.thelazygeniuscollective.com/blog/the-best-granola-ever?rq=granola Missy's Summer Camp Planning Spreadsheet https://docs.google.com/spreadsheets/d/1ZFBk-ER6cDRtxfurSkQbMs0s6iiBbzNS6HDZaMgDGnU/edit?usp=drive_link Connect with Missy: LinkedIn: https://www.linkedin.com/in/missy-couch-5626b8176/ About CheckBox Pro: CheckBox Pro helps school leaders create sustainability through added capacity—taking repetitive tasks off their plates so they can focus on what matters most. https://www.checkboxpro.com/ Licensed music ID: ILRNI9DIEHE4JTVQ Music: Energizer by Chris Phaze licensed through Premium Beat by Shutterstock ID: ILRNI9DIEHE4JTVQ

    24 min
  5. 47: CEO: "Chief Everything Officer"

    MAR 16

    47: CEO: "Chief Everything Officer"

    In this episode of the CheckBox Pro Series, Missy sits down with Nicholas Ditto, Founder of Fort Worth STEAM Academy, for an honest look at life in the middle of a school's planning season. Nicholas shares his journey from aspiring public defender to educator and now founder, driven by a deep belief that access to high-quality education shapes opportunity. He explains why middle school is such a critical moment—before students begin disengaging—and why that urgency led him to launch a new charter campus in Fort Worth. The conversation explores the realities of the planning year, where "CEO" quickly becomes "Chief Everything Officer." From nonprofit paperwork and marketing to facilities and finance, Nicholas reflects on the steep learning curve founders face long before students arrive. He also shares the energizing moments that make it worthwhile—like gathering founding families and staff and watching a community begin to form. Nicholas names his superpower as staying focused on the few priorities that truly drive outcomes. He also shares practical systems for managing time, communication, and task—simple structures that help sustain him during an intense season of leadership.  Key Takeaways: Why middle school is a pivotal moment for student trajectory. The hidden business-building side of founding a school. How focusing on "one to three" priorities drives results. Practical systems to streamline time and communication. The importance of building community from day one.  Connect with Nicholas: Learn more about Fort Worth STEAM Academy https://www.fwsteamacademy.org/ Connect with Nicholas Ditto on LinkedIn https://www.linkedin.com/in/nicholasditto/ About CheckBox Pro: CheckBox Pro helps school leaders create sustainability through added capacity—taking repetitive tasks off their plates so they can focus on what matters most. https://www.checkboxpro.com/ Licensed music ID: ILRNI9DIEHE4JTVQ  Music: Energizer by Chris Phaze licensed through Premium Beat by Shutterstock ID: ILRNI9DIEHE4JTVQ

    29 min
  6. 46: From Vision to Reality

    MAR 2

    46: From Vision to Reality

    In this episode of the CheckBox Pro Series, Missy sits down with Shonqualla West, Founder and Superintendent/CEO of Unparalleled Preparatory Academy, for an honest conversation about what it really means to lead during a school's founding year. Shonqualla shares how growing up in a small rural town with limited school choice shaped her belief that students deserve early opportunities to explore who they are, what they're good at, and what's possible for their future. That belief now lives at UPA, a career immersion middle school where students "try on" careers through STEM-focused, hands-on, and interdisciplinary learning. She reflects on the realities no one prepares founders for—the constant zooming in and out, the many hats, and the tension between staying deeply involved while learning when to step back. Shonqualla also talks candidly about building her first leadership team, the importance of strong operations support, and the joy of seeing students and families choose—and take pride in—a school that began as an idea on paper. She closes by naming her leadership superpower—bringing bold visions to life through community buy-in—and offers hard-earned advice for other founders: pace yourself, give yourself grace, and keep going.  Key Takeaways: What makes the founding year uniquely challenging—and uniquely formative. Why founders must constantly "zoom in and out" to lead effectively. The importance of hiring strong operations leadership early. How UPA helps students explore identity, strengths, and careers starting in middle school. Why community pride and student joy are powerful indicators of success. A reminder that grace is essential for sustainability in leadership.  Connect with Shonqualla: Learn more about Unparalleled Preparatory Academy https://upaschools.org/ Connect with Shonqualla on LinkedIn https://www.linkedin.com/in/shonqualla-west-m-ed-35b463229/ About CheckBox Pro: CheckBox Pro helps school leaders create sustainability through added capacity—taking repetitive tasks off their plates so they can focus on what matters most. https://www.checkboxpro.com/ Licensed music ID: ILRNI9DIEHE4JTVQ Music: Energizer by Chris Phaze licensed through Premium Beat by Shutterstock ID: ILRNI9DIEHE4JTVQ

    34 min
  7. 45: The Long Game of Leadership

    FEB 16

    45: The Long Game of Leadership

    In this episode of the CheckBox Pro Series, Missy sits down with Rosalind DaCruz, Founder and Executive Director of RISE Prep Academies. Rosalind shares her journey from Teach For America corps member and high school history teacher to founding a charter school just three years into her teaching career—and what it's been like to lead and grow that organization for nearly a decade. Rosalind reflects on the evolution of her role from Founding Head of School to Executive Director, naming the often-unspoken challenges of scaling a school network: letting go of daily classroom life, resisting the urge to solve every problem personally, and learning to trust others with work she once owned. She speaks candidly about the emotional weight of this transition, especially as RISE Prep expands from a single kindergarten class into a K–12 network serving up to 1,400 students, with multiple campuses and major facilities projects underway.  The conversation also explores how Rosalind sustains herself through this demanding season of leadership. As a working parent and long-time school founder, she shares the practical systems that help her stay grounded—including a weekly closeout and look-ahead routine that brings clarity, accountability, and grace to both her professional and personal life. This episode is an honest, encouraging listen for school leaders navigating growth, transition, and longevity in the work.  Key Takeaways: What it really feels like to transition from founder to Executive Director as schools scale. Why stepping back from day-to-day school life can be both painful and necessary. How executive coaching and time audits supported Rosalind's leadership shift. The role of grit, strategic pivots, and persistence in sustaining a growing charter network. A simple weekly planning practice that supports leadership, parenting, and well-being.  Connect with Roz: Learn more about RISE Prep Academies: https://www.riseprep.org Connect with Rosalind DaCruz on LinkedIn https://www.linkedin.com/in/rosalind-dacruz-3a3a4177/ About CheckBox Pro: CheckBox Pro helps school leaders create sustainability through added capacity—taking repetitive tasks off their plates so they can focus on what matters most. https://www.checkboxpro.com/  Licensed music ID: ILRNI9DIEHE4JTVQ Music: Energizer by Chris Phaze licensed through Premium Beat by Shutterstock ID: ILRNI9DIEHE4JTVQ

    34 min
  8. 44: Strong Systems, Strong Relationships

    FEB 3

    44: Strong Systems, Strong Relationships

    In this episode of the CheckBox Pro Series, Missy sits down with Luke Savidge, Principal of Compass Midtown High School in Memphis, Tennessee. Luke shares his journey into education—from growing up in a family of educators, to teaching middle school, to stepping into high school leadership for the first time in his 15-year career. Luke offers a candid look at the realities of leading a high school, including the steep learning curve of credits, scheduling, and compliance, as well as the ongoing work of building relational trust with staff, students, and families. He explains why strong relationships are the foundation that make everything else possible—and how investing in people ultimately creates better outcomes for students.  The conversation also dives into Luke's leadership superpower: organization. He walks Missy through the system he's built to keep himself grounded and focused—a single, living document that tracks priorities, data, staff celebrations, walkthroughs, and even self-care. Luke shares how becoming "Type A by necessity" helped him protect his time, lead more sustainably, and show up better for his school community.  This episode is a practical and human look at what it takes to lead well in a complex environment—and a reminder that systems and relationships aren't opposites, but partners.  Key Takeaways: Why high school leadership feels like a different ballgame than middle school—and what makes it uniquely challenging. How Luke prioritizes attendance and discipline data with a clear weekly rhythm. The importance of building relational capacity quickly when stepping into a new leadership role. How one well-designed system can reduce overwhelm and increase follow-through. Why small, consistent acts of care matter more than grand gestures for staff morale.  Connect with Luke: LinkedIn: https://www.linkedin.com/in/luke-savidge-ed-s/ Learn more about Compass Midtown High School: https://www.compassmidtown.org  About CheckBox Pro: CheckBox Pro helps school leaders create sustainability through added capacity—taking repetitive tasks off their plates so they can focus on what matters most. https://www.checkboxpro.com/ Licensed music ID: ILRNI9DIEHE4JTVQ   Music: Energizer by Chris Phaze licensed through Premium Beat by Shutterstock ID: ILRNI9DIEHE4JTVQ

    36 min
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5
out of 5
9 Ratings

About

CheckBox Pro founder, Missy Couch, 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.

Information

  • Creator
    Missy Couch
  • Years Active
    2024 - 2026
  • Episodes
    51
  • Rating
    Clean
  • Copyright
    © 2024
  • Show Website
    CheckBox Pro Series