Jennifer Cheatham Leads Evaluation Revelations & Discipline Transformations
An Imperfect Leader: The Superintendents and Leadership Podcast
Release Date: 08/13/2024
An Imperfect Leader: The Superintendents and Leadership Podcast
I am thrilled to share a very special crossover episode between our podcast, An Imperfect Leader, and from the ! Together, we sat down with , a professor at MIT, to explore the the history of Junior Republics and the cutting-edge work of Embodied Education. Here are two key takeaways from our conversation: 🏙️ The Legacy of Junior Republics: Imagine a miniature city or nation run entirely by kids. Starting in 1895, Junior Republics gave children the power to act as senators, run businesses, and even debate major issues like women's suffrage (often reaching progressive...
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This week on An Imperfect Leader: The Superintendents and Leadership Podcast I’m joined by , COO and Chief Academic Officer at Fullmind and host of the . In a world where the education landscape is constantly shifting, Hayley makes a compelling case that adaptability isn’t optional, it’s essential. We explore how strong leaders connect the dots of data through storytelling - transforming numbers into a shared purpose and collective action. In a powerful “After Action Review,” Hayley shares a hiring mistake from early in her tenure and the lesson that reshaped her approach: skills can...
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I recently sat down with , Superintendent of Winchester Public Schools, to talk about what it really means to lead in a messy, high-pressure moment for public education. Jason embraces being an “imperfect” leader. In a field often paralyzed by the pressure for perfection, that mindset matters. Three takeaways that stayed with me: 🏛️ A Cathedral to Possibility: Winchester’s Emil and Grace Shahadah Innovation Center brings students together to explore a true buffet of options. It’s about social cohesion and shared opportunity, not silos. 🔄 Doubling Down on Agency: Amid...
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🚨 Are schools preparing students for a world that no longer exists? I recently had the privilege of sitting down with the force behind Most Likely to Succeed and Multiple Choice, and author of What School Could Be (with a new book on math coming soon!). Our conversation centered on one big idea: the status quo isn’t enough anymore. 🤖 AI changes the game: If we’re training students to do what computers now do best, we’re aiming at the past. We need to shift from compliance and percentile rankings to creativity, empathy, purpose, and real problem-solving. 🛠️...
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In the latest episode of An Imperfect Leader, I sat down with , author of , to explore how schools can move beyond compliance and toward deeper focus, connection, and self-management in the digital age. Here are three ideas that really stood out during our conversation: 1️⃣ From compliance to self-management: We often say we want creativity and collaboration, yet we still design systems around compliance. Patrick challenges that mismatch. The real goal isn’t control. It’s helping students develop self-management. 2️⃣ Leading with curiosity, not “tech panic”: How we...
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Leadership isn’t about finding the perfect solution. It’s about learning from the daily grind of complexity. In this week’s episode of An Imperfect Leader: The Superintendents and Leadership Podcast, I had the chance to speak with , former superintendent, Stanford professor, and author. A few insights that stayed with me, especially for leaders working in high-stakes environments: 1️⃣ Conflict isn’t a failure, it’s the work: Dr. Cuban shared that he couldn’t recall a single conflict-free day as a superintendent. Leadership is a constant balancing act (boards, unions,...
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What if the problem in our schools isn’t a lack of voice, but a lack of connection? In this episode, I had the opportunity to sit down with , author of , for a conversation that challenged many of the leadership norms we’ve inherited, especially the idea that effective leaders must remain stoic, distant, or emotionally neutral. Matt makes a compelling case that this model is no longer serving our schools. Instead, he invites leaders to rethink community, voice, and presence; and to move from making people feel heard to making them feel truly held. Here are three insights from our...
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🎙️ New Episode Alert: If We Get Ninth Grade Right, Everything Changes In this episode of An Imperfect Leader: The Superintendents and Leadership Podcast I get to talk with , National Director of the . This conversation zeroes in on why getting 9th grade right can dramatically improve graduation rates and disrupt long-standing inequities in our system. Here are three big ideas we dig into: 1️⃣ Ninth Grade: The Strongest Predictor of Graduation: Kaaren shares a powerful (and sobering) insight: students who are “on track” in ninth grade are three to four times more likely to...
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I’m excited to share the latest episode of An Imperfect Leader: The Superintendents and Leadership Podcast, featuring , Superintendent of Veribest ISD. Mandy offers a powerful look at what it means to lead with transparency, humility, and deep community trust. A few takeaways that stayed with me 👇 🤝 Shared Vision, Real Buy-In: Through a Texas Strategic Leadership pilot, Mandy brought together the board, staff, and local businesses to define what a Veribest graduate should be. The result? A vision everyone owns because they created it together. 🎓 Preparing Students for...
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Are you leading from a place of fixing… or from a place of presence? 🌱 In the latest episode of An Imperfect Leader: The Superintendents and Leadership Podcast, I had the honor of sitting down with Elena Aguilar, the visionary behind Transformational Coaching and author of eight bestselling books, including The Art of Coaching and Arise. 📚✨ Leadership can be a lonely journey. We’re often expected to have the answers, solve the problems, and move fast. But Elena reminds us that real transformation doesn’t come from quick fixes—it comes from going deeper and...
info_outlineHello, Imperfect Leaders!
INTRO: Evaluations. In every single profession, employees are evaluated. They are evaluated by their direct supervisors or evaluated by a board of directors. Often they are evaluated by the people they lead in the form of a survey (often referred to as a 360 survey). Plus, there are informal evaluations conducted by the community over social media (those can be brutal).
Formal evaluations can be difficult to navigate if there is not a clear process and protocol established at the very beginning. How often have you entered an evaluation meeting only to discover that what you thought you were being evaluated on was very different than what your evaluator thought?
My guest this week Is Dr. Jennifer Cheatham and she has incredible advice for school and district leaders about goal setting, reporting on progress, and even tips for how leaders can formally request authority over the evaluation process as part of their contract (I hadn’t thought of that one – so wise!). In Part 2, during her After Action Review, Jennifer talks about something very important to me: the tackling of a major system of oppression - a district’s code of conduct (also known as discipline).
It’s a great episode full of incredible insights! Thanks for tuning in!
BIO: With over twenty-five years of experience in the field of education in San Diego, Chicago, and Madison, Wisconsin, Dr. Jennifer Cheatham has served as a teacher, a teacher leader, a professional developer, a central office leader, an area superintendent, and a superintendent. In each of these roles, she focused on a number of things, including cultivating strong teams, designing enduring systems, and strengthening routines for organizational learning – all to make the lives of children better. She is now a Senior Lecturer on Education and Co-Chair of the Public Education Leadership Project at the Harvard Graduate School of Education.
FURTHER INFO: A few months ago, I had a chance to speak with Max Silverman at the University of Washington’s Center for Educational Leadership. Our conversation was wide ranging, but we kept returning to the role of evaluations. Leaders in every profession are interested in growth. Personal growth and the growth of those they supervise. This is a big topic for educational leaders as well. It wasn’t a day or so later that I came across this article by Jennifer: Can Superintendents’ Evaluation Lead to Their Own Growth? In the article she points out the unintended consequences of a traditional school board process of evaluation and how that the lowering of one point might lead to a superintendent’s quick demise. She references the incredibly disturbing national trend when it comes to leader longevity (we are losing superintendents at alarming rates). As we continue to read the article, we learn more about the shared process she created with your board in Madison, Wisconsin, which included self-reflection. Give it a read!
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At the end of every interview we have for teacher candidates, we say, “What questions do you have for us?” And they always ask, “What kind of support can I expect?” And we always say, “Don't worry, we'll give you a mentor.”
But it's not real mentorship. I mean, it's support with the difficult kid, or the field trip form, or the grade card. But it isn't coaching.
That's where partners like EdConnective step in. Because they provide real coaching, observations and feedback with practice. EdConnective ensures that every student thrives by facilitating exceptional educator growth. If you're looking for support for your people, for your leaders, for science of reading efforts, for recruitment and retention initiatives, check out EdConnective.com.
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An Imperfect Leader: Leadership in (After) Action is supported by ILAA, LLC, a firm dedicated to supporting aspiring, new, and established leaders. For more information, please find them at www.human-centeredleaders.com.
Music for An Imperfect Leader was written and arranged by Ian Varley.
Sam Falbo created our artwork, a wood-print inspired daruma doll butterfly.