The Education Equation with Jeremy Singer

Jeremy Singer sits down with Rebecca Winthrop, senior fellow and director of the Center for Universal Education at the Brookings Institution and co-author, with Jenny Anderson, of The Disengaged Teen: Helping Kids Learn Better, Feel Better, and Live Better.

In a Brookings survey of more than 65,000 U.S. students, 75% of third graders say they love school. By 10th grade, it's 25%. Winthrop explains why disengagement is still hard to spot, starting with how she misread her own two sons during COVID.

The book's core finding: engagement isn't a yes-or-no question. Students move among four modes (Passenger, Achiever, Resister, and Explorer), and these are states, not traits. More than half of middle and high schoolers spend most of their time in Passenger mode. Fewer than 4% regularly experience Explorer mode.

Key Highlights:

• Achievers aren't the goal. They follow instructions well but avoid risk, focus on grades over learning, and cheat at high rates.

• Autonomy moves disengaged students fastest. More scaffolded freedom, not less, moved struggling students into Explorer mode more quickly. At Iowa BIG in Cedar Rapids, one disruptive student became a standout within two months.

• Focus on interests, not passion. "Find your passion" adds pressure. Adults can help kids notice what sparks their curiosity.

• AI introduces a new divide. AI accelerates students who are already exploring and makes it easier for everyone else to coast.

• For parents: Ask what your child learned, not how they scored. Ask Passengers for a plan instead of nagging. Tell Achievers their worth doesn't depend on grades.

• For teachers: Johnmarshall Reeve's autonomy-supportive practices need no curriculum changes and have been tested in more than 35 randomized controlled trials across 20 countries. Expect about two weeks before students respond.

• For system leaders: Don't use GPA cutoffs to bar struggling students from extracurriculars. Stop assigning work AI can complete, and pair knowledge with applied learning.

• On Advanced Placement: Winthrop asks what it would take to make every AP course project-based.

Referenced in the Episode:

• The Disengaged Teen by Rebecca Winthrop and Jenny Anderson

• Brookings and Transcend research on student engagement

• Johnmarshall Reeve's research on autonomy-supportive teaching

• Iowa BIG

• Democracy and Education by John Dewey

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Timestamps:

00:00 Show Intro

00:34 Meet Rebecca Winthrop

01:41 The Engagement Cliff

02:26 Why Write The Book

04:22 Four Engagement Modes

05:02 Achievers And Passengers

07:16 Resisters Vs Explorers

09:00 Moving Toward Explorer

11:33 Family And Classroom Levers

13:58 Counterintuitive Autonomy

16:45 Stop Saying Find Passion

18:16 Making Learning Relevant

19:55 AI And Engagement Modes

20:44 AI Equity Divide

22:21 Parents Key Takeaways

23:54 Breaking Passenger Cycles

26:01 Teacher Agency Nudges

28:43 Policy Moves at Scale

31:19 Rethinking AP for Agency

34:04 Project Based AP Vision

35:25 Rapid Fire and Wrap

In this episode of The Education Equation, host Jeremy Singer talks with former and current Executive Directors of Partners in School Innovation: founder Julien Phillips, Becky Crowe, and Derek Mitchell. The conversation covers the organization's 30-year history in public education, tracing its transition from an early AmeriCorps talent model to a fee-for-service continuous improvement partner.

Key Topics:

🌱 Origin Story: Founder Julian Phillips explains how combining his background in the Peace Corps, McKinsey, and Ashoka led him and co-founder Kim Gross to launch the organization alongside the creation of AmeriCorps.

📊 Navigating Policy and Funding Shifts: Former ED Becky Crowe details managing through the No Child Left Behind era, handling federal funding instability, and shifting to a fee-for-service model with experienced School Improvement Fellows.

🚀 Geographic Expansion: Current ED Derek Mitchell outlines expanding the model outside California into districts like Philadelphia and Battle Creek using an anchor funder strategy.

💼 National Service and Early Talent: The panel discusses national service, the impact of AI on entry-level positions, and the long-term value of early-career work experience.

Advice for Leaders and Funders:

🏫 Focus on Implementation: Derek Mitchell notes that for every $1 spent on materials or programs for schools, systems should invest $7 helping educators use them effectively.

🎯 Funding Human Capital: Becky Crowe calls on philanthropy to prioritize sustained funding for educator and school leadership pipelines.

🤝 Collaborative Partnerships: Julian Phillips stresses that school improvement relies on equal, reciprocal partnerships and continuous learning.

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In this episode of The Education Equation, host Jeremy Singer talks with Trevor Muir—an educator, author, speaker, and founder of Epic PBL. Recorded at College Board's Advanced Placement Annual Conference, this conversation explores how project-based learning (PBL) can address the ongoing relevance crisis in today's classrooms and prepare students for the durable skills needed in an AI world.

Trevor shares his journey from a classroom teacher to a leading advocate for "main course" PBL—learning experiences that require students to think critically, collaborate, and solve real-world problems. They discuss the difference between meaningful applied learning and "dessert" projects, how AI can serve as a powerful project-planning partner, and practical ways for AP teachers and school leaders to effectively incorporate and scale PBL while maintaining content mastery.

Key Highlights:

Dessert vs. Main Course Projects: Trevor explains the difference between projects tacked onto the end of a unit (like a model volcano) and projects where a meaningful problem drives the core learning of the subject.

The Relevance Crisis: With growing student disengagement, making content relevant through applied learning is critical. Even traditional subjects like calculus and grammar can be grounded in purposeful, real-world problems.

AI as a Co-Pilot: While AI brings challenges to the classroom, it can serve as a helpful brainstorming partner for teachers looking to generate authentic, localized project ideas aligned with their standards, while still preserving the student thinking that learning requires.

PBL in AP Courses: PBL doesn't mean abandoning direct instruction or lowering expectations. Trevor shares how teachers can gradually introduce problem-solving units into their packed curriculums and why allowing students to grapple with real constraints leads to better outcomes.

Referenced in the Episode:

Timestamps:

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Global Tech, Local Impact: Unlocking Classroom Bottlenecks with Emma Dorn

How can we let data drive student success? On this episode, host Jeremy Singer talks with Emma Dorn, a Senior Knowledge Expert at McKinsey & Company, about how school systems improve and sustain progress at scale. While the US debate focuses on whether to use technology, the Global South innovates out of necessity due to resource constraints. From solar tablets in Malawi to WhatsApp coaching in Pakistan, Emma shares how to solve the core instructional bottleneck.

Emma outlines five case studies from around the world where technology solves real instructional problems: 

• First, design for the instructional bottleneck, not the tech. In Malawi, where class sizes reach 150, Imagine Worldwide deploys offline, solar-powered tablets running adaptive software, doubling literacy and math fluency. 

• Second, technology designed for teachers can be more transformative than direct-to-student devices. McKinsey's analysis of global PISA data shows tech in the hands of teachers adds a year or two of learning, while student devices reduce outcomes due to distraction. New Globe utilizes teacher tablets to deliver structured lesson plans offline. 

• Third, technology works better when aligned with the curriculum. Mentu's AI assistant in Colombia and the Dominican Republic maps to local curricula to scaffold lower-skill teachers. 

• Fourth, technology is most powerful when scaling proven interventions like teacher coaching. In Pakistan, Talimabad created a WhatsApp-native digital coach analyzing classroom audio to give immediate feedback. 

• Fifth, think beyond the Scantron. Using the Teaching at the Right Level (TaRL) methodology, Pratham and Wadhwani AI developed oral reading fluency assessments operating on $50 cell phones, reducing assessment time by 50% across millions of learners.Listen in to learn how a global perspective can provide unique insights into how to leverage emerging technologies to solve real world educational challenges at scale.

Research and Links:

Malawi Scale-Up: globalpartnership.org/blog/malawi-strengthening-edtech-evidence-community-perspectives

McKinsey PISA Study: https://www.mckinsey.com/industries/education/our-insights/drivers-of-student-performance-insights-from-europe

Structured Pedagogy: https://www.wwhge.org/resources/implementing-structured-pedagogy-programmes-effectively-at-scale/

New Globe Impact: https://newglobe.education/impact/

Taleemabad Profile: https://taleemabad.com/

Mentu AI: https://mentulabs.com/en/

Pratham TaRL: https://www.pratham.org/about/teaching-at-the-right-level/

Wadhwani AI: https://www.wadhwaniai.org/

Join the Conversation:

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Time Stamps:

00:00 Show Introduction

00:38 Meet Emma Dorn

02:03 Why Look Globally

04:14 Constraints Drive Innovation

06:20 Lesson One Bottlenecks

12:21 Lesson Two Teacher Tech

19:00 Lesson Three Curriculum Alignment

23:37 Lesson Four Scaling What Works

29:28 Lesson Five Oral Assessments

34:18 Big Picture Takeaways

35:42 Rapid Fire Questions

37:40 Five Year Vision

38:51 Closing Thanks

AI and the Future of Learning with Ethan Mollick

Jeremy Singer sits down with Ethan Mollick, professor at the University of Pennsylvania's Wharton School and author of Co-Intelligence: Living and Working with AI, a New York Times bestseller and a best book of the year from The Economist and Financial Times. Mollick is a defining voice in the AI space, testing generative tools in real-world classrooms and authoring the widely read newsletter One Useful Thing. He is the Ralph J. Roberts Distinguished Faculty Scholar, Rowan Fellow, and Associate Professor at the Wharton School, where he directs the Generative AI Lab and studies the effects of AI on work, entrepreneurship, and education. He was named one of TIME Magazine's Most Influential People in Artificial Intelligence. 

Despite the rapid pace of development, Mollick argues that the AI we use today is the worst it will ever be, necessitating a proactive shift from denial to engagement. In this episode, he explains why the "homework apocalypse" is already here and how the traditional writing assignment has been fundamentally disrupted. The discussion moves beyond simple prompt engineering to explore the "jagged frontier" of AI capability, where the technology excels at complex tasks while occasionally stumbling on simple ones. Mollick and Singer break down the varying impacts of AI on human performance, describing it as a leveler for those with skill gaps and a "king-maker" for experts who can leverage the tool to achieve massive productivity gains.

The conversation also tackles the existential questions of human agency and the future of assessment. Mollick advocates for a "flipped classroom" model where AI serves as an infinitely patient universal tutor outside of school, leaving class time for active learning, debates, and creative projects. He and Singer discuss testing in the age of AI and how educators can teach students to develop "durable skills" like taste, judgment, and a unique personal style . By viewing AI as a teammate rather than just a tool, Mollick suggests that teachers can reclaim hours of their week and focus on the deeply human aspects of education.

Featured References:

Episode Timestamps:

00:00 — Introduction to Ethan Mollick and the pace of AI evolution 02:26 — The "homework apocalypse" and the shift in educational thinking 04:45 — Why today’s AI is the worst version we will ever use 09:15 — Lessons from the 1970s calculator debate for modern curricula 13:55 — AI literacy vs. a fundamental reshaping of human interaction 17:30 — Developing taste and agency as essential "durable skills" 19:00 — The Leveler, Elevator, and King-maker effects on human skill 29:10 — The promise of the universal tutor to close equity gaps 32:55 — Using AI to enable the flipped classroom and active learning 36:55 — Shifting from "tool" to "teammate" in teacher workflows 41:50 — Why AI detectors fail and the move toward in-class assessment 45:45 — Rapid Fire: Retirement of AI literacy, Neal Stephenson, and the importance of humanities 48:45 — A three-year vision for positive change in education

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Cognitive Science in the Classroom with Dan Willingham

Jeremy Singer sits down with Dr. Daniel Willingham, professor of psychology at the University of Virginia and author of Why Don’t Students Like School?: A Cognitive Scientist Answers Questions About How the Mind Works and What It Means for the Classroom.

Despite decades of robust research into how the human brain learns, a significant gap remains between laboratory findings and daily classroom instruction. In this episode, Dr. Willingham shares the origin story of his career pivot from memory researcher to educational translator following a transformative 2001 conference with teachers in Nashville. The discussion moves beyond the hype of educational trends to explore the fundamental constraints of the human mind. Willingham and Singer break down why students are naturally averse to thinking, explaining that the brain is designed to save effort by relying on memory rather than slow, hazardous problem-solving. They discuss why spacing—revisiting content over time—is scientifically superior for retention but often resisted by students due to its impact on immediate motivation.

The conversation also tackles the modern challenges of AI and declining reading scores. Willingham argues that the issue isn't necessarily a lack of leisure reading among youth, but rather a decrease in the rigor of texts and expectations within schools. He advocates for knowledge-rich curricula that sensibly sequence factual, procedural, and conceptual information to provide the necessary engine for critical thinking.

Featured References:

Book: Why Don't Students Like School? by Daniel Willingham Book: The Reading Mind by Daniel Willingham

Book: Cultural Literacy by E.D. Hirsch

Research: Sam Wineburg (Stanford University) on digital literacy and vetting information

Data: American Time Use Survey (Bureau of Labor Statistics)

Episode Timestamps:

00:00 — Introduction to Dr. Daniel Willingham and the gap between science and classrooms 03:00 — The Nashville story: Why Willingham pivoted to education 09:00 — The science of spacing: Why laboratory findings don't always translate to classrooms 13:50 — Advice for superintendents: Choosing CogSci-aligned curricula 22:45 — The core thesis: Why the brain is set up to save you from thinking 33:45 — Defining factual, procedural, and conceptual knowledge 41:50 — AI in education: Generalizable skills vs. domain-specific knowledge 51:40  The Reading Mind: Addressing declining scores and the importance of rigor 01:03:50 — Rapid Fire: Retirement of learning styles, the importance of probability, and the future of teacher education

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Jeremy Singer, president of the ⁠College Board⁠, is joined by Jennie Magiera, Google’s Global Head of Education Impact, to discuss the transformative role of AI in schools. Magiera, who began her career as a math teacher and tech skeptic at Chicago Public Schools, explains her shift toward viewing technology as a powerful vehicle for educational equity when it is used to addressspecific instructional challenges. The discussion highlights ⁠LearnLM⁠, Google’s family of AI models fine-tuned specifically for education and grounded in five core learning science principles: active learning, managing cognitive load, adapting to learners, stimulating curiosity, and deepening metacognition.

Magiera shares ⁠a study⁠ showing that students who used LearnLM for short tutoring sessions experienced a 5.5% performance boost on novel topics compared to those working with human tutors alone. ⁠A six-month Northern Ireland pilot⁠ further demonstrates AI's impact, with teachers reporting an average of 10 hours saved per week on administrative tasks like lesson planning, risk assessments, and parent outreach. This efficiency provides critical breathing room for educators, helping to reduce stress and prevent burnout while allowing them to reinvest time into professional learning and deeper student engagement. The episode concludes with an exploration of durable skills like empathy and critical thinking, which Magiera argues will only increase in importance as AI handles more routine technical tasks.

Resources Mentioned in This Episode:

⁠Google for Education Communities and Tools⁠

⁠Switch by Dan and Chip Heath⁠

⁠Weekend Language by Andy Craig and Dave Faustino⁠

⁠OECD AI Capability Indicators Report⁠

Google for Education Research in Northern Ireland

Google Research with Eedi Labs about AI Tutoring

Episode Timestamps:

00:00 — Jeremy Singer introduces the Education Equation 01:05 — Meet Jennie Magiera, Global Head of Education Impact at Google 05:43 — From tech skeptic to innovation leader 08:14 — The Lead with the Need philosophy 18:10 — Understanding LearnLM and learning science principles 22:30 — Research on AI tutoring and student performance boosts 29:25 — Saving 10 hours a week: The Northern Ireland Pilot 37:45 — Durable skills and what makes us uniquely human 43:15 — Rapid Fire: Book recommendations and the importance of empathy 48:10 — Hopes for education in the next three years

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In this episode of The Education Equation, host Jeremy Singer, President of the College Board talks with Sal Khan, founder and CEO of Khan Academy, about the evolution of their decade-long partnership and the transformative role of AI in the classroom. They reflect on the early days of providing free, world-class SAT practice to tens of millions of students and share the "beast mode" origins of Sal’s instructional videos. The conversation moves into the launch of a new collaboration between the College Board and Schoolhouse.world, which provides free, peer-to-peer SAT tutoring to help students stay accountable and motivated.

Sal discusses insights from his book, Brave New Words: How AI Will Revolutionize Education (And Why That’s A Good Thing), and describes his first experience with GPT-4 as a "benevolent alien moment" that signaled a new era for educational technology. He explains how AI tools like Khanmigo serve as Socratic tutors that nudge students toward answers without doing the work for them, while also acting as powerful assistants for teachers by handling administrative tasks and lesson planning. Despite the rapid growth of AI, Sal argues that teaching remains one of the most human-centric and secure professions in the modern world.

The episode also covers the ethics of AI in schools, where Sal advises educators to avoid fool's errands like AI detection and instead embrace transparency and in-class assessments. He shares personal anecdotes about AI’s potential to support mental health and family dynamics, illustrating how these tools can provide meaningful advice for young people. Finally, Jeremy and Sal envision a future where technology makes classrooms more joyous and interactive, allowing teachers to focus on student engagement rather than paperwork.

Sal's book recommendation: The Foundation Series by Isaac Asimov

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Timestamps

(00:00) – Introduction: Jeremy Singer and the mission of The Education Equation

(02:18) – The origin story of the Khan Academy and College Board partnership

(05:47) – Sal’s "beast mode" process for creating instructional content

(08:35) – Data and evidence: The impact of free personalized practice

(12:12) – Evolution from supplemental tool to district-wide integration

(15:58) – The birth of Schoolhouse.world and the future of peer tutoring

(22:20) – Balancing pedagogy with engagement: The Duolingo vs. Khan Academy approach

(24:49) – The "Benevolent Alien" moment: First contact with GPT-4

(29:50) – Mastery learning and addressing "unfinished learning" with AI

(33:00) – Guardrails: Ensuring AI helps students learn without cheating

(37:25) – Vision for the AI-enabled classroom of the future

(40:55) – AI's role in mental health and family dynamics

(45:43) – Advice for educators on using AI ethically and responsibly

(47:50) – Rapid Fire: Educational buzzwords, favorite books, and the "AP Law" idea

(51:00) – Closing thoughts and where to follow

🎧 The Education Equation: Dr. Janice Jackson on Scaling Solutions

On this episode of The Education Equation, host Jeremy Singer speaks with Dr. Janice Jackson, former CEO of Chicago Public Schools (CPS) and Executive Director of the Aspen Institute's Education and Society Program.

Dr. Jackson, a CPS alumna, discusses her journey leading one of the nation’s largest school districts. She notes that her time as a principal provided the best preparation for the superintendency. Under her leadership, CPS boosted its graduation rate from 55.8% in 2010 to 82.5% in 2020. This dramatic turnaround was driven by intentional work, including making students take a college entrance exam to graduate and implementing the Freshmen on Track system, which was informed by data from the University of Chicago Consortium on School Research. This success was built on data transparency, accountability, principal empowerment, and strong public-private partnerships.

The conversation moves to Hope Chicago, the two-generation debt-free scholarship model she founded. Hope Chicago provides debt-free support (tuition, books, fees, and a stipend) to students from neighborhood high schools. By reducing financial risk, the model has significantly increased matriculation rates from about 57% to about 85% today. First-year persistence also increased from 61% to about 75%, demonstrating that removing debt and providing one-on-one support boosts college success.

Now at the Aspen Institute, Dr. Jackson is exploring the future of student outcomes on a national level. She emphasizes the need for leadership to address major challenges like economic preparedness, the impact of AI and EdTech, and the rise of alternative schooling models. Her goal is to translate her lessons from Chicago to a national context, advocating for a return to non-political accountability to ensure every child can succeed.

Dr. Jackson's education book recommendation: "It's Being Done": Academic Success in Unexpected Schools

Key Takeaways:

- Principal Power: The principalship is the single best leverage point for large district change.

- Data-Driven Turnaround: CPS used the "Freshmen on Track" indicator to drive a dramatic increase in its graduation rate from 55.8% to 82.5%.

- The Affordability Barrier: Hope Chicago's debt-free scholarship model significantly increases college matriculation and persistence rates for low-income students by eliminating financial risk.

- National Education Gaps: At Aspen, Dr. Jackson is focusing on creating a new course for education that addresses economic preparedness, AI integration, and the regulation of alternative schooling models.

Why You Should Listen:

Dr. Jackson offers a rare perspective, having led one of the country's largest school districts through a period of significant positive change. Her work provides clear, data-backed examples of how systemic improvements can be achieved. Listen for her insights on transforming a large school system and why her work now focuses on setting a new, accountable course for American education.

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Time Stamps

[00:00:54] Introduction to Dr. Janice Jackson's background

[00:05:37] The principalship as the best preparation for CEO

[00:14:15] Achieving CPS’s historic graduation rate increase

[00:29:21] Launching and scaling Hope Chicago

[00:36:06] Setting a new course at the Aspen Institute

In this special live episode, Jeremy Singer interviews Liz Cohen, author and VP of Policy at 50Can, as part of the College Board Forum 2025. Cohen, an expert in K-12 education, discusses her new book, The Future of Tutoring: Lessons from 10.000 School District Tutoring Initiative. She argues convincingly that tutoring is one of the few interventions with clear evidence of improving educational outcomes.

The conversation explores how the COVID-19 pandemic and federal ESSER funds created a unique opportunity for the research and scaling of tutoring, which Cohen refers to as an "accidental experiment". By May 2023, 80% of U.S. school districts were offering some form of tutoring. Cohen shares data on significant academic gains from initiatives in places like Washington D.C. and Guilford County, North Carolina.

Key Takeaways:

Defining High-Impact Tutoring (HIT): Effective elements include tutoring at least three times a week for a minimum of 30 minutes, a student-to-adult ratio of no more than 4:1 (ideal), and the use of a consistent tutor.

Virtual vs. In-Person: The data shows that the modality—virtual or in-person—does not significantly impact outcomes, and virtual tutoring increases access and flexibility.

The Power of Embedding and Alignment: Success is enhanced by integrating tutoring into the regular school day (often via an intervention block) to reduce student stigma, and by aligning the tutoring with the core curriculum.

AI’s Role: Cohen is optimistic about AI's potential to reduce costs and enhance human tutoring, for example, by creating "AI tutor coaches" to provide instant guidance and eliminate the "learning curve" for new tutors.

Navigating Cost and Scale: The discussion addresses how to sustain costly HIT programs after ESSER funds expire, exploring solutions like outcomes-based contracts and increased efficiency.

Why You Should Listen:

Liz Cohen’s insights provide a blueprint for education leaders seeking to implement proven, scalable interventions. She argues that the successful adoption and scaling of tutoring demonstrates the education system can embrace big, hard changes. The episode concludes with thoughtful questions from the live audience on tutor preparation, combating student stigma, and measuring the return on investment by reducing future remediation costs.

Liz’s education book recommendation: The End of Education: Redefining the Value of School by Neil Postman.

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Timestamps:

03:18 The Impact of COVID on Education

06:11 The History and Evolution of Tutoring

13:09 High Impact Tutoring Defined

19:07 Success Stories and Data Insights

20:04 Embedding Tutoring in School Schedules

26:40 Strategies to Reduce Tutoring Costs

31:43 The Role of AI in Tutoring

37:47 Rapid Fire Questions and Audience Q&A