Jacob Kantor was the number one sales rep everywhere he went - McGraw Hill, LAUSD, Varsity Tutors, Revolution Prep. He could have kept doing that forever. Instead, he created JK K12 Consulting and gave himself a title nobody had ever heard of: Chief DODO, which stands for District Office Door Opener.

In this episode, we dig into what it actually took to design a career from scratch, why the best first meeting is one where you never mention the product, what the post-ESSER trust gap looks like from someone who sits between EdTech companies and district leaders every day, and how he built a weekly practice of giving people their flowers publicly on LinkedIn that changed everything.

If you're a school or district leader, this conversation shows you what trust-building looks like from the other side of the table. If you're someone thinking about designing your own path instead of following a traditional one, Jacob's story is proof that it's possible, and that the messy middle is part of it.

Dr. Sabba Quidwai is the CEO of Designing Schools and author of "Designing Schools: How Design Thinking Makes YOU Irreplaceable in the Age of AI." She works with schools and districts worldwide to help educators thrive in an AI-powered world.

• Jacob Kantor's website: https://thejacobkantor.com
• Jacob on LinkedIn: https://www.linkedin.com/in/thejacobkantor

Drawing on Microsoft's new Preparing Students for the Future of Work report, Dr. Sabba Quidwai challenges the common narrative that AI is replacing workers. Instead, she argues that AI is eliminating traditional entry-level tasks and accelerating graduates into roles that require judgment, leadership, and decision-making from day one. Through examples from workforce research, organizational change, and personal stories about AI use, she explores why schools must redesign learning experiences to prioritize human skills, visible thinking, and frameworks like SPARK and WISE that help people partner effectively with AI. 

Timestamps

00:00 – Everyone Got a Promotion

• Introduction to Microsoft's latest workforce report and the idea that AI isn't eliminating jobs—it's removing traditional entry-level work and elevating expectations for new graduates. 

05:00 – The New Fundamentals: Context Engineering and Voice

• Exploration of the emerging workforce skills employers need most, including organizing context for AI systems and developing a distinct human voice that stands out in an AI-generated world. 

09:30 – What Laundry Teaches Us About AI

• A historical look at how technology shifts work rather than eliminating it, using the evolution of laundry and household technologies as a powerful analogy for today's AI transformation. 

11:00 – The Behavior Gap and Losing Your Voice

• Lessons from Canva's AI learning initiative and Amy Blankson's personal story reveal why AI adoption challenges are often human and organizational, not technological. 

18:30 – The SPARK Framework: Prompt the Human First

• A deep dive into the SPARK framework and how educators can redesign learning experiences by clarifying the Situation, Problem, Aspiration, and Results before involving AI. 

22:00 – Stop Policing AI, Start Designing Better Work

• Why leading organizations and universities are shifting away from AI detection and toward assignments that make reasoning, judgment, and human thinking visible. 

Resources Mentioned

• Microsoft, 2026 Work Trend Index (the 67/32 stat): Work Trend Index: Microsoft’s latest research on the ways we work.
• IU Kelley AI Playbook for Faculty (detectors, defensible work): kelley.iu.edu/Kelley_AI_Playbook.pdf
• Rob Giglio / Canva, Fortune (the behavior gap): We gave our 5,000 employees a week to do nothing but learn AI. We learned the biggest blockers are human ones
• Amy Blankson, Confessions of a Writer Who Used Too Much AI: Confessions of a Writer Who Used Too Much AI
• HBR, How to Move from AI Experimentation to AI Transformation (the 90% / INSEAD-Harvard study): How to Move from AI Experimentation to AI Transformation

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For questions, email: [email protected]

In this thought-provoking episode, Dr. Sabba Quidwai explores how the narratives we tell about AI are shaping our perceptions, decisions, and sense of agency. Through stories ranging from a viral Monet experiment to commencement speeches that sparked student backlash, she argues that the real challenge isn't AI itself—it's the stories institutions, leaders, and individuals tell about the future.

Drawing from personal experiences navigating economic uncertainty, research on hope, and her work with students and educators, Dr. Quidwai makes the case that agency, pathways, and purpose—not technology—are the foundations of a hopeful future.

Timestamps

00:00 – The Monet Experiment: When a Masterpiece Was Mistaken for AI

• A viral social media post reveals how AI narratives are changing our ability to recognize authenticity and shaping what we believe is real.

03:00 – Why Graduates Are Booing AI Commencement Speeches

• Examining the backlash against AI-focused graduation speakers and what student reactions reveal about fear, uncertainty, and the search for agency.

06:00 – The Power of Storytelling: Wozniak, Jensen Huang, and Hope

• Contrasting approaches to talking about AI and why stories rooted in humanity, vulnerability, and purpose resonate more deeply than technology-first narratives.

11:00 – The Perfection Problem in Education

• How decades of rewarding perfection have left schools struggling to articulate why human creativity, process, and imperfection matter in the AI era.

28:00 – Hope Is a Skill: Goals, Pathways, and Agency

• Exploring research from C.R. Snyder and Brené Brown that reframes hope as a teachable cognitive process rather than a feeling.

36:00 – Students Co-Designing the Future in Roseville

• A powerful example of students, educators, and leaders collaborating to define the skills, mindsets, and agency needed to thrive alongside AI.

41:00 – The Story You Tell Yourself Shapes Your Future

• A personal reflection on resilience, agency, and why changing your narrative can transform what becomes possible.

Resources Mentioned

• The Monet painting experiment — Fortune, Nick Lichtenberg
• Graduates booing commencement speakers — The Verge, Janus Rose
• Steve Wozniak at Grand Valley State — Futurism, Frank Landymore
• Jensen Huang CMU Commencement Speech — YouTube
• "Too Much Is Happening Too Fast" — The Atlantic, Charlie Warzel

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🎓 Prepare Your Students for an AI Future: The Future Ready Student AI Playbook a 10-hour course experience to graduate your students AI ready.

For questions, email: [email protected]

In this deeply reflective episode, Dr. Sabba Quidwai explores the emotional question underneath today’s AI conversation: Do I still matter? Through stories of corporate layoffs, classroom innovation, leadership transformation, and emerging AI practices, she unpacks why the future of work and education depends not just on technical skills, but on preserving human agency, identity, empathy, and meaning.

Drawing on research, real-world district examples, and frameworks like SPARK and Clark & Estes’ Knowledge-Motivation-Organization model, this episode challenges listeners to rethink AI not as a replacement for people, but as a tool that amplifies the uniquely human capacities machines cannot replicate. 

Timestamps

00:00 — “No Pure Managers”: AI Restructuring the Workforce

• Dr. Quidwai examines layoffs at Coinbase, Cisco, LinkedIn, and Microsoft, and asks the deeper emotional question many professionals are silently carrying: Do I still matter?

07:00 — Why AI Training Alone Isn’t Enough

• Introduction to the Clark & Estes framework (Knowledge, Motivation, Organization) and why most AI initiatives fail when organizations focus only on tools instead of people.

10:00 — What Real AI Literacy Looks Like in Schools

• A powerful classroom example from English teacher David Norenberg shows how students critically evaluated AI outputs rather than simply using or banning the technology.

21:00 — The SPARK Framework and Prompting the Human Before the Machine

• Dr. Quidwai explains how empathy, aspirations, and human-centered thinking create stronger AI partnerships and restore motivation and agency.

29:00 — What Innovative Schools Are Doing Right with AI

• Real examples from Wichita Public Schools, Bangor Township Schools, Community High School District 117, Roseville, and Desert Sands Unified show how leaders are redesigning systems, culture, and learning around AI.

42:00 — Roald Dahl, AI Writing, and the Fight for Human Voice

• A reflection on The Great Automatic Grammatizer explores why human creativity, struggle, and meaning still matter in a world of polished AI-generated content.

Resources Mentioned

• Coinbase CEO memo — "Building a Leaner and Faster Coinbase" (the original memo)
• Cisco confirms 4,000 layoffs despite strong Q3 earnings and $15.8B revenue
• Read LinkedIn CEO's Internal Memo Announcing Layoffs
• Why the 'Middle Path' of AI Literacy May Be the Future of English Class — The 74
• Your article on Designing Schools — Innovation Gap Analysis: Using the KMO Method in Schools
• Clark & Estes (2008) — Turning Research Into Results (ResearchGate) (the original book)

Explore More from Designing Schools

🤝 Partner with Us: Join the AI Power Circle and collaborate with forward-thinking educators building the future with AI.

📘 Get the Book: Designing Schools - a practical blueprint to transform your campus with creativity, leadership, and innovation.

🎓 Prepare Your Students for an AI Future: The Future Ready Student AI Playbook a 10-hour course experience to graduate your students AI ready.

For questions, email: [email protected]

In this episode, Dr. Sabba Quidwai explores the growing challenges facing today’s graduates as AI, economic instability, and outdated educational systems collide. Drawing from Microsoft’s latest Work Trend Index, historical research on the digital divide, and real-world examples from business and education, she argues that the real issue is not access to AI tools, but whether young people have guides, systems, and learning environments that help them see opportunity instead of fear. Through frameworks like SPARK, backwards design, and design thinking, this episode challenges educators and leaders to redesign learning experiences, organizational systems, and community partnerships so students can build a meaningful human advantage in an AI-driven world.

Timestamps

00:00 – The “Cursed Generation” and the Broken Promise of Stability

• Dr. Sabba reflects on the difficult realities facing new graduates and introduces the tension between individual grit and systemic barriers in today’s workforce.

03:45 – Microsoft’s Work Trend Index and the 67% Problem

• A deep dive into Microsoft’s latest findings showing that organizational systems matter twice as much as individual effort when it comes to successful AI adoption.

10:15 – The Digital Divide We Never Solved

• Revisiting Paul Atwell’s research on the “digital use divide” and why schools still struggle to redesign learning tasks instead of simply adopting new technology.

17:30 – The Guidance Divide and Why Relationships Matter Most

• Examples from Mark Cuban, college students building AI-powered tools, and school leaders reveal that access to mentors and guidance may now matter more than access to technology itself.

21:45 – Four Strategies Schools Can Start Using Immediately

• Practical frameworks for redesigning learning, partnering with businesses, creating AI-safe experimentation cultures, and focusing on workflows instead of tools.

28:00 – Story, System, Strategy: Designing Schools for an AI Future

• Dr. Sabba outlines how districts and schools can move beyond isolated innovation toward sustainable organizational transformation.

Resources Mentioned

• Microsoft 2026 Work Trend Index Annual Report - Agents, Human Agency, and the Opportunity for Every Organization

• Wiggins & McTighe, Understanding by Design
• The Cursed Generation -  Ryu Spaeth 
• Mark Cuban on Big Technology Podcast 
• Hey Dad! We Built an App - Axios

Explore More from Designing Schools

🤝 Partner with Us: Join the AI Power Circle and collaborate with forward-thinking educators building the future with AI.

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🎓 Prepare Your Students for an AI Future: The Future Ready Student AI Playbook a 10-hour course experience to graduate your students AI ready.

For questions, email: [email protected]

This episode explores the overwhelming pace of AI advancements and the anxiety it creates, arguing that the real solution isn’t chasing every new tool but building intentional systems. Through stories from educators and students, Dr. Sabba highlights the growing gap between how AI is used in schools versus the real world—and why designing thoughtful frameworks for learning is more critical than ever.

Timestamps

00:00 – AI Overload & The Stress Response

• OpenAI’s new agent features spark widespread panic and highlight the emotional toll of constant tech updates.

03:00 – Systems Over Tools

• Why reacting to every AI update is unsustainable—and how having a system changes everything.

05:30 – A Student’s AI Dilemma

• Joey’s story reveals confusion around ethical AI use and the lack of clear guidance in education.

10:00 – Schools vs. Reality

• Educators revert to paper-based methods while the workforce accelerates toward AI fluency.

12:00 – Beneficial vs. Detrimental AI Use

• New research introduces “cognitive offloading” and how AI can either support or weaken thinking.

Resources Mentioned

• NYT - Dana Goldstein - How AI Killed Student Writing and Revived It
• Medium - Joey and Devon - AI Literacy is the New Digital Divide
• CNBC & Handshake — Entry-level jobs calling for AI skills nearly doubled from a year ago, says report
• UTS Cognitive Offloading - Artificial intelligence, cognitive offloading and implications for education
• RAND - More Students Use AI for Homework, and More Believe It Harms Critical Thinking
• OpenAI Workspace Agents - Introducing workspace agents in ChatGPT
• Open app - Open: Nervous System Reset

Explore More from Designing Schools

🤝 Partner with Us: Join the AI Power Circle and collaborate with forward-thinking educators building the future with AI.

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🎓 Prepare Your Students for an AI Future: The Future Ready Student AI Playbook a 10-hour course experience to graduate your students AI ready.

For questions, email: [email protected]

This episode unpacks the recurring cycle of adopting, blaming, and retreating from new technologies in education—highlighted by LAUSD’s recent screen restrictions. Dr. Sabba Quidwai argues that the real issue isn’t technology itself, but the failure to redesign learning experiences and build systems that empower educators and students. From classrooms to workplaces, the message is clear: without agency and intentional design, new tools only reinforce old problems.

Timestamps

00:00 – LAUSD’s Screen Ban Announcement

• A major policy shift sparks debate: banning screens for young learners and limiting usage for others.

00:02 – The Real Problem Isn’t the Technology

• Historical pattern: adopt → disappoint → blame → remove. The issue lies in task design, not devices.

00:05 – A Personal Story of Transformation with Tech

• How reimagining a task—not just using a tool—changed teaching practice and career trajectory.

00:10 – The Digital Use Divide Explained

• Equal access doesn’t mean equal learning; how students use technology determines outcomes.

00:16 – AI in the Workplace: Same Mistake, New Context

• Research shows organizations succeed with AI only when they rethink workflows, not just adopt tools.

00:23 – From Literacy to Agency

• Why teaching tools isn’t enough—true impact comes from empowering people to use them meaningfully.

Resources Mentioned

• LAUSD Screen Time Policy Details — EdSource
• Reese Witherspoon Confronts AI Backlash — Variety
• Meta Keystroke Tracking — TechCrunch
• Attewell — The First and Second Digital Divides (ERIC)
• Employers Struggle to Find Graduates with AI Skills — Higher Ed Dive
• Mapping AI into Production — INSEAD/Harvard (SSRN)

Explore More from Designing Schools

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🎓 Prepare Your Students for an AI Future: Free Course – AI Skills for College and Career to equip your school community with future-ready skills.

For questions, email: [email protected]

In this episode, Dr. Sabba Quidwai challenges the dominant narrative that AI is eroding students’ ability to think, arguing instead that the real issue is a lack of human agency in how technology is used. Drawing on new research, workplace trends, and classroom insights, she reveals how students and workers alike are struggling not with AI itself, but with systems that fail to empower them. The episode offers a powerful reframe—and practical strategies—for designing learning and work environments that prioritize agency, empathy, and intentional AI use.

Timestamps

[00:00:00] The Cognitive Offloading Debate Begins

• Reflections from education conferences and the growing concern that students are “outsourcing” their thinking.

[00:03:00] It’s Not a Thinking Problem—It’s an Agency Problem

• Why disengagement predates AI and what research reveals about student experience.

[00:05:00] The AI Frontier Is Moving Faster Than We Realize

• Anthropic’s unreleased model and what it signals about the future students are entering.

[00:10:00] Gen Z’s Emotional Reality with AI

• New data shows rising anxiety, anger, and lack of control despite widespread usage.

[00:14:00] The Classroom Insight That Changes Everything

• Students aren’t cheating—they’re using AI for feedback, but without the framework to evaluate it.

[00:18:00] When Agency Is Missing, People Push Back

• Why 44% of Gen Z workers are actively sabotaging AI in the workplace.

[00:26:00] Five Shifts to Move from Compliance to Agency

• Practical strategies for educators, leaders, and parents to redesign AI integration.

Resources Mentioned

• Lumina/Gallup Gen Z AI Sentiment Report
• Gen Z Workers Sabotaging AI Rollouts
• Anthropic Claude Mythos - Project Glasswing
• Ryan Roslansky & Aneesh Raman - Open to Work: How to Get Ahead in the Age of AI

Explore More from Designing Schools

🤝 Partner with Us: Join the AI Power Circle and collaborate with forward-thinking educators building the future with AI.

📘 Get the Book: Designing Schools — a practical blueprint to transform your campus with creativity, leadership, and innovation.

🎓 Prepare Your Students for an AI Future: Free Course – AI Skills for College and Career to equip your school community with future-ready skills.

For questions, email: [email protected]

This episode explores the tension between fear and opportunity in the age of AI, drawing parallels from history to show that technological disruption is not new—but our response to it matters more than ever. Through real-world examples from Oracle, Stanford research, and student behavior, the conversation highlights a critical truth: success with AI depends less on the technology itself and more on how we invest in people, redesign systems, and build human agency.

Timestamps

00:00 – A Story from 1920s Madrid

• A powerful reflection on telephone operators and how past generations faced automation—reminding us that technology evolves, but human value endures.

05:00 – Oracle’s Layoffs & Leadership Failure

• A case study of what happens when organizations prioritize infrastructure over people, including the controversial 6:00 AM layoff emails.

07:30 – What Successful AI Adoption Actually Looks Like

• Insights from Stanford’s Enterprise AI Playbook reveal that the biggest challenges aren’t technical—they’re human.

12:30 – Students, AI, and the Critical Thinking Crisis

• New data shows students are using AI more while simultaneously believing it harms their thinking—highlighting a gap in guidance and frameworks.

16:00 – Building Agency: The Real Competitive Advantage

• Examples from LinkedIn and KPMG demonstrate how organizations are investing in human skills, experimentation, and AI fluency.

Resources Mentioned

• Hadiya Quidwai, "They Called It Automation Too," Substack

• Jensen Huang on the Lex Fridman Podcast (#494) | April 2026
• Pereira, Graylin & Brynjolfsson, "The Enterprise AI Playbook: Lessons from 51 Successful Deployments," Stanford Digital Economy Lab, April 2026
• Schwartz & Diliberti, "More Students Use AI for Homework, and More Believe It Harms Critical Thinking," RAND Corporation, 2026
• Hanson & Shroff, "AI Adoption Isn't the Hard Part, It's Building Employee Agency," Fortune, 2026

Explore More from Designing Schools

🤝 Partner with Us: Join the AI Power Circle and collaborate with forward-thinking educators building the future with AI.

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For questions, email: [email protected]

In this episode, Dr. Sabba Quidwai explores why the biggest barrier to effective AI adoption isn’t the technology—it’s the lack of systems and mindset. Drawing parallels to the iPad rollout in education, she explains how history is repeating itself and why a “mobile mindset” is essential for success in an AI-driven world. The episode challenges listeners to shift from tool usage to intentional design in order to unlock real transformation.

Timestamps:

00:03:00 – The rise of “AI slop” and why generic outputs are getting worse, not better

00:08:00 – AGI debate and what it actually means for everyday professionals

00:11:00 – AI agents that can control your computer and why systems matter more than ever

00:19:00 – The 2014 iPad story and the origin of the “mobile mindset”

00:25:00 – Research reveals why experienced AI users outperform beginners

Resources Mentioned:

• Free Masterclass: From AI Slop to AI Systems - Join Us Live
• Anthropic Economic Index: Learning Curves Report
• Lex Friedman Interviews Jensen Huang
• Instructure Canvas Introduces AI Agents
• USC - Students Share Experience with iPads

Explore More from Designing Schools

🤝 Partner with Us: Join the AI Power Circle and collaborate with forward-thinking educators building the future with AI.

📘 Get the Book: Designing Schools — a practical blueprint to transform your campus with creativity, leadership, and innovation.

🎓 Prepare Your Students for an AI Future: Free Course – AI Skills for College and Career to equip your school community with future-ready skills.

For questions, email: [email protected]