Lassoing Leadership

Summary

In this episode, we explore the future of independent schools, leadership challenges, and the impact of AI with Anand Mahadevan, Executive Director of CAIS. Discover insights on continuous improvement, community engagement, and adapting to rapid technological change.

Keywords

independent schools, leadership, AI in education, continuous improvement, community engagement, school accreditation, educational trends 2026

Key Topics

• The role of AI in education and school design
• What it means to be a CACE school and the accreditation process
• Leadership characteristics for thriving in complex environments
• Trends in education for 2026 and beyond
• The importance of community and social health in schools

Sound Bites

"AI is a tsunami or paradigm shift in education."

"The future's already here, it's just unevenly distributed."

"Leaders need intellectual humility, humor, and courage."

Chapters

00:00 Introduction and guest introduction

01:52 Guest background and journey into educational leadership

04:10 Highlights from the 2025-26 academic year in schools

06:45 What makes a school a CAIS school?

08:36 Defining the essence of CAIS schools

14:02 Emerging trends for 2026 and beyond

16:03 The impact of AI on education and school design

17:36 Schools as community centers and social health hubs

21:38 Leadership qualities for flourishing in education

23:53 The alchemy of leadership: humility, humor, and courage

28:28 The importance of financial and institutional sustainability

30:16 How to learn more about CAIS and connect

Resources

CAIS Official Website - https://www.cais.ca

Summary

In this episode, Joe Wilson discusses the human stories behind AI development, the hidden labour involved, and the importance of critical thinking about AI narratives. He emphasizes understanding the human stack and encourages skepticism and curiosity in AI adoption.

Keywords

AI, human stories, labour, critical thinking, AI narratives, technology, ethics, education, AI development, societal impact

Key Topics

• The anthropological perspective of AI and the human stories behind it
• Hidden labour and ghost workers in AI development
• The role of entrepreneurs and narratives in AI's future
• Critical thinking and skepticism about AI stories
• The impact of data centers and environmental trade-offs
• Grassroots innovation and youth engagement with AI

Sound Bites

"The humans who do the science are almost always erased from that process"

"I've been told, AI was just gonna solve the opioid epidemic... I'm not sure about this claim."

"These are brains and they are thinking and they are doing human work"

Chapters

00:00 Introduction to Joe Wilson and his book 'Humans of AI'

03:07 Joe's background in science, technology studies, and AI research

04:14 The importance of understanding the human stories behind AI

06:22 The erasure of human labor in scientific narratives and AI

08:46 Diverse personas in AI development: pioneers, ghost workers, believers, and detractors

11:39 Hidden labor in self-driving cars and data centers

14:22 The reorganization of human labor through AI and entrepreneurial narratives

17:23 The dangers of believing AI as human-like intelligence

18:45 Critical thinking and skepticism in AI adoption and education

24:11 Grassroots innovation and youth creativity in AI

26:56 Environmental trade-offs and community reactions to data centers

28:46 The importance of curiosity and skepticism in AI understanding

29:22 Where to find more of Joe Wilson's work and research

Generative AI in Education: Insights from Leading Thought Leaders

Summary

Discover the transformative potential and practical applications of generative AI in education through discussions with top educators and industry experts. This episode explores innovative use cases, leadership strategies, ethical considerations, and how schools can prepare for an AI-driven future.

Take Aways

• Diverse perspectives on inspiring AI applications in schools, from research tools to personalized student support
• Strategies for resource-efficient AI implementation and developing sovereign AI foundations
• Leadership guidance for integrating AI into school culture, policymaking, and curriculum
• Critical conversations around data privacy, academic integrity, and ethical AI use
• Practical steps for educators and leaders to navigate AI's rapid evolution and ensure responsible adoption
• The importance of fostering a growth mindset, critical thinking, and cognitive bilingualism in students
• Examples of innovative projects like vibe coding and AI clubs that demonstrate student engagement and creativity
• Insights on building AI literacy across all levels of education and ongoing professional development

Timestamp

00:00 - Introduction to AI in education and episode themes02:10 - Inspirational examples of generative AI applications04:14 - Sovereign AI: building custom, ethically governed systems06:43 - Resource strategies for AI integration amid staffing challenges08:26 - Innovative uses from higher education and public schools09:23 - Creative AI solutions supporting diverse student populations11:00 - The evolving conversation on data privacy and academic integrity12:45 - How skilled teachers leverage AI for personalized learning13:12 - Practical AI projects like vibe coding and student-led initiatives16:02 - The role of AI clubs and student-focused AI literacy18:14 - Platform options and safety considerations for schools19:19 - Data analytics and research tools empowering school leadership21:10 - Transformative possibilities: live translation and collaborative insights23:38 - Preparing schools for the AI revolution: strategic guidance27:06 - Leadership guardrails: values, guiding principles, and growth mindset30:49 - Balancing safety, ethics, and well-being in AI adoption34:12 - Addressing educator concerns about curriculum overload36:11 - Framing AI as a facilitator rather than an additional burden38:43 - Developing agentic skills and responsible AI oversight in students42:38 - Advice for new school leaders navigating AI's impact45:38 - Connecting with the experts: resources and ongoing learning opportunities

Resources

• Shape of Tomorrow newsletter - Michael Ianni-Palarchio's insights and updates
• Future of Education Report - Case studies and leadership guides
• Vibe coding - Creative AI-driven app development for educators and students
• Claude Platform - Educator-friendly AI tools for classroom innovation
• Gemini & Flint Platforms - Official tools used by Lakefield College School

• Jason Rogers - Twitter | LinkedIn
• Garth Nichols - Twitter | LinkedIn
• Michael Ianni-Palarchio - LinkedIn | Newsletter
• Beth Nichols - LinkedIn
• Les McBeth - Future Design School | LinkedIn
• Myke Healy - Head of School at St. John's Ravenscourt | LinkedIn

This episode is a must-listen for educators, school leaders, and policymakers aiming to harness AI responsibly and creatively, ensuring a future-ready education system.

Summary

There is a question sitting underneath most conversations about generative AI in schools right now. Not whether it belongs in the classroom. That debate is largely settled. The harder question is what happens to the parts of learning that cannot be automated.

For this episode of Season 3, Garth Nichols and Jason Rogers put that question to a panel of education experts: Alan Gertner, Justin Medved, Natalie Vera, and Eric Hudson. Rather than a single guest working through a single book, this conversation brings several voices into the room together, each carrying a different vantage point on where AI is already reshaping classrooms and where it still has no business being.

The panel moves quickly, but it stays grounded. Talk of curriculum and tools gives way to something more personal: student agency, the discipline of keeping a human in the loop, and what it might mean for a generation of students to grow up fluent in tools built to think for them.

What lingers longest is a claim offered almost in passing, that real education happens in the parts that cannot be Googled. Not because the tools are unwelcome. Because the parts that cannot be searched are the parts that were never really about information in the first place. Literacy, ethics, leadership. Everything the panel touches keeps circling back to that idea.

Chapters

00:00 setting the stage: why ai matters for schools right now
04:00 the panel introduces itself, and where each perspective differs
09:49 stories of ai already at work in classrooms
20:12 practical strategies for bringing ai into a school
29:59 the ethics of ai, and why a human still needs to be in the loop
40:03 a future vision for ai and school leadership
50:10 helping educators and parents step into ai with confidence
59:57 closing thoughts and where to find more

Key Takeaways

Agency, not automation. The panel keeps returning to student agency as the center of AI literacy. The goal is not a generation that defers to the machine, but one that knows when to.

Inspiration before implementation. The most convincing case for AI in schools comes not from policy, but from small classroom stories. The panel offers several, and they do more work than any framework could.

A human still has to be in the loop. Ethical use of AI is treated as a design constraint, not an afterthought. Every strategy discussed assumes a person is still making the final call.

What cannot be searched. For all the ground the panel covers, the conversation keeps returning to the same idea. The most important parts of education are the parts a search engine was never built to hold.

Quotes

"Centering student agency in AI literacy."
"Real education happens in the parts that can't be Googled."
"Generative AI can push civilization forward."

Resources

Learning on Purpose Newsletter: https://substack.com/learnonpurpose
Cohort21 Blog and Resources: https://cohort21.com
Kinship, Precision Learning: https://buildkinship.ai (double check, see note above)
NETI, Network for EdTech and Innovation: https://linkedin.com/groups/12345678

Guest Links

Justin Medved, LinkedIn: https://www.linkedin.com/in/justinmedved/
Natalie Vera, LinkedIn: https://ca.linkedin.com/in/natalie-vera-3b1ab840
Eric Hudson, LinkedIn: https://www.linkedin.com/in/ejhudson/
Alan Gertner, LinkedIn: [needs confirmation, placeholder]

Summary

Some leadership lessons arrive through frameworks. Others arrive on four legs.

In this episode, Garth and Jason sit down with Robyn Meagher and Jason Dorland, whose book Ike traces the impact one animal had on how they think about vulnerability, joy, and connection. Their journey is not a typical leadership origin story, and that is part of what makes it worth hearing. Ike became a mirror for both of them, a way of seeing self-worth and relationship differently, and that shift carried directly into how they now coach and lead others.

The conversation covers journaling as a practice for processing emotion rather than just recording events, and how psychological safety is not a policy but a condition built through real, sustained connection. Robyn and Jason return often to joy and play, not as a break from high performance but as one of its actual sources. Resilience, in their telling, is less about grinding through and more about protecting the capacity to feel light even under pressure.

What emerges most clearly is the honesty in how they describe vulnerability. Not as a leadership buzzword, but as something they learned had to be lived before it could be taught.

This is a conversation for leaders who sense that the science of performance only gets you so far, and that heart has to be part of the equation too.

Chapters

00:00 introduction to leadership and passion
02:32 the journey of Robyn Meagher and Jason Dorland
05:02 exploring the book Ike and its emotional impact
07:58 the influence of Ike on vulnerability and relationships
10:12 leadership practices: journaling and psychological safety
18:32 the role of fun and joy in leadership
24:59 Ted Lasso: a model for heart centered leadership
28:55 Beards Book Club outro

Key Takeaways

Vulnerability, practiced honestly rather than performed, deepens both connection and leadership effectiveness.

Joy and play are not indulgences. They are part of what sustains high performance and resilience over time.

Animals can reshape how we see our own worth, offering a kind of unguarded reflection that is hard to find elsewhere.

Journaling gives leaders a way to process emotion in real time, rather than letting it accumulate unexamined.

Psychological safety is built through authentic connection, not declared through policy.

Leadership sits at the intersection of science, heart, and lived experience, and none of the three is optional.

Sound Bites

"Animals profoundly impact our self-perception."

"Psychological safety is foundational for growth."

"Joy builds resilience and enhances performance."

Resources

yourmindset.ca - https://www.yourmindset.ca

Summary

What does it mean to achieve something today, when the paths that used to define success are shifting under everyone's feet?

That question sat at the center of our conversation with Asheesh Advani, CEO of Junior Achievement Worldwide and author of Modern Achievement. Ashish has spent his career watching how young people define success, and what he is seeing now is a generation navigating career paths that no longer move in a straight line. AI is part of that shift, not as a threat to outrun but as a tool that, used well, frees people up to do the harder, more human thinking.

Asheesh walked us through a framework he calls fixed, flexible, and freestyle, a way of thinking about leadership and career decisions that accounts for how much certainty we actually have in a given moment. We spent time in the tension between meritocracy and effort, and why rewarding habits and persistence may matter more right now than rewarding outcomes alone. Mentorship came up again and again, not as a program to run but as a relationship that lets people find purpose at their own pace rather than someone else's timeline.

What stayed with us was his point about meta-learning, the idea that reflecting on how we learn is becoming as important as the learning itself. In a world moving this fast, that kind of self-awareness may be the most durable skill a leader or a young person can build.

This is a conversation for leaders and educators trying to make sense of achievement in a world that keeps redefining it.

Chapters

00:00 introduction and updates on Junior Achievement Worldwide05:13 the changing landscape of success and achievement08:19 path dependency and career flexibility10:55 the fixed, flexible, and freestyle framework13:58 meritocracy and the role of effort17:11 generative AI and education19:56 the structure of modern achievement23:18 mentorship and purpose in education26:12 Ted Lasso: leadership lessons29:13 conclusion and final thoughts

Key Takeaways

Success no longer follows a fixed path, which means leaders need frameworks flexible enough to hold uncertainty rather than pretending it away.

The fixed, flexible, and freestyle framework offers a way to match your approach to how much certainty a situation actually allows, rather than defaulting to rigid planning everywhere.

AI is most useful when it takes on the easy tasks and frees people to spend their effort on the hard thinking that actually builds judgment.

Rewarding effort and habits, not just outcomes, builds a healthier relationship to achievement, especially for young people still figuring out what success means to them.

Mentorship works best when it makes room for someone to find their own purpose at their own pace, rather than steering them toward someone else's definition of arrival.

Meta-learning, the practice of reflecting on how you learn, may be one of the most important skills to build in a world that keeps changing what success requires.

Sound Bites

"Use AI to do hard thinking, not just easy tasks."

"We should be rewarding effort and habits, not just outcomes."

"Let people find their purpose at their own pace."

Resources

Modern Achievement by Asheesh Advani - https://www.amazon.com/s?k=Modern+Achievement+Ashish+Advani
Junior Achievement Worldwide - https://jaworldwide.org
Marshall Goldsmith - https://www.linkedin.com/in/marshallgoldsmith
Generative AI tools - https://openai.com/blog/chatgpt
Meta-Learning and Reflection Science - https://www.sciencedirect.com/science/article/pii/S0160289619301244

Guest Links

LinkedIn - https://www.linkedin.com/in/ashishadvani/
Website - https://jaworldwide.org

Keep Leading the Lasso Way.

Summary

Hospitality is not a department. It is a posture.

That was the thread running through our conversation with Mia Berloni, CEO of Teatro Group, as Garth and I dug into the idea of unreasonable hospitality and what it actually asks of a leader. Mia has spent her career inside rooms where the smallest gesture, a remembered name, a note passed at the right moment, can matter more than the meal itself. What she has learned in those rooms translates directly to how schools and organizations build culture.

We talked about clarity as an act of kindness rather than its opposite, and how feedback delivered with care becomes one of the most generous things a leader can offer a team. Mia's approach to hiring is not built around credentials first. It is built around who fits the culture and who will carry it forward, because culture is not something you announce, it is something you practice in a hundred small decisions a day.

What stayed with us was her insistence that kindness has to hold even when it is inconvenient, even when it costs you time or comfort in the moment. That is where unreasonable hospitality stops being a nice idea and starts being a discipline.

This is a conversation for any leader who wants their culture to be felt, not just stated.

Chapters

00:00 introduction to unreasonable hospitality05:47 Mia's journey into hospitality08:50 the role of culture in leadership11:51 hiring for culture and team dynamics14:49 leading with kindness and clarity17:56 feedback as a tool for growth21:00 rapid fire questions and final thoughts33:04 Beards Book Club outro

Key Takeaways

Unreasonable hospitality means going beyond expectation in ways that are small, specific, and personal. It is not about grand gestures, it is about noticing.

Clarity is kindness. Leaders who avoid hard conversations in the name of being nice are often doing the opposite of what their people need.

Culture is built through hiring. Bringing in people who already carry your values forward is easier than trying to teach values after the fact.

Feedback, given well, is a form of investment in someone's growth rather than a correction of their shortfall.

Kindness that only shows up when it is convenient is not really a value. It becomes real in the moments it costs something.

Sound Bites

"Clarity is kindness."

"Sometimes the smallest things are the biggest things."

"Leading with kindness even when it's inconvenient."

Resources

Unreasonable Hospitality by Will Ghidara - https://www.amazon.com/s?k=Unreasonable+Hospitality+Will+Ghidara
Mia Berloni - Teatro Group - https://www.linkedin.com/in/miaberloni/

Summary

In this inspiring episode, psychologist and author Dr. Jody Carrington shares insights on the importance of authentic connection, emotional regulation, and leadership in education. Discover practical strategies to foster social health, build resilient teams, and lead with heart in challenging times.

Keywords

leadership, education, emotional regulation, social health, authentic connection, resilience, teacher well-being, school leadership, mental health, community building

Key Topics

• The importance of feeling seen and deeply understood
• Neurobiological wiring for connection and its implications
• The impact of social health on happiness and performance
• Strategies for leaders to regulate themselves and others
• The role of joy and vulnerability in building community

• Feeling Seen: The Key to Connection in Schools
• How Authentic Interaction Transforms Education

Quotes

• "We are neurobiologically wired for connection"
• "The hardest thing is to look at each other"
• "Misery loves miserable company"

• drjodykarrington.com

Chapters

00:00 - Introduction to Lasso and Leadership

05:07 - The Importance of Connection in Leadership

08:08 - Understanding 'Feeling Seen' in Education

11:01 - The Role of Educators in Emotional Well-being

14:18 - Burnout and the Need for Rest in Leadership

17:13 - Investing in Educators for a Better Future

20:00 - The Importance of Social Health

26:37 - Understanding the State of Education

32:57 - Leadership Lessons from Ted Lasso

Summary

Every school has a plan. Fewer schools have a strategy.

That distinction is where Garth and I began our conversation with Tom Olverson, author of Leading Through Strategy and The Architect Leader. Tom has spent years helping organizations separate the two, and what became clear early on is that a plan is a list of things to do, while a strategy is a set of integrated choices about where you will win and where you will not even try.

For heads of school, that reframe changes everything. It means naming a winning aspiration, understanding the culture you are actually working within rather than the one you wish you had, and accepting that saying yes to one direction means saying no to several others. Tom walks through five questions that help leaders get there, and we spent real time in the tension between honoring tradition and still being willing to move a school forward.

What stayed with us most was Tom's language around the head as architect. Not the person who does the building, but the person who designs the conditions under which good building can happen. That shows up in how you hire, how you develop culture, and how much trust you place in talented people to do the work once the conditions are right.

This is a conversation for heads of school and aspiring leaders who are tired of plans that sit on a shelf and want language for the harder, more honest work of strategy.

Chapters

00:00 introduction to leadership and strategy11:49 understanding strategy vs. planning17:39 balancing tradition and progress20:55 the role of heads in leadership27:55 common pitfalls in strategic planning32:25 leaders as architects36:08 hiring talented faculty40:05 the importance of faculty culture43:45 Beards Book Club outro

Key Takeaways

Strategy is not the same as planning. A plan lists actions. A strategy makes a bet on where value will come from, and that bet requires real trade offs.

A winning aspiration is the starting point. Before a school can build a strategy, its leaders need clarity on what winning actually looks like for that specific community.

Heads of school are architects of systems, not just managers of tasks. The job is to design the structures and conditions that let good work happen, then get out of the way.

Culture eats strategy without careful attention, which is why understanding the culture you already have matters as much as the plan you are trying to build on top of it.

Hiring well and then trusting the people you hired is one of the clearest levers a leader has. Talent thrives inside the right conditions, and creating those conditions is leadership work.

Sound Bites

"Strategy is a set of integrated choices."

"Your winning aspiration defines your vision."

"Strategy is about making a bet on value."

Resources

Leading Through Strategy by Tom Olverson - https://www.amazon.com/s?k=Leading+Through+Strategy+Tom+Olverson
Resource Group 175 - https://resourcegroup175.com

Guest Links

Website - https://resourcegroup175.com

Keep Leading the Lasso Way.

ABOUT THIS EPISODE

We have been circling this topic for a while. AI is everywhere in our schools right now, and the loudest conversations tend to be about policy and tools, about what students should or should not be allowed to do. But in this episode, Garth and Jason slow down and ask a different set of questions: What is this moment actually asking of us as leaders? What does it mean to be literate when a machine can write? And how do we build the kind of trust in our communities that makes navigating all of this possible?

This is not a how-to episode. It is more of a thinking-together episode. And we think that is exactly what this moment calls for.

WHAT WE GET INTO

00:00 - Setting the table: why this conversation, why now

05:55 - What does literacy actually mean when AI can tell your story for you?

08:20 - Revisiting mission, vision, and values through an AI lens

11:28 - Coherency and clarity: the leadership work only humans can do

14:17 - Why imperfection might be the most important thing we can model right now

16:22 - Finding the balance: technology in service of connection, not instead of it

18:34 - Where we go from here, and what we are still figuring out

A FEW LINES THAT STUCK WITH US

"What does it mean to tell your own story?"

"Trust is becoming more important in our society, not less. And schools are one of the few places that can actually build it."

"How are we going to build trust through imperfection? Because that might be the whole game right now."

KEY TAKEAWAYS

The question of AI in schools is not primarily a technology question. It is a values question. When we sat with that, it shifted the whole conversation.

Literacy has always been about more than decoding words. It is about authorship: the ability to find your voice, to make meaning, and to put something of yourself into the world. AI makes that question urgent in a new way. If a student can generate a polished essay in 30 seconds, what are we actually teaching them to do, and why?

What we kept coming back to was trust. Not just the institutional kind, but the deeper kind: the trust a student has that their teachers see them, that imperfection is safe, that taking a risk will not cost them everything. Schools that can build that kind of trust will be the ones that find their footing in this moment. And the leaders who model curiosity over certainty will be the ones worth following.