The Market's New Demand: Why industry leaders are prioritizing conflict resolution, priority sorting, and emotional intelligence over software proficiency.

The "Clunky" Nature of Change: How institutional evolution is rarely gradual, usually requiring a crisis or a significant shift in data to force a new paradigm.

AI in the Trades: A look at how entrepreneurs in blue-collar industries are using AI to build training databases and improve field operations.

Killing the Written Exam: Drew's innovative approach to "oral defenses" in crisis communication, where students must defend their strategies in real-time rather than submitting a paper.

The Difference Between Output and Outcome: Shifting the metric of success from "how fast can we do a task" to "how much have we actually grown as leaders."

Season 2 opens with a raw and timely conversation between Bob Hutchins and Tim Howes about one of education's biggest challenges: academic integrity in the age of generative AI.

As schools race to adapt, many are responding with surveillance and bans, but Bob and Tim ask a deeper question-what if the problem isn't AI, but the system itself?

They explore how generative tools are not creating dishonesty but revealing cracks in outdated assessment models, why detection software erodes trust, and how educators can rethink learning through transparency, reflection, and prompt literacy instead of punishment.

Redefining Academic Integrity:
Integrity is no longer about "doing your own work," but about demonstrating your own judgment and transparency in using AI responsibly.

Policing vs. Trust:
Detection tools and AI surveillance create a culture of suspicion. True integrity grows from relationships, mentorship, and open dialogue.

Systemic Rot in Education:
AI didn't cause dishonesty—it exposed how transactional learning and grade-focused systems fail to nurture genuine understanding.

Prompts as the New 'Show Your Work':
Instead of grading AI outputs, teachers can assess the quality of a student's prompts, which reveal depth of knowledge and critical thinking.

Inequity and the AI Divide:
Well-resourced schools teach AI fluency. Others teach avoidance. Without intervention, AI will widen the digital divide between students who learn to use it creatively and those who are punished for it.

"Detection doesn't build honesty. Relationships do." – Tim Howes

"If AI can do the task, maybe it's the wrong task." – Tim Howes

"Integrity wasn't working before AI. Generative tools just made the cracks visible." – Bob Hutchins

"Grading the prompt, not the output, reveals the student's understanding." – Bob Hutchins

In this special episode, we pause our usual conversations with educators and leaders to reflect on an essay I wrote, Teaching Humans, Not Machines. For decades, schools trained students to follow procedures, memorize answers, and perform for tests. The irony is that artificial intelligence now does those things better than we ever could.

We look at how systems shaped students to value compliance over curiosity, performance over presence, recall over reasoning—and how that left us vulnerable to disruption. But we also ask a deeper question: what capacities remain irreducibly human?

From attention and intellectual courage to real curiosity and creativity, these are the skills that can't be automated. They're also the very foundation of citizenship and meaningful life. If we want education to serve people instead of machines, we need to reclaim and cultivate them.

The article is here at https://bobhutchins.substack.com/p/teaching-humans-not-machines

📝 Episode Summary:
In this back-to-school conversation, Bob Hutchins sits down with Tim Howes to explore how schools can embed AI literacy into the core of teaching and learning—without losing the skills, creativity, and human connection that make education meaningful.

Together, they tackle questions on what belongs on a "must teach" list when AI can already perform so many traditional academic tasks, and how to ensure AI literacy isn't siloed off as a tech elective. They discuss the importance of transferable skills like critical thinking, collaboration, and adaptability, as well as emerging competencies such as prompt engineering, evaluating AI outputs, and blending human judgment with AI-generated insights.

The discussion also dives into the balance between AI-assisted learning and friction-rich, manual experiences that build resilience, the role regional service centers like ACES can play in shaping state and national AI priorities, and how today's first-graders might graduate looking very different from today's seniors.

🔍 Topics Covered:

What to prioritize on the "must teach" list in an AI era

Why AI literacy should live alongside—and within—core subjects

Skills that will gain importance because of AI, not in spite of it

Prompt engineering as a foundational literacy skill

Evaluating and interpreting AI outputs with a critical eye

Balancing AI-assisted learning with productive struggle

The role of service centers in piloting curriculum and influencing policy

A vision for the AI-literate graduate of the future

🧠 Key Quotes:

"AI shouldn't be a siloed tech skill—it's an appliance we'll use in every discipline."

"Prompting well is just asking better questions—and that's a skill we've always needed."

"We can use AI to create more manual learning experiences, not fewer."

📌 Who It's For:
Educators, administrators, policymakers, curriculum designers, and anyone shaping the future of learning in the age of AI.

🔗 Resources & Mentions:

ACES Innovation and AI initiatives

AI literacy integration models for K–12

Federal AI literacy funding announcements

Prompt engineering strategies for educators

📝 Episode Summary:
In this powerful episode, Bob Hutchins sits down with Dr. Lisa Simone—licensed clinical social worker, longtime educator, and director of Youth Justice and Education Services at ACES—to explore what it means to build systems that actually serve our most vulnerable youth.

From court-involved students to young people navigating trauma, disconnection, and deep educational gaps, Dr. Simone shares how her team is transforming what school can look like. Together, they discuss how AI and digital tools—when used with intention—can support student voice, promote real-world readiness, and break cycles of institutional failure.

But this conversation goes beyond tech. It's about leading with empathy. About earning trust, not demanding compliance. About building something new with students instead of designing around them. Whether you're in a classroom, a district office, or working in justice reform, Lisa's insights are an invitation to reimagine what it means to educate with care and purpose.

🔍 Topics Covered:

• Designing schools with students, not for them

• The shift from deficit models to strength-based education

• How AI can support trauma-informed practice without replacing human connection

• Tools that promote dignity, not difference, in the classroom

• Why "student voice" isn't optional—it's foundational

• Reentry models that prioritize healing and career pathways

• What truly personalized learning looks like for justice-involved youth

• The difference between repackaged compliance and transformative tools

🧠 Key Quotes:

• "It's not about demanding respect. It's about building safety so trust can grow."

• "Don't design a plan for a student—design it with them."

• "AI doesn't have to push students further apart. If used wisely, it can bring them back into the fold."

📌 Who It's For:
Educators, school leaders, social workers, policy makers, juvenile justice advocates, and anyone working to create equitable, human-centered learning environments.

🔗 Resources & Mentions:

• ACES Youth Justice and Education Services

• Connecticut Juvenile Justice Policy Oversight Committee (JJPOC)

• 21st Century Ed

• Gardner Holt Education maker spaces

• Trauma-informed care, SEL, and project-based learning

• Reentry pathways and postsecondary transitions for justice-involved youth

In this thought-provoking conversation, Bob Hutchins sits down with Dr. Kris DeFilippis, a former K–12 educator turned NYU professor, to explore the collision of AI, education systems, and equity. With experience ranging from custodian to assistant superintendent, Kris brings a rare, ground-level and systems-wide perspective to what's happening in schools as artificial intelligence gains traction.

They unpack the myth that AI is just a tool—and discuss how it may instead be a disruptive force demanding a full rethinking of how schools operate, assess, and serve. Kris shares candid reflections on how AI risks becoming a shortcut that bypasses meaningful equity work unless leaders adopt a mindset of epistemological humility and deep systems inquiry.

They also dig into real-world use cases, emerging policy gaps, and the paradoxical possibility that AI—if implemented wisely—could return us to the human core of education: agency, relationships, and community engagement.

🔍 Topics Covered:

The system-level tension AI is creating in public education

Why AI should not be treated as a neutral tool

The danger of automating existing inequities

Reframing assessment beyond regurgitation

Giving teachers and leaders time back for human-centered work

What transformation means vs. mere adoption

The myth of AI cheating and what it reveals about student motivation

Redefining educational leadership in the AI era

🧠 Key Quotes:

"If AI is giving you time back, use it to ask better questions—not just do more of the same."

"AI can't replace human judgment, but it will reflect it. So we better be sure we know what we're putting in."

"Equity isn't a side hustle. It has to be embedded into how we implement every single thing—including AI."

📌 Who It's For:
Superintendents, school leaders, policy-makers, professors, tech developers, and educators who want to engage AI thoughtfully, ethically, and systemically.

🔗 Resources & Mentions:

NYU Educational Leadership & Policy programs

Rutgers Disproportionality & Equity Lab

21st Century Ed & https://pdgogy.ai/

https://www.linkedin.com/in/kris-defilippis/

In this insightful episode, Bob speaks with Olga Simoes, CFO of the Association of Educational Service Agencies (AESA), about the financial realities behind educational innovation. Drawing from her time at ACES and her current national role, Olga shares how leaders can navigate limited budgets while making forward-thinking decisions that prepare students — and schools — for an AI-driven future.

Olga opens up about:

• The tension between what's needed and what's possible in today's educational funding landscape

• How to evaluate new technologies and avoid investing in the "shiny object" trap

• Building a culture that embraces change — not just in tools, but in mindset

• Why financial leaders need to zoom in and out — from spreadsheets to classrooms

• How to budget for long-term transformation, not just short-term fixes

• What future-ready hiring and workforce development will require

Whether you're an educational leader, financial administrator, or someone interested in how change happens behind the scenes, this episode offers a grounded, thoughtful look at how money, mission, and innovation meet.

Links & Resources:

• Learn more about AESA- https://www.aesa.us/

• ACES (Area Cooperative Educational Services)- https://www.aces.org/

• Connect with Olga Simoes on LinkedIn- https://www.linkedin.com/in/olga-simoes-804007112/

• Subscribe to Future Proof Education: AI and Beyond for more episodes on technology, leadership, and the future of learning

👤 Guest: Autumn Caraglio, Reading Specialist at ACES Mill Road School, North Haven, CT

📝 Episode Summary:
In this episode, Bob Hutchins speaks with Autumn Caraglio, a reading specialist at ACES Mill Road School, where she works with K–8 students facing profound emotional, behavioral, and academic challenges. Autumn brings over a decade of experience in trauma-informed, individualized literacy instruction—and she's not afraid to ask hard questions about what edtech gets right, and where it still falls short.

Together, they explore how AI tools—when used thoughtfully—can support students' self-confidence, personalize reading interventions, and remove the social stigma around struggling readers. Autumn shares real-world examples of how tools like speech-to-text, AI-powered feedback systems, and offline prompt engineering help her students learn, express, and grow. She also highlights the danger of relying on "shiny" tools that aren't built for nuance—and how she evaluates which tech tools to bring into her practice.

If you've ever wondered what real personalization looks like for students with complex needs, or how AI can quietly empower rather than overwhelm, this episode offers a grounded and deeply human perspective.

🔍 Topics Covered:

• How trauma-informed reading instruction reshapes traditional literacy models

• The role of trust, repetition, and relationship-building in reading interventions

• How AI can enhance offline instruction and reduce screen dependency

• What to look for—and avoid—in AI-powered literacy tools

• Why personalization must be relational, not just algorithmic

• The emotional benefits of private, self-paced AI feedback

• Ethical concerns and emotional intelligence gaps in edtech

• How Autumn helps staff adopt and adapt tech with curiosity, not pressure

🧠 Key Quote:
"AI should never lead—it should support. Especially when you're teaching kids who've been told they can't." – Autumn Caraglio

📌 Who It's For:
Literacy coaches, special educators, administrators, edtech designers, and anyone committed to creating inclusive, compassionate, and future-ready classrooms.

🔗 Resources & Mentions:

• ACES Mill Road School, CT.

• AI-powered fluency and IEP goal-writing tools

• Tools mentioned: ChatGPT, Claude, MagicSchool, Adobe, Canva, HMH Ed

• Trauma-informed reading practices