Help One Hundred Schools

Pete Upham has worked inside schools across multiple functional roles, from admission and development to college counseling, before spending 15 years leading a school association and working with hundreds of institutions. Today he runs his own consulting practice, and about 70% of his projects circle back to the same challenge: enrollment. What draws him to this work isn’t just the analytics. It’s the gap he keeps seeing between the data schools already have and the decisions they’re actually making.

Most schools are sitting on years of untapped information. They collect it, store it, and rarely interrogate it. Pete’s work is about changing that, helping schools move from anecdote and assumption to patterns, clarity, and smarter choices.

This conversation covers what good data practice actually looks like, where schools most commonly go wrong, and why the schools still standing in 20 years will almost certainly be the ones who took this seriously.

Help 100 Schools Podcast is underwritten by Spiral Marketing for Schools, a national enrollment marketing agency serving independent schools.

Heads of School and senior leadership teams may request a listener invitation for a complimentary 7-Point Enrollment Visibility Analysis. This assessment provides actionable insights into your school’s digital presence, inquiry pipeline, and growth opportunities.

Request a listener invitation here.

How is your school using data to drive enrollment decisions, and where would you honestly rate your data practice on a scale of 0 to 10?

Share your thoughts on social media and tag #Help100Schools

Subscribe to the Help 100 Schools Podcast for more conversations on enrollment strategy, leadership, and what it takes to build a school that lasts.

Rich Suttie got into the ChatGPT beta nearly four years ago and hasn’t stopped experimenting since. As a former Navy Top Gun instructor turned school head turned educational consultant, he’s delivered over 50 webinars on AI to private schools across the country. His consistent finding? Most educators still rate themselves a 2-4 out of 10 on AI familiarity.

Meanwhile, students are already logged in.

This conversation isn’t about whether AI belongs in schools. That ship has sailed. It’s about moving from paralysis to practical strategy: understanding the three types of resistance holding schools back, identifying low-risk starting points that deliver immediate value, and building the policies and practices that let you leverage technology without losing your soul.

Whether you’re curious, skeptical, or already knee-deep in prompt engineering, this episode offers a clear-eyed look at what AI adoption actually requires and what it makes possible when done right.

1. The Adoption Gap Nobody’s Talking About
   Why most school leaders still hover at beginner-level AI literacy after years of availability, and what that delay is actually costing.
2. Three Patterns of Resistance
   The real reasons educators avoid AI: time scarcity, fear of the downsides, and concern about dehumanizing education. Plus how to address each one.
3. Where to Start Without Risk
   Communications, policy drafting, data analysis, and marketing plans where AI delivers fast wins and builds confidence for harder applications.
4. The Task Force Method
   How to use AI itself to charter a team, build your policies, and create guardrails that align with your school’s mission and culture.
5. Training AI to Know Your School
   Why feeding your strategic plan, mission, and context into AI transforms it from generic tool to personalized assistant.
6. What Integration Actually Looks Like
   From browsers to Microsoft Office, AI is already embedded in the tools you use daily. The question is whether you’ll manage it intentionally.

• Three barriers dominate: “I don’t have time,” “I’ve only heard negatives,” and “Won’t this just encourage cheating?”
• Schools avoiding AI aren’t protecting their mission. They’re losing ground while students use it anyway.
• Start with administrative tasks where bias and accuracy matter less: calendar communications, policy templates, spreadsheet analysis.
• Different AI tools have different strengths and biases. 
• Training AI is iterative. Feed it your context, correct its assumptions, and it learns over time.
• Form a multidisciplinary task force. Include parents and teachers who are already curious, not random assignments.
• The person who embraces AI to improve their performance won’t lose their job. The person who ignores it might.

• Connect with Rich Suttie: LinkedIn
• Explore More Episodes: help100schools.com/podcast

Help 100 Schools Podcast is underwritten by Spiral Marketing for Schools, a national enrollment marketing agency serving independent schools.

Heads of School and senior leadership teams may request a listener invitation for a complimentary 7-Point Enrollment Visibility Analysis. This assessment provides actionable insights into your school’s digital presence, inquiry pipeline, and growth opportunities.

Request a listener invitation here.

How is your school approaching AI adoption, and where do you honestly rate your familiarity on a scale of 0-10?

Share your thoughts on social media and tag #Help100Schools

Subscribe to the Help 100 Schools Podcast for more conversations on innovation, leadership, and navigating change in education.

In this episode of the Help 100 Schools Podcast, host Karl Boehm speaks with Highley Thompson, Partner and Search Consultant at Educational Directions, about how independent schools can approach leadership transitions as moments of opportunity rather than disruption. Drawing on his decades of experience as a teacher, coach, division head, and consultant, Highley shares a deeply human perspective on how to find and nurture the right leaders—those who not only match a school’s mission, but also elevate its culture and community.

Their discussion explores the intersection of strategy and heart in school leadership searches: why timing, alignment, and authenticity matter as much as credentials, and how teams can use reflection and collaboration to ensure lasting success. Whether you’re a Head of School, board chair, or educator aspiring to leadership, this episode offers invaluable insights into the evolving world of executive search and team development in education.

1. The Transformational Approach to Leadership Search
   Why successful hiring isn’t about filling a vacancy—but about aligning a school’s vision, community, and timing for long-term impact.
2. The Power of Team Dynamics
   How adopting a coach’s mindset helps school leaders build high-functioning administrative teams grounded in trust, communication, and shared purpose.
3. The Three Variables for a Successful Match
   Highley’s framework—the person, the position, and the timing—and how these factors combine to create sustainable leadership fit.
4. Embracing AI with Integrity
   How artificial intelligence is reshaping search processes and candidate preparation—and what both schools and applicants should do to stay authentic in an AI-assisted world.
5. The Future of Independent School Leadership
   Why the next generation of leaders may come from both within and outside traditional education pathways, and how that diversity can strengthen schools for the long term.

• Every leadership transition is an opportunity to clarify mission, culture, and direction.
• A great search balances skill alignment with emotional intelligence and institutional fit.
• AI can be a helpful tool—but only human insight can determine true compatibility.
• Reflecting on team dynamics leads to more cohesive, forward-looking school cultures.
• Schools that invest in authentic, transparent hiring build trust that lasts beyond the transition.

• Connect with Highley Thompson: LinkedIn
• Educational Directions: https://www.edudx.com
• Email: [email protected] 
• Explore More Episodes: help100schools.com/podcast

Help 100 Schools Podcast is underwritten by Spiral Marketing for Schools, a national enrollment marketing agency serving independent schools.

Heads of School and senior leadership teams may request a listener invitation for a complimentary 7-Point Enrollment Visibility Analysis. This assessment provides actionable insights into your school’s digital presence, inquiry pipeline, and growth opportunities.

Request a listener invitation here.

How is your school approaching leadership transitions, and what does “the right fit” really mean in your community?

 Share your thoughts on social media and tag #Help100Schools

Subscribe to the Help 100 Schools Podcast for more conversations on leadership, growth, and building stronger school communities.

Most schools do not struggle because of strategy. They struggle because of staff culture that was never intentionally built.

Meredith Herrera works with school leadership teams navigating conflict, transition, burnout, and alignment challenges. In this conversation, she explains how staff culture shapes leadership effectiveness, retention, and ultimately enrollment stability.

Meredith didn’t plan to start a consulting business. She left school administration after years as a senior leader and, like she puts it, was fully intending to watch Netflix. Then her phone started ringing. Friends at schools needed help with a new Dean of Students, or a team that couldn’t move forward. One favor turned into another, and Meredith Herrera Consulting was born.

Her background is in counseling and human development, and that lens shapes everything she does. She coaches mission-driven leaders, works with teams navigating conflict or transition, and specializes in supporting historically marginalized leaders who are often promoted into high-stakes roles with very little runway. Her core conviction: most schools don’t have a talent problem. They have a support problem. And the cost of ignoring that shows up everywhere, in burnout, in turnover, in enrollment, and in the students who absorb all of it.

When staff culture weakens, families feel it long before anyone talks about strategy, and enrollment eventually reflects it.

In this episode of the Help 100 Schools podcast, we explore what becomes possible when schools stop assuming leadership takes care of itself and start treating culture as something worth building on purpose.

• Heads of School navigating staff turnover or burnout

• Division Directors and Deans stepping into leadership

• Enrollment leaders seeing retention pressure

• Boards seeking stronger internal alignment

1. What Culture Actually Is

Staff culture is defined by daily experiences, not formal plans or kickoff meetings.

Culture isn’t the strategic plan or the August kick-off session. It’s what people experience every single day. Meredith explains how much of a school’s culture forms completely by accident, through habits and traditions no one has examined in decades, and what it takes to start shaping it intentionally.

2. Why Alignment Is Not Agreement

Functional teams structure disagreement instead of avoiding it.

Healthy teams disagree. What separates functional teams from dysfunctional ones isn’t the absence of conflict, it’s having clear norms for how to work through it. Meredith breaks down what that structure actually looks like: decision-making roles, meeting agendas, communication sequences, and knowing who needs to be consulted before a call gets made.

3. The Bilateral Relationship Between Adults and Students

The wellbeing of staff and students continuously shapes each other.

If students aren’t doing well, look at the adults. If adults aren’t doing well, look at the students. Meredith traces this connection throughout the conversation, making the case that enrollment and retention are a direct reflection of how your team feels when they show up to work.

4. Why So Many Leaders Are Set Up to Struggle

Promotion without structured support creates preventable leadership failure.

Most people get promoted because they were excellent in their previous role. That is not the same as being prepared to lead. Meredith talks honestly about the gap between being promoted and being supported, and why assuming internal mentorship will fill that gap usually doesn’t work when the mentors have no white space in their own calendars.

5. What Sustainable Leadership Could Look Like

Intentional systems of support are the difference between burnout and longevity.

Meredith shares what she hopes to see change over the next decade: less crisis-driven leadership, clearer pathways for leaders of color and neurodivergent leaders, and schools that stop losing talented educators simply because no one built the systems to keep them.

• Culture is formed whether you shape it or not. The only question is whether you’re doing it on purpose.
• A culture of nice and a culture of kind are not the same thing. Nice avoids hard conversations. Kind has them.
• People aren’t resistant to change. They’re resistant to being surprised. Clear communication resolves more resistance than any persuasion strategy will.
• Job descriptions are a culture tool. When people don’t know the scope of their role, they try to do everything at full intensity and burn out.
• The leaders who need coaching most are often the ones no one thinks to invest in: academic deans, deans of students, division directors. Future heads of school who are burning out right now.

• Website: mherreraconsulting.com 
• Email: [email protected]
• LinkedIn: Meredith Herrera
• Explore More: help100schools.com/podcast 

Help 100 Schools Podcast is underwritten by Spiral Marketing for Schools, a national enrollment marketing agency serving independent schools.

Heads of School and senior leadership teams may request a listener invitation for a complimentary 7-Point Enrollment Visibility Analysis. This assessment provides actionable insights into your school’s digital presence, inquiry pipeline, and growth opportunities.

Request a listener invitation here.

How is your school moving from a “culture of nice” to a “culture of kind” while building sustainable leadership systems?

 Share your thoughts on social media and tag #Help100Schools

Subscribe to the Help 100 Schools Podcast for more conversations on leadership, growth, and building stronger school communities.

Sylvie Mensah lives in two worlds that rarely overlap. By day, she guides privileged families through admissions at the British School of Lomé in Togo. The rest of her time, she runs La Touche, providing education and hope to youth in juvenile detention centers and underserved communities across the same city.

Moving between these extremes—opportunity and abandonment, resources and deprivation—has fundamentally reshaped how Sylvie sees potential in every child. Her work embodies a philosophy rooted in Togolese culture: the child belongs to the community. It’s a perspective that challenges Western assumptions about success, access, and who deserves investment.

In this episode of the Help 100 Schools podcast, we explore what becomes visible when you refuse to see children through a single lens, and what American educators might learn from a culture where collective responsibility isn’t just a value, but a way of life.

1. How Context Shapes Perception of Potential

Why the same intelligence looks different in a detention center versus a private school, and what that reveals about opportunity rather than ability.

1. Cultural Models of Collective Responsibility

The Togolese principle that “the child belongs to the community”—how neighbors, strangers, and institutions share accountability for every young person’s success.

1. Barriers Beyond Money

Why language anxiety, cultural fear, and confidence gaps keep families from pursuing opportunities—and how lived experience can bridge those divides.

1. Education as Rehabilitation

How La Touche provides the only formal schooling in Togo’s juvenile detention system, and Sylvie’s vision for making it a national model.

1. Reciprocal Transformation Through Service

The story of a privileged student who volunteered for one month and stayed over a year—and what both sides gained from the exchange.

• Every child has potential—what varies is awareness, opportunity, and who’s willing to invest in proving it.
• Language and cultural confidence can be bigger enrollment barriers than tuition for international families.
• When communities embrace collective responsibility, safety nets emerge that individual families cannot create alone.
• Cross-cultural service experiences teach values and perspective that no classroom curriculum can replicate.
• Advising families to prioritize education today over other investments plants seeds with generational returns.

La Touche: latouche-tg.org/
Contact: Facebook (WhatsApp Number Available)| LinkedIn
Help 100 Schools Movement: help100schools.com

How is your school preparing for crisis management while building community trust?

Share your thoughts on social media and tag #Help100Schools

Subscribe to the Help 100 Schools Podcast for more conversations on leadership, growth, and building stronger school communities.