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What happens when your organization is optimized for yesterday?
We know that for most schools and not-for-profits, business as usual is a recipe for decline—gradually and then suddenly. This is what keeps most of our clients up at night.
Boards and leaders are the first line of defense when the stakes are high. We might sound like a broken record, but we are convinced that to lead change, there must be a clear and committed alignment of board and leadership about when to change, what to change, how to change, how to communicate change, and how to course correct when change brings unintended consequences.
Change leadership is tricky. And sometimes quite risky. In this Blueprint, we examine three examples of how systems and mindsets that brought success in the past can put your organization at risk today.
- Stephanie
| | Optimized for Obsolescence:
Mathematics Education as an Example | | During a recent podcast conversation, when asked how he would describe American education right now, my dear friend Ted Dintersmith—author, venture capitalist, and executive producer of the film Most Likely to Succeed—said: | | “People will say it’s not working. It actually is working really well. It’s just with an obsolete model.” | | | |
So often we hear that the education system is “failing” or “broken.” Reframing is helpful because it answers the question “How did we get here?” and points the way to possible solutions—that have implications far beyond our schools.
Dintersmith offers his perspective (one we've been articulating since I had the honor to premiere Most Likely to Succeed with Ted at Sundance in 2015):
| | “We adhere to the model that goes back to 1893, and that model was designed to equip young kids with rote skills and intentionally erode their creativity and curiosity and audacity and agency. And our decision, which I think was quite fateful, was as technology started to really shift things and move us out of the industrial era to the innovation era, we just doubled down on obsolete. And so it’s working in terms of its goal. It just has the wrong goal.” | | | “I think that’s a gross mismatch between what we not only insist on in school but devote thousands of hours to, versus a world that doesn’t care about that anymore, but cares about all these really powerful, interesting math ideas, ideas that absolutely shape our lives. You know, the more we do that, the longer we persist, the more kids leave school with really dismal prospects and hallowed-out sense of purpose.” | | | |
Relatedly, the Deloitte report on 2026 Higher Education Trends, emphasizes that “By embracing today’s transformative trends, higher education leaders have a remarkable opportunity to reimagine their institutions as agile, resilient centers of learning and innovation.”
Relevance and value are the most important considerations: “To do so, leaders must reconcile two realities: Students overwhelmingly seek degrees that lead to meaningful employment, and employers need graduates who not only have immediate skills but also the agility to adapt as work continues to evolve—especially under the influence of AI.”
If schools of the past were optimized for rote jobs and “being good at doing tasks you are assigned,” then today we need to optimize for the capacity to continually and rapidly learn. And every organization—not just schools—needs to think about how to facilitate continual learning.
Lifting this discussion back up to our larger thesis about change, we ask: How often is the “why” of what you do unclear? Start by testing some long-held assumptions—and notice what you do that is no longer relevant or valuable. Increasingly, schools and organizations that fail to adapt are seeing consequences in the bottom line—if they know where to look.
| | Change Your Focus:
What the Numbers Aren’t Telling You | | |
In "The Looming Crisis" and "Your Local College Is Running Out of Cash," Michael Horn highlights that many colleges are on the brink of becoming insolvent unless dramatic steps are taken. One of the most alarming aspects is that colleges can seem fine and then suddenly announce crisis and closure. We see similar problems in not-for-profits and private schools that find themselves constantly strapped for cash.
Drawing upon a new study by Steven Shulman, Horn writes,
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“Instead of focusing on operating budgets or net assets that are often illiquid, Shulman’s research examined a basic but critical financial question: Given current cash flow, how long could each college survive based on the cash and equivalents available for operations? For a surprising number of institutions, the answer is: not long.
Even assuming enrollments remain steady—an optimistic scenario given the coming demographic decline—more than one-third of the colleges studied have less than five years before becoming fiscally insolvent without significant changes. That means they will have less money coming in annually than they are spending, and will need to start drawing down their unrestricted endowments, or borrowing—if they can—to keep operating. On average, those schools have less than a year before their financial position falls into that territory. Colleges can appear stable right up until the moment they are not.”
| | | There are many parallels for K-12 schools and nonprofits—in both the source of the issues and the potential solutions. Horn’s description of the forces impacting colleges is highly relatable: | | “The cause of these challenges isn’t one single factor, but a set of pressures building from demographic changes, shifts in the public’s perception of the value of a college education, increased operating costs, emerging alternatives to traditional colleges, and, of late, possible changes in federal policies and programs.” | | | |
The question is: with multiple external forces breaking the old model, what do we deliberately build in its place?
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Start with your teams. Raising the bar for your board and executive team is essential work. Begin with board composition and your leadership team—focusing on the mindsets and conditions to get the best out of both.
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Confront reality. As Horn points out, many financial measures can fail to show the true picture. And we encounter too many organizations who cannot answer his question: Given current cash flow, how long can your organization survive based on the cash and equivalents available for operations?
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Recognize that surviving is not the true mark of success. Almost a decade ago in our paper, “From Financial Sustainability to Thriveability," we called for a shift in focus from financial sustainability to “thriveability.” The paper is written for schools, but the provocations within have wider applications for any organization ready to test assumptions and ensure its relevance and value into the future.
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Reassess the scope of your mission and how your school or nonprofit truly adds value. What problem are you solving today? Why does it matter? What do your clients or learners want? Who are they? It’s not enough to just incrementally improve on old approaches. You need to rethink mission and develop a winning strategy.
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Consider options for addressing fixed costs. Horn notes that while M&A has previously been resorted to only after a college fails, there are a growing number of strategic M&As between colleges and other NFP organizations that are designed to address challenges that feel intractable. Competitors can collaborate effectively when they appreciate each other's distinctive value. Start by examining where administrative costs and back office infrastructure might be consolidated. Where can two or more organizations share staff, spaces, and resources in order to increase impact for all?
| | Change is Human Work:
Leading People in an Age of Technology | | |
Change leadership is tricky and risky because the human dimension of change is at the center of the work. It’s often the most crucial element in successful transformations.
As one example, this BCG article “AI Has Made Work Reinvention a CEO Mandate” highlights the critical role of the leader in relation to AI advancements:
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“Too many leaders see AI as a technology transformation rather than a work and people transformation. They’re thinking about today’s work, and today’s processes—simply overlaying technology on top of them. The critical mindset shift is this: We must rethink why we do this work in the first place. What value does it create? Who should do this work? How must we redesign the work to unlock enterprise value, not just individual productivity?
This kind of transformation must be driven by the CEO because these shifts cut directly across existing structures, incentives, and power dynamics. They challenge roles, organizational boundaries, and professional identity. In many cases, the people closest to the work itself, and most impacted by how it will change, are also the ones being asked to help redesign it.”
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In change work, people need to know answers to three big questions:
- Why are we changing?
- What are we changing?
- How will this affect me?
This work requires as much (if not more) attention to the people as to the technology.
The Stanford Social Innovation Review article “Welcome to the Age of Relational Intelligence” offers helpful insights. Enter Ms. Ricks, a retired office manager who volunteers at 74th Street Elementary School in South Los Angeles as part of Generation Xchange, and Celeste, a fourth grader, who feels like her school work has more value because Ms. Ricks takes the time to care. “I feel like I know somebody is counting on me,” said Celeste.
Writes the author: “As artificial intelligence grabs headlines and investment dollars, Ms. Ricks and Celeste are practicing an intelligence that cannot be automated. It’s the intelligence of attunement, of care, of knowing, and knowing how to know each other. We might call it relational intelligence (RQ), the deeply human ability to build trust, navigate tension, repair ruptures, and create meaning with others.
Relationships are the foundation when we do work with other humans: when we focus there first, we can pursue the work with greater efficacy, purpose, and meaning.
| | The Emotional Work of Change | | |
Strategic clarity and relationships are just the start. Emotions and reactions will shape your organization’s ability to pursue its strategy in real time—and when you embark on changing long-established structures and processes, you are guaranteed to encounter a range of emotions: often these emotions are experienced as resistance, opposition, or a lack of accountability. Let's reframe this by examining underlying emotions, and how that can dramatically improve your ability to lead.
Reframing Resistance
Resistance is often experienced as defiance and criticism. The HBR article “Leaders Treat Resistance as Valuable Data” unpacks why it is helpful to shift your view and see what the resistance can tell you:
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“A colleague recently asked me a question about change that seemed so normal: ‘How do you tell the difference between legitimate concerns about a change and kneejerk resistance to it?’ At first glance, it sounds like a practical leadership question. But the more I sat with it, the more I realized it’s not actually answerable. It rests on a flawed assumption: that some resistance is legitimate and some isn’t. That assumption is exactly what gets leaders into trouble.
But here’s what years of studying and guiding organizational change have taught me: All resistance is meaningful data. … In my experience, what we call resistance is almost always something else: fear, loss, confusion, overload, or sometimes a legitimate flaw in the change itself.”
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The author outlines four emotional responses to help leaders understand and respond to resistance:
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Loss: “What am I losing?”
Every change, no matter how positive, involves an ending. … The mistake leaders make is trying to “sell” the future without acknowledging what’s being left behind. Name the loss directly. Don’t euphemize or rush past it. Re-anchor their value in the future.
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Anxiety: “What does this mean for me?”
Uncertainty is one of the brain’s most powerful stress triggers. … When anxiety is high, people don’t process information well. Communicate consistently, not just clearly.
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Lack of control: “Why is this being done to me?”
Often people don’t resist change as much as they resist feeling powerless or excluded in the face of it. Many organizations unintentionally make this worse through “faux-inclusion”: asking for input after key decisions have already been made.
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Flaws in the change: “This doesn’t actually work.”
Sometimes resistance isn’t about emotion at all. It’s about execution. Feedback may come wrapped in frustration or bluntness, but don’t let tone disqualify the content.
While this is where leaders must begin with change, seeing resistance as data is not a blank check for ongoing behavior that undermines the well-being of the team. We are not encouraging you to drag your feet when someone is actively undermining progress—to the detriment of all. There is a point at which behavior that consistently undermines forward movement demands that leadership step in. Our guiding principle is to invest the majority of your energy in the people who can lead you forward.
Own and Choose Accountability
Another powerful reframing that supports leading through relationships is offered in the HBR article “Accountability Must Be Chosen Not Mandated”:
| | “Leaders should stop asking ‘How do I hold people accountable?’ and start asking ‘What’s preventing them from choosing it?’” | | | |
When you enable your team to shift from a defensive stance (“Will I get blamed for this?”) to a mindset where they see themselves as essential to the outcome, you unlock the potential for growth, shared problem-solving, practices that create psychological safety, and a sense of ownership that drives positive outcomes.
As the author notes, it starts with clarity about the “why”: “When the meaning is clear, accountability stops being about compliance and starts being about care and commitment. At the individual level, meaning might come from values like integrity or reliability. At the team level, it’s often a shared goal that transcends any one person’s contribution.”
Trust and connection cannot be rebuilt with words that don’t match the realities. Looking at difficult realities is not easy. And no matter how thoughtful we are about how we lead and communicate, transformations of this scale involve loss and change—in ways that are personal as well as structural. You can't duck the emotions associated with loss or change—but you can offer new pathways of purpose, productivity, meaning, and impact.
| | What We Learned: Your Survey Responses | | |
Thank you, Blueprint readers!
A few weeks ago, we asked what you think and so many of you responded—we’re deeply grateful for the time and thought you put into the feedback!
Your engagement affirmed our sense that Blueprint readers are a remarkable group—nearly half of those who responded are Heads of School, CEOs, or Executive Directors and almost another 20% are board members. We also appreciate our many readers who are faculty, staff, and senior administrators that are taking the time each month to think about enterprise-wide topics and their own leadership: the current and future success of your organization (and your own career) depends on it!
Reflected in your responses, the topics that matter most to you are:
- Strategy & Planning
- Board & Leadership Assessment
- Trends on AI, workforce culture, etc.
We’re inspired to see that Board Education and Executive Coaching also ranked high—reflecting your dedication to ongoing learning.
When asked what you find most valuable, GLP’s insights and commentary came out on top, followed by our curation of resources and the white papers we author. You’re not just looking for a roundup of links—you want the "so what"—and we’ll keep that front and center.
You’re loyal readers—and you generously recommend the Blueprint. And you want more. The open-ended responses were full of thoughtful details—requests for deeper dives on AI, spotlights on schools and organizations that are innovating, and resources for middle management. We’re taking notes.
One big discovery for us is that most of you didn't know you can access the archives of past Blueprints! They are available on the GLP website—and they are full of resources you can return to.
At the bottom of this page https://www.greenwichleadershippartners.com/the-blueprint just enter your name/email to unlock access to the archives.
You are always welcome to email me with additional thoughts and suggestions at stephanierogen@greenwichleadershippartners.com. One of the best parts of sending the Blueprint each month is getting emails about how it helps your work and how you share the Blueprint with your team!
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