Chess, Not Checkers
May 9, 2026
“Fast is fine, but accuracy is everything.” — Wyatt Earp
Over the past month, meetings in Albany, NY and Washington D.C. reminded me of something I learned very early in my career as a district technology leader: education policy is a game of chess, not checkers.
When companies enter the education market, they often assume success is primarily about product innovation, speed, or market timing. Those things matter, but they are only part of the equation. The reality is that when you choose to work in education, you are signing up to operate inside systems built around public trust, student protection, local governance, and taxpayer accountability.
One of the biggest things I was reminded of during these conversations is how much education policy still starts locally. It is easy for founders, investors, and executives to think policy begins in Washington D.C. or at the state capitol. In reality, many of the most important decisions happen much closer to the classroom. School boards interpret state laws into district policy. Superintendents operationalize those decisions. Technology leaders evaluate risk and implementation. Teachers and families ultimately determine whether trust is earned or lost.
Years ago, when I was a fairly young Chief Technology Officer in Texas, I remember sitting with a freshman Texas legislator discussing education policy. He talked about trying to push a button in Austin that would create change across more than a thousand school districts, all with different communities, leadership teams, histories, and needs. That conversation shaped the way I think about policy to this day. Laws are rarely one size fits all in education. They become interpreted through local context, local leadership, and local trust. That is why companies selling into schools cannot simply study legislation. They have to understand the environments where those laws are actually being applied.
In Albany, I was reminded again how complex education governance really is. You may have alignment with legislators on both sides of the aisle and still discover they have limited influence over decisions, especially near term. You may align with a governor’s office and realize an independent state education agency operates separately with different authority and priorities. At the federal level, the conversations can be incredibly valuable, but federal leaders often have limited jurisdiction and influence over what ultimately happens at the state or district level.
None of that makes those meetings less important. In fact, they are critical. Policymakers want to hear from practitioners and operators. They want to understand what is actually happening in schools and classrooms across their states. But those conversations also reinforce an important reality: policy work in education requires patience and long term thinking. Like I said, chess, not checkers.
One of the biggest misunderstandings I see from companies entering the market is the belief that the rules are negotiable if the product is innovative enough. They are not. When you choose to work in education, you are agreeing to operate inside a specific set of guardrails. Whether that is student data privacy agreements, procurement requirements, accessibility standards, or state level regulations, those rules become part of your go to market strategy whether you like it or not. And the most important thing to remember is that those guardrails exist for a reason. They are there to protect students.
Data breaches and cybersecurity incidents in education have been in the news a lot recently, and they are important reminders that student data is not just another business asset. It is deeply personal information connected to children, families, and futures. Student data is uniquely sensitive. In many ways, it is some of the cleanest identity data that exists because young children do not yet have credit histories, financial complexity, or long digital records attached to them. That creates enormous responsibility for companies operating in this space, and the challenge becomes even more complicated with artificial intelligence.
Many student privacy laws on the books today were written years before AI reached its current capabilities. Technology is moving exponentially faster than policy frameworks can evolve, and policy most likely will never move as fast as technology. That does not remove responsibility from companies. If anything, it increases it. The companies that endure in education are the ones that understand this early. They recognize that trust is not a marketing strategy. It is infrastructure.
I have written before about trust velocity, and I believe trust in education is both slower to build and more fragile once broken than in many other industries. Education is deeply personal work. Schools are responsible not only for student learning, but also for student safety, family trust, and stewardship of public resources. That changes the way decisions get made. Yes, there are RFPs, compliance reviews, procurement processes, and legal agreements. Those things matter. But underneath all of it is reputation. District leaders want to know whether they can trust you. Teachers want to know whether your product actually helps students. Families want to know whether their children are safe.
I also think it is important to approach these conversations with empathy. In education technology, it is easy to criticize competitors when something goes wrong. The reality is that every company operating at scale faces risk. Cybersecurity threats are real. The technology landscape is changing rapidly. What matters is how companies prepare, how seriously they take the responsibility, and how transparently they respond when issues occur.
The organizations that endure are usually not the ones chasing shortcuts. More often, they are the ones willing to build carefully, listen closely, and strengthen foundations before scaling aggressively. I have been fortunate to help grow organizations very quickly during my career, and the reason those companies were able to move fast was because they had already invested heavily in trust, architecture, operational discipline, and customer alignment before the market noticed the momentum. Fast growth is not the problem. Weak foundations are.
The companies that flame out are often the ones moving faster than their understanding of the systems they are entering. Sometimes they launch too many products too quickly. Sometimes they prioritize speed over architecture. Over time, that creates operational complexity and increases the surface area for risk. The companies that last for ten or twenty years usually look different. They listen carefully to customers. They involve practitioners in product discussions. They pilot thoughtfully. They learn in controlled environments before scaling broadly. They understand that long term trust compounds far more effectively than short term momentum.
One of the lessons ranch life continues to reinforce for me is that shortcuts eventually reveal themselves. Fences that are not built correctly fail under pressure. Foundations that are rushed create problems later. The same principles apply in education technology. The organizations that endure in this market are rarely the loudest or the fastest. More often, they are the ones willing to understand the system deeply enough to move with it responsibly.
Because in education, trust is not a growth tactic. It is infrastructure.
