Seek First to Understand… A View from Both Sides of Education

March 21, 2026

“You don’t understand it until you’ve lived it.” ~ Texas saying

Out at the ranch, I’m still learning that lesson.

Horses have a way of exposing what you don’t know. You can read about them, watch them, or talk about them, but until you spend time around them, you don’t really understand how they think, how they react, what they need, or even how you will react to them.

The same is true in education.

There are a lot of opinions about education and Education Technology right now. You see them online, at conferences, and in conversations across the industry. Most are well intentioned. Many are right about specific frustrations. But very few tell the whole story.

And that is not a criticism. It is just the reality of perspective.

Over the course of my career, I have had the opportunity to see education from multiple angles as a teacher, a principal, a district leader, a Chief Executive Officer, and inside Education Technology companies. What I have learned is simple, but not always easy to live out. It is really hard to understand a system you have not sat inside of.

When you are a teacher, it is hard to fully understand the pressures your principal is navigating. When you are a principal, it is easy to forget how decisions made at the district level are shaped by budgets, constraints, and competing priorities you do not always see. And when you move into district leadership, you begin to understand just how many variables influence a single decision.

The same thing happens in Education Technology.

What is discussed at the leadership level of a company does not always translate the same way once it moves through the organization. By the time it reaches a district, it may come through a sales conversation, a support interaction, or even something as simple as an email. Along the way, things get filtered, simplified, or misunderstood. Sometimes it feels like a game of telephone.

Across every role, the pattern is the same. Without intentional effort, we default to our own perspective. That is where most of the friction begins.

From the outside, it is easy to assume breakdowns happen because of bad intent. In reality, they usually happen because of misalignment. Schools operate within real constraints including timing, budgets, staffing, and limited capacity for implementation. Education Technology companies operate within their own pressures including growth expectations, product timelines, and revenue targets.

When those realities collide without understanding, things break.

I remember sitting as a Chief Technology Officer in a school district and having vendors talk to me about quarters, quotas, and end of fiscal year urgency. The truth is, I did not even speak that language at the time. We were not being difficult. We were just operating in completely different systems.

On the other side, I have seen Education Technology companies try to move too fast, selling into districts without fully understanding implementation capacity, professional development limitations, or how many initiatives a system can realistically absorb at once. Speed often creates the gap.

Trust takes time. Understanding takes time. Alignment takes time. When we try to shortcut that, we create problems that did not need to exist.

Early in my career, I did not always have this perspective. As a district leader, I had a clear view of what I thought about vendors and salespeople. Like most people in education, I had a mental model of what good and bad looked like.

Then I moved into the private sector and found myself sitting alongside hundreds of sales professionals, later selling myself and eventually leading national sales organizations. I had to learn. I had to understand how they were trained, what they were measured on, and what it actually takes to be effective in that role. There is far more discipline and intention behind it than most people realize.

That shift in perspective changed how I saw the entire ecosystem. It also reinforced something I already knew from the district side. Relationships matter more than transactions.

As a Chief Technology Officer, I had what I would call my Mount Rushmore of account managers. The ones who listened, who were patient, who understood my constraints, and who showed up when things were not going well. Those were the people I trusted. Later in my career, I hired some of them into organizations I was leading. Not just because they could sell, but because they knew how to serve.

One of the biggest gaps in these conversations is a lack of understanding of how complex both sides really are. Running a school or district is incredibly challenging. There are governance structures, community expectations, and operational realities that most people never fully see.

At the same time, building and scaling an Education Technology company requires patience and a deep understanding of how schools actually operate. The companies that last are not the ones that move the fastest. They are the ones that listen, adapt, and build based on real needs. Too often, products are built based on assumptions instead of actual problems schools are trying to solve.

Schools do not need more problems. They need partners who help solve the ones they already have.

Most breakdowns between schools and Education Technology companies do not come from bad intent. They come from a lack of communication, a lack of relationship, and a lack of a genuine effort to understand what is really happening on the other side.

The best partnerships I have experienced, on both sides, always started the same way. Someone took the time to understand the strategy, the constraints, and the real problem trying to be solved.

If I could offer one piece of advice to educators sharing feedback with Education Technology companies, it would be this. Try to understand the why behind what you are seeing. Not to excuse poor behavior, but to better understand what may be driving it. There is often more happening beneath the surface than what is visible.

And if a company consistently behaves in a way that does not align with your needs or values, it is okay to move on. That signal matters more than most people realize.

For Education Technology companies, the advice is simple. Build for schools. Not for your roadmap, not for your competitors, and not for what you think might be needed. Build for the real problems that educators are trying to solve. If that is your North Star, it will force you to listen, to understand, and to build the right way.

The longer I have been in and around education, the more I have realized that most friction is not caused by people trying to do the wrong thing. It is caused by people seeing only part of the picture.

Out on the ranch, that lesson shows up every day.