Think New Software Will Solve All Your Problems? Give Me Five Minutes.

The problem isn't always the technology. Sometimes it's how we're using it, what we're asking it to do, or what we haven't thought to ask.

There's a particular kind of conversation I find myself having with schools. Someone tells me they need a new system.

The admissions team is frustrated with its CRM. Advancement needs a better way to manage relationships. The business office is reconciling information across platforms. Sometimes, they're right. They genuinely need something different.

Having worked in schools and in edtech, I've experienced technology from both sides: relying on these systems to get the work done and helping schools select, implement, and make better use of them. That experience has taught me that knowing what a system can do is only part of understanding whether it's the right solution.

Before a school starts evaluating tools, I want to understand something else: What are you trying to accomplish, and what's preventing you from doing it today?

The answers often take us somewhere entirely different from where we started.

Start with the work, not the software.

When I look at a school's technology stack, I'm not starting with a list of their systems and asking whether they're good products. I'm starting with the people who use them.

What does each office need to accomplish? What information do people need, where does it come from, and who else needs access to it? Where does that information need to go next?

And perhaps most importantly, what are people spending time doing that they shouldn't have to do at all?

A school might have invested in a sophisticated enrollment management platform, but the admissions team is still maintaining separate spreadsheets to track inquiries, manage events, or produce reports. Why?

Perhaps the platform already has those capabilities, but the team doesn't know about them. Maybe the original implementation didn't account for how the office works, or staff turnover left the team without the knowledge to use the system well. The spreadsheets might be familiar and comfortable, even if they create extra work and make information harder to share. Or perhaps the platform genuinely can't produce the reports the school needs.

Those are very different problems, and they require very different solutions.

Not every department needs to use the same tools. But the school should understand how those tools fit together.

One of the most interesting things that happens when I start asking questions across departments is discovering how often teams are trying to solve the same problem independently.

Admissions has one system for communicating with prospective families. Advancement has another for alumni and donors. Marketing has its own email platform. The business office maintains separate records. And somewhere in the middle, someone is manually moving information from one place to another.

Each department may have made perfectly reasonable decisions about what it needed. But those decisions weren't necessarily made with an understanding of what was happening elsewhere in the school. The result can be overlapping subscriptions, disconnected information, duplicated work, and multiple versions of what should be the same data.

The opportunity isn't necessarily to consolidate everything into one system. It's to understand where the work intersects and whether the technology supports those connections.

Sometimes the problem is that we don't know what we need. When someone says, "Our CRM doesn't work for us," I want to know what that actually means.

Is it difficult to use? Does it lack a feature? Is the team struggling to produce useful reports? Are people entering information inconsistently? Or has the school not yet defined what it wants to measure and how the process should work?

I've found that it's easy to confuse a technology limitation with a process that hasn't been fully thought through.

That distinction matters when deciding who should evaluate a new system. A school's IT leader may be excellent at managing infrastructure, security, and technical support, but understanding the day-to-day work of every department requires a different perspective. The people using the system need to explain what they're trying to accomplish, and someone needs to ask enough questions to uncover the real problem(s) beneath the initial request.

School leaders also have to consider what happens after a purchase. Every additional platform brings responsibilities for implementation, integration, maintenance, and support. Those considerations need to be weighed alongside the opportunities a new tool might create.

The strongest technology decisions bring together the people who understand the work, the people who understand the technology, and the leaders who understand the school's broader priorities. Each brings a perspective the others may not have.

Consider a school that wants better enrollment reporting. It might be tempting to purchase another analytics tool. But if the admissions team hasn't agreed on how it defines an inquiry, when an applicant moves from one stage to another, or which metrics leadership needs, a new dashboard won't solve the problem. It will simply display inconsistent information in a more attractive format.

Before investing in another solution, we need to define the questions we're trying to answer. Only then can we determine whether the existing technology can answer them.

The most revealing question might be: "Why are you doing that?" I don't mean that critically. I mean it with genuine curiosity.

Why does someone spend two hours every Friday compiling a report? Why is the same information entered into three systems? Why does the marketing team manually export lists that could potentially be generated automatically? Sometimes there's a good reason. But sometimes the answer is, "That's how we've always done it." Or, "I didn't know there was another way."

Those answers can reveal opportunities that don't require a new purchase. A feature might never have been activated. A workflow could be automated. Two departments could agree on a shared process. A team might simply need training on a platform it already owns. And sometimes, the task itself no longer serves a useful purpose.

The goal isn't just to make existing work more efficient. It's to determine whether that work needs to happen in the first place. Automating an unnecessary process doesn't make it necessary.

Before recommending a technology change, I want to understand what the school already has, which capabilities aren't being used, where systems overlap, how information moves between offices, and why people have created workarounds. I also want to know whether staff have the training, capacity, and support to use their tools effectively.

Schools have invested more than the purchase price in these platforms. They've invested time in implementation, data migration, training, and learning new ways of working. That investment deserves a thoughtful assessment, not an automatic decision to replace everything. If a problem can be solved with better training or a more thoughtful workflow, let’s figure that out before making a change.

But sometimes, after asking these questions, the conclusion is that the school really does need something new. At least now we know what we're looking for and why.

The best technology decisions start with better questions.

I don't believe schools should hold on to technology simply because they've already invested in it. Sometimes a system has reached its limits, the school's needs have evolved, or a platform is creating more work than it's eliminating.

Schools can be reluctant to replace a system because of the money, time, and effort they've put into it, even when it's no longer serving them well. But the sunk-cost fallacy is real and continuing to use the wrong tools has a cost, too. That's especially important in offices responsible for enrollment and fundraising, where inefficient processes and missed opportunities can directly affect the school's revenue.

The objective isn't to have the newest platform, the most sophisticated tech stack, or the fewest systems. It's to have the right tools, used thoughtfully, supporting the right work. So before swapping in a new product, ask whether you're getting everything you need from what you already have and really listen to the answers. You might be surprised by what you discover.

Not sure where to start? This is the kind of work I do alongside independent schools. I help leadership teams understand what's working, where their systems and processes are getting in the way, and whether the next step is better use of what they have or exploring something new. If your school is wrestling with these questions, let's talk.