Why I 'Sentenced' My IT Professional to Probation: The Crisis of Tech Talent in Courts

People often mistake me for some kind of technology expert. The reality? I'm just a judge with a finance background who happens to care deeply about modernizing our justice system. Sure, I can work my way around a website builder and chat with AI, but my technical expertise stops right about there. You might say I once stayed at a Holiday Inn Express - but that's about as close as I am to being a tech wizard.

This misperception, though amusing, actually highlights a serious problem in our justice system: judges aren't technologists, and technologists aren't judges. We're trying to modernize a complex system, but we're missing the expertise to do it right. My own journey trying to bridge this gap taught me just how deep this problem runs.

When I served on the trial court, I started small - building basic DIY solutions like websites and online calendars with text reminders. Nothing fancy, just practical tools to make the court more accessible and efficient. But here's the thing about being a judge: when you're presiding over hundreds of cases, you can barely find time to eat lunch, let alone manage and scale technology solutions. I needed help.

I thought I'd hit the jackpot when I managed to hire a bright computer science graduate fresh out of college. Young, enthusiastic, armed with coding skills - finally, someone who could help take our basic solutions to the next level. But we immediately hit a wall. I kept imagining all these amazing possibilities without understanding what it would actually take to build them. Meanwhile, my tech wizard had absolutely no idea what our workflows looked like or what defendants actually experienced while on probation.

So I did something that probably seemed crazy at the time: I "sentenced" him to probation. Not legally, of course, but I made him stand before me in court and go through the entire process. He had to visit multiple probation offices, meet with case managers, find the drug testing facilities - all scattered across different parts of the city, of course. He experienced firsthand the confusing paperwork, lack of signage, poor instructions, and the endless waiting.

That single exercise was worth more than a hundred planning meetings. Suddenly, he understood why we couldn't just "build an app for that." He saw our workflows not as neat flowcharts on a screen, but as the messy, complex, human processes they really were. That's when the real innovation began.

But here's where the story takes a frustrating turn that perfectly illustrates the challenge courts face. After a year of incredible work and innovative ideas, we lost him to the private sector. We simply couldn't compete with tech company salaries.

This pattern plays out in courts across the country every year. Instead of building real solutions with dedicated tech talent, courts end up buying expensive "court management systems" from vendors who don't truly understand court operations. These companies roll in with flashy demos and impressive PowerPoints, but two years and millions of dollars later, you've got a system that's about as useful as a chocolate teapot.

Don't get me wrong - court IT departments are full of heroes. These folks keep our systems running, our networks secure, and our printers printing (most of the time). But courts need more than traditional IT support. We need people who can bridge the gap between technology and the actual practice of law, between flowcharts and human experience.

Here's the hard truth: getting this expertise won't be cheap. Try telling your local municipality that you need to hire senior developers at tech company rates - watch how fast they show you the door. But here's what those budget hawks need to understand: you either pay now for expertise, or you pay later for failure. Every clunky system, every failed technology rollout, every hour wasted wrestling with inadequate tools - it all costs money. More importantly, it costs justice.

Let me be crystal clear though: the lack of a dedicated technologist is not an excuse for courts to do nothing. Any court can start modernizing today with basic off-the-shelf tools and a willingness to learn. I did it with a website builder, online calendars, and form software that cost less than $1,000 a year. These simple tools can make a real difference in accessibility and efficiency.

And while I understand that not every court will be able to afford their own technologist, there's a solution that could help bridge this gap: every state Supreme Court should have at least a small team of dedicated court technologists. These teams could design modular, standardized solutions - like LEGO kits - that individual courts could easily deploy and customize to their needs. Imagine having pre-built "kits" for essential court functions: one for digital record-keeping, another for case management, and another for public access. Each piece would work on its own but also fit perfectly with the others. This way, courts could start with what they need most urgently while ensuring they're building toward a cohesive, integrated system.

But if we truly want to transform our justice system - to build custom solutions that address the unique complexities of court operations - we need dedicated tech talent on our teams. It's not an either/or proposition. Start with the basics now, absolutely. But let's also fight for the expertise and resources to build something better.

Until we get serious about bringing in real tech talent, paying them properly, and funding their innovations, we're just putting digital band-aids on analog wounds. And trust me, as someone who gets called a "tech expert" for basically heating up the equivalent of a TV dinner, I know we can do better. We must do better. Because at the end of the day, this isn't about having the coolest new tech toys. It's about building a justice system that actually works for everyone.

For more posts like this, visit www.schlegal.tech.