Start Small With AI: Lessons From a Digital Court Calendar

For many in-house lawyers, AI feels overwhelming. The pressure to “keep up with change” collides with the reality of overstuffed inboxes, scattered contracts, and a never-ending list of urgent requests. The result? Paralysis. You know innovation matters, but where do you even start when contemplating how to start small with AI for in-house lawyers?

Judge Scott Schlagel of Louisiana’s Fifth Circuit Court of Appeal offers a surprisingly simple answer: start small. His journey from paper calendars to digital scheduling is a case study in how the smallest step can unlock lasting transformation. Even in-house teams can find inspiration to start small with AI for in-house lawyers from his story.

Watch the full conversation with Judge Scott U. Schlegel here:

When Judge Schlagel joined the bench in 2013, his courtroom still relied on a giant red scheduling book. Lawyers had to call chambers, leave voicemails, or send assistants just to check dates. The process wasted time, created errors, and frustrated everyone involved.

So he digitized it. He put the court’s calendar online, set standard times for motions and pre-trials, and allowed lawyers to coordinate with opposing counsel before booking. He even included Zoom links years before the pandemic made them standard.

The investment? Around $150 a year.
The impact? A smoother, faster, more reliable court system.

For corporate counsel, the parallel is obvious. AI isn’t magic it’s a layer that depends on clean, digital workflows underneath. If your contracts are buried in email, if your matter tracker lives on one paralegal’s desktop, or if compliance processes are managed in spreadsheets no one shares, AI has nothing to work with. Start small with AI for in-house lawyers by first creating a digital foundation.

Judge Schlagel calls this “laying the foundation.” In-house teams need to think the same way: digitize, standardize, and centralize first. Only then can AI tools analyze contracts, flag risks, or predict trends with accuracy.

The brilliance of Judge Schlagel’s calendar wasn’t in its sophistication it was in its simplicity. It didn’t require a massive budget, enterprise software, or a culture overhaul. It was a pilot project. And once lawyers experienced the benefits, resistance faded.

In-house teams should take the same approach when deciding to start small with AI for in-house lawyers. Don’t wait for a multimillion-dollar AI solution. Instead:

• Automate NDA intake.
• Use AI to summarize board minutes.
• Move matter tracking into a shared, collaborative platform.

Start small. Fail small. Learn fast.

The role of in-house counsel is evolving. Businesses expect legal to be collaborative, data-driven, and tech-enabled. Lawyers who embrace that shift by experimenting, learning, and laying a foundation for AI position themselves as leaders, not laggards.

As Judge Schlagel put it: “Start today. Don’t be afraid to fail. In a week you’ll be better off, in a year you’ll be stronger, and in 10 years you’ll have the legal system you always dreamed of.”

For in-house counsel, the message is clear: the future won’t wait. But it doesn’t require a leap. Just a first step to start small with AI for in-house lawyers.

If you’re considering how AI fits into your legal department, don’t get stuck chasing the big picture. Ask yourself:

• What’s one process we could digitize today?
• What’s one task AI could help simplify?
• How do we build momentum from there?

Your first move doesn’t have to be perfect. It just has to start.

Watch the full conversation here:  Notes to My (Legal) Self: Season 7, Episode 8 (ft.Judge Scott U. Schlegel)

At Notes to My (Legal) Self®, we’re dedicated to helping in-house legal professionals develop the skills, insights, and strategies needed to thrive in today’s evolving legal landscape. From leadership development to legal operations optimization and emerging technology, we provide the tools to help you stay ahead. AI risks, including mid-level ones, are an essential component of these discussions.

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