Beware the Tech Stackers

Paul Wilkins

02 Apr 2025 — 2 min read

There’s a popular idea going around that every business challenge can be solved with the right tech stack. Pick the right combination of AI tools, bolt them together with a little automation, and boom—you’ve got a system. Something scalable. Something impressive. Something that solves problems while you go make coffee.

This mindset has made its way into the world of litigation. And while I’m no stranger to technology, I’m going to offer a contrarian view: if you’re a trial lawyer, and you’re thinking in terms of a tech stack, you’re probably thinking too small.

Here’s why.

A Tech Stack Is Fixed. Litigation Is Not.

Stacks are great for processes that don’t change. Think billing systems, document management, scheduling workflows. Those are plumbing problems.

Litigation is something else. Strategy shifts. Facts evolve. Jurors surprise you. Witnesses implode. The story you thought you were telling on Monday is sideways by Thursday. If you’re locked into a rigid set of tools with predefined outputs, you’ll never see the pivot coming—much less make it.

I work with AI tools every day. But the system I’ve built isn’t a stack. It’s a strategy augmentation framework. It’s a pool of flexible, evolving tools that get selected and combined differently depending on the problem, the timing, and the person holding the reins.

What Tools Can’t Do (Yet)

AI tools are brilliant at synthesis. They can analyze, summarize, extract, compare. But they still can’t reason from first principles. They don’t know what matters to a jury. They don’t feel the tone shift in a deposition or recognize when a damages story needs to be flipped upside down to make sense.

That’s you. That’s your job.

The tools I use don’t try to do it all. They:

Analyze discovery responses and draft motions to compel.
Extract themes and contradictions from depositions.
Summarize medical records into clear, human narratives.
Help evaluate how a story lands with a jury before it ever sees a courtroom.

They don’t spit out answers. They give you better questions. They push your thinking forward. And yes, they generate real output—outlines, motions, visuals—but that’s the residue of good thinking, not the point of the exercise.

The Most Valuable Part of the System Is Still You

If you’re waiting on AI to automate your way out of strategic decision-making, you’re going to be waiting a long time. Because the real value in trial work isn’t in having all the data. It’s in knowing what the data means. It’s in shaping a story that turns facts into stakes.

That’s where people still matter. That’s where they always will.

The system I use is designed to elevate good thinking. To help trial lawyers do what only they can do: connect the dots, tell the story, and persuade a jury to care.

So yes, beware the tech stackers. They might be building tools.

But you? You’re building cases.

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