Creativity Hacks for Trial Lawyers: Think Like a Software Engineer

Rumpole Meets the Robot

Picture this: Horace Rumpole, the witty and idealistic barrister in the British TV series Rumpole of the Bailey, finds himself in chambers with a peculiar new assistant. It's not a law student or a junior associate—it's a machine. 

A machine that claims it can read thousands of pages of documents in minutes, suggest themes for his next closing argument, and even draft the bones of a cross-examination. Imagine Rumpole's skeptical raised eyebrow. Could this digital whiz really help him craft a better argument or bring order to the chaos of case files piled on his desk?

Horace Rumpole / Rumpole of the Bailey

We don’t live in Rumpole's era, but many trial lawyers today face a similar conundrum. Having been trained in the classic traditions of trial advocacy—persuasion, intuition, and meticulous fact-gathering, it can be difficult to believe that tools like generative AI can augment those essential skills. 

Working alongside the engineers building our company’s software for trial lawyers opened my eyes to the possible. In fact, I’ve discovered there’s much to learn from how they approach their work. Especially when it comes to handling complexity, adapting strategies, and embracing automation, trial lawyers can learn from the practices of software engineers—without having to write a single line of code.

Crafting a Case Theme
Litigation always starts with a dispute—an injury, a breach of contract, discrimination, or other wrongful act—that frames what the case is about. But there is far more to developing an effective theme than the underlying dispute. An excellent trial lawyer will first seek to learn every available detail about the dispute and collateral facts before developing a case theme. One must account for both the good facts and the bad facts to create a unified narrative, one that harmonizes them in a way the jury will accept as true for your client to win.

Software engineers take a surprisingly similar approach when designing systems. They start with a foundational product idea—say financial services, communication, or a unique business process. Before writing the first line of code they must learn about user requirements, types of data, desired functionality, and potential tradeoffs before they can design a system harmonized for the user’s needs.  

Because software engineers are immersed in technology—unlike lawyers—they are quite open to using new ones to help get the job done. Once they have explored and tracked user requirements with tools such as Airtable and Notion, they will turn to writing code. More often than not, they will use a product like GitHub Copilot to write the first draft.

So how might Rumpole use generative AI to develop a case theme? Imagine him sifting through a pile of documents, trying to understand the key facts of the case, both favorable and unfavorable. AI could assist by analyzing documents, highlighting significant evidence, summarizing critical facts and contradictions—all in minutes, not hours. It could even answer follow-up questions and point to specific evidence supporting its responses. 

Rumpole’s time is freed up to focus on revising it into a credible theme that brings together every part of the story that can withstand the attacks of opposing counsel. Instead of starting from scratch or getting bogged down in tedious document review, AI provides a comprehensive map of the case landscape in a fraction of the time. This helps ensure that nothing is overlooked, and all facts—good and bad—are accounted for and synthesized in Rumpole’s case theme.

Test, Refine, Repeat
Crafting legal arguments is similar to the process engineers follow when testing a piece of new software they have developed. Arguments are like complex software systems—they need to be logically sound and able to withstand unexpected challenges. Engineers refine their code by running tests, identifying weak points, and making improvements using products like Ellipsis Code Review. They also test it with users. It is an iterative process. 

Trial lawyers do something similar. The best arguments don’t happen overnight; they evolve. Arguments are refined by pressure-testing them against opposing counsel's likely responses or by mooting (rehearsing) them with colleagues. The process is also iterative. Each refinement makes the argument more resilient—able to hold up when opposing counsel (or the judge) tries to poke holes in it. 

The lesson here? Don’t settle for your first version of an argument. Keep testing and refining until you’re confident it can withstand the adversarial pressures of the courtroom.

Your Digital Associate
While some trial lawyers might bristle at the idea of technology handling trial preparation, imagine if Rumpole or his partners had a junior associate who could sift through thousands of documents, summarize depositions, or draft early versions of motions—all in a fraction of the time it would take a human. Today, generative AI is that junior.

Software engineers already embrace tools which assist in writing code, offering suggestions, and automating parts of their workflow. These tools act like an extra brain, anticipating needs, suggesting solutions, and freeing up time for more creative problem-solving. 

In the same way, generative AI can be a copilot for trial lawyers, helping manage the tedious and time-consuming aspects of a case, ensuring that they can focus on crafting winning arguments and responding dynamically to the facts as they emerge.  Of course, all lawyers, not just trial lawyers, must protect confidential client information when using generative AI tools. But, assuming you are doing that, instead of seeing generative AI as a threat, think of it as an extra set of hands—allowing you to focus on what you do best: advocacy.

An "Agile" Mindset
Software engineers often use an "agile" approach, characterized by working in short sprints, usually two weeks, and holding brief daily standups to discuss progress, roadblocks, and goals. These structured cycles and quick, scheduled check-ins help ensure that the team stays focused, avoids distractions, and constantly makes progress toward their objectives using tools like Shortcut. The agile approach helps engineers adjust quickly to changes rather than sticking rigidly to an original plan. 

Trial lawyers can benefit from this approach. Setting and evaluating case objectives every two weeks (or some other cadence that works for you) will help ensure consistent progress. Likewise, daily standups to address blockers and track progress allow the team to cover what is happening in real time, not weeks later after going down the wrong path, potentially requiring substantial rework. 

The discovery process often takes unexpected twists. Witnesses provide damaging testimony, documents turn up late, new evidence can even emerge during expert depositions. By setting regular, scheduled times to evaluate and reassess developments and strategies—akin to an agile sprint cycle—the litigation team can ensure it stays focused and aligned, while keeping everyone aware of any challenges. 

Sprints can be used to manage different phases of preparation, such as fact and expert discovery, pre-trial motions, mediation, or final trial preparations. The goal is to ensure that lawyers are continually evaluating and, where necessary, iterating on their case strategy, rather than letting any surprises throw them off course.

The most effective advocates aren’t those who rigidly stick to their original script; they’re the ones who can adapt their themes and strategies on the fly.

Blending Tradition with Innovation
Rumpole, the curmudgeon of the Old Bailey, had a reputation for razor-sharp instincts, eloquent arguments, and tireless dedication. But if he had access to the tools we do today—generative AI, insights from engineering workflows, and automation—he would surely use them to become an even more effective advocate.

By blending our traditional skills with lessons from the tech world, trial lawyers can not only improve their efficiency but also elevate their advocacy—better equipping them to serve clients in an ever-evolving legal landscape.

So, the next time you find yourself knee-deep in a stack of case files, think about what a little automation, a dash of adaptability, and an engineer’s perspective could do for you. 

Rumpole would raise his glass in approval.

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