2013 was a simpler time. Everyone was doing the Harlem Shake, we collectively wondered what the fox says, and AI was just beginning to make waves in the legal world. When I started at Relativity in 2013, technology-assisted review was the hot new tool. We’d often compare it to Netflix—it was an easy, attainable way to explain how the technology recommends documents for review.
We’ve come a long way since that once-simple analogy, and while the world is considerably more comfortable with AI, there’s still … a hesitation. A tendency to dip a toe, rather than dive in headfirst.
Then, there are the AI Visionaries. The legal professionals who cannonball into the deep end—and help others do the same.
So, we asked a few of members of our 2025 cohort: What should legal professionals know about learning to work with AI?
#1: Ask questions like a lawyer.
According to Aaron Crews, partner at Holland & Knight, AI hasn’t changed the core of legal work.
“What we lawyers do, if we're good at this job, is ask really good questions. We take information in, apply the rules, and based on that, we advise. Using AI to be quicker and deeper in how you can do that means you’re going to be more effective as an advocate and advisor for your client.”
Prompting is a natural fit for this skill set. If you want to learn how to prompt effectively, start with a few resources from the experts:
- Generative AI for e-Discovery and the Importance of Prompt Engineering – Blog post written by Starling Underwood of Kilpatrick Townsend
- 6 Tips for Better Prompting – Blog post written by AI Visionary Benjamin Sexton of JND eDiscovery
- AI Advantage: Aiming for Prompt Perfection? Level up with Relativity aiR for Review – A webinar recording featuring Troutman Pepper eMerge and Foley & Lardner
#2: Educate yourself on what makes a good—and not-so good—AI provider.
AI tools aren’t one-size-fits-all, and not every vendor is a fit. Ben Sexton, senior VP of innovation and strategy at JND eDiscovery, emphasizes the importance of choosing providers who are honest about their tools—and willing to listen.
“We’re still early in the ‘AI-enabled future,’ and today’s products have strengths and weaknesses. A good provider will be transparent about where their products succeed and where they might not. Be cautious if you attend a demo and don’t feel heard, or if your questions weren’t answered directly and satisfactorily. Trust your instincts.”
If a provider can’t answer your questions clearly, move on. The right partner will be upfront about the strengths and limitations of their models, as well as how they approach security and privacy. You can also refer to resources like the NIST AI Risk Management Framework to understand what responsible AI should look like—and use that as your benchmark in vendor evaluations.
#3: Get comfortable coloring outside the lines.
For Aaron, the best way to build AI fluency inside an organization isn’t to push strict rules; it’s to lean into the creativity and curiosity already bubbling up.
“In every organization, you have people using AI off the books,” Aaron says. “They're using it to do things faster and better. Rather than fighting against that, bring those people into the fold. If you're trying to build a culture that is pro AI adoption, connect with your internal hackers and turn them into heroes. It is a strategy that works.”
This mindset—encouraging experimentation and rewarding curiosity—can drive more organic, sustainable AI adoption. Legal teams don’t need to spin up a full AI department overnight. They just need enough freedom to play a little.
Foster a safe environment for experimentation. Google’s “20 percent rule” may not be realistic for law firms, but encouraging attorneys and staff to spend a few hours each month exploring AI tools can yield big insights.
#4: Make AI work for you.
AI doesn’t have to replace you—it can relieve you. That’s a shift Tracey Vinson, senior assistant general counsel and director of e-discovery at Bayer, thinks more people need to consider.
“Read about what AI applications are available in your field and think about work that you don’t particularly like to do. How might you use AI to lessen that burden on your workday?”
Whether it’s sifting through huge document sets or drafting outlines for deposition prep, AI can take the heavy lifting off your plate and make your work life—heck, your personal life—better. In fact, these tools are already alleviating the drudgery and opening space for higher-value work.
“The integration of AI into the e-discovery landscape has already begun to transform the practice, bringing accuracy and efficiency to the massive job of finding the truth in the masses of data we are charged with parsing,” Tracey says.
Start small. Pick one workflow that could use a boost, and then experiment with AI tools to see how they can help. For instance, ask your team to try AI-powered document review for the next case or to use AI for preliminary contract review. (You know where to find us if you need help getting started.)
So, What Now?
If you’re waiting for the right moment to start exploring AI in your legal work, consider this your gentle nudge.
The Visionaries featured here weren’t going to wait for a perfect roadmap—they jumped in, asked smart questions, and found a place for AI in their workflows. Not because it’s trendy, but because it’s useful. As Ben Sexton put it:
“AI shows promise at solving some of the biggest challenges in e-discovery. It saves time and costs, but also increases access to justice.”
You don’t need to master it all at once. Start with one question, one workflow, or one tool. See where it takes you.
Graphics for this article were created by Caroline Patterson.
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