TL;DR: As artificial intelligence transforms legal practice, how should companies build teams prepared for this technological revolution? At our SpotDraft Summit 2025, industry leaders shared their strategies for developing AI-ready legal teams—from hiring practices to skill development and organizational restructuring.
The legal industry has historically been slow to adopt new technologies, but artificial intelligence is proving too transformative to ignore. For legal departments looking to stay competitive, building teams that can leverage AI effectively has become a strategic imperative.
Our panel of legal leaders, including representatives from Fortune 500 companies and innovative tech firms, offered practical insights on preparing legal teams for the AI era. Their diverse perspectives revealed common themes around skills development, hiring practices, and the changing nature of legal work.
Meet our expert panel
Our discussion featured insights from industry leaders representing various facets of the legal ecosystem:
- Anna Richards, Transformation Lead at Eudia
- Andrew Epstein, General Counsel at Demandbase
- Micki Nute, Associate General Counsel and Chief of Staff at Pure Storage
- Anne Kerwin, Managing Director at Kerwin Associates
The changing landscape: Legal talent in the AI era
Anne Kerwin opened the discussion with a thought-provoking observation: "AI is humanizing lawyers." Rather than replacing legal talent, AI is helping attorneys work more efficiently and focus on higher-value activities. This shift is creating new opportunities—and challenges—for legal departments.
"This is the prologue of the story of AI," Kerwin noted, describing the pressure legal leaders feel to integrate AI into their operations. "Some are behind the eight ball, some are ahead of the curve, but there's a general sense of 'What do I do? Where do I go?'
The changing landscape has significant implications for hiring. According to Kerwin, "We're going to see more of every lawyer really being a technologist." She described recent interviews with commercial heads who enthusiastically shared their AI implementation experiences—conversations that wouldn't have happened just a few years ago.
Skills-based hiring: Beyond traditional legal credentials
A recurring theme throughout the discussion was the shift toward skills-based hiring rather than focusing solely on credentials like law school prestige or Big Law experience.
Andrew Epstein challenged the notion that lawyers are resistant to change: "There's a fallacy that lawyers are not willing to change, and I think we all need to stop saying that. I think it's very rare to find GCs or hiring managers now who are saying folks need to be at this specific law school or have specific big law experience."
Instead, our panelists emphasized the importance of curiosity, adaptability, and business acumen. For his team at Demandbase, Epstein prioritizes hiring contract managers and legal operations professionals over traditional commercial lawyers, noting these roles often make the most impact for teams of his size.
Micki Nute shared that Pure Storage has begun hiring specialists rather than attorneys for certain roles: "We have opted in the privacy space and in some of our ethics and compliance to go with a specialist role as opposed to a strict attorney role. We're looking for a more business-legal combination."
Allocating resources strategically with AI
How should legal departments allocate resources in this changing landscape? Our panelists offered several innovative approaches.
Anna Richards described John Deere's strategic decision to invest in a process automation specialist rather than another attorney: "Her entire purview is, where in the department are there opportunities for automation? This may be gen-AI related or technologies like Power Automate that are preparing us for the future."
Richards added that their team is analyzing work at the task level to identify AI opportunities—which has led them to slow down hiring while they assess potential impacts. "We anticipate AI will impact everywhere," she noted, adding that this creates opportunities for legal service providers and requires new partnerships with outside counsel.
Andrew Epstein shared how his team at Demandbase has automated NDA processing using AI: "We made a shift about a year ago where all of our NDAs are negotiated by AI." After identifying five key issues they cared about in NDAs, they trained an AI tool to automatically approve agreements that meet their criteria, significantly speeding up the process and freeing lawyer time for higher-value work.
Building AI skills within your team
For legal teams embracing AI, developing new skills becomes critical. Our panelists shared various approaches to upskilling their teams.
Micki Nute emphasized the importance of encouraging AI consumption to build personal skill levels: "We had to really focus in and get our attorneys focused on the consumption aspect, pushing the consumption of the technology to increase the personal skill level and encouraging the team to be very curious about how this could apply to their jobs."
For more traditional organizations like John Deere, Anna Richards described their approach to building comfort and adoption: "We are doing the first department-wide co-pilot pilot in our team with about 400 licenses deployed within our legal and regulatory affairs groups. We have built five weeks of cohort training where they'll ride shotgun with us."
Their initiative includes usage tracking, adoption goals, and a requirement that each participant develop at least one meaningful use case for their area of expertise. To support this effort, they've partnered with consultants to build a prompt library covering legal topics that matter to their team.
Using AI in the hiring process
The panelists also discussed how AI can enhance the hiring process itself.
Andrew Epstein shared that he uses generative AI to prepare interview questions based on the STAR method (Situation, Task, Action, Result). This helps him assess not just what candidates have accomplished but how they approached challenges and what they learned.
Tom Stephenson suggested using AI to simulate different interview scenarios: "I would encourage anyone who is looking for their next role to play around with your Gen AI model. Ask it to pretend like it's the interviewer from HR. Then pretend like it's the associate general counsel...And what would they ask? What are they looking for?"
Looking ahead: The future of legal teams
Looking to the future, our panelists offered predictions about how legal teams will continue to evolve.
Anne Kerwin suggested that junior roles might shift dramatically: "In terms of paralegals, contract managers, I think that may shift to legal engineers, prompt engineers potentially." She also predicted a return to more experienced in-house counsel, with lawyers staying at firms longer before transitioning in-house.
Micki Nute described how Pure Storage is reconsidering its organizational design: "We are taking a pause on our organizational design model and actually going back to the drawing board with that. I'm very fortunate to be in this kind of chaotic space at the moment because I think that I can lean in and really dictate—not dictate, aggressively persuade—my C-suite into what that ROI is actually going to be for our legal team."
Key takeaways for building your AI-ready legal team
Based on our panel's insights, here are key considerations for legal departments looking to build AI-ready teams:
- Prioritize curiosity and adaptability over specific credentials when hiring
- Look for business-minded individuals who can think strategically about AI implementation
- Consider specialists and legal operations professionals to complement traditional attorney roles
- Invest in upskilling through structured training programs and prompt libraries
- Start with focused automation efforts in areas like NDA processing that offer clear ROI
- Analyze work at the task level to identify the most promising AI applications
- Be strategic about resource allocation, potentially slowing traditional hiring while assessing AI's impact
- Consider flexible talent models that allow for adaptation as needs evolve
As Anna Richards aptly noted, "We're really talking about augmented intelligence, not artificial intelligence. We are not trying to take the human touch out of it, but we are trying to augment what our humans are capable of doing."
By embracing this perspective and implementing the strategies shared by our panel, legal departments can build teams that are ready to thrive in the AI era—teams that use technology to enhance human capabilities rather than replace them.
This blog post is based on the panel discussion "Building a Legal Team that's Ready to Embrace AI" from our recent SDSF event, featuring Anna Richards (John Deere), Andrew Epstein (Demandbase), Micki Nute (Pure Storage), and Anne Kerwin (Kerwin Associates), moderated by Tom Stephenson (Legal.io).
