How to Build AI Fluency Across Your Legal Department

For in-house legal teams, there are two dimensions to the AI shift: the tools and the people. Software gets a lot of attention, but the harder work is getting the department to use it well: improving collaboration and productivity while preserving the accuracy of legal judgments. 

Comfort levels on AI vary from enterprise to enterprise, and it all starts with top-level leadership. As Docusign’s Chief Legal Officer, Jim Shaughnessy has firsthand experience fostering an AI-fluent culture. In a candid conversation, he shared his perspective on how legal leaders can overcome hesitancy about using AI to reduce the monotony of contract tasks, accelerate the agreement cycle, free up legal bandwidth, and empower departments to become strategic partners and unlock insights that can drive growth. 

Key Takeaways

• Meet teams along the AI readiness curve: In-house teams naturally fall into three tiers—AI Leaders, AI Learners, and AI Skeptics. Tailor training to each group rather than mandating a one-size-fits-all rollout.

• Institutionalize peer-led learning: Celebrate successful use cases publicly in department town halls to normalize safe experimentation and peer-to-peer knowledge sharing.

• Implement risk-adjusted governance: Calibrate human oversight against contract complexity—automate low-risk agreements while reserving intensive legal review for high-consequence negotiations.

• Reinvest productivity gains into strategic roles: Automating repetitive administrative tasks opens up legal capacity, fostering new legal roles that interface with sales, customer success, and product governance.

What is the state of AI maturity for in-house legal teams?

AI-maturity levels vary across legal teams and roles, whether a junior lawyer or a general counsel. The differences often come down to AI experience rather than professional abilities. Shaughnessy referenced a recent biannual survey of the Docusign legal department which revealed three categories of AI-readiness:

1. AI leader: These pioneers already take full advantage of how AI can improve productivity and enrich their professional lives, testing new use cases and workflows to accelerate the contract lifecycle.

2. AI learners: These professionals are overwhelmed by the available AI capabilities. They want more clarity on what the tools do and specific, practical guidance on integrating them into their process.

3. AI skeptics: This small segment is resistant to the AI transition and the tools.

Shaughnessy predicts a future in which AI is ubiquitous, and the people who fully embrace the new era will be best-positioned for career growth. But for the people in the middle of the spectrum, he puts the onus on himself. “That’s on me as a leader, and on our company as leaders, to provide more clarity.”

Some people need more time than others, as with any tech transformation. Shaughnessy recalled years ago a colleague who printed out emails, uncomfortable with the shift to a new paperless system. Over time, that person came around. 

With software evolving daily, leaders need to find a balance that makes employees comfortable with the tools and the risks that are identifiable and manageable, without leaving anyone behind. “We have to be able to help folks on all points of that spectrum.”

How can legal leaders create an encouraging environment for AI use? 

For Shaughnessy, creating a culture of AI experimentation means leading with positive reinforcement. “We celebrate successes in front of our entire department,” he said. “We also look for opportunities to take the best experiments and turn them into tools we can use across our department, or even influence some of our business processes and workflows.” 

Instead of leaving behind those who are struggling, he advises offering courses and educational materials at different levels, from the basics to sophisticated use cases.

“One of the things we’ve done that has been great is giving people a forum in our monthly town halls to demonstrate the AI applications they’ve developed.” Shaughnessy describes a recent town hall where a junior lawyer shared how a specific AI tool helped to organize and prioritize her workflows. That five-minute presentation spawned a staff meeting discussion and learning moment for the whole team.

What can legal do to address concerns about AI risk and accuracy?

Trust is a common source of hesitation before legal teams hand tasks over to AI. Teams ask, “How can we be sure the output will be accurate?” or “What is the right level of human review?” and “What safeguards are in place to ensure alignment with our playbooks?”

It’s a natural response, and the solution is familiar: risk-adjusted decisions. Just as legal spends more time on high-value or high-risk contract negotiations, leaders can apply greater human oversight to these documents and rely on AI for standard, lower-risk agreements.

Shaughnessy notes, “As you move up the value or complexity chain, the consequences of a lack of accuracy become greater, and so it’s necessary to apply more rigorous analysis and judgment into when and how you use AI.”

Consider risk factors like data quality, tool effectiveness, intended use, and the potential consequences of getting it wrong. “It’s easy to identify the poles where you’d feel very comfortable using AI and the poles where you’d never use it,” says Shaughnessy. “The in-betweens are going to take some time to develop and involve a fair amount of judgment. And the judgment will change over time, as it becomes informed by experience.”

Giving lawyers a tool for quick research is one thing. Incorporating AI agents with decision-making power is another. Following up on his recommendation to start with low-risk contracts, Shaughnessy says. “Given that there are possibilities of errors, is [AI] being used in places where you can live with the errors? If it’s something where there will be significant financial, personal, or business consequences, you will want the right sort of safeguards in place to validate the results.”

How are legal roles changing because of AI productivity gains?

AI fluency has become an implicit expectation for legal hiring at Docusign, even when not stated in job descriptions. The productivity gains are evolving the legal role, and not just for junior lawyers. “We’ve implemented some AI applications that have resulted in some of the work that was done by more senior people being automated,” says Shaughnessy. “It liberated their time and made it possible for them to turn their attention to higher value and more strategic initiatives.”

As AI takes on tedious, low-skill tasks, more dynamic legal positions are emerging. One focuses on giving peers, customers, and prospects a clearer idea of how the legal department uses its Docusign technology, including ways AI has improved the contracting process. Another pairs lawyers who deeply understand Docusign’s capabilities with customer success and sales teams, so they can help implement and configure AI-powered agreement workflows.

“As a company, we’re investing in growth,” Shaughnessy explains. “So when we have AI productivity gains, we determine how to invest those back into growth.”

How can legal leaders embrace AI with Docusign?

AI is already reducing routine work and increasing the impact of everyone on the legal team, from junior lawyers to senior leaders. It’s a trend Shaughnessy’s department expects to continue. Docusign Intelligent Agreement Management (IAM) is at the heart of the evolution, using automation and AI agents to accelerate contract workflows and inform legal decision-making.

“We can all learn. The wonderful thing about the way that knowledge is developing here is that nobody has a monopoly on all the good ideas and all the ways that they can improve what they do and how they do it,” he says.

Built on our native AI, Docusign Iris, IAM gives legal departments a unified place to innovate, collaborate, and streamline the agreement lifecycle, from playbook analysis and redlines to routing and obligation management. The IAM platform has ingested more than 300 million consented, real-world agreements to support legal’s specific agreement challenges and governance needs. By starting with low-risk workflows, scaling oversight with complexity, and sharing their learnings, legal can move from early AI experiments to having department-wide impact.

See how Docusign brings legal teams through the AI shift with stronger controls, faster agreements, and more room for strategic work.

Frequently asked questions

How should legal leaders introduce contract AI without overwhelming their teams?

Begin with high-volume, low-risk contract workflows such as first-pass NDA reviews or clause extraction. Pair each pilot with clear internal usage guidelines, peer demonstration forums during team town halls, and optional tiered training modules.

What is the most effective way to balance AI speed with legal contract accuracy?

Apply a risk-adjusted governance framework that matches the depth of human review to the complexity and risk exposure of the task. Keep experienced attorneys in the loop for high-liability negotiations while allowing automated AI analysis for standard agreement types.

How can organizations ensure legal AI tools meet enterprise data security standards?

Prioritize enterprise software providers that offer explicit contract data consent boundaries, contractually guarantee that confidential client information is not used to train public foundation models, and maintain audited compliance standards (such as SOC 2 Type II and ISO 27001).