5 Ways AI Is Changing Legal Contracting Workflows

Commercial contracting is going through a seismic shift, with AI at the center. To commercial legal teams, it means a new way of approaching their work.

Historically, legal’s part in the agreement cycle was seen as uniquely human: reasoning, analysis, comparisons of laws to terms. That work included strategic, complex, client-facing judgments, but it was also frequently accompanied by tedious, low-skill contracting tasks that trapped valuable lawyer time. AI-powered agreement technology is challenging traditional thinking. Between intelligent automation, including autonomous agents, AI is helping to identify patterns in data and text that previously lay hidden, recommending redlines, flagging risks, and initiating the next action in the workflow.

As Vice President and Deputy General Counsel of Commercial, Growth and Trust at Docusign, I optimize and automate the commercial legal function through people, process, and technology. In this role, my team and I have experienced the AI shift firsthand. What follows is how our commercial legal team has evolved with AI-driven workflows and where similar teams can implement AI with valuable human oversight still in place.

In describing this transformation, I often say "AI is becoming more and more like a co-lawyer or like a junior lawyer that can help you execute ever more complex tasks."

Why isn’t it enough to just give legal AI tools?

Commercial legal teams are facing two simultaneous conditions: the pressure to automate and  the fatigue around the constant influx of new AI tools and messaging. In the in-house context, legal departments are not getting more headcount, so everyone is being pushed by their leadership or peers to automate and do more with less.

Simply sending an email to announce a new AI-powered capability isn’t enough to improve efficiency. Rather than a general mandate, a successful rollout involves articulating real use cases and tangible examples of how they can work technology into their processes.

It isn’t like you can magically do your work better because you now have a new kind of hammer. Somebody has to show you how to use it.

Here are a few of the workflows where the Docusign commercial legal team has found success in its AI journey:

1. AI streamlines first-pass reviews and redlining

In Docusign’s commercial legal team, AI automates the first pass of every contract review. For nearly every document that comes from a counterparty, human eyes take a first look at any changes and redlines.

Part of the Docusign IAM platform, the AI-Assisted Review feature analyzes the draft against a commercial playbook, flagging potential risks or noncompliance, suggesting changes, and explaining those changes for the human reviewer. This saves legal’s time and focus for the more intricate reviews and edits.

2. AI agents can field repetitive internal questions

Every day, commercial contracting teams field internal questions. These are often repetitive, time-consuming, non-legal or quasi-legal questions, with attorneys forced to manually write each response. AI cuts out this process through a self-help storefront.

At Docusign, AI agents automate query answers (under the oversight of human eyes), so the internal client gets a faster response. The future state goes even further: the same questions are resolved without human involvement. 

For legal teams, this type of automation moves the needle. It’s the kind of thing that when we show our team, ‘Hey, AI can do this. You no longer have to answer these low-level questions, that in some cases aren't even legal,’ the lawyers say, ‘Oh good! I hated answering those.’

3. AI makes it easier to share institutional knowledge

All legal teams face the problem of institutional knowledge concentrated in just a few individuals. In the cycle of retirements and new employee onboarding, organizations have to go through ‘campfire-style’ knowledge sharing to get everyone on the same page: let’s all sit around while I tell you the story of the big German bank deal I did back in 1983.

AI technology lets legal teams create a ‘digital twin’ of seasoned commercial attorneys, capturing the deals they’ve negotiated, the frequency of specific clauses, the language they use in different situations. It’s a way of more efficiently sharing the lived experience and knowledge of senior lawyers so that their decision-making becomes replicable in automated responses, new employees can quickly get up to speed, and everyone’s time is optimized.

4. AI helps us stay on top of post-signature obligations

Even after a contract is signed, with their huge contract volume, commercial legal teams can struggle to make sure what’s in the contract is acted upon, either immediately or in the future. What’s the data incident notification period for this customer? What’s our SLA? Are we entitled to service credits? Did we miss the payment deadline for this vendor?

With AI, more and more of your corpus of agreements becomes a living, breathing record that you can work with and leverage. Our AI-powered agreement repository, Docusign Agreement Manager, lets us easily organize executed agreements and quickly identify which have an SLA clause, an autorenewal deadline, a required credit, or other obligation. AI agents can surface these milestones, send out notifications, and kick off next steps.

Finished agreements can’t just sit in the digital file cabinet. With this AI-powered repository, they become assets you can access and understand, and use to inform better dashboarding and reporting.

5. AI agents help speed up commercial negotiations

Over the next year, AI agents will likely play an even bigger role in negotiations, accelerating the sales cycle while keeping final judgments in human hands. Right now, negotiations are still heavily manual and a very human process. The lawyer redlines in Microsoft Word. The human counterparty lawyer talks to their human client and drops a comment in the document.

The emerging alternative is agent orchestration on both sides. In minutes, AI agents could exchange language, track positions, and produce a revised draft. A human attorney reviews and approves the final markup, rather than making every change themselves. Looking forward to low-risk areas, teams could even authorize agents to provide signatures, a possibility already contemplated under the US ESIGN Act.

I talk more about this transformation in this interview.

How can legal move from example use cases to real AI implementation? 

In speaking nearly daily with customers about how Docusign’s legal department is optimizing commercial contracting, I hear hesitation from risk-averse legal teams about inserting AI into critical contract workflows. Here are three strategies I suggest to ease fears about AI.

3 strategies for commercial contracting leaders

With these in place, CLOs will come to realize: ‘We are automating a massive amount of agreement negotiation. We don’t have any lawsuits. I’ve saved so much time. We’re so much faster.’

What does a commercial contracting lawyer look like in the AI era?

Skilled commercial lawyers will always have a place in the corporate landscape, but their exact work is changing. They’ll have new skills and more time for high-value deals and customer interactions. 

"Everyone I’ve talked to recognizes that the world has changed. There’s no one I talk to who believes this is hype."

The commercial legal teams of the future are technically savvy. The industry refers to an emerging role: forward-deployed lawyers. This new form of lawyer combines their legal expertise with solutions engineering. They deeply understand a customer’s specific agreement workflows to deploy flexible, AI-powered software that alleviates pain points. This is taking shape in my own department and its workflows.

Modernize your commercial legal workflows with Docusign IAM

Docusign’s Intelligent Agreement Management (IAM) platform, founded on the native AI engine Docusign Iris, is built for the new era of commercial contracting. Trained specifically on documents and document workflows, AI automation and agents can be embedded in the agreement cycle. With this rich foundation of data and process insights, commercial legal teams can relieve their low-level, repetitive, and manual processes to close deals with more speed, control, and consistency.

Find out how your legal team can use AI to accelerate contracting workflowsLearn more

Frequently asked questions

How is AI changing commercial contracting?

Commercial contracting is moving from a largely human-driven process to AI-driven workflows, such as redlining and post-signature management, while human judgment and oversight remain in place.

Where should commercial legal teams start with AI?

Begin with lower-risk, higher-volume work, such as first-pass reviews of routine agreements or repetitive internal questions. This keeps dense human involvement on high-stakes matters and slowly expands confidence as performance data accumulates.

How does governance help teams adopt AI more comfortably?

Clear rules, the ability to roll back decisions, and full visibility into what agents are doing address the natural risk aversion of legal leaders, justifying AI decisions and making broader use feel more manageable.