In this episode, I'm talking with Sandy MacDonald, Senior Director and Head of Legal Operations at DocuSign. Sandy is recognised for building an "ahead of the curve" team that treats AI not just as a tool, but as a collaborative digital assistant embedded into the very fabric of their workflow.

We talk about the cultural shift of AI adoption and how focusing on individual "pain points". You’ll hear perspectives on "human-in-the-loop" governance and why the most successful legal teams are moving away from "AI slop" toward high-value, verified automation that lawyers actually trust.

Overcoming the Fear of Replacement: Sandy explains that the primary cultural hurdle is fear; however, she emphasises that AI won't replace lawyers, but lawyers who use AI will replace those who do not.

The "Foot in the Door" Strategy: Instead of massive overhauls, the team focuses on "narrow use cases" such as using Gemini to generate images for presentations - to build curiosity and comfort.

"Human-in-the-Loop" Governance: DocuSign implements a strict governance model where humans remain responsible for validating every piece of AI-generated output.

Peer-to-Peer Learning Over Formal Training: Sandy shares why monthly "AI wins" segments in Town Halls are more contagious and effective than top-down mandates or formal one-hour training sessions.

Criteria for AI Adoption: How to identify the best starting points for automation by looking for tasks that are high-volume but low-risk, such as processing customer questionnaires.

The Evolution of Legal Ops: The shift in the Legal Ops role from being CLM (Contract Lifecycle Management) experts to becoming "AI evangelists" and builders who design their own custom workflows.

--------

Each week I take what I'm hearing in conversations with legal leaders.

I analyze the market and track emerging trends in this AI era.

In my newsletter called The Future Lawyer Market Intel for the AI era

I'm focused on:

What AI is exposing

The opportunities

The blind spots

And the shifts shaping the next five years.

This is how you see the chessboard before everyone else does:

https://hollycope.my.canva.site/thefuturelawyer

Hosted on Acast. See acast.com/privacy for more information.