An AI-First Culture Looks Like This with DocuSign's Head of Legal Operations

Are Compliance Jobs the "Safest" in an AI World? With Global Head of Risk Management at Freshfields

In this episode, I'm talking with James Smither, Global Head of Risk Management at Freshfields. James is a self-described "risk geek" dedicated to redefining how law firms perceive uncertainty as both a massive upside and a critical downside. We talk about the "apocalyptic spectrum" of AI risks - from the common trip-ups like hallucinations and citation errors to the looming threat of quantum computing breaking modern encryption. You’ll hear why the traditional graduate recruitment model is officially obsolete and how firms must pivot to training "AI natives" who can balance technical curiosity with human scepticism. Defining Risk 101: Why risk is the "impact of uncertainty on objectives" and why that matters for your bottom line. The Talent Gap: The disconnect between "AI natives" who instinctively use the tools and the "analogue generation" who know how to spot their mistakes. The End of the Billable Hour?: Why AI efficiency is creating a tangible, existential threat to traditional legal pricing models. The Human Value-Add: Why your unique insight and reliability are the only things that will distinguish winners from losers when everyone uses the same machines. -------- 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 [https://hollycope.my.canva.site/thefuturelawyer] ---------------------------------------- Hosted on Acast. See acast.com/privacy [https://acast.com/privacy] for more information.

An AI-First Culture Looks Like This with DocuSign's Head of Legal Operations

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 [https://hollycope.my.canva.site/thefuturelawyer] ---------------------------------------- Hosted on Acast. See acast.com/privacy [https://acast.com/privacy] for more information.

How To Create a Claude- Native AI Law Firm with Zack Shapiro

In this episode, I'm talking with Zack Shapiro, founder of an AI-native law firm, Rains LLP. Zack is a corporate lawyer focused on startups and business law who has transformed his two-person practice into a high-leverage powerhouse serving over 200 clients. Despite describing himself as "uniquely bad at using tech tools," he has pioneered a "Claude-native" workflow that uses agentic AI to handle his legal work. We talk about the shift from "billable hours" to "high-judgment lawyering" and how prompting is becoming the most critical white-collar skill of the next decade. You’ll hear perspectives on why most legal tech "wrappers" are actually counterproductive that most lawyers are missing. The Power of "Bare Metal": Why Zack avoids expensive legal AI platforms in favor of direct, "bare metal" interaction with reasoning models like Claude. Prompting as an Essay: Moving beyond simple queries to 2,000-word "context dumps" that capture the nuance of a client's specific leverage and goals. Building Custom "Skills": How to use your own past work as a reinforcement learning environment to create agentic workflows that compound in value over time. The Entrepreneurial Opportunity: Why now is the greatest time in history for small, AI-empowered legal teams to steal market share from rigid, legacy firms. The Hallucination Filter: Practical strategies for using AI to check itself, ensuring that "turning your brain off" never becomes an option. -------- 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 [https://hollycope.my.canva.site/thefuturelawyer] ---------------------------------------- Hosted on Acast. See acast.com/privacy [https://acast.com/privacy] for more information.

What AI Really Means for the Next Generation of Lawyers

I'm talking with: Peter Boyce, one of the legal deputy directors in the civil service and AI lead for his agency. Amy Cronin, senior director of legal at Skyscanner. Alexander, Co-lead of AI Research at Thomson Reuters.  David Mazur, Vice President, General Counsel & Compliance Officer for Nestle. In this episode, we explore how AI is reshaping entry-level roles in law firms and what it means for the next generation of legal professionals. With firms increasingly investing in AI tools for high-volume, foundational tasks, like disclosure and early-stage case preparation, junior lawyers are facing a changing landscape. This shift raises important questions about skills development, career progression, and the future of legal education. We dive into: * The evolving role of junior lawyers: How AI is taking over manual, high-volume tasks and what that means for experiential learning. * Essential skills for the AI era: Why critical thinking and an "AI-first" mindset are becoming the most valuable human contributions in law. * Hybrid expertise: How future lawyers will need to combine legal knowledge with technical acumen to guide AI effectively. -------- 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 [https://hollycope.my.canva.site/thefuturelawyer] * New approaches to hiring and professional development: Why portfolios, business proposals, and problem-solving abilities may become more important than traditional CVs. * Opportunities amid change: How junior lawyers can add value by spotting inefficiencies and leveraging AI to deliver smarter solutions. ---------------------------------------- Hosted on Acast. See acast.com/privacy [https://acast.com/privacy] for more information.

Who Really Holds the Power in Law Now? (with Head of Legal Regulatory at Revolut)

In this episode, I'm talking with William Finlay, Head of Legal Regulatory at Revolut. He leads the group regulatory team within the legal department. A global fintech powerhouse that is leading the charge in integrating AI into both customer-facing products and internal back-office workflows. We talk about the "top-down" vs. "bottom-up" approach to AI adoption and how Revolut balances its dual role as both a user and a reviewer of the technology. You’ll hear perspectives on why the traditional law firm revenue model is under threat. "Fill Your Boots": Instead of a restrictive culture, Revolut encourages a "bottom-up" approach where employees are empowered to find creative, efficient ways to use AI in their daily tasks. The Future of Private Practice: A prediction that the "army of juniors" model in law firms will be disrupted as AI takes over low-level tasks, forcing firms to rethink how they train the next generation of senior partners. AI as a "Guidance Counselor": A lighter look at how teams are using AI for non-legal tasks, such as analyzing the tone of messages to ensure they are being empathetic to colleagues. -------- 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 [https://hollycope.my.canva.site/thefuturelawyer] ---------------------------------------- Hosted on Acast. See acast.com/privacy [https://acast.com/privacy] for more information.