CLM Simplified: From Theory to Real Outcomes ft. Lucy Bassli

In this episode of "The Counsel's Code," we are joined by the renowned Lucy Bassli, a true pioneer in legal operations. She shares her no-nonsense insights on why CLM initiatives fail, how to actually use AI, and what legal teams need to stop doing right now.

Meet the Speaker: Lucy Bassli

We are thrilled to feature Lucy Bassli, the founder of InnoLaw Group and author of "CLM Simplified." A former Assistant General Counsel at Microsoft, she is one of the most recognized thought leaders in legal ops and contracting. Her journey began as a commercial transactions lawyer at Microsoft, where she was tasked with bringing "predictability" to a high-volume procurement contracting process, a mission that sparked her passion for optimizing legal workflows.

Key Insights from the Conversation

How did your passion for optimizing contracts develop, and what broke CLM for organizations?

Lucy's passion was a "completely unplanned progression." As a commercial transactions lawyer at Microsoft supporting procurement (a $17 billion/year spend), she was faced with immense volume and zero predictability. Her Chief Procurement Officer told her, "it's death by paralegal over there... I hope you're here to fix it."

This became her mission: to provide the business with "predictability" on what to expect from legal. She spent 13 years streamlining processes, creating templates, and even outsourcing live contract review. She realized she enjoyed this "people, process, tools" work "way more than the editing and redlining of yet another limits of liability provision."

What’s the biggest predictor of CLM success despite unreadiness and misaligned expectations?

The "single biggest predictor" of success is "an appetite for change." Lucy states this is more important than being tech-savvy or knowing the latest gadgets. She believes that 99% of CLM systems fail "because of the lack of change management" and a lack of readiness for that change.

With legal teams drowning in AI noise, how should they realistically use AI in CLM?

Lucy advises teams to "walk back the question." Instead of "I need a CLM with AI," they should start with, "I want to automate some of my contracting processes." Her team approaches this by looking at the contracting life cycle's eight phases.

AI, she explains, plays a different role in each phase. "In some phases, it's extremely helpful... and has revolutionized that particular phase... while in other phases, it just isn't there yet." The key is to avoid "throwing more tech after tech" and instead get "very crisp on where you want to use it" to solve a specific, clear problem.

Where does CLM deliver the most value—speed, risk, or visibility?

Lucy first clarifies her definition: CLM is Contract Life Cycle Management—the people and process—not just the technology. When evaluating the technology's value, she believes it's in the "workflow."

The most value comes from automating "the movement of the four corners of the document across the phases," such as intake, triaging, and assignment. This end-to-end process management is, in her view, more critical than focusing on inside the four corners—the "clauses, the redlining, the editing, the playbooking." She feels solutions are often great at one or the other, but not both.

What are your top criteria for evaluating CLM vendors beyond the product?

Since the "differentiation is pretty minimal" among top-tier tech, Lucy says the "people behind that tech becomes much more important." Her team is "agnostic but opinionated" and evaluates vendors based on:

• Implementation: Do they do it internally or use a third party? What is the expected "lift" on the customer's team?

• Customer Success: What happens after go-live? What support is included versus extra?

• Holistic Service: Does the vendor just provide "technical implementation" (the piping), or do they also provide the "professional service" to ask the "why questions"—like "Why do you do it that way?" She favors vendors who understand that their tech "can't be successful without professional services."

What CLM practices should legal teams stop right now?

Lucy's answer is blunt: "Stop doing nonsense work." She argues that "no lawyer goes to law school so that then they can spend their days reviewing NDAs or... the exact same template MSA over and over again." She calls this a "misuse of corporate resources."

She urges legal teams to "assume smart risk" on these repeatable contracts, noting that most of the risk is "actually commercial." The goal is to "empower the business to do a little bit more" and get legal to "step out" of work that "does not make a difference to the business."

Where do you see CLM and AI in 2–3 years?

Lucy predicts we'll see "more and more focused point solutions" that target specific parts of the contracting life cycle. She also hopes buyers will become "more focused on the pain points they're trying to solve."

She boldly "rains on a lot of parades" by bursting the bubble of a "one CLM system" for all contracts. She says the "end-to-end CLM for all contracts across an enterprise—just don't see it happening successfully."

Most underrated part of CLM, top resource, and one tip for new teams?

Lucy jokes that CLM is mostly "overrated" because "the expectations are so high and the sales pitches are so promising."

However, she says the most "underappreciated" part is "the ability to automate approvals in a smart way that gets legal out of some sort of a default approver all the time." She suggests this capability is a potential "game-changer," allowing teams to "get the business to do their part" first, perhaps even before the negotiation phase begins.

About "The Counsel's Code" Podcast

"The Counsel's Code" is your go-to podcast for exclusive interviews with top legal executives. Discover the strategies they've employed to cultivate their careers, excel in their positions, and emerge as true leaders in their organizations.

Throughout our discussions, we delve into the challenges of leadership and how these accomplished professionals manage the pressures that come with it. Our mission is to provide valuable insights and support for in-house counsel, fostering mutual growth and development.

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Disclaimer: The views expressed in this podcast are the speaker’s personal opinions and do not necessarily reflect the positions of the podcast, Volody, or any current or former employers.