The Legal AI Game: Why Waiting Might be Better Than Rushing ft. Myah Bowermaster

Applying AI to an already bad process is just automating a bad process,” says Myah Bowermaster, Head of Legal Operations at Cvent, in this episode of Between the Briefs by Steno. Tune in as hosts Adrian Cea and Joe Stephens sit down with Myah to explore the truth behind AI adoption in the legal landscape.

What You’ll Learn:

How to position legal operations as strategic partnership
Why waiting for AI maturity beats first-mover adoption
The framework for assessing legal tech readiness
How to build credibility as a non-lawyer legal operations leader
The “help me help you” approach to process implementation
Why contract data integration unlocks revenue-generating insights
How to hire for legal operations success without a legal background
The human-AI balance that protects cognitive capability

AI is shiny, but not all that glitters is gold. And, it turns out waiting, rather than rushing, might be the smarter choice when it comes to the AI game.

Highlights:
00:00 Introduction & Meeting Myah Bowermaster

01:43 From Paralegal to Legal Operations Leader: An Unconventional Path

05:48 What Legal Operations Actually Does and Why It Matters

10:16 Strategic Patience: Why AI Adoption Should Follow Market Maturity

13:29 Myah’s Advice to Legal Teams

15:40 Input Quality Determines Output Reliability

18:27 Descriptive Context Over Prompt Engineering

20:41 Building Credibility Without a Law Degree

23:05 Ownership, Maturity Models, and Growing Legal Operations Teams

25:50 The Real Resistance: Centralization and User Interface Design

27:20 Three-Year CLM Implementation and Cross-Functional Excellence

29:32 Hiring for Legal Operations: Soft Skills Over Legal Background

32:33 Crisis Management and the Chaos Coordinator Role

34:23 The Evolution of Legal Operations: From Admin to Chief of Staff

35:57 When to Hire Your First Head of Legal Operations

37:33 AI Tool Evaluation: Consistency, Integration, and User Experience

40:02 Turning Contract Data Into Revenue-Generating Intelligence

44:20 Myah’s Hot Take: Just Because AI Can Doesn't Mean It Should

45:16 Key Takeaways and Final Thoughts

Quotes:

"Legal operations is doing everything it takes to run a legal department that doesn't involve practicing law. We're the connective tissue bringing the process to compliance. Lawyers are really good at being lawyers, but lawyers are not typically process oriented or tech oriented, and so a big part of what legal ops does is we empower lawyers to do what only lawyers can, and then we automate and operationalize the rest."
“Everyone kept saying we need to catch up with AI, but all the pain points that we have were not something that AI could do yet in the legal space. I could purchase this right now and address 25% of the pain point, but we haven't done the internal work to get to that 40%. Why don't I just wait and let the market catch up to us so they can address 70 to 80% of our pain points?"
"You don't need to be a prompt engineer. You need to be descriptive and then let the AI do the prompt engineering for you. Start every prompt with: I want you to refine this prompt so it works best with my tool. Do not run the prompt. This shows you how descriptive you actually were and what the AI understood from what you said."
"It is all about relationship building. I went out to everyone and said, help me help you. What are your pain points? Instead of telling you the best way to do something, I understand what your pain points are and tell you everything I do is to help you and enable you and make your life better. It all comes back to trust."