AI & The Law: An Operator's Guide to AI Risk, Governance, & Contracts
AI & the Law: An Operator's Guide to AI Risk, Governance, & Contracts
AI is reshaping how organizations operate and most leaders are navigating it without a map. This three-session live course equips Chiefs of Staff, Legal Ops professionals, and business operators with the strategic and legal fluency they need to guide their organizations confidently. By the end, you'll know the right questions to ask, the red flags to watch for, and how to become the most informed person in the room when AI decisions are on the table.
This course is a collaboration between Operators (Chief of Staff Network, Legal Operators, BizOps Network) and Briefly (www.brieflynow.com).
Session 1: AI Risk vs. Reward: Building Your Organization's Adoption Strategy
Tuesday, May 19 at 12pm ET
Speaker: Damien Riehl, Clio
Your CEO wants to move fast on AI. Your legal team wants to pump the brakes. Your job is somewhere in between. In this kickoff session, Damien Riehl, lawyer, engineer, and one of the most in-demand AI speakers in the legal world, cuts through the noise to give you a clear-eyed framework for thinking about AI adoption. From risk-tolerant tech startups to compliance-heavy healthcare systems, every organization faces the same fundamental tension. This session gives you language, scenarios, and strategies to navigate it — and to help your leadership team make smarter decisions faster.
You'll come away able to:
Articulate the real risks and rewards of AI adoption in plain language
Advise your C-suite on balancing speed with compliance
Understand how different organizational cultures require different AI strategies
Speak confidently about legal tech capabilities and what's actually possible
Session 2: AI Governance Crash Course: What the Law Actually Says Right Now
Thursday, May 21 at 12pm ET
Speaker: Shannon Yavorsky, Orrick
There's no single AI law - and that's exactly what makes this complicated. The EU AI Act is coming into force. Hundreds of state bills are actively being debated in the U.S., and in the meantime, existing laws like GDPR, CCPA, Title VII, the FTC Act, and huge numbers of state laws are already being applied to AI in ways most leaders don't realize. This session is a practitioner's guide to the current state of AI governance. We’ll cover what’s in force now, what's coming down the pipeline, and critically, what your organization probably needs to be doing right now that it isn't.
You'll come away able to:
Understand which existing laws govern AI use at your organization today
Understand the basics of AI risk categories under the EU AI Act and how they may or may not apply to your company
Identify the highest-risk areas in your organization
Track what to watch for as federal and state legislation continues to evolve
Session 3: AI Contracting: Protecting Your Organization in Every Deal
Tuesday, May 26 at 12pm ET
Speaker: David Tollen, Tech Contracts Academy & Sycamore Law Group
Most AI law is happening in contracts, not in legislatures. Whether you're buying AI tools, selling AI-powered products, or managing a vendor relationship that predates the AI era, the terms of your agreements matter more than ever. Data privacy clauses, indemnity provisions, and DPAs that seemed routine two years ago now carry entirely different weight. In this practical closing session, David Tollen, one of the country's leading experts on technology contracts, walks through what non-lawyers need to know to negotiate smarter, avoid costly mistakes, and work effectively alongside their legal and commercial teams.
You'll come away able to:
Identify the key provisions in AI-related contracts that require extra scrutiny
Understand what questions to ask before signing any AI vendor agreement
Know when to revisit existing contracts in light of AI developments
Work more effectively with your commercial lawyers and revenue teams
Bonus: Office Hours Session
Following the three core sessions, an optional open-format office hours will be available for registered attendees. No formal teaching, just open Q&A and peer conversation moderated by Adam Stofsky (Briefly) and the Sylva team. It will be a space to connect, share real situations, and get perspectives from others navigating the same challenges.