When Legal Opts Out, AI Opts In: If Legal Isn’t in the Room, the Model Decides

Hello friends and colleagues,

A few months ago, a seasoned General Counsel I admire faced a quiet crisis.

It was late on a Friday. A Slack ping arrived from product leadership. Friendly tone. Casual ask. “Just a quick gut check, we’re rolling out dynamic AI-powered pricing Monday. All good?”

She opened the document. Read it twice. Her instinct kicked in. Dynamic pricing. User profiling. AI-driven decisions. The legal issues were there, but buried. And worse, she had not been in the room when it was built.

She opened a new browser tab. Typed, “How to explain AI risk to a board.”

And then she froze.

She realized she didn’t need more answers. She needed fluency. A framework. A process for navigating new technology with calm and clarity, not panic and pressure.

That weekend, she built it.

She didn’t just read. She ran an "explain it to a 12-year-old" drill with her team, just like the one I recommend in The First AI Drill for Your Legal Team. She restructured her board briefing approach using the What, So What, Now What framework. And she mapped exactly where AI was already operating quietly in her company, a method I outline in Three Places AI Is Already in Your Company.

By Monday, she was not just ready to explain the risk. She had become the one everyone turned to for clarity.

You Don’t Need to Learn AI. You Need to Learn to Lead in It.

When lawyers say they feel behind on AI, they are often looking in the wrong direction. You don’t need to become a machine learning engineer. You need to become fluent in translating AI systems into a business context and risk clarity.

That’s why I created the AI Literacy Starter Pack for General Counsel. It’s not a list of definitions. It’s a set of battle-tested tools to help you guide your team through ambiguity and show up to leadership conversations with confidence.

In-house leaders are using this to run simulations, rewrite escalation playbooks, and turn board reports into clear action frameworks. When it’s time to present to the board, you don’t need tech jargon. You need to tell them, simply: what the system does, why it matters, and what they need to decide, just like I explain in How to Explain AI Risk to Your Board in Ten Minutes.

That’s not just a communications skill. That’s leadership.

NDAs, Non-Standard Clauses, and the New Legal Fluency

Not all risks announce themselves like AI. Sometimes they hide inside “routine” contracts, like NDAs.

I’ve seen legal teams assume AI tools can draft and redline their way through confidentiality language. But AI cannot yet reason through nuance. It cannot weigh context, assess downstream use, or evaluate whether your carve-out aligns with your company’s risk posture.

That’s why I’ll be speaking at the upcoming Contract Nerds webinar on October 30, where we’ll go deep into the new landscape of non-standard NDA terms. Alongside Sterling Miller , Jessica Nguyen , and Nada Alnajafi , I’ll explore how to spot, draft, and negotiate complex clauses around data restrictions, AI system disclosures, and multi-tiered confidentiality frameworks.

We'll also look at how to pair human expertise with the right tools. At TermScout, we’ve launched Certify™ AI to meet this exact need. Certify™ AI independently verifies AI-related contract terms by analyzing your agreements against evolving industry standards. The result is a trusted certification badge that builds confidence with customers and helps accelerate deals. It’s not about drafting faster; it’s about contracting with credibility.

The Modern GC Is Not Waiting to Be Asked

The most effective legal leaders I know aren’t sitting back, hoping AI clarity shows up. They’re building new operating models from scratch.

They are embedding legal inside the product lifecycle, something I unpack in From Tech Support to Strategic Partner with Kevin Keller and Kate Aishton .

They are rewriting their own roles, from responder to architect. Minh Hoang Merchant did just that when she took the pen and drafted the earnings script herself, not because it was required, but because it was the fastest way to learn what mattered.

They are building around frameworks like the Six I’s Model to modernize legal operations, and leading with confidence, not certainty, but clarity and context.

Goodbye: AI Changed the Game. You Get to Change the Role.

That GC didn’t have a perfect answer. But she had a system. And in this era, that is more powerful than instinct alone.

She no longer googles “AI board risks” at midnight. She builds the frameworks that others Google later.

And that is the shift. From reacting to shaping. From compliance to fluency. From passive to powerful.

If your legal function still thinks NDAs are boilerplate, or AI is a “later” conversation, now is the moment to lead.

Join me on October 30. Bring your hardest clause. Bring your AI anxiety. We’ll unpack it all together.

Until next time,

Olga

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Olga V. Mack is a leading innovator in the legal field, driving digital transformation and championing the use of technology to modernize law. With a focus on efficiency, accessibility, and client-centric solutions, she has redefined traditional legal practices through groundbreaking tools, strategies, and advocacy. As an award-winning CEO, General Counsel, accomplished author, and sought-after thought leader, Olga is dedicated to empowering the legal profession to embrace transformative technologies and stay adaptable in an ever-evolving world.