It usually starts in a Slack message or an offhand comment after a board meeting. “Why are we spending three weeks reviewing this NDA when ChatGPT can do it in ten seconds?” And if you’re the only lawyer at a 400-person company, you know the subtext: Why are we paying you for this?
We talked to three general counsel at mid-market companies who’ve had this exact conversation in the past six months. Their approaches were different, but the through-line was the same: the GCs who came out of it well didn’t fight the technology — they reframed the conversation around risk.
Perspective 1: “I Said Yes — With Guardrails”
Rachel K., GC at a 320-person SaaS company, knew that if she blocked AI outright, her CEO would just go around her. So she came back within a week with a one-page proposal: three specific use cases where AI was low-risk. She built a simple intake form — “if you want to use AI for legal-adjacent work, run it through here first.” The key was speed. She didn’t disappear for a month to write a 40-page AI policy. She gave him something workable in a week and positioned herself as the person who enables smart adoption, not the department of no.
Perspective 2: “I Made It About the Board”
David M., GC at a 510-person healthcare IT company, didn’t argue about whether ChatGPT was “good enough.” He asked one question: “What do you want me to tell the board if PHI ends up in a training dataset?” That reframed the whole conversation. They ended up doing a formal vendor evaluation of three enterprise AI tools with proper BAAs, data handling agreements, and audit rights. His advice: if your industry is regulated, you don’t have to invent reasons to be cautious. The regulations are the reasons.
Perspective 3: “I Used It as Leverage”
Sarah K., GC at a 280-person manufacturing company, had been asking for a CLM tool for two years. When her CEO brought up AI, she bundled an enterprise AI tool with the contract management system she’d been wanting. Pitched it as a “legal technology modernization” initiative. The CEO got his AI story for the board. She got the infrastructure she needed. Sometimes the best move isn’t to fight the ask — it’s to expand it.
What We Took Away
Speed beats perfection. A one-page framework delivered in a week beats a comprehensive policy delivered in three months. Reframe around risk, not capability. Don’t argue about whether AI is “good enough” — talk about what happens when it’s wrong. Position yourself as the enabler. The companies that handle AI well aren’t the ones with the best policies — they’re the ones where legal is in the room when decisions get made.
