S2: E8 | Nate Kostelnik | How to start using AI for contract review, one clause at a time

In this episode of Brief Encounters, Juro’s Richard Mabey is joined by Nate Kostelnik, attorney, contract expert, and one of LinkedIn’s most original voices on how AI is transforming the way we draft and review agreements.

Nate has worked on thousands of contracts and built a following for his creative, human-centered takes on legal tech. In this conversation, he explains how AI can help lawyers get to agreement not just faster, but further apart faster, and why that distinction matters for anyone building playbooks or automating reviews.

Together, Richard and Nate explore:

• Why “playbook maximalism” slows teams down - and what a smarter alternative looks like
• How to start using AI for contract review one clause at a time
• The “drafter’s” and “reviewer’s dilemmas” in an AI-powered world
• Whether AI could one day move beyond review into full negotiation
• How lawyers can balance fairness, efficiency, and scale without losing context or judgment

For legal teams wondering where to begin with AI, Nate’s advice is clear: don’t overthink it, start small, stay thoughtful, and keep your playbooks alive.