Where AI Actually Helps and Fails in M&A Legal Work

Aaron Binstock, Partner, Co-Head of Private Equity Practice at Cooley LLP

AI can now draft, review, and benchmark deal documents in a fraction of the time it used to take, but knowing when to trust the output is a different skill entirely.

Aaron Binstock, a partner at Cooley with nearly 20 years of transactional experience, has seen both sides of that tradeoff firsthand.

Where does AI actually save time on a deal, and where does it create false confidence? What happened when a client's AI-generated tax step chart was built on the wrong assumption? How does reverse prompting produce a better first draft than a single one-shot prompt? And what's changing about how junior lawyers build judgment, and how firms bill for their time?

What You'll Learn

• Where AI reliably speeds up NDA markups versus bespoke merger agreements
• How reverse prompting turns a mediocre AI output into a usable first draft
• The tax step chart mistake that nearly cost a client millions in consideration or tax
• How cross-deal benchmarking pulls survival periods, caps, and baskets into one reference chart
• Why some clients and counterparties are opting out of AI entirely, and how firms track it
• What junior lawyer training looks like once document grinding stops teaching judgment
• Why AI can produce a report but still can't own the result

If you're dealing with AI tools that sound confident but don't actually know M&A, DealPilot, powered by M&A Science experiential data, has guidance built from practitioners who've actually run the deal to help you catch what AI can't see coming.

____________________

The Buyer-Led M&A™ Summit is back

August 18th, free and virtual. We're releasing the State of AI in M&A 2026 report live at the event before it goes public. Benchmark your program, hear from practitioners across the industry, and leave with a clearer picture of where dealmaking is headed.

Register here: https://hubs.ly/Q04kBhzV0

____________________

Episode Chapters

[00:00] Intro

[03:12] Aaron's Path Into M&A

[05:12] Cooley's Public AI Commitment

[07:22] Where AI Fits On A Deal

[11:37] Quality Control And AI Playbooks

[16:33] The Tax Step Chart Mistake

[18:41] How Reverse Prompting Works

[22:19] Benchmarking Past Deals With AI

[23:13] Lockbox Pricing And Prompt Quality

[25:33] When Clients Say No To AI

[33:06] AI's Impact On Legal Billing

[35:44] Training Lawyers In The AI Era

[42:20] Why AI Can't Own The Deal

[44:07] Craziest Moments In M&A Deals