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.
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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
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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
