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

M&A Science

Release Date: 08/13/2026

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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...

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, , , , , , , and Eight deal professionals share the M&A moments that never make the CIM. A birthday cake in a management presentation that confirmed a culture fit and influenced a bid. A buyer who died before close, forcing a nine-month restart from scratch. Eight years of customer revenue data on a 1980s IBM that management claimed did not exist. A target quietly heading toward Chapter 11 while diligence was underway. Unexpected events mid-deal are not exceptions. They are the deal. How you read them is what separates experienced practitioners from everyone else. What You'll Learn:...

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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