The AI due diligence dilemma

Why more questions and faster answers aren’t always better

The promise of AI in mergers and acquisitions (M&A) due diligence is hard to argue with: faster question generation, detailed issue identification, real-time tracking of outstanding responses. But the lawyers at Fasken who work on M&A every day are seeing something more complicated play out in practice.

In a September 2026 bulletin, partners Nicole Park, Alexandra Lazar, Antonella Penta, Shanlee von Vegesack and Reina Mistry, along with counsel Paul Blyschak, look at where AI is genuinely adding value in the due diligence process and where, if managed poorly, it can undermine transactions. Their core argument cuts against the assumption that more capability automatically means better outcomes.

On the buy side, one problem is volume. AI can quickly generate extensive due diligence question lists, but quantity is not the goal. Excessive questions can frustrate sellers, damage negotiating dynamics and obscure the issues that actually matter. Human judgment remains the only reliable tool for deciding what is truly material to a given client in a given transaction.

On the sell side, the stakes are higher. A due diligence response that turns out to be inaccurate or misleading does not just slow a deal down; it can expose sellers to liability in contract or in tort. Anecdotal reports of buyers walking away after receiving AI-generated responses that management could not explain or defend are increasingly common. One investor cited by Pitchbook pulled out of a live sales process after receiving responses that were, in their words, clearly AI-written and unrefined. In another case, a deal collapsed after a founder was found to have used an AI tool to answer fundamental questions about how his business had grown.

The bottom line: AI accelerates both sides of the due diligence equation, but human experience and expertise must still drive the deal.

Read the full Capital Markets and Mergers & Acquisitions Bulletin now.

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Nicole Park | Toronto, ON - Nicole Park is a partner and seasoned corporate/commercial and M&A lawyer revered for her adept management of private mergers and acquisitions. Her extensive experience spans domestic, cross-border and international transactions, as well as insolvency-based transactions. With a focus on private equity transactions across a broad range of industries, Nicole also lends her experience to corporate reorganizations, corporate governance matters, and provides day-to-day and strategic advice on business partnerships, corporate finance matters and commercial agreements.

Alexandra Lazar | Montréal, QC - Alexandra Lazar is a partner in the Corporate/Commercial group in Montréal. Her practice touches on all areas of corporate law, including mergers and acquisitions, corporate reorganizations, equity financing and general corporate and commercial matters.
 

Antonella Penta | Montréal, QC -  Antonella Penta is a partner within the Corporate/Commercial law group. Antonella is effective in leading negotiations and realizing private company mergers and acquisitions, venture capital and private equity transactions. Antonella regularly manages cross-border and international transactions, corporate reorganizations and private placement financings. She has assisted companies in various industries from initial stages of incorporation to divestiture, including structuring, drafting of shareholder and partnership agreements, as well as drafting various commercial agreements.

Shanlee von Vegesack | CFA – Calgary, AB; Vancouver, BC - Shanlee von Vegesack is a partner at the firm. Her practice is focused on securities and capital markets, mergers and acquisitions, private equity, start-ups, shareholder activism and corporate governance. Shanlee has a business-friendly, “get the deal done” mentality, enabling her to develop close and trusting business relationships while delivering practical, timely and high-value advice on an array of complex legal issues and transactions. 

 

Reina Mistry | Vancouver, BC - Reina Mistry is a partner and corporate/commercial lawyer providing strategic counsel to companies in the technology sector on a range of issues, from inception of the business to the growth and procurement phases.

 

Paul Blyschak | Calgary, AB - Paul Blyschak's practice is focused on mergers and acquisitions, private equity, corporate and commercial matters, and project development. His experience includes advising clients regarding private and public M&A, including share purchases, asset purchases, and plans of arrangement. His experience also includes other complex and high value commercial contracts and arrangements such as commodity purchase and sale agreements, corporate restructurings, joint venture agreements, shareholder agreements, and project development agreements.