Instead of using behavioral questions in initial calls, Salas O'Brien views the entire three-month diligence period as the real interview. How a target's leadership responds to the inevitable challenges that arise reveals more about their character and working style than any prepared answer could.

To get past a founder's polished pitch, ask about their core motivations (like ambition) multiple times throughout the diligence process, using different phrasing. This repeated, layered approach can reveal inconsistencies and expose their genuine life goals versus what they think investors want to hear.

To vet potential investors or acquirers, founders should ask them to articulate their vision for the startup's next five years. Hearing their story told through the buyer's eyes reveals the depth of their strategic thinking and helps assess whether their vision aligns with the founder's, ensuring a better post-transaction fit.

Contrary to standard M&A practice where integration begins post-close, Brad Jacobs makes immediate, unrestricted access to a target company's employees and operations a non-negotiable term upon signing. This allows his team to begin the integration process weeks or months earlier.

Traditional private equity questioning feels like an interrogation, yielding guarded answers. An operator asking peer-to-peer questions creates a conversation, resulting in deeper, more authentic information—the primary input for better investment decisions.

Instead of focusing on transactional details, Milliken's M&A lead connects with founders on an emotional level. By understanding their ultimate vision, he frames the acquisition as the fastest path to achieving their dream, a question that has proven highly compelling and effective in closing deals.

By the time a strategic acquirer enters due diligence, the desire to do the deal is already high. The process's primary purpose is not to hunt for deal-breakers but to confirm key assumptions and, more importantly, to gather the necessary data to build a robust and successful integration plan.

Despite extensive online and third-party checks, Jacobs considers multi-day, in-person interviews with the target's senior management to be the most crucial part of due diligence. This direct interaction is essential for uncovering hidden risks, opportunities, and the intangible "skeletons" that don't appear in financial statements.

A key part of buy-side M&A is conducting 'reverse diligence,' where the buyer transparently outlines post-close operational changes (e.g., new CRM, org charts). This forces difficult conversations early, testing the seller's cultural fit and willingness to integrate before the deal is finalized.