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.

A compressed diligence process relies heavily on projections. A superior approach is building a relationship over 1-2 years, which allows an investor to witness the company's actual execution against its stated goals, providing far greater conviction than any financial model.

Instead of just tracking hard numbers, AI tools can systematically analyze years of transcripts to map out qualitative or "soft" guidance (e.g., "revenue will accelerate in H2"). This creates a picture of a management team's guidance style and credibility, a crucial but historically painstaking analysis to perform.

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.

Experience taught Herb Wagner that great leaders consistently surprise on the upside. He now weights leadership quality far more heavily, assessing CEOs not by interviews or charisma, but by their verifiable track record and through trusted backchannel references who have worked with them directly.

Management interviews are not equally valuable across all industries. In sectors like tech, understanding a CEO's vision is critical for alpha. In commodity businesses like coal, where external factors dominate, financial analysis is more important than management's qualitative input.

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.

To increase the value of expert calls, investors should use them to validate or invalidate a pre-existing thesis. This structured approach yields more satisfying and insightful conversations than open-ended fact-finding.