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.

The most effective way for operating partners to integrate post-acquisition is not by presenting a strategic plan, but by asking "What do you need help with?" and performing hands-on, tactical work to fill immediate talent or resource gaps, which builds trust and yields deep insights.

During due diligence, the most revealing portfolio company reference checks involve asking CEOs leading questions. Frame inquiries to suggest the private equity sponsor is taking undue credit for successes. This tactic encourages frankness and uncovers the true dynamics of value creation and deal sourcing.

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.

PE investors often fail to unlock a portfolio company's full potential by only interacting at the board level. Engaging deeper with operational leadership is crucial to understand the team's true quality and identify opportunities to transform the value proposition, which are often missed from the boardroom.

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.

Centana Growth uses its deep diligence process to uncover operational insights for founders. In one case, they collaboratively identified a flaw in a company's core matching algorithm during a diligence session, leading to immediate improvements before the deal even closed. This reframes diligence as a value-add activity.

To stand out from the flood of PE firms, acquirers must demonstrate deep operational knowledge specific to the seller's industry. Discussing granular details like inventory management, billing rates, and software challenges builds trust and proves you are a credible partner, not just a financier. This operator-led approach resonates with founders.

Bringing a C-suite operator into the core deal team as an equal, not just an advisor, is a revelatory experience. Their peer-to-peer conversations with management unlock a different level of information and interpretation, making it impossible to go back to a traditional, finance-only diligence model.