A silent dissenter won't respond to "What are your concerns?". Instead, "soft-float" several potential objections, like giving them a multiple-choice question (e.g., "Is it our integrations, our pricing, or something else?"). This lowers the barrier for them to engage and allows them to latch onto a specific point, revealing their true apprehension.

CEOs provide a curated view of their company's culture. To get an accurate picture, talk to people who have left the organization on good terms for an unfiltered perspective. Also, ask behavioral questions like 'What would you tell a friend to do to be successful here?' to uncover the real cultural DNA.

Transactional questions get transactional answers. A "story-worthy" question, like "Tell me about the moment you first sensed trouble with your supplier?", prompts a narrative. This approach extracts the emotion, context, and deeper story behind an issue, leading to more authentic connection and insight.

Formal cultural diligence can be staged. A more authentic assessment comes from informal settings. Observing how a target CEO and their team treat service staff reveals their true character and provides a powerful, unfiltered indicator of cultural compatibility or potential red flags for integration.

To gauge an expert's (human or AI) true depth, go beyond recall-based questions. Pose a complex problem with multiple constraints, like a skeptical audience, high anxiety, and a tight deadline. A genuine expert will synthesize concepts and address all layers of the problem, whereas a novice will give generic advice.

A founder asking an investor about their biggest blind spot during evaluation is a disarming and intelligent question. As shared by Maytha Agarwal of Defy, it forces the VC to self-audit their decision-making process in real-time, revealing their introspection and leading to a more honest, transparent conversation.

At the end of an expert call, ask the expert to consider a scenario where your agreed-upon conclusions are incorrect. This prompts them to reveal second and third-order risks and blind spots that may not have surfaced during the main discussion.

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.

The chaotic, underdog nature of a startup is a binary filter. Frame this reality honestly during interviews. The right candidate will be energized by the challenge, while the wrong fit will be stressed. This question quickly reveals cultural suitability.