After a promising sales call, combat 'happy ears' by feeding your meeting notes into an AI. Ask it to identify the top three reasons the deal might *not* go through. This provides an unbiased third-party analysis, revealing red flags and potential objections you can address proactively.

Effective call planning goes beyond setting a goal; it involves scenario planning for failure. A powerful question for managers to ask reps is, "If this call were to go sideways, what would be the most likely way that it does?" This forces reps to anticipate and prepare for common objections or derailments.

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.

Buyers won't openly state their career risks, such as getting fired for a failed project. To uncover these fears, ask: 'What does success look like for you three months after this is deployed?' Their answer reveals their key success criteria, which are directly tied to their biggest perceived risks.

AI models tend to be overly optimistic. To get a balanced market analysis, explicitly instruct AI research tools like Perplexity to act as a "devil's advocate." This helps uncover risks, challenge assumptions, and makes it easier for product managers to say "no" to weak ideas quickly.

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.

Before starting a project, ask the team to imagine it has failed and write a story explaining why. This exercise in 'time travel' bypasses optimism bias and surfaces critical operational risks, resource gaps, and flawed assumptions that would otherwise be missed until it's too late.

To test an expert's overall sentiment, ask an unrelated "burner question," such as about company culture. A sudden shift in tone can reveal underlying biases or problems not apparent when discussing business models or market structure.

Instead of asking broad discovery questions, present your pre-call research and immediately ask the prospect to correct you. This demonstrates diligence, makes them feel like an expert, and gets to the core issues much faster than starting from scratch.