Generic discovery questions like "what's your pain point?" yield generic answers. A better question is, "If you hired someone to sit next to you, what would you have them do?" This reveals the tedious, unglamorous tasks that are ripe for an automation-focused product solution.

The desire to appear intelligent causes founders to avoid simple questions and instead anticipate needs. This leads to incorrect assumptions. Asking basic, even "stupid," questions like "Why did you take this call?" is the key to understanding the customer's real needs and ultimately closing the deal.

Many founders mistakenly use discovery calls to qualify leads or set up a pitch. The true objective is to determine if a customer has "pull"—an urgent, unsolved problem they're actively trying to fix. This reframes the entire goal from selling to understanding deep customer motivation.

At the end of customer conversations, asking this simple, open-ended question can reveal larger, more urgent problems than the one you initially intended to solve. For MobileIron, it led to focusing on the iPhone; for BlueRock, it pointed them toward AI security, proving its power in finding true market needs.

Instead of asking vague questions like "would you use this?", Decagon's founders were aggressive with initial discovery. They immediately asked prospects about budget, ROI justification, and key stakeholders. This sales-oriented approach, which many founders avoid, provided clear signal and killed bad ideas quickly.

The goal of a discovery call isn't to secure a 'yes' but to understand the prospect's true sentiment. End calls by asking for transparency, not a commitment. Questions like 'Does this feel like a problem worth solving?' and '...worth solving now?' provide an accurate read on the deal's viability, preventing an overinflated pipeline of deals that die later.

The classic "If you had a magic wand, what problem would you solve?" is insufficient. To find true "hair-on-fire" problems, you must follow up by asking prospects to rate their satisfaction with their current solution and the problem's importance on a 1-10 scale.

When a product fails to get traction, don't just discard it. Use it as a tool to open conversations with target customers. Once it's clear they don't want the existing product, pivot the discussion to ask, "What would you pay me to do?" to uncover true, unmet demand.

When pivoting, the first step isn't just finding a problem you're excited about, but one customers will pay to solve. Asking "How much will you pay for this?" early avoids building a business around a problem that, while real, has no budget allocated to it. Start by following the money.