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Don't ask a candidate to pitch your product; they don't know it well enough. Instead, ask them to pitch their current product as if you were a customer. Critically, evaluate the discovery questions they ask and what they listen for to gauge their true customer focus.
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To get unbiased feedback, don't mention your product. Instead, ask prospects about their #1 challenge. If they organically bring up the problem your product solves, you've found a real pain point and strong market pull.
To efficiently screen sales reps, hold a group interview where candidates perform a pre-sent script. Then, provide live feedback and ask them to try again. This quickly assesses their preparation, ego, and coachability.
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.
Asking a candidate when they first encountered the brand can reveal whether they are a true customer and believe in the mission. This question invites a conversation that helps suss out their level of preparation, empathy for the customer, and genuine interest beyond just seeking a job.
When a prospect asks if your product does something, it’s a confession that their current process is failing. Instead of just answering "yes," use it as a discovery opportunity. Ask, "How do you currently do that today?" to uncover the underlying problem and tailor your demo to solve it directly.
Traditional sales separates discovery from the demo. A better approach is to start the demo immediately and ask discovery questions in context. Asking "How do you track applicants today?" while showing your applicant tracking dashboard grounds the conversation in reality and makes your product's value more tangible.
To gauge if an executive is a true 'builder' with customer empathy, ask them to design a new feature for a product they use daily. Their ability to solve a problem for themselves reveals their capacity to be empathetic to new customers.
Instead of guessing your competitive advantage, ask potential customers which other solutions they've evaluated and why those products didn't work for them. They will explicitly tell you the market gaps and what you need to build to win.
Instead of immediately providing a technical answer, top-performing sellers first qualify the question itself. Asking "Why do you ask?" reveals the customer's underlying strategic intent, turning a simple query into a deeper discovery conversation and uncovering true needs.
When hiring a sales leader, founders often fall for the most enthusiastic candidate. Ben Horowitz advises picking the one who rigorously qualifies the opportunity—questioning the product and customers. This demonstrates the critical discovery skills they'll apply when selling.
