Instead of asking leading questions that corner an interviewee, use open-ended prompts starting with 'how,' 'what,' or 'why.' This encourages expansive answers and genuine information gathering, whereas closed questions allow for simple, uninformative deflections, achieving no learning.
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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.
Direct questions in sales or leadership can feel confrontational. Prefacing them with 'I'm curious...' completely changes the dynamic from an interrogation to a collaborative effort to understand. This simple linguistic shift builds trust, encourages openness, and turns transactions into lasting relationships.
The goal of asking questions isn't just for you to gather information. It's a Socratic dialogue designed to help stakeholders think differently and arrive at the real need themselves. By guiding their thought process, you build deeper alignment and co-create a better solution, rather than just extracting requirements for yourself to fulfill.
Instead of asking standard discovery questions, top performers pose strategic questions that require joint exploration. This shifts the dynamic from a sales pitch to a collaborative problem-solving session, creating a deeper partnership and revealing unforeseen opportunities that standard questions would miss.
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.
Originating from research with terminally ill children, the 'spill question' (e.g., 'Tell me about X') is a powerful, open-ended prompt. It allows people to reveal their primary concern organically, bypassing the researcher's assumptions about what is important.
Citing Oprah Winfrey, Rubenstein argues the key to great interviewing is not having the best questions but being a great listener. True listening allows the interviewer to pivot and follow up on unexpected answers, turning a rigid Q&A into a genuine conversation that uncovers far deeper insights than a prepared script ever could.
When a prospect gives one-word answers, repeatedly and politely ask "Can you give me an example of that?" or "Can you be more specific?" This simple loop forces them to move from vague statements to the concrete details needed to build a case for your solution.
An interviewer's goal is to learn, not to talk. By dominating the conversation, as when the interviewer's question was twice as long as the answer, nothing is learned. A good rule of thumb is to limit your own speaking time to 10-15% to maximize information gathering.
Ineffective interviews try to catch candidates failing. A better approach models a collaborative rally: see how they handle challenging questions and if they can return the ball effectively. The goal is to simulate real-world problem-solving, not just grill them under pressure.