Stupid Questions

Stupid questions aren’t stupid, and to be successful in Tech Sales- you NEED to answer them with a smile.

Let’s get one thing straight: I’m not saying stupid questions are a bad thing. In fact, I welcome them—all of them. Even the ones that make me pause and think, “Why on earth would anyone ask that” or better yet “How does someone in your role not know the answer to that?”

If you’ve been in tech sales for even one day, you’ve experienced this: a prospect asks a question so baffling that your brain does a double take. But the truth is “stupid” questions can tell you a lot about a deal – as long as you can see through them. No matter how outlandish or misinformed they might seem, they actually tell you something important:

• The prospect is engaged.
• The prospect trusts you enough to ask.
• They’re trying to fill gaps in their understanding.
• They’re exploring how your solution fits their needs.

Every question—no matter how off-base—represents a point of interest. And that IS something to work with.

How to handle the stupid questions

How you handle the stupid question will absolutely determine how the rest of your relationship with go with that prospect. If you handle it with grace and keep you cool – you’ll maintain credibility and continue to solidify yourself and your team as a trusted advisory in the call.

1. Pause and Reframe the Question

When a prospect asks a question that seems baffling, take a moment to reframe it. Often, what they’re asking isn’t what they mean. They might be struggling to articulate their real concern.

For example:

• Question: “Can your platform guarantee a 50% revenue increase in the first quarter?”
• Reframe: “It sounds like you’re looking for solutions that can drive measurable results quickly. Let me walk you through how we help clients achieve growth and the kind of timelines they’ve seen.”

2. Lead with Empathy

Even if the question seems silly, don’t dismiss it. Everyone has their own knowledge gaps, and prospects might be under pressure to deliver solutions. Start with understanding.

• “I’d glad you asked. Let me clarify that for you.”
• “I see where you’re coming from. Let’s break this down.”
• “I love that question. Let me dig into that further for you.”

A little empathy goes a long way in making the prospect feel respected, no matter how silly their question may seem.

3. Or Ask Questions Back

Turn the conversation into a dialogue. Often, questions stem from deeper concerns or misunderstandings. Ask follow-ups to uncover their real needs.

• “What’s driving that question?”
• “Can you tell me more about what you’re hoping to solve?”

This not only helps you address their concerns but can also uncover opportunities to position your solution and its value more effectively.

4. Use Humor (When Appropriate)

Sometimes, a lighthearted approach can defuse the awkwardness of a wild question. Just make sure it’s good-natured and not dismissive.

For example:

• Question: “Can your platform read minds?”
• Answer: “Not quite yet, but we’re working on it! Until then, let me walk you through how we anticipate user needs using predictive analytics.”

5. Say No—But Make It Positive

When the answer is no, be honest. If you can try to deliver it a positive spin. Focus on what your solution can do. If available, explain the logic behind the no. Delivering a no can make you AE panic. But my take is that a no will not destroy a healthy deal.

Why Stupid Questions Are a Good Sign

As much as these questions might make you want to facepalm, remember – they’re actually a good thing. They mean the prospect is engaged, curious, feel safe to ask a question and interested in what you’re offering. Sure, their understanding might need a little shaping, but that’s part of your job.

When you welcome every question—yes, even the “stupid” ones—you create an environment where prospects feel comfortable exploring their concerns and ideas. And that engagement? It’s priceless.

Final Tips for Handling Stupid Questions

• Stay Calm: Resist the urge to roll your eyes or react defensively. Pause. A patient response reflects professionalism.
• Educate, Don’t Lecture: No mansplaining. No talking down. Use these moments to gently guide the prospect toward a clearer understanding.
• Encourage Questions: Thank and continue to invite questions throughout the process. It builds trust and keeps the conversation flowing.

At the end of the day, there’s no such thing as a truly stupid question in sales—only opportunities to clarify, educate, and build trust. So the next time you’re hit with a head-scratcher, pause, take a deep breath, put on your best smile, and turn it into a chance to shine.

How do you handle off-the-wall questions in your sales calls? Share your tips—I’d love to hear them!