Curveball sales questions test composure more than actual selling skill
The 55 Interview Answers That Get People Hired gives you proven structures and examples for the questions employers ask most.
"Sell me this pen."
It's become something of a cliché, but it and its variants still show up regularly in sales interviews, and plenty of candidates freeze the moment it happens.
The actual pen doesn't matter. What the interviewer is watching is how you think under a sudden, unscripted ask.
What This Question Is Really Checking
Can you ask questions before pitching, rather than launching straight into features?
Do you sell benefits relevant to the person in front of you, or just recite generic features?
Can you stay composed and even a little playful under an unexpected, slightly awkward ask?
Do you know how to close, or does the pitch just trail off?
The Best Structure to Use
Ask → Tailor → Close
Ask: Start with a question about their actual need, rather than immediately pitching.
Tailor: Connect the product to what they just told you, not a generic feature list.
Close: End with a direct, low-pressure ask, not an open-ended trail-off.
Answer template
Before I sell you anything, can I ask what you're currently using to [relevant task, e.g. sign documents, take notes]? [Based on their answer] It sounds like [specific need they mentioned] matters to you. This pen [specific benefit tied to that need, not a generic feature]. Would it make sense to grab a few for your team?
Notice the structure works for literally any object. The pen is irrelevant. The process is what's being evaluated.
A Live Example
Interviewer: Sell me this pen. You: Happy to. Quick question first, what do you currently write with day to day? Interviewer: Just whatever's around, usually a cheap ballpoint. You: Got it. So reliability probably matters more to you than looks. This one won't skip or dry out mid-meeting, which sounds like exactly the kind of small annoyance you're dealing with now. Want me to leave a couple on your desk?
Handling Other Curveball Variants
"Convince me to switch banks"
Same structure. Ask what they value in a bank first, then tailor the pitch to that specific answer.
"How would you handle an angry customer right now, pretend I'm the customer"
Stay calm, acknowledge the frustration directly, then move toward a specific resolution rather than generic reassurance.
What to Avoid
Launching straight into features with no questions
"This pen has a comfortable grip and smooth ink flow" without knowing what the person actually needs skips the most important selling skill: qualifying.
Getting visibly flustered or laughing it off entirely
A little humor is fine and often works well, but treating the question as too silly to actually attempt misses the point of it.
Never actually closing
A pitch that just ends without an ask leaves the most important selling moment out entirely.
Final Thought
This question isn't really about pens, banks, or any specific product.
It's about whether you default to genuine selling technique the moment you're put on the spot.
Use the structure:
Ask → Tailor → Close
Prepare for 55 Common Interview Questions
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Have You Been Hit With a Curveball Like This?
What was it, and how did you handle it? Reply and tell me. It may become the next OwnerPath guide.