Fun & viral · Sales Roleplay
Sell me this pen: practice the 30-second test out loud
The classic answer is to ask before you pitch: when did you last use a pen, what for, and what happens when you don’t have a good one at the moment it matters. Then sell the outcome he just described rather than the pen, handle “I already have a pen,” and ask for the sale. Practice the 30-second test with Grant Whitmore, an impatient investor who says he owns fifty pens.
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Updated October 2026
Who it's for
Who this practice is for
- Sales job candidates practicing the classic interview question before the real one.
- Sales trainers who want to show what asking before pitching sounds like.
- Anyone who freezes when someone says 'sell me this pen' at a party.
- Reps working on discovery when the buyer says they already have one.
What happens
How a session goes
- Grant Whitmore speaks first. He says he already owns fifty pens and gives you 30 seconds.
- You ask questions about when he last used a pen and what for. He answers in his impatient style.
- He pushes back with 'I already have a pen' and decides whether to commit, give a conditional next step, or say no with the real reason.
Real lines from a test session
What Grant Whitmore said in a test session
“Here's a pen. I already own fifty of them. Sell me this one. Go.”
“That's better. … Can you guarantee this pen will make me close deals faster, or are you selling me insurance against a problem I've never had?”
“You sold me on the signal it sends across the table, not the ink inside it. That's good.”
From a test session of this practice in the app, lightly trimmed. Your session goes its own way: the character reacts to what you say.
The scorecard
What the scorecard looked like for Sell Me This Pen
“I can’t put an exact number on that—it really depends on the day and the situation, honestly. But I’ve seen people feel more confident with it, and that confidence might speed things up. I just think it’s a really good p”
You backed off from your confident value framing and defaulted to vague feeling, which the buyer rightly dismissed as not a business reason.
Try instead: “You're right, I can't guarantee a specific deal closes faster. But I can guarantee zero misfires on your signature stroke — and in my experience, that removes one variable from your stack of worries. Want to test it on your next contract signing?”
What went well: You adapted mid-session, shifting from space tech to the psychological signal of the pen in a negotiation setting.
Real scorecard output from one of our test runs. In test runs the practice answers are written by a test script, not by a customer.
What good looks like
What a strong answer does here
- You ask when he last used a pen and what for before you mention the pen.
- You turn his answer into urgency instead of listing features like smooth or blue.
- You frame the pen around the signal it sends across a table, not the ink inside.
- You close with a clear next step, even if it is a conditional one.
Scored on:
- Discovery
- Objection handling
- Value framing
- Next step
Common mistakes
Weak lines, and what to say instead
Weak: “This pen is smooth and blue and writes really well.”
Better: “When did you last use a pen, and what were you doing?”
Listing features skips discovery, which is the first thing the scorer rewards.
Weak: “It's a great pen. You'll love it. Trust me.”
Better: “You said you own fifty. What would make this one worth picking up over the others?”
Asking about his answer creates the need instead of assuming it.
Weak: “So, do you want to buy it?”
Better: “Based on what you said, would it help to try this one in your next meeting?”
A clear close tied to his answer beats a vague ask.
Weak: “I can guarantee this pen will make you close deals faster.”
Better: “I can't promise faster deals, but this pen is the one you'll reach for when you sign.”
Overpromising sounds like insurance against a problem he doesn't have.
Sell Me This Pen: start talking in a few seconds. Your own side stays yours to fill in.
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Your sales roleplay practice plan
- Discover the buyer’s problem
- Handle the real objection
- Agree a specific next step
Start with a free worksheet, then test your own response with a voice or text roleplay. Your first complete coaching report is free once across all areas. Create a free account to save your goal, actual words, and downloadable notes.
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FAQ
Questions about Sell Me This Pen
Who is Grant Whitmore?
Grant Whitmore is an impatient, rich investor, about 55, running the classic test. He says 'sell me this pen' and gives you 30 seconds. He owns fifty pens and is decided. He speaks first. He is a 3D face whose voice matches it. He pushes back, then commits, gives a conditional next step, or says no with the real reason. Try it free →
Is this only for sales interviews?
No. Sales job candidates and sales trainers use it, but anyone who wants to practice the classic 'sell me this pen' test can try it. You practice out loud or by typing, against an AI character who pushes back. It is practice, not advice for a real interview. Try it free →
Why do interviewers ask “sell me this pen”?
To see whether you ask questions before you pitch, listen for a need, connect the product to it, handle an objection and ask for the sale, all in a minute. It is less about pens than about whether you sell to the buyer in front of you or recite features. Try it free →
Try Sell Me This Pen free
4 free rounds now, no signup. 7 with a free account. Then $4.99 for 100 rounds, one time, with no subscription. Plans are there if you practice every day.
Try it free, no signupBuilt by Matthew, a solo founder. Questions? Email support@getadversaryai.com, I read every message.