A viral post about the "sell me this pen" interview question reminded me how deep the emotional ties on this question run. Now that I've had room to think, I want to talk about what actually happens the second you ask it - both inside the room and out on your existing team.
The Candidate Was Never Fooled
Somebody walks into your interview room having researched your company, studied your buyers, and prepped a POV on the market you sell into. You know what breaks their confidence in your process fastest?
Asking them to sell you a pen.
The question comes with 20 years of baggage from Jordan Belfort and the Wolf of Wall Street. It's cultural shorthand for the version of sales built on manipulation, misogyny, and drug-fueled hustle theater. You cannot separate the question from the lineage, and you shouldn't try.
The candidate you actually want is selling a $50k + product or service not a $20 bag of pens. That role runs on preparation, consultation, and collaboration. They clock the pen question in a second and it gives them the ick. They know you aren't screening for the skills the job requires. You're screening for who can do a Belfort impression under fluorescent lighting.
Most reps will play the game in the moment, but reject the offer once they leave the room & you may never realize why.
Where Earn The Right Comes In
Earn the Right is the philosophy at the center of my sales work. The short version: you don't get to demand access to a buyer's time or money. You earn it through preparation, curiosity, and showing up with real value. Earn the Right is a deliberate rejection of the aggressive, manipulation-based tactics that dominated sales for decades (and unfortunately still do sometimes).
The kind Belfort is STILL famous. Mind you he currently has over 3.7 M followers on TikTok where he once bullied me so aggressively I was genuinely afraid his stans were going to DOX me (but that’s a different story)
Look at the pen question through that lens. The candidate walks in prepared. They researched your company and buyers and built a POV on the market. You throw them off their prep to see if they can improvise a Belfort-style pitch. You're testing the opposite of the philosophy your buyers demand your reps embody.
Trust Isn't Built Once
That's one of the core philosophies I talk about in my book, Profit Generating Pipeline: Proven Formula to EARN TRUST and Drive Revenue.
Trust and an idea I’ve labeled the “Trust Economy” is so important to me that in addition to making it a cornerstone of my book, I also partnered with a handful of big creators to launch a free video masterclass series called State of Revenue.
Watch all 35 free Masterclass videos HERE, but thinking about starting with mine - The Trust Economy: Why Traditional GTM is Dead (& What Works in 2026).
As important as it is to build and maintain trust with your customers, leaders can sometimes forget that earning the right extends to earning the right to ask our team to trust us.
Now think about what "sell me this pen" signals through that lens.
Nothing about a Belfort-era ambush question reads - yes trust me with your professional future and financial security. It reads as a leader cosplaying Wolf of Wall Street.
The first interaction with a candidate you might one day lead is not the moment to erode it.
What I’m Reading & Watching For The Month
Business Book Club:
Mattering, by Jennifer Breheny Wallace. The book explores why people want to feel seen and how to build stronger relationships at work and at home.
Pleasure Reading:
I Who Have Never Known Men by Jacqueline Harpman « I am a SUCKER for a deeply depressing dystopian book with a female narrator
My Sister. The Serial Killer by Oyinkan Braithwaite « Found this gem in Italy looking for English-language used books. Thriller set in Nigeria and written by a Nigerian woman so it’s a different take on of my fav genres.
Mr. Salary by Sally Rooney « super short story and I loved it. I’ve been trying to talk myself into one of her novels but just can’t so it was nice to get a feel for her writing.
Galatea by Madeline Miller « Another short story from the Author of Song of Achilles and Circe (one of my all-time FAVS). Another beautifully Green-inspired story from fantastic author.
Watching:
I’m rewatching the series Person of Interest, it may be even more timely now.
Finally watched the ANTM doc and WOW I forgot just how utterly wild that series was.
Don’t forget to bookmark the free video masterclass series!!
Watch all 35 free Masterclass videos HERE, but thinking about starting with mine - The Trust Economy: Why Traditional GTM is Dead (& What Works in 2026).
