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“Do you love to win, or hate to lose?” - How to Crush This Interview Question Like a Nerd!

by Todd Caponi

· neuroscience,Transparency,transparency sale

(note: I'm using a publicist. After writing this article, I asked her to run it by a few publications. They all said no...which is probably why I like it so much!)

I was first asked the question during an interview way back in 2001, “Do you love to win, or hate to lose?” After my meandering response, the interviewer explained that the answer he was looking for is, summarized, “True winners in sales always expect to win, and therefore hate to lose”.

Now, when I hear this question, it upsets me...mostly because I’m a nerd for the neuroscience behind it, but...

...“hating to lose” drives toxic sales cultures, typically resulting in behaviors that eventually prevent more frequent winning.

The Neuroscience Nerd Answer
I hope I’m asked the question again at some point in my life, because here would be my totally geeky answer. Ready? Buckle-up.

“Scientifically speaking, if we’re comparing a short-term reward versus a short-term loss, our brain’s loss aversion is stronger. A number of studies support this, one specifically led by Professor Daniel Kahneman identified that it may actually be 3x stronger.

"However, if we’re comparing a short-term reward against a long-term risk, we’re actually drawn to the short-term reward. In one example study led by Martin Lindstrom, he showed how a smoker’s brain’s craving center lights up when reading a cigarette warning label. Essentially, a cigarette warning label has the opposite effect of what it’s intended to, as it reminds the brain that they’d desire a cigarette.

"So, in summary, all human beings are more averse to loss than drawn to reward...unless that loss or risk is long term and uncertain. In that case a shorter term reward is preferred.”

Take that, jerk!

The Non-Nerdy Explanation
There is a tremendous amount of value to losing. While winning is what pays the bills, the best way to make that happen more often is to actually celebrate the losses for their effort, then investigate transparently the lessons learned.

Part of this comes from the jackass leaders in my past who have, with bluster and pageantry, essentially stoned reps for losing deals. “How did this happen?” “We were clearly out-sold!”

As a result, guess what happened?

Loss rates went down - for the wrong reasons: Mysteriously, deals that I swear we lost weren’t showing up on the loss report. Upon further review, their close dates were now in 2022, or they had been moved back to “suspect”.


Excuse making went up: Remember, in the movie The Blues Brothers, when Jake proclaims to his ex all the reasons why he left her at that altar? They included, “There was an earthquake! A terrible flood! Locusts!”. According to himself, it wasn’t his fault. In never-lose sales environments, reps would find anything they could latch onto which would lead the court of leadership opinion to render a not-guilty verdict.

Winning sales leaders create environments where transparency is rewarded. When a loss happens, mark it, and recognize the efforts of the team who engaged in the effort. The rep whose opportunity resulted in a loss already recognizes the fact that their wallet and their quota would have greatly preferred a win. Draw as much value from that loss as humanly possible - for the rep, but also for the entire organization (leadership, product, marketing, operations, etc.).

Now, I hope someone asks you during an interview, “Do you love to win, or hate to lose?” you’ll be ready to pummel them with your answer!

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Todd Caponi is the author of the book, The Transparency Sale. He also is a keynote speaker, workshop leader and trainer as Principal and founder of Sales Melon LLC.

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