“Um, this pen comes in multiple colors, and uh . . . ”

“I don’t write in multiple colors.”

“Oh, I see. Well, this one here . . . it has a modern design that, uh . . . ”

“I don’t like the design of that pen. It is too modern for my taste.”

“OK, well, if you buy it today, I can get you a deal for half off.”

“I didn’t want it at $2.00 and don’t want it for a buck, either.”

So it goes until one of three things happens.

  1. The candidate gets frustrated and quits trying to sell.
  2. Awkward silence forces me to switch to a different question.
  3. The candidate figures out that selling has no correlation with product features, and everything to do with my needs.

If you have interviewed with me, chances are good that you have attempted to sell something to me. Perhaps, it was your pen. I might have asked you to sell me your necktie or the stapler on my desk.

I have listened to over 500 answers to this question. I have a good sense of the type of answers that correlate to great employees. In this post, I share what I am looking for and the reason I love this question.

Do You Like A Challenge?

This question takes the intensity of the interview up a few notches. As soon as I hand you the pen, I am reading your face. Do your eyes light up or do you look like you just saw a ghost?

“Sell me something” differs from other interview questions in one key component. I insinuate that this question will be Pass/Fail, and you will get immediate feedback.

All other interview questions are left open where the interviewer nods, writes something down and moves to the next question. When I ask you to sell me something, it is clear that there can only be two results.

  1. You sell me a pen.
  2. I convince you that I don’t want a pen.

A great candidate gets energized by the challenge. They smile, lean forward and become animated, like a racehorse walking into the starting block.

The opposite happens with someone who doesn’t like a challenge. They shrink into their chair, sigh deeply and start mumbling to themselves to stall for time.

Business is hard. On a daily basis, you must be convincing. If you don’t sell to customers, you still need to persuade your manager and peers.  If not, you are just an order-taker and how much value can you add to your organization saying yes to everything?

You will be asked to walk into offices every day and ask for someone’s time, attention or money. They are not going to give it up easy, and you’ll need to handle every kind of objection and personality while keeping calm and thinking on your feet.

An interview is a great place to simulate an environment where one person is attempting to sell themselves to another with the prize being a high-paying job. Your response can signal how strong your growth mindset is. I am much less interested in sales skills than the traits that make up successful people.

Your enthusiasm and approach matter more than your effectiveness as a salesperson.

Do You Attempt To Understand What I Need?

In the movie, Pulp Fiction, Jules Winnfield and Vincent Vega are mob enforcers finishing up a contract.

All goes swimmingly until one of their targets, who looks strikingly like a young Jerry Seinfeld, storms out of hiding with a loaded revolver. Before the hitmen can defend themselves, Seinfeld closes his eyes and squeezes off six point-blank rounds in their direction.

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Jules and Vince check themselves for bullet holes and glance at the wall behind them. The look on Seinfeld's face is one of a man who realizes he should have measured twice and cut once.

The hitmen do not make the same mistake in return.

Jules looks over the bullet holes and sees divine intervention. I see poor execution, planning, and an inexperienced operator nervously rushing through his job.

In short, I see the same mistakes that poorly trained salespeople make. Rather than wasting bullets, incompetent salespeople fire off as many "features" of their product as possible.

This is the "machine gun method" of selling. Perhaps, you have encountered this with an annoying representative in a mall, desperately attempting to convince you to stop walking.

Salespeople employing the "machine gun approach" nervously rush to blurt every feature they can recall.  They "spray and pray," unloading their entire clip in hopes that one of their selling features might be of interest. It comes across as desperate, even pathetic.

If someone is applying for a sales position and has sales experience, my expectations are much higher. Any trained sales professional should understand the importance of discovery in the persuasive process.

Still, most dive right into features, which only serves in making me defensive. After all, you are assuming that you know what I want.

  • Do you tell me that your pen has the most beautiful blue ink in the world? I tell you that I hate the color blue.
  • Do you tell me that your pen has an ergonomic rubber grip? I tell you that I am allergic to rubber.
  • Do you tell me that you are proud of the sturdy frame that never breaks? I will tell you that it feels too heavy and that I need light pens for my arthritis.

How Resilient Are You?

Most sales experts teach that you should get the customer saying yes. Ask questions that have obvious "yes answers" and condition your customer to agree with you, like a dog getting a treat for barking.

This is a cynical and manipulative method of negotiating. Most smart prospects will figure out what you are doing and resent it.

  • "Do you like to save money?"
  • "Do you want top quality at the best value?"
  • "Do you want peace of mind?"

Those questions make me want to take a shower.

People see through that game. Sure, you get a customer who agrees with you as long as they are in front of you.  You leave the meeting with a false sense of confidence. Two weeks later, the customer hasn't responded to any of your voice messages.

Any real negotiation hasn't started until someone says no. Rejection is necessary because it informs us. It forces us to ask better questions, to understand our counterpart on a deeper level.

If "yes" is a blow-off answer, "no" sends a signal from someone who is not being listened to.

The same applies to any internal negotiation. If you want your boss to implement a change, expect resistance. If the change was so obvious, your manager would have implemented it already.

Expect to be turned down several times. Expect that you will need to conduct more research and provide more evidence. Embrace every rejection as an opportunity to learn more about what it will take to get to yes.

I purposely throw up barriers early when I ask the "sell me" question in an interview. The only way you can lose is if you quit, and so many people give up after a rejection or two. I have to encourage half of the candidates to "keep going," when they throw up their hands like Tommy Boy selling his first brake pads.

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Even if you've never sold anything in your life, you can demonstrate tenacity in an interview. Careers are built on setbacks and our willingness to persevere. Take a few early hits and keep coming.

Are You Adaptable?

At some point, I need to see that you are paying attention. Resilience is great, but "Willing to bang head on the wall the longest" is not a trait that is advancing a company forward.

If you've been shut down on every feature for five minutes, can you figure out that it might make more sense to ask a question or two?

If I want to sell a stapler to you, the first thing I need to know is how often you use a stapler.

  • How often do you use a stapler?
  • What kind of stapler do you use?
  • What do you like about it?
  • What do you wish was different about your stapler?

These are open-ended questions that force someone to share more than just a one-word answer. These questions help me understand how you might interact with my product. They help me understand your needs and give me permission to offer a feature that might satisfy those needs.

This approach works for any product, service or idea that you are trying to sell.

  • How often do you use pens?
  • Where do you keep your pens?
  • What do you like about the pens that you currently use?
  • What do you look for when you purchase a pen?
  • What bothers you about your current pen?

Ask me questions, listen with intent, and take notes. Ask until you have an incredible amount of information about my preferences, then repeat what you heard and ask if you summarized correctly. Mirroring makes me feel special, akin to a waiter reciting your full order after writing it down at a restaurant.

Now that you know what I am looking for in a pen, tell me how your pen meets every need and how it exceeds what your competition is currently providing me.

  • If I said that my current pens run out of ink too fast, tell me about how long your ink cartridges last.
  • If I mention that I love a smooth flowing blue ink, explain the unique aspect of your pen's color.
  • If you hear me complain about getting cramps from writing too much, lean on the ergonomic handle designed for comfort.

Only tell me the features that match the needs that I expressed. This keeps me from objecting, as I would be contradicting myself. Features are not benefits until they match with an expressed customer need.

"If I heard you correctly, comfort is important to you. One aspect of our pen that makes it a favorite with our customers is this soft, rubber handle. Feel free to sign your name with it to get a feel for what I am talking about."

I ask this interview question to learn about your confidence, energy, tenacity, creativity, and ability to pay attention and adapt. You don’t need decades of sales experience to demonstrate those things. Lead by asking questions and get me talking, which will buy you time to be creative in how to help me.

As a hiring manager, I use this question to gauge much more than sales acumen. Sales skills can be taught but the aspects of your personality that this question exposes are inherent and not likely to change.

Most of all, have fun with this question. Some of my favorite hires bombed this question in spectacular fashion but had the self-confidence to laugh about it in the interview.

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