I spent the better part of the past 20 years interviewing candidates for sales positions and rarely missed an opportunity to ask someone to sell me something. I have listened to over 500 answers to this question.

Selling is difficult. Every day, you ask for someone’s money. They won’t give it up easy. You need to handle every kind of objection while keeping cool and thinking on your feet.

An interview is actually a great place to simulate that environment where one person is attempting to sell themselves to another with the prize being a high paying job.

First and most importantly, I look for people whose eyes light up when I ask the question. This is a challenging question. It puts you on the spot and differs from other interview questions in one key component. I am insinuating 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, one of two things will happen.

A great candidate loves 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 to sell.

They look like they just saw a ghost. They shrink into their chair, start mumbling and asking multiple nonsense questions to stall for time.

Once you begin, I am looking for one thing and one thing only. Do you attempt to understand what I need?

Inexperienced candidates will immediately start talking about features of the pen, which means they assume that they understand what I want. This is a mistake in any sales situation.

This makes me defensive.

Do you tell me that the pen has the most beautiful blue ink in the world? I will tell you that I hate the color blue.

Do you tell me that the pen has an ergonomic rubber grip? I will 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.

Avoid telling me about the features of the pen until I give you permission.

Instead, ask open-ended questions. This makes me elaborate versus closed-ended which will only get you a one-word response.

“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 about writing, listen 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. This makes me feel special, akin to a waiter repeating 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 pen runs out of ink too fast, address how your ink cartridges might help.

If I mention that I love a smooth flowing blue ink, talk about how your blue pen is different than competitors. Only tell me the features that match the needs that I expressed, which will keep me from objecting. How can I object after I already told you something was important to me?

Bottom line is that most people don’t crush this question. Many still impress me with great energy and persistence. I am looking for confidence, high energy, tenacity, creativity and someone who is paying attention to what is important to me.

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 put the close on me later.

This question is not going to keep you from getting the job if you have performed well in the interview up to this point. Like every other question, it provides another indicator.

I often use it as an opportunity to coach and have hired many people who have bombed when asked this question (we still laugh about their answers today).

Have fun if you are asked this question. Bring some energy and start asking questions. You’ll be fine.