I’m going to break the magician’s code here and give you insight into the questions I ask and why. Sales has a bad rap but in Daniel H. Pink’s book, To Sell is Human, he describes the paradigm shift between “buyer beware” to “seller beware”. If you can understand the intereaction of sales, and stay informed of the process, you will have a higher success rate of finding the product suitable to your needs.

… prospective purchasers are on notice. When sellers know more than buyers, buyers must beware. It’s no accident that people in the Americas, Europe, and Asia today often know only two words of Latin. In a world of information asymmetry, the guiding principle is caveat emptor—buyer beware.

Imagine a world not of information asymmetry, but of something closer to information parity, where buyers and sellers have roughly equal access to relevant information. What would happen then? Actually, stop imagining that world. You’re living in it…

Buyers today aren’t “fully informed” in the idealized way that many economic models assume. But neither are they the hapless victims of asymmetrical information they once were. … The belief that sales is slimy, slick, and sleazy has less to do with the nature of the activity itself than with the long-reigning but fast-fading conditions in which selling has often taken place.

The balance has shifted. If you’re a buyer and you’ve got just as much information as the seller, along with the means to talk back, you’re no longer the only one who needs to be on notice. In a world of information parity, the new guiding principle is caveat venditor—seller beware.

We have all interacted with salespeople who are just not good at their job, they ask questions like “What brings you in today?”, their goal is to get you to the cash register as quickly as possible. Then there are the people who have been trained, they ask questions like, “How is it 65 in December?!”, to get the banter going, get you comfortable and then usually default to “so what brings you in today”.

Then come the elite. I won’t name names. They are the people who are in sales don't come to mind when you think of “salesperson”. Asking questions about your lifestyle, what makes you tick, did you catch the new Knives Out movie yet? Banter and rapport are quickly established, and every single question gives us an answer we need.

The Interview

I try to work food or movies into the conversation: this allows me to better understand your willingness to to experiment, your eye for detail, and even spending habits. If you tell me you go to restaurant x every Friday, you are looking for durability, reliability, nothing too fancy, BUT I now have a point to launch from. Maybe deep down you know you’re too comfortable, and the reason we are meeting is to broaden that horizon.

I’ll ask what the people at work wear: this is usually a gold mine. The client will start by describing what the overall vibe is, then the pieces they see most regularly, then what they like and don’t like. I’ll ask further about certain people, and it always turns out Bill dresses for attention, Carol is constantly dressed for the wrong job, Frank is a killer at work but is a straight up slob, and Tiffany and Stephen have amazing style but the client knows they can’t pull it off. - oh my…we hit the jackpot. Now I know: how you perceive people, what you look for, what is important too you, what items you recognize as status vs merit, how you compare yourself to others, and so much more.

I want to hear about your past purchases: what items you have bought, why you like them and what you paid for them. This helps me understand what you look for in a garment and what you see as “value” in each garment. But it also opens up the conversation for what you may not have thought of. If you tell me, “I buy my pants cheap because I’m tough on them and they rip.” Well maybe it’s not you that’s the problem, it’s the cheap pants. If you tell me, you love patterns to make you stand out, have you thought about dialing down the patterns and upping the details? If you tell me, you love stretch because it’s comfortable, have you thought about changing styles so your measurements are accommodated more effectively?

In a sale there is an infinite amount of possibilities, even if there is a finite amount of products. The goal here is to help you understand as a buyer that the answer you give may or may not land with the seller as you are intending. Questions that seem irrelevant are often, more relevant than “What do you have in navy?” - Be conscious of the answers you give and the questions being asked.