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The Most Important Question in Sales

Sales can often be too much about talking and not enough about listening. Here’s some quick tips to help you remember to ask the most important question.

Published in

The Art of Sales

4 min readApr 8, 2016

As a young and quickly growing startup, we pride ourselves on our ability to sell our products to a wide variety of clients, but we know that we still have much to learn. When it comes to asking questions in sales, there is one particular lesson that stands out above the rest. Learn to ask “why?”

The Importance of Asking “Why” in Sales

It’s easy to get caught up in all the bells and whistles, cool features and fancy gamification gadgets that we have created and completely miss asking the most important question. This isn’t just a problem that we faced, it’s actually one of the most common problems in sales. Sales reps get caught up talking about the product and explaining its features and benefits and they forget to slow down to ask… WHY?

Companies buy a product for one primary purpose: to solve a problem or ease a pain they are facing. So, if you can start your conversations by understanding what your customer’s motives are, you can avoid a whole lot of jumping through hoops and unnecessary dialogue. When it comes to business, people want to come in, solve their problem and get out as quickly as possible with a strong sense of confidence that their purchase will achieve their desired goals and eliminate their current pains.

Many times, your prospect may not be clear on exactly what the problem is or even what type of solution they are looking for. It is your job as a sales rep to help them. Don’t pretend that your product solves some problem when you know it really doesn’t… be honest with your client and with yourself. Build trust. Once this is established, clearly articulate why your product is the best on the market, why the pricing is justified and what benefits your potential customer should expect after buying. In order to do this, you need to start with “WHY”?

Here are a few examples:

Why did you contact us for a demo today?
Why do you believe this product is right for you?
Why is this issue important?
Why do you want to fix this now?
Why have you chosen to speak with us instead of our competitors?
Why have you been unable to solve this problem thus-far?

I recently attended an entrepreneurship where we were asked to explain why our product was created… and then ask why again and again and again. The purpose was simple: by continuing to ask “why?” you will eventually get to the true underlying logic or purpose.

“Start With Why”

Simon Sinek gives some great examples of how “start with why”. Generally, he suggests people begin the process something like this: “I want to_____ so that ______”. By refining this over and over, you will eventually reach the true purpose or passion behind what you’re doing or the true problem that you are trying to solve within your life or business. Simon’s TED talk on this topic has over 26 Million views and can be viewed here:

If there is one thing in particular that we should learn from Simon Sinek, it’s that by understanding the “why” you can shape the “how” and the “what”. In other words, if you understand why the issue is important then you can explain “how” your product helps and “what” it does. Thus, essentially shortening the discussions and cutting through most of the usual objections.

Two of the most important keys to sales are:

Let your prospects sell themselves
Eliminate every obstacle to a sale

The best way to accomplish both of these are by asking your prospects “why?”. The truth is, you can’t really sell anything effectively unless you understand the motivations, desires and rationality of your prospects… and the only way to achieve this is by simply asking them “why?”. So, get out there, test it out and see how much more you are closing.

But don’t forget, if for some reason you’re still not selling, you should sit down and ask yourself “why?” ;)

Sales Motivation Software

If you have a problem that you’re currently facing and would like to learn how to overcome it by enabling your sales reps with all of the tools they need to stay motivated, engaged, informed and competitive, please feel free to request a demo to learn more what sales motivation software can do for you.