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Selling Starts With the First Question

2 min readApril 1, 2021

Selling doesn’t start until you ask a question.

This is counter-intuitive to many sellers. Yet, it’s a hard truth that you can’t sell if you’re doing all the talking.

If a buyer wanted a one-sided conversation with you about your product, they’d visit your website. Where they’d be able to gather the same information without someone blathering at them.

In fact, if you’re having an actual sales conversation with the buyer, chances are high they’ve already done that. Therefore, if you can’t provide more value to the buyer than your website, what are you doing?

Think about it this way. You invest your time and effort to capture a few precious moments of a prospect’s attention. When you succeed and get the chance to actually talk with a potential buyer, do you immediately launch into your pitch? Or, do you lead off with a question that requires a thoughtful answer from the buyer?

If you pitch first then all you’re doing is advertising, like a commercial on television. Except without the entertainment value.

How many buyers do you know that are prepared to invest their limited time to listen to an advertisement?

However, if you start a sales conversation with a question, then you begin to build interest. When you create a spark of interest in the mind of the prospect, it increases their level of engagement with you. That’s when real selling begins.

The key is to be prepared to ask your prospect one or more insight questions. An insight question is one that asks the prospect something about their business that they should know. But don’t. It forces them to pause. And, think.

This is the cool part. When the prospect has to stop and consider their answers. Because many buyers have become scripted, like sellers. They have become so conditioned to answering the same set of scripted questions from sales reps that they often are on autopilot. When scripted sellers talk with scripted buyers, it’s not a great experience for either party.

Insight questions break from the script. They demonstrate a level of understanding and acumen about the buyer’s business that immediately engage their attention and interest. Unlike those asked by the other sellers they’re talking with. (Companies have to enable their sellers with an inventory of insight questions that they can ask.)

There is a simple sales behavior sellers can learn to start sales conversations on the right footing. I call it the “Ask. Don’t Tell” habit.

It’s simply this: when you begin a conversation with a buyer, always ask an insight question before you talk about your product, service or company. Ask. Don’t Tell.

The choice is yours. It’s the choice between instantly engaging the attention and energies of the buyer or having them wonder whether you’re wasting their time.

How do you want to start your connection with a prospect?

Follow Andy on LinkedIn.