The art of masterful questions


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The average salesperson asks potential customers up to 48,000 questions a year.

How did we come to that figure? Simply do the math. If you consider 20 conversations a day, 10 questions per conversation, five days a week, 48 weeks in a year — we get 48,000 questions! Give or take a few thousand questions, this number is impressive.

So, if we’re asking so many questions every year, you’d assume most salespeople would be masters at delivering them? You’d be wrong – this skill still alludes most.

The reason is the average salesperson doesn’t think too deeply about what they say. As such, most questions are surface level and don’t penetrate or stray too far from the norm.

Average salespeople are so focused on what they want to say, they aren’t truly listening for the response, or triggers to help them determine exactly where to dig deeper and take the conversation to a place that’s more personalised and meaningful.

What are masterful questions?

  • Questions that dig deeper towards the customer drivers;
  • Questions that challenge or jolt a reaction;
  • Deeply thought-provoking questions;
  • Questions that encourage the recipient to speculate about their goals and aspirations;
  • Questions that prompt customers to express their thoughts or feelings;
  • Questions that support customers to evaluate and prioritise what’s important to them;
  • Specific questions asked in negotiations and objection handling; and
  • Questions that are most certainly not for the average.

The average salesperson digs on the surface. This is due to a lack of skill, will, confidence or perhaps a genuine lack of interest or care for the other person.

We all know the more you dig, the more you will find. And the more you find, the more value you unlock for the customer.

The best salespeople ask better questions, and the most successful salespeople demonstrate the art of Masterful Questions™. No, not for the average.

Trent Leyshan is the founder of sales training company BOOM! Sales and author of Outlaw and The Naked Salesman


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