Sales Questioning: Drilling Down 3 Times

Sales Questioning: Drilling Down 3 Times

Sales Questioning:  Are you drilling down 3 times?

I like to feel that I’ve done a thorough job when I’m selling to my prospects. By this I mean I like to feel that I’ve done a very thorough job with my ability to ask good questions.

A big part of this, for me, is drilling down 3 times on the things that I would regard as paramount factors in all of my deals:

Money, Authority and Timing

I’ve mentioned before that a lot of us tend to be hard wired optimists about our deals and really need to work on our inward/outward honesty. The reality of the situation is that we are far too often told what we want to hear and the problem comes in where we tend to just accept what we’re told.  Our Sales Questioning skills need to be sharper than ever if you want to spend your time in the right places

Let’s look at a genuine example I’ve come across based around Timing.

I’m sure every person reading this article has been in a position where they’ve asked for the order and a prospect has told them…

“We should be able to give you an order in 2 weeks time”

At this point, the average (too many!) sales people will leave a sales meeting or end a call believing that they’ve done a good job and will be getting a decision in 2 weeks.

I disagree.

We need to be drilling down three times so rather than adding this to my pipeline I’d be inclined to spend 30 seconds asking a few more good, subtle questions to truly qualify the timing aspect of the deal…

“Why in 2 weeks?”


“Just so I understand, what kind of process does this go through in the next 2 weeks to get signed off?”

“It goes through Brian our Technical Director and once he’s signed it off it goes to Barry the MD for final approval”

It’s important to understand as much as you can about your prospects buying processes and who’s involved in them so I find timing is usually related to authority in these conversations.

By drilling down a second level the better sales person is likely to find out a little more about how things work but I still think there’s one extremely good, under-utilised question that we should always be asking in this situation.

Drilling Down 3 Times Sales Questioning

My view is that when we get to the third stage of questioning we can safely say we’ve done a good job because depending on the answer to the third question, you may not be putting it on your forecast this month at all…

“What are the risks of this not happening?” (“What are the risks of this slipping into next month?”)

“Actually Barry’s going to Canada tomorrow and won’t be back for 6 weeks”

And there you have it.

You can probably see quite clearly from this example how the average sales person would have ended up feeling quite disappointed 2 weeks later when they went back to ask for the order only to find nothing had moved forward whereas the smartest sales person, through more effective questioning has a far more detailed knowledge of the opportunity and knows that the prospects not likely to be able to make a decision for 6 – 8 weeks rather than the 2 weeks they initially mentioned.

You can avoid uncertainty like this by making sure you’re being thorough with your sales questioning. This should really be standard practice for all of us but there are not a lot of people doing it.

Make a conscious effort to drill down 3 times on every opportunity using good sales questions to truly qualify aspects and within a few months you’ll become unconsciously competent, asking great questions, forecasting accurately and more productive through spending less time chasing deals that won’t happen yet.

If you’re already doing this with your sales questioning, give yourself a pat on the back. If not, time to start.

Pete Stuckey

Pete Stuckey Training & Consultancy provide first class Telesales Training,LinkedIn Training for Sales People & Sales Outsourcing Solutions.

If you’ve found this article useful, you’re welcome to follow us for regular sales advice and feel free to get in touch if you’ve got any questions.