Effective Selling, Means Asking Effective Questions

If anybody is thinking that asking ‘effective questions’ is the same as asking ‘open ended questions’, then you are about 20% correct.sherlock-110x150

But really…..asking open ended questions is like table stakes in a poker game; it’s the price of admission and everybody does it.

Using questions effectively is one of the most important skills a sales professional, or a sales leader, can have. It’s also one of the most poorly executed.

Most Sales pros know about:

  • Open Ended questions
  • Leading Questions
  • Probing Questions
  • Making a Statement, but disguising it as a question

But one of the most effective, and least well-leveraged is the skill of asking 2nd, 3rd, 4th… level questions.

What exactly is a 2nd or 3rd level question? It’s actually very simple; I ask you a question (that’s a first level question), you give me an answer, then I ask you a question building off of the answer you just gave me (2nd level question), you give me another answer, I ask another question building off of that answer (3rd level)….

This is the natural way that comfortable and meaningful conversation goes in ‘real life. So why not do it in our business life? There are a bunch reasons why this happens, or doesn’t happen – the sales person or leader isn’t curious enough…or doesn’t know how to process the impact of the answer they just received and doesn’t really know what question to ask next…or has fear of feeling like they are interrogating the prospect… There are a myriad of reasons, but frankly, none of them are good enough.

By NOT asking multi-level questions, we are having superficial discussions and we are not engaging the prospect in a meaningful way; we’re just like everybody else.

Most sales reps ask 5 questions when they speak to a suspect or prospect:

B – Do you have budget?

A – Do you have the authority to make a decision?

N – What do you need?

T – When do you need it?

The BONUS QUESTION – Can I have an appointment?

Waaaaaay too often we leave a TON of valuable information on the table because we don’t drill down in levels. Most often, a sales person or leader asks a question; example – “What problem are you trying to solve with this project”? The Prospect answers with something that usually sounds like “My current system no longer gives us what we need”. The most common thing that happens next is that the questions become about ‘What do you need in a new system”?

(Interestingly, most sales people and sales leaders ARE comfortable asking multi-level questions when asking about features and capability needs.)

But the real value would come from asking questions like “What, exactly, is it about your current system that is causing you problems”? (2nd level question) “Why is that happening”? (3rd level question) “What kinds of business problems is that causing you”? (4th level question) “How is that affecting you and your company”? (5th level question).

This doesn’t apply only to sales reps, this applies to sales leaders as well. When we are doing pipeline and forecast and deal reviews with our team members, we should dive in and ask more meaningful questions.

This helps our sales team mates to learn and to ‘see’ things in their sales cycles that they may not have seen before. Also (and if you’re a sales leader and you remember nothing else from this blog, hang on to this piece), every sales rep does some amount of prep work prior to coming into a pipeline / forecast / deal review meeting with you. Most will anticipate 1 or maybe 2 levels of questions you might ask them. If you simply ask a 3rd level question, you and the sales rep will get much closer to the facts in a deal.

Asking multi-level questions when speaking with prospects, and with each other, helps us to see the situation from different angles and depths. It helps us all to learn and find new issues, new answers. It also helps separate us as sales professionals from the rest of the herd.

Be different. Be curious. Ask ; you’ll be very happy that you did.


– Software Delivered as Promised. No Surprises.

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George Brown

Insight written by George Brown

Senior Vice President at Rand Group

A thought leader and pioneer in the areas of cloud computing, sales and marketing, George is a highly regarded subject matter expert and leader with over 30 years’ experience in strategically propelling businesses forward.

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