Powerful sales questions are one of the most impactful tools that any sales professional has. Sales questions designed to influence. To persuade. To uncover the truth. To identify options. And to get your prospect to think differently about you, your product or service, and your company.

As Voltaire once said “judge a man by his questions rather than his answers.”

Good questions can help you uncover a prospect’s reasons for buying, help identify underlying needs and aspirations, and build the relationship by positioning you as a thoughtful, valuable ally.

But sometimes, you need a little more.

Sometimes, you need a pattern interrupt.

Sometimes, you need to ask a prospect a sales question that stops them dead in their tracks, and causes them to explore an entirely new aspects of what you’ve been discussing.

The questions that I’ve included in this post do just that – they are counterintuitive, impactful, and they require a certain dose of courage to even ask them. But bring them up at the right time, and they’ll help you expose the real truth about what your prospect is thinking.

First, let me start by saying this. Please don’t ask these questions literally, and/or right off the bat. It’s always best to preface them with a “softening statement”. Softening statements are short prefaces that help the prospect prepare for the fact that you’re going to do something that is unexpected, and may (at first sight) run counter to your best interests.

Some of my favourite softening statements are:

  • I hope you don’t mind, but can I ask you an honest question ?
  • There’s something I’m struggling with. Do you mind if we … ?
  • I can’t quite put my finger on it, but ….
  • Can we stop pretending I’m trying to sell you something for a second ? There’s something I’d like to ask you

I recommend that you always use a softening statement before asking any of the following questions. It gives your prospect a chance to prepare for what’s coming, sets the tone for a change in the conversation and – perhaps most importantly – indicates that you’re willing to take the conversation to a deeper, more meaningful level. 

(Can you tell me) what’s really going on ?

When we speak with prospects, especially when it’s early on in the relationship, there’s a real desire on both sides to stay at the surface level. Prospects talk about their “needs”, but stay high level and don’t provide a lot of detail and/or clarification.

The stated need, however, is almost never the real need. And the difference between sales people and sales professionals is that sales pros dig deep. Asking a question like this entices your prospect to “dig deeper”, and in a very subtle way gives them permission to let you in on what’s really happening.

What can you see going (horribly) wrong ?

In any sales process, there are five different buyer personas at work. And one of them is the person with whom sellers like to spend the majority of their time with. It’s the champion.

After all, the champion is the person who wants to see you get the deal. Who wants to work with you. Who actively lobbies and advocates on your behalf.

The problem is, when both of you are on the same side, it’s often hard to see where things could go wrong. Until they do.

Asking this question is a great way to get out of the “feel good” vibe of sitting around the table together, and exploring the reasons why things may not turn out the way you’d like them to.

What don’t you know right now ?

This one’s a real head turner. Which is why it’s one of my favourite questions.

Asking this question in a very subtle way invites your prospect to explore aspects they haven’t thought of, information that needs to be uncovered or angles they’ve missed thus far.

And even though at first it may seem counterintuitive (after all, who really knows what they don’t know), you’ll find that when you ask, you often get the most surprising, delightful answers.

What/Who’s your preferred choice right now ?

I’m a huge fan of this question. Let me tell you why.

Traditionally, sellers have been taught to ask a variation on the question “how are we doing so far ?” in an effort to qualify the deal and see how they/their firm are positioned. The challenge with that question is that it’s very easy for the prospect to give a fuzzy, non-committal answer (think “you’re doing great” or “I really like what I’ve seen thus far”).

This question makes that very hard. It forces the prospect to give you a direct, clear answer. It’s either you, or not you. (By the way, if the prospect avoids the question or declines to answer, that should also tell you something).

What’s your best alternative ?

A very subtle variation on the previous question, this one aims to uncover which alternatives exist (if any) to working with you or purchasing your product or service. It’s a very nice, gentle way of helping your prospect put on the table which options they have.

What don’t you like about _____ ?

This one again takes a “text book” sales question (“What do you like about _____ ?”) and flips it on its head. The effect is powerful, yet effective. By inviting your prospects to explore and divulge the reasons against working with you (or your competitor), you encourage them to open up – thereby getting valuable information on where you’d need to beef up in order to win the business.

What’s missing for you to be able to move forward ?

This is one of my “go to” questions, especially in the proposal phase. Asking it allows me to identify what’s missing for my prospect to be able to move forward, and to be able to move forward with us.

BONUS question: if I ______ , will you _______ ?

Look. We all know that sometimes people say one thing, and then do something else entirely. This question helps you get a clear commitment from your prospect that they will move forward with you, if you do what they’re asking.
Variations on this question can be:

  • If I give you ____ , are you saying you’ll move forward with us ?
  • If I can ______, will you take this to your boss for approval ?
  • If we could eliminate ___________, do we have a deal ?

Einstein’s well-known definition of insanity was “to do the same thing over and over again, and expect a different result”. Next time you find yourself in a situation where a deal is not moving forward, but you’re not quite sure why, try one of these questions.

And when you do, leave me a comment below. I’d love to know how it went.