Tested And Proven: The Only 3 Sales Questions You'll Ever Need

Sales questions. Ask the right ones, and you’ll build trust, uncover opportunities and cement your relationship as a trusted advisor. Ask the wrong ones, and you’ll become known as “a salesperson”.

Voltaire once said “Judge a man by his questions rather than his answers.” Yet, it seems that most sellers do a poor job of asking great questions. We ask leading questions. Questions we already know the answers to. Qualifying questions. Rhetorical questions. Yes/no questions.

When instead, we should be asking great questions.

For decades, we’ve all been told to “find the pain”. “No pain, no sale”. Problem is, most buyers today either don’t have (much) pressing pain, don’t want to be reminded of it or put off doing something about it until the very, very last minute. Plus, do you really want to go in and start by putting the finger on the sore spot of someone you just met for the first time ? Didn’t think so.

Most buyers today think in much broader terms than pain. If you focus only on pain, you’re missing out on (at least) 50% of the opportunity you could help uncover.

Sales questions: The 3 Only Questions You’ll Ever Need (In A First Sales Meeting).

If you want to uncover the full range of how you could potentially help them, these three sales questions can give you an excellent start.

Where do you want to be/go next ?


First, get your buyer to paint a picture of the future they seek or desire for themselves, their career/business and their family (remember, emotion trumps ratio every time). Be specific. Ask for clarification. Ask “what would that look/feel like ?”. Dig for details (how much ? how soon ? in what form ?).

Don’t be afraid to spend a good chunk of time on this. You’ll be surprised at how many things they’ll say that you can help them with.

Where are you/things now ?


Now (and only after you’re fully done exploring where they want to go), ask them where they are now. Get them to paint a detailed picture of where they are now. Specifically, how it’s different from where they want to be. What’s not going well ? What’s the “thorn stuck in their toe” ? What do they wish would be different, or they could change ?

By simply asking these two sales questions, you’ll cover fully 100% of the opportunity that is (potentially) there. You’ll understand not only what they want to move away from (the “pain”), but also what they want to move towards (the “pleasure”).

At RAIN Group, we call this pair “Afflications and Aspirations”.

But, there’s one more question you should be asking.

“What’s holding you back, or stopping you right now ?”


Ask this question, and you get what I like to call the “Discovery Question Triumvirate” (DQT – just kidding, I made that up). You’ll know everything you need to know to get started on the path towards positioning your services and seeing if there is a fit.

For 95% of my (new) clients, if they just stick to these three sales questions, dig until they find the true answers and help their prospect see how they can help them get from A (where they are now) to B (where they want to be), the quality and results of their sales meetings increases instantly and dramatically. I personally use these questions (or variations on them) in every single first sales meeting.

If you’ve ever been in a sales meeting with me, you’ll know that’s true. Fact.

And here’s the real reason I religiously follow these – and recommend all my clients do the same.

No more waste.

No more fluffing around in meetings where no one has any idea of what is being accomplished. No more “let’s just get to know each other a little”. No more “shall we see if there’s a fit.” And – more importantly – no more time wasted on prospects who have no need, desire or plan to buy from you. Try these three sales questions, dig and present a plausible solution. All you need to do to instantly increase the quality of your sales meetings.