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Last month, I had an opportunity to attend Sales Kickoff Summit 2016 organized by amazing HireVue people! It proved to be a very valuable experience. Sometimes it is surprising how much value could be found for free on the internet when you know where to look at.

However, one presentation really stuck to me. Personally, I adore practical application when it’s possible and this really hit the nail on its head. The presentation that stood out to me was by Juliana Crispo, Founder & CEO at Startup Sales Bootcamp and was called “3 questions to find the pain”. As of today, 19th March 2016, the video is still available here.

Before we start, I should let you know that the whole talk is applicable to B2B and doesn’t really work in B2C, unless you’re selling a complex product. A car, let’s say. If it’s pens & pencils – this article & the talk isn’t for you.

Anyway, the whole idea behind finding pain is asking questions to find the main problem of the customer. And it is done, so product demo would only reflect the features that are relevant to the buyer. Therefore, this enhances the likelihood of closing the deal. By the way, have I told you that Juliana kept the consistent 40% close rate over 5 years! I hope now you will start taking notes!

Why would you need to discover the pain of the customer? To be able to eliminate it with your product! And generally at these times, a majority of buyers are numb to their pain. Meaning that things could be better, but they are good enough the way they are. 80% of deals turn out to be to buyers who are numb to their pain. These are the ones you’re after. And they require skill to be able to close them.

sales questions_luck-deals-skill-deals

“Modern buyers are numb to their pain”

The cornerstone of the closing these deals would be asking the right questions to reveal those pain points. Even if the customer is not aware of them.

In total, there are 3 types of questions according to Juliana: pain openers, pain inducers and digging questions. If you follow these questions and select the ones that are relevant to you, you will receive a pretty well image of what the person is looking for and you would be able to decide if your solution is right for a customer.

Pain Openers – Great Conversation Initiators

If you’ve done your homework and know what the type of business or customer you’re dealing, you could start with: “Typically these business work with us because of pain x, pain y etc. – are these the same challenges that you face?”

From this point, it can go both ways: “Yes! This salesman knows what he’s doing!” Or it can go “No… They have no clue what I’m looking for”. That is why preparation so relevant. You can literally make or break the deal with one sentence.


The whole array of questions could be built around this practice. It is the matter of knowing your target audience and researching before qualifying for a demo or even a phone call. Just don’t forget the formula:

sales questions_dont-forget-formula

However, do not worry if the answer is “no”. You can admit that this customer is different from others and ask for their challenges. Just beware! Ask them to prioritize the main challenge. That is where the money goes. Because solution-to-all might appear inefficient and you might lose a potential customer, because he might decide to look for cheaper alternatives that fix just 1 issue. And don’t forget, there is the reason why the customer is taking his time to attend a meeting with you. He is already interested in your product.

sales questions_likelihood-of-sale

Pain Inducers – Sell to Numb Buyers

These set of questions are there to emphasize the pain. To make a customer think of what would happen if I don’t take the action now. However, the main point is to make the customer admit that it would happen. This is what makes them so keen on purchasing your solution. If they admit something bad could happen – they would automatically want to prevent it from happening. You have to help them portrait the future. And show how daunting it is if they don’t have your product.

The basic formula for pain inducers:

“What? How? Let’s image that? If?” + “Future” = “Pain Inducers”

But to really make them shine, you would have to design your own questions:

  1. Your solution to a problem (your unique value proposition)
  2. Offer your value proposition and get denied by prospect (not worth the investment)
  3. Prove them wrong (with pain inducer question).

The whole list by Juliana is present here:

sales questions_pain-inducing-examples

Digging questions – Find more about customer

Now, if your customer appears to have a problem that your product solves – don’t jump around and get all excited. Do not underestimate the deal!

That is where the digging questions come. They are there to make you seem thoughtful and keep you cool. Ask for details, examples – just make them talk. Even if you’re extroverted – keep yourself quiet on this one and look for details.

And, there is not much a formula for making a digging question, but remember: the goal is to make them talk. Avoid questions that you can answer only by “yes” or “no”. Ask why? How? Ask for exact examples of their problems.

Juliana offered some of the examples in her presentation, you can use those.

sales questions_keep-calm-ask-questions

If you are really stuck. Just use an up-tone. Everything in an up-tone sounds like a question. If you’re interested how it should be said – watch the presentation.

What if they start asking questions? Good news, everyone! These are the masked pain-points. They care about those and want to know if you can really help them. But instead of start bragging about your helpful support and fancy solutions. Ask them what is the reason that they’re asking? You will be able to extract more information and answer it the way they want to hear it.

So this was a brief overlook of 3 types of questions to find pain, but if you’re looking for more. Be sure, to check Juliana’s Crispo Buy-in method on StartupSalesBootcamp. These techniques are used by many successful startups and I’m sure you can find something relevant there. However, let me know in the comments if you already had a chance to use these techniques. Also, don’t forget to share if you find this article worth reading.



by Jonas Matkevicius

Jonas is a marketing specialist at SalesChakra. He is a certified inbound marketer who drives social media engagement and optimizes content for audiences. He loves to write on sales, non profits and entrepreneurship.