Top Questions to Implicate Pain in Discovery

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In a blog I wrote about a year ago, I talked about the five most important things to do in a discovery call. The most important of them all is implicating pain. Implicating pain means that you help the customer to understand the literal implications of not solving the problem that their pain represents. 

For example, if you sell a fraud solution to a bank, you might try to understand how much fraud is happening at the bank in the absence of your solution. Through that lens, there is a literal dollar amount affixed to the pain. But the implications of that pain may be experienced in other ways. On a personal level, if it is your responsibility to mitigate fraud for the bank, other things may be at stake, like your ability to get a promotion or bonus pay, or even to keep you job altogether. 

It’s certainly very important to help customers become aware of their pain. While it is certainly the case that many times customers will come to you in search of a solution because they are already aware that they are experiencing some level of pain, a lot of times they are not aware of the problem whatsoever.

For example, in the quest to prevent fraud at the bank, the fraud manager might be putting customers through a tremendous amount of friction. Customers might need to answer two questions about themself, enter a pin number, and then receive a one-time passcode via text message to perform a basic check of their account. What the fraud manager might not realize is how much he or she has dampened the customer experience in their effort to solve a different problem. That may lead to fewer users transacting with the bank. In that sense, it is much easier to quantify fraud losses because they are easily quantifiable, whereas in the latter case, the amount of dropout or loss of revenue due to poor customer experience is more difficult to measure and not necessarily obvious to the naked eye. This is where creating awareness of the pain becomes critically important if you were selling the inverse of a fraud solution: a customer authentication solution.

However, pain implication is arguably just as important as pain awareness. The reality is, our clients are always dealing with a variety of different pains. Even in our personal lives, we have a myriad of problems to fix all the time. Problems are what give our lives meaning. If we never had any problems to solve, our lives would not be very challenging or rewarding. Therefore, it is incredibly important for our customers to understand that the problem we are looking to solve for them is their number one problem to solve. And the only way they come to that realization is by understanding the magnitude of their pain and comparing that to the magnitude of other pains they might be experiencing. 


With that in mind, I’ve put together a few of my favorite questions to help implicate pain. They are ranked in no particular order.

How are you measured in your role?

The implications of pain are not strictly felt by the company, the business unit, or even the individual team. The pain is also felt by the specific individual with whom you are interacting. In enterprise selling, it is typical to find a champion within the organization who will “go to bat” for you and your product. That individual always has something personal at stake: a promotion, a bonus, or even just positive perception. That individual may be struggling in their job and could be looking for some sort of sparkplug or innovative idea that will help them preserve their job.

In all the aforementioned scenarios, the individual has massive personal stakes. Fundamentally, in order to understand how much is at stake for that individual, you need to know how they are measured.

I used to sell products to call centers for many years. Some of my clients were responsible for the IVR, which is the interactive voice response system that tries to field customer inquiries without needing to route the call to an agent. The product I sold helped to contain callers in the IVR so that more expensive call center agents would not be required to resolve those issues. Naturally, the people I sold to were directly measured by the IVR containment rate. They literally received bonuses commensurate to their ability to increase the containment rate. This meant that you could draw a direct line to their pockets by the success of our product. 

If you implemented our solution today and a year from now you were having a leadership meeting about how it is going, what would you want to be able to say in that meeting?

I love this question for a variety of reasons. First off, it’s a less cheesy way of asking a similar question: “What does success look like for you?” I say that it’s less cheesy because the latter question just does not feel organic, whereas the former is much more realistic. In real life, if a client adopts our solution, down the road they will of course need to justify the results of the campaign provided they work in a mature organization that cares about data-driven approaches to solutioning. 

More importantly, this forces the customer to think about the tangible gains they hope to achieve with the product. Most buyers make decisions emotionally, so it is important to get them to also consider implications beyond just how they feel about something. When they are forced to think about what they might tell their boss about the success of the product a year from now, they cannot just say they feel good about it. They need to be able to say it increased revenue by X% or decreased costs by Y%. It needs to be meaningful.

Lastly, this question is fantastic because it forces the buyer to visualize a scenario in which they are successfully using your product. Visualization is a proven tactic to help athletes succeed when preparing for a big competition. If we know it works in sports, why would we not apply it to consultative selling?

What happens for you if you do not solve this problem today, and why didn’t you try to solve it a month ago?

You might be noticing a trend here already: we are asking open-ended questions. It goes without saying for experienced sellers that “yes or no” questions are a bit taboo – all you get is a one-word answer. Generally speaking, the more information we can glean from the prospect, the better job we are doing of executing proper discovery. Open-ended questions force the prospect to say more than one word, and if you still feel dissatisfied by the answers you are receiving, you can always ask a follow up: “Can you elaborate on that?” or “Tell me more about that.”

As it pertains to this question, there is usually some sort of critical event that occurs that gets a potential buyer to act. We need to understand what that critical event is and why it matters so much. In theory, whatever pain the client was experiencing has probably been somewhat painful for awhile now. Usually the problem just gets worse and worse until the proverbial dam breaks and the client feels that now this is their most pressing problem. So what was the straw that broke the camel’s back?

Understanding the critical event that makes this pain their top pain is core to being able to sell a solution. Fundamentally, it helps you understand what type of state is acceptable to the client and what type of state is unacceptable. You cannot sell a solution to anyone unless you understand not only what is an acceptable state, but what is indeed a desirable state.

Hypothetically, if you could achieve [X], would it be your number one priority?

In my book “Authentic Selling,” I talk about the idea of Inception, where you plant an idea in the mind of the buyer. Inception is powerful because people are much more likely to adopt an idea if it is their idea and not your idea. So it’s important we get people to make it their own idea that they have pain.

A great way to do that through the backdoor is to get the customer to admit that a certain percentage improvement in performance would make them drop everything they are doing and pursue it. If you think about it, if someone admits that that would be the case, then they are saying in so many words that they do indeed have pain. They are not saying it out loud nor are you asking about the pain directly, which makes it all the more powerful. The selling has now occurred deep in their subconscious, and now they are intrigued by the idea that you might actually be able to deliver on the promise in your hypothetical question. 

More importantly, the answer “No” is telling. It could be that your prospect is genuinely unqualified, in that solving the problem you solve is just not important to them. It might also be that they are making some faulty assumptions that need to be challenged. You fundamentally need the client to agree that the pain you solve is not only worth solving, but must be solved immediately if you want to get anywhere with them. This is a great way to ask.

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