How to Get Sales Prospects to Discuss Pain

In my previous blog on Customer Pain, I discussed the importance of focusing on a prospect’s (or customer’s) pain. Customers, particularly in the information security space, do not buy products or services so much as they buy pain relief.

NOTE: in this blog I use the terms prospect and customer interchangeably although they are different. The concepts of pain apply to both prospects and paying customers.

Consequently, it is important to focus conversations around the pains your prospects experience.  This requires sales and marketing people who are able to get prospects to discuss their pain.  Most people are not going to reveal their weaknesses to a sales person.

I spent many years selling security products and services.  I found that the way to get prospects to open up, was to simply be curious.


Curiosity is amazing. It creates a safe environment where people can openly discuss their pain.  However, you need be careful. Too much curiosity to quickly can make people defensive.

Over the years, I developed a set of questions to ease into discussions about pain.

  • Tell me about the problems you are experiencing.
  • How is this impacting (harming) you?
  • How long has this been going on?
  • What have you done to make things better?
  • What results did you get?
  • Have you tried anything else?
  • Are you satisfied with your current efforts?
  • Do you think there are better ways?
  • How do you feel about this?

When people open up and reveal pain, you must show empathy, concern, and more curiosity. Then you are building a relationship based on support and care, rather than a merely transactional sales engagement. Curiosity is magical in how well it disarms people and reveals truth.

Being curious also refocuses the conversation away from you (and your products) and on the customer. People like to talk about themselves. They will like and trust you when you let them talk about themselves.


However, not every customer will be receptive to curiosity. It may cause the customer to take up a defensive posture where they will reveal nothing. In this case, you need to nudge them back to a safe space. Telling a story can do this.  But not any stories, rather a stories with the specific intent of communicating “I am like you, I get you.”

Again, most salespeople mess this up, as they tell stories about themselves. For example, anybody blathering about what a big shot they were when they worked at some big boy company, is not communicating empathy. They are communicating ego.

What are these stores like? I tinkered around with this for years. I found that stories that are tangentially relevant, were the most effective. A tangentially relevant story is about pain that is similar (not identical) to the prospect’s pain.

For example, when I was meeting senior level security people, I would often tell stories about when I did security operations (SOC) work for a customer. I did not focus on me (or confidential customer information), but rather on the clumsy tools and soul-crushing politics of the organization. In other incidents, I would tell stories about the frustrations of deploying particular technologies which were similar (but not identical) to the technology the customer was installing.

The intent of these stories was twofold:

  • I have “been there done that”
  • I understand your pain

The reason my stories worked, was the tangentially relevant details.  For example, when I mentioned the politics of the organization.  Superficially, this sounded like innocuous complaining, but when people hear these details, it reinforces the credibility of the story. Moreover, it communicated to the listener, “I have had to put up with this stuff too.”  Small, unusual details are what make stories more real.

Once I had reassured the customer I understood them, they were more receptive to a question such as “tell me about your pain.”

Incidentally, while I did draw upon my experiences for stories, I also altered the details so as not to reveal confidential information. Stories do not need to be absolutely accurate. Removing key details ensures you are not violating confidentiality while still benefiting from those experiences.

Training Sales to Tell Stories

Invariably, this prompts the question, how do you train salespeople to do this?

  1. Stop pitching. Reorganize your sales methods to stop all pitching. The first few meetings with a customer should be 100% listening and gathering information. Any discussion of your product or services should be relegated to later.
  2. Build Buyer Personas. While not discussed in this blog, it is vital you understand who you are selling to. Buyer Personas help define these people. More specifically, they should define what is important to these buyers.
  3. Role Play: Gather your sales team and role play scenarios.  Hire a sales coach to help.
  4. Remove Ego and Collaborate. You do not need to actually experience something to tell a story about it. With an ounce of creativity and a lot of humility, you can borrow stories (and be honest with customers that you borrowed it.) Remember, the story is not about making you seem smart or cool, but rather reassuring the prospect you understand them and have credibility. Collaborate with other’s and listen to their stories. The stories you need are everywhere around you.

That last item is the real magic. The gateway to stronger relationships with customers is to remove your ego from every engagement. I can tell in an instant when a salesperson cares about me or themselves. It is all in how they present information.

If you can tell a genuine story, that shows you care, you can build a strong relationship based on trust, and not merely selling.


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