How do you know when a prospective customer is a “real” prospect and not just someone who’s too nice or too embarrassed to say “no” or someone who’s so indecisive he or she will never say “yes”?

Think about the time and effort you’d save and the resources you could reallocate, if you could only cut through the chafe and tell right away whether someone ultimately will or will not close a deal with you. No more spending hours (or days) with back and forth phone calls, emails, meetings, reports and proposals, or (worse yet) food and drinks to court a prospect in hopes of a sale.

Sales professionals know what I’m talking about as the “discovery call” or in 2017 terms that the digitally savvy can embrace, the “discovery email” (or tweet or message or post or skype) or even the “discovery meeting.” Whatever you prefer to call it—and I prefer to call it the “discovery connection”—this is the time when you first connect with the prospect to check him/her out and vice versa.


A prospect could be someone looking to you for a job (a job candidate) or to buy your product or service or some other resource from you (a customer or client). Regardless of your prospect’s intention, the purpose of your discovery connection with him or her remains the same. You want to:

  • Establish a relationship
  • Better understand his or her pain points or needs
  • Give the prospect a reason and/or reassurance to believe that you are the one best suited to understand and meet those pain points or needs.
  • Leave the prospect with a positive impression of you and/your brand even if a sale does not take place. He or she (or a colleague or friend) could need you at some point in the future.

As with any relationship, discovery connections are a two-way street. The prospect will want to:

  • Learn about your brand, product, or service
  • Better understand your value proposition and what differentiates you from others
  • Feel reassured that you understand the nature of his/her challenge and are well positioned to help address it.


The key to getting a good sense of what makes your prospect tick and whether he or she will ultimately “close the deal” starts with asking good questions. First you’ll want to start with the basics. This is where you “vet” the prospect and you let him or her “vet” you:

  • What pain point or need/challenge is he or she experiencing?
  • What is the prospect’s current understanding of your product or service? Is he or she already a raving fan, or does the prospect need education and convincing?
  • How serious is he or she is about making a purchase? Does the prospect understand your pricing, and can he or she afford what you are selling?
  • How will the prospect make the purchase decision (and, importantly, is he or she the decision maker)?

While there are bound to be occasional insurmountable logistical barriers with some prospects (such as pricing, geography, legal or regulatory issues), the obstacle that’s most tough to overcome is when your prospect lacks the business pain/need to buy your product or service. With that in mind, your discovery connection line of questioning should focus on the main challenge being faced by the prospect and what he/or she has done (or hasn’t done) to solve that challenge and why:

  • What problems/challenges are you trying to solve?
  • When must this problem be solved?
  • What is preventing you from solving the problem now?
  • Have you tried other solutions? If so, what was the outcome?
  • Why do you think these other solutions did not work?
  • What does success look like for you? How will it be measured?
  • If the problem can’t be solved, what happens?
  • What resources are available to address this challenge?
  • Do you have a process in place for choosing someone to help you find a solution?
  • How can I help you make your decision?
  • Who else is involved in solving the problem/making decisions?

Of course, every one of these discovery questions is an opportunity for you to educate the prospect about “why you” and what you can do better than anyone else to help him/her find a solution.


What exactly disqualifies your prospect is up to you. Perhaps it’s affordability, or you feel he or she needs so much convincing that it’s not worth your time and effort, or personality-wise you can “tell” it’s not a good fit, or you simply don’t offer what he or she needs. Is it one strike and you’re out, or does everyone make the cut and you simply triage them as A, B, and C level prospects, with the latter levels getting less attention than your top tier?

Just as every prospect is different, every business is too. What makes sense for one business, won’t necessarily make sense for another due to things such as timing, business maturity, your bandwidth for new sales, and how many other prospects you already have in the pipeline.


Your discovery connection isn’t necessarily a one-and-done interaction. While you’d like to be able to make one call or do one meeting and intuitively “know” where the engagement is heading, that’s not always possible. If you’re unsure, pick up the phone, meet again—do whatever it takes to feel more certain about whether a particular prospect is the real deal or not.

How do you approach prospect discovery? Do you maintain an “any breathing prospect” mentality, or do you seek to vet prospects so you can determine good fits vs. bad ones?

Share your thoughts and processes here. Inquiring monkeyz want to know!

Paul June is King Monkey of BARREL O’MONKEYZ, a San Diego-based strategic marketing agency specializing in the Sports and Active Lifestyle markets. Barrel O’Monkeyz serves as a seasoned, outsourced marketing team for companies looking to ramp up sales and launch new products. Our barrel is full of talent and creative arms ready to prove we don’t just monkey around!