How to Overcome 3 Common Prospecting Conversation Challenges

Jamie Shanks
Jamie Shanks
Share on email
Share on facebook
Share on linkedin
Share on twitter


Prospecting conversations are some of the hardest conversations in the sales process, even for the most experienced sellers. Though difficult, they’re also the critical beginning of what should be an enjoyable customer experience. As you’re coaching your sales team, consider using these methods to overcome three common prospecting conversation challenges.

Challenge 1: Getting in the Door
Problem: Prospects won’t give you the time of day.

Thirty-five percent of salespeople say it’s more difficult to elicit a response from buyers than it was only two or three years ago. The reason for this is two-fold: 1) the seller is reaching out to cold prospects; or 2) the prospect thinks he or she has heard this pitch before, and the seller isn’t breaking through the noise.

Solution: Leverage the up-front contract method.

During the initial call, if a prospect is convinced there’s no value to having the conversation, he or she will disengage quickly. You can overcome that response by getting to the meat of the discussion early on through use of the up-front contract.
The up-front contract is a conversational way to structure a meeting, wherein you clearly define what you’re asking and empower the prospect to feel in control. The method includes five components:

  1. The purpose of the meeting.
  2. The client or prospect’s agenda for the meeting.
  3. The sales rep’s agenda for the meeting.
  4. The date, location and duration of the meeting.
  5. The expected outcome of the meeting.

By using the up-front contract, you overcome the prospect’s initial questions: who is this person, what do they want to talk about, and — most importantly — how long am I going to be on the phone. When you define all of those elements for them in about 30 seconds and then ask if it makes sense that you continue the conversation, you stay in control of the process while simultaneously making them feel like they’re in the driver’s seat.

Challenge 2: Earning Attention
Problem: Sales reps are too heavy-handed too early.

Many beginner sales reps are eager to jump into a sales pitch during an initial phone call and skip over a critical component: challenge discovery. Before you can offer your solution to a problem, you need your prospect to self-identify a pain point. 

Solution: Add structure with the 30-second commercial.

A 30-second commercial is a tactic to get a prospect’s attention by guiding them through a series of questions that in turn answer for the prospect, “why is this person and their business relevant to me?” 
The 30-second commercial contains four elements:

  1. Opening statement: Give a brief introduction of the sales rep and company.
  2. Pain statement: Identify pains the prospect may be feeling through a statement like, “I work with clients who experience [insert three common customer pain points].”
  3. Positioning statement: Gently earn buy-in for continued discussion through a statement like, “If you’re dealing with some of those pain points, maybe we should continue this discussion.”
  4. Contact information: Ask for the time to discuss more in detail.

Through this methodology, you get your prospects to self-discover the problem before you begin talking about a solution. They have an “aha” moment when they realize the pain, and the rest of the conversation becomes a bridge between problem and solution. At that point, you’ve earned their attention and can gracefully usher them toward what will help end their pain — you and what you’re selling.

Challenge 3: Overcoming Decision Reluctance
Problem: Buyers won’t make a decision.

While decision reluctance is a major roadblock in the sales process, the problem isn’t actually that the buyer won’t make a decision. The problem is they haven’t fully realized the impact and manifestation of their pain — and the responsibility of getting them to that point falls on the seller.

Solution: Guide prospects through the Pain Funnel.

People make decisions emotionally; if you’re operating in a state of logic with a prospect, you’ll have a hard time getting them to buy. The key is to ask questions that uncover the emotional impact of the issue at hand. 

This can be done through the Pain Funnel, a path that takes an intellectual problem and boils it down to an emotional issue, thus empowering decision-making. There are four steps in the Pain Funnel:

  1. Begin the Pain Funnel: Ask questions that get at the true pain points.
  2. Identify surface problems: Ask for more detail to understand those pains deeply.
  3. Identify reasons: Ask questions that uncover why those pains exist.
  4. Identify impact: Ask questions that guide the prospect to realize how those pain points cause real problems that need to be addressed.

This method is similar to how a doctor diagnoses a patient; like a quality salesperson, they work to understand where the pain is coming from to recommend the right treatment. You’re both driving them to make a decision and also learning information that will help you make a difference by adding true value.

While the sales process continues to become more social and digital, the importance of the salesperson in that process grows; each human interaction is a critical moment to move a prospect closer to close. Use these tactics as you continue to refine those moments with your sellers who struggle during the prospecting phase. 


Follow Us

Subscribe to our Newsletter

Get our latest blogs direct to your inbox


Subscribe to receive more sales insights, analysis, and perspectives from Sales For Life.

The Ultimate Guide to Social Selling