Pain Points — Can Your Team List Them All?

Sam Merlo
3 min readJan 3, 2022

If you don't know what problems you're solving, you cannot consistently book healthy demos or manage a healthy pipeline.

That's because Pain Points are the primary motivators behind a business's willingness to spend money.

True, sometimes people buy for reasons beyond pain, but the strongest and most reliable sales come by solving business problems. In other words, "pain" is like "need," but with the clear difference being not a "nice to have" but instead, "we need to solve this."

Training Pain Points

How can you help your reps not just remember Pain Points but really understand them? I use pain point tables.

The key idea here is to summarize and explain. Paint the picture, but don't overload your reps with too much information. Give them just enough to cover the basics, and they'll color in the details by listening to prospects.

Here's an example:

Pain Point 1: Data is hard to reach.

Why is this a pain?

  1. The business has a strategic objective to use data-based decision making, and hard to reach data means information could be underutilized or delayed.
  2. Data that is hard to reach might require lots of time and mundane work, thus draining resources away from higher-value projects.

Questions to Ask:

  • What data sources require the most time to make available? Would it help your team free up time and better meet SLAs if it were easier and faster to get that data?
  • What insights is the business hoping to generate with this data?

Practicing Pain Points

Repetition is the secret to successful training. Understanding a concept can happen quickly, but comprehending it enough to use in different circumstances takes time.

  • Consider gamifying Pain Point review sessions.
  • Quizzes, even simple ones using Google Forms, help hold reps accountable to learning — plus, you get clear visibility into where each person still has knowledge gaps.
  • My favorite: Opp Reviews — meet as a team to discuss the “why” behind a demo; why do they want a demo, and why now? At first, your reps will likely offer long answers, probably listing features, but after a few sessions, answers will evolve. Instead of “they want more web data,” a rep might say, “right now they make web data available once a week, and their goal is to make a steady stream available because their new CMO wants marketing to be more data-driven.” As a bonus, other reps will learn new ideas for booking a demo from their own colleagues.

3 Tips for Takeaway

  1. I like to offer helpful prompt questions so my reps can get a conversation started more easily. Once the conversation has begun, they use value-based talking points to keep it moving forward and demonstrate relevancy.
  2. The title and role of your prospect will dictate which of the pain points you solve are most applicable. It also determines how your prospect experiences the pain — do they encounter the problem every day, or do they see it through the impact on strategic objectives?
  3. For extra power, tie your unique differentiators into the pains you're solving. If you can solve a problem in a unique and compelling way, you'll cut out a lot of competition and possibly shorten your sales cycle.

Learn more about using Pain Points in "Outbound Sales Demystified: Generate Leads and Close Deals." Available on Amazon in paperback & ebook

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Sam Merlo

Sales Enablement Champion for Early Stage B2B Startups