3 steps to understanding your prospects’ problems

In today’s newsletter, I’m going to share my 3 steps to gaining a clear understanding of your prospects’ problems.

If you can replicate this process, you’re much less likely to get ignored by prospects and much more likely to get replies and book meetings.

Unfortunately, most SDRs don’t have a solid process for understanding their prospects daily struggle, so they are constantly throwing USPs and features, and getting no replies as a result.

Getting replies is about showing you understand your prospects’ problems.

Without a proper understanding of your prospects’ problems, there are a number of challenges that arise:

Challenge 1: Prospects can feel they are in a sequence. They know you’re sending this email to everyone else, and they hate it.

Challenge 2: Your messages are ignored. Prospects don’t even read the entire message.

Challenge 3: You destroy relationships instead of building them. You are seen as an annoyance and your email parked in the spam folder.

You can overcome all of these challenges by building a better system for understanding your prospects’ problems.

Here’s how I do it, step-by-step:

Step 1: Understand their goals and metrics

Prospects are typically evaluated on a set of 1 to 3 metrics. They get promotions or get fired based on their performance against these metrics.

When building a new sequence, I list the metrics my prospects are evaluated on. Here are a few places where I look for information:

  • Podcasts/webinars where my Ideal Customer Profiles are interviewed

  • Job descriptions

  • SDRs/AEs I have trained in companies I worked with (or similar)

When I have an idea of the metrics my prospects are evaluated on, my next step is understanding their goals. I ask myself the following questions:

  • Are they trying to maximize or minimize this metric?

  • What happens if they miss it? What are the concrete consequences on their jobs/lives?

  • Do they have stretch goals?

Step 2: Find their initiatives and the problems they face

Once their goals and metrics are clarified, I start digging into their initiatives and symptoms.

What are they working on right now to achieve their goals? What are the tools/training sessions/services they are evaluating to avoid missing their goals?

Now that I know more about their initiatives, I can start listing problems they would typically face.

Are they having a hard time finding/implementing the right tools? Did they try training their teams, without success? Are they going to miss their goals because they can’t find a service provider to do a job they are incapable of doing?

(Note: if you’re interested in doing this exercise, step-by-step, go check my Cold Message System.)

Step 3: Study the exact symptoms of these problems and and highlight them

Finally, I list the exact symptoms of these problems, and I highlight them in my cold messages.

Problems are often not enough to get a reply. They tend to be vague and full of jargon. For example, “Not having an upsell playbook” is a problem a lot of my prospects have.

Symptoms of this problem are:

  • AEs are missing on easy expansion revenues

  • Customer Success Reps are only order takers, they have no sales skills

  • Expansion metrics are missed, quarter after quarter

I like to compare this with a doctor consultation. When you say “I have a cold”, you’re mentioning a sickness (a problem), but when your doctor asks you about your symptoms, you’ll say you:

  • have a runny nose

  • have regular headaches

  • feel exhausted

  • have fever

Think about what is more vivid in your mind? Problem or symptoms? It’s the same with prospects.

When you have a clear list of symptoms, you can highlight them in your outreach, like below:

Symptom table

And these are my 3 steps to understanding my prospects’ problems.


  • Step 1: Understand their goals and metrics

  • Step 2: Find their initiatives and the problems they face

  • Step 3: Study exact symptoms of these problems and highlight them

Before you go, I’m considering launching an outbound sequence building/correction service. If you’re interested, just hit reply and tell me:

  • Who are your selling to?

  • What’s your reply rate?

  • What is your biggest challenge?



P.S. When you’re ready, here are 4 ways I can help you.
  1. Build your outbound prospecting system from scratch here (200+ students)
  2. (NEW!) Write cold messages that get a 38% reply rate and 27% meeting rate here (20+)
  3. Book me 1:1 or for your team here
  4. (NEW!) Sponsor my newsletter & get 3k+ eyeballs on your ad!

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