142: How to Sell the Problem (When They Don't Know They Have it Yet)

Welcome back to the Practical Prospecting newsletter!

Most outbound messaging fails because the prospect doesn’t feel the problem yet.

Whether you’re selling something niche, new, or in a crowded space, you can’t just pitch the product. You have to make them feel like they’re missing something.

That’s what execs care about more than anything: “What am I not doing that my peers already figured out?”

You can’t force your way onto their priority list. But you can trigger their curiosity, their FOMO, and their instinct to stay ahead.

In today’s newsletter, I’ll show you how to do exactly that.

Agenda

• The Awareness Ladder

• Sell the Problem (Not the Solution)

• 3 Tactics You Can Use Today

Todays newsletter is brought to you by Aligned!

I’ve used Aligned for years in one specific way: to make my emails to high-value prospects stand out.

It’s one of the best “offers” you can include in a cold email.

Aligned lets you create digital sales rooms, which are basically custom landing pages built for a single prospect. Instead of sending a normal email, you send them a link with a tailored page just for them.

The best part is the tracking. You can see who opens it, who they forward it to, and how long they spend on each section.

You can steal the exact template and framework I use for free here. No trial or credit card required.

My recommendation: create a batch of these, send them to your top prospects, then follow up (call + LinkedIn) with the people who engage with the page the most.

The Awareness Ladder

There are four stages of buyer awareness:

1. Unaware – They don’t feel the pain yet. Life’s good (or so they think).

2. Problem-Aware – Something’s off. They’re annoyed, but not enough to look around.

3. Solution-Aware – They’re actively researching options.

4. Product-Aware – They’re comparing you to competitors and trying to justify the budget.

Most people only go after stages 3 and 4. That’s fine. If you catch a buyer here, you don’t have to be clever, you just have to show up at the right time.

But those campaigns are not scalable.

It’s stages 1 and 2 that transform an average outbound motion into something that your competitors can’t copy.

Here’s how…

Sell the Problem (Not the Solution)

Nobody cares about your product if they don’t believe they have a problem.

That’s why most emails that pitch the product fall flat. Especially when you’re selling something new or nuanced.

Here’s an example from a client that sells a recruiting automation tool:

Bad message:

“Save hours per week using our AI-powered recruiting assistant.”

Better message:

“Most hiring managers are still spending 5–8 hours per week screening resumes manually. We found that most of them don’t realize how much qualified talent they’re missing because they can’t get to every applicant in time.”

This reframes the product from "automation" to "talent loss". A much harder problem to ignore.

Here’s another example from a client selling an internal knowledge platform:

Bad message:

“Centralize your company knowledge in one easy-to-use platform.”

Better message:

“Most teams don’t realize how much time they waste answering the same internal questions over and over. When knowledge lives in Slack threads and individual brains, scaling breaks down fast. Especially when onboarding new hires.”

3 Tactics You Can Use Today

Here are three go-to strategies when your prospect isn’t actively shopping (i.e. engaging prospects in stages 1 and 2):

1. The Comparison Bomb

“Teams on Datadog are spending 20–30% more on monitoring than those using PulseCore, and they’re still missing key incident alerts. Want a side-by-side breakdown?”

Create a little FOMO. You're not saying they're doing something wrong, you're hinting that others are doing it better.

This works especially well with execs. Because what do execs care about more than anything?

What their peers are doing that’s new, cutting-edge, and just might make them look behind.

You can’t get on their priority list if they aren’t in the right awareness stage. But you can make them think they’re missing something that already is.

2. The Invisible Cost Angle

“Engineers spend 5–10 hours a week untangling legacy code and chasing down undocumented dependencies, but that time never shows up on any report. It just quietly kills sprint velocity.”

The best problems to highlight in outbound aren’t always the loud, obvious ones — they’re the silent ones your prospect has learned to live with.

3. The “Why Now?” Trigger

“Google’s phasing out third-party cookies, and marketing teams without a first-party data strategy are already seeing weaker retargeting performance. The gap’s only going to widen this quarter. Want to see how others are adapting?”

This works because it:

• References a clear, time-sensitive shift

• Creates urgency

• Positions the solution as part of what top performers are already doing

Thanks for reading,

Jed

P.S. Don’t forgot to grab my free deal room template here