Some quick context before we dive in.

Over the last few issues, we’ve been writing about something we call the Story System. It’s one of our most popular frameworks inside the Growth Program, and after the last newsletter, a bunch of you replied asking for more practical ways to apply it.

So we’ll stay on the topic for an issue or two to help dial in your messaging.

Today’s focus is a simple way to figure out where your messaging is breaking before you go rewrite anything.

The Four Failure Buckets

Most messaging problems fall into one of four buckets:

1. Audience — You’re talking to the wrong person.
2. Problem — You’re focusing on the wrong pain.
3. Value prop — You’re not giving a sharp enough “why us.”
4. Sequence — You’re telling the right story in the wrong order.

Let’s walk through each one with quick checks you can run this week.

1) Audience: “This sounds great, but not for me.”

This is what it looks like when your message is technically clear, but not personal enough to pull the right people in.

What to look for

• You see impressions, but engagement is low.
• People land, skim, and bounce.
• Or you get signups, but not the customers you actually want more of.

How to diagnose it

The job test

Look at your homepage or a core ad and ask:

Could three very different roles all reasonably think this is for them?

Example:

“The all-in-one platform to help teams move faster.”

A founder could read this and think it’s for them. A product manager could too. So could an ops lead.

That’s the problem. When everyone can see themselves in the message, no one feels specifically addressed.

Compare it to:

“Keep product launches moving without chasing approvals across Slack and email.”

Now the audience narrows naturally. The wrong people self-select out. The right ones lean in.

The “they” test

Scan your copy for vague language like “teams,” “businesses,” or “users.”

Then ask:

Could the person I actually want read this and immediately think, ‘That’s me’?

Example:

“We help teams stay aligned and move faster.”

Versus:

“Built for RevOps leaders who are tired of babysitting handoffs between sales and finance.”

In the second version, the reader doesn’t have to translate. They either see themselves or they don’t.

How to fix it

Start small. Rewrite one headline or one email as if you’re speaking to a single, specific person in a specific situation. Name their role. Name what they’re responsible for. Anything written for “everyone” should be the first thing to go.

2) Problem: “That’s true, but not what hurts most.”

This is what happens when your story is accurate, but doesn’t create urgency.

What to look for

• Prospects say you’re interesting, but don’t move forward.
• Sales calls feel friendly, then stall.
• You hear, “This isn’t a priority right now.”

How to diagnose it

Ask yourself whether your message names a surface pain or the real consequence behind it.

Example:

Surface-level pain:

“Approvals get lost in email.”

Most teams will agree with this. It’s true. But it sounds more like an annoyance.

The deeper problem:

“When approvals get lost, deadlines slip, launches get delayed, and I’m the one who looks bad.”

That’s what people actually rearrange their week to fix.

If your messaging never names the downstream consequence, it rarely earns urgency or budget.

How to fix it

Anchor your story to the risk and responsibility your customer carries, not just the inconvenience they complain about.

3) Value prop: “You sound like everyone else.”

This is where a lot of messaging falls apart under real comparison.

What to look for

• Your pitch works until competitors enter the conversation.
• Buyers say they’re comparing you to X and Y, and you don’t have a clear angle.
• Your site reads like a features list.

How to diagnose it

Write your main value prop in a doc. Then replace your logo with your top competitor’s.

Example:

“The fastest way to manage projects.”

Could Asana say this? Yes.

Could Monday.com say this? Yes.

Could ClickUp say this? Also yes.

That means it’s not a value prop. It’s table stakes.

Compare it to:

“The only project tool that shows where work is stuck before leadership asks.”

Most competitors would struggle to say this without lying or changing their product. That’s the difference.

How to fix it

Force clarity by writing three things side by side:

• What customers are doing instead today.
• Why you’re better, in one clean sentence.
• Which persona actually cares about that difference, and why.

Pick three to five value props that hit real problems and aren’t easy to copy. Those should show up everywhere.

4) Sequence: “Good story, wrong moment.”

Sometimes the story itself is fine. It’s just showing up too early. (We discussed this concept last week in a bit more detail.)

What to look for

• People bounce on strong offers.
• Mid-funnel content performs better than top-of-funnel.
• Things only work when a founder is there to explain.

How to diagnose it

Map one core path end to end:

Ad → landing page → CTA → first product or onboarding touch.

For each step, ask:

What single belief is this step trying to create?

Example:

Top-of-funnel ad:

“Book a demo to see how our AI-powered workflow engine integrates with your tech stack.”

Versus:

“Still chasing approvals across five tools?”

Same product. Same story. Different moment.

The first message belongs later, once interest exists.

The second earns the first belief: this is my problem.

How to fix it

• Top of funnel earns interest.
• Middle builds understanding and contrast.
• Bottom removes risk.
• Post-purchase pays off the promise.

Each step does one job, then hands off.

Want this system set up for your own startup?

The diagnostic you just read is one slice of the Story System, our proprietary framework inside the Growth Program.

It’s what we use to help teams define one clear narrative, then map how that story should show up at different moments in the buyer journey.

When teams go through it, messaging stops drifting. Funnels get simpler. Tests start compounding instead of resetting.

Because everything lives in a single system, the diagnosis is faster and less emotional. You’re not guessing. You’re checking failure points against a framework you already trust.

If you want a repeatable way to debug your messaging instead of guessing every time performance dips, this is worth a look.

👉 Learn the Story System inside the Growth Program​

​Devon Reynolds​
Demand Curve Creative Strategist