please take this messaging help… (Dave's Newsletter)

Today let’s take your messaging from good to great [with the help of Diane Wiredu]

Editor's Note: Hi there. Me again. Editing this 4:21 PM sitting in front of the woodstove with my daughter (she’s reading, I’m typing) Do you know Diane Wiredu? She’s awesome as a person I found out; AND she’s one of the best resources for messaging for your company. This newsletter is based on her lessons from our event earlier this year; first time writing about them here. Enjoy.

The Meaning Gap (And Why It’s Key to Clear Messaging)

Marketers have been following the same messaging advice for years.

Be clear. Show the value. Make it compelling.

The result? B2B homepages all looking something like:

“Made easy.”
“Repeatable revenue.”
“All-in-one.”
“Network. Harmony. Optimized.”

Technically words. Functionally nonsense. And they mean nothing. Where did the fun go? Where did the inspiration go? I just want to go GAHHHHHHHHH.

Answering questions buyers aren't asking yet. Jumping into the story three pages too late.

And that giant void between what teams think is being communicated and what buyers actually take away?

Diane calls it the Meaning Gap.

Luckily, it’s fixable. And it all starts with a flagship message.

1️⃣ A Flagship Message

Most companies have messaging bloat. They list 8 benefits. 4 value props. 6 reasons to buy.

But people can only retain about 7 pieces of information at a time. And when you say everything, you say nothing.

You need one flagship message. One thing you want to be known for.

Start with this question: If you could only be known for ONE thing, what would it be?

Then pressure test it:

• Is it memorable?
• Is it defensible?
• Does it push your brand forward?

Here are two ways to find your flagship message:

1. Name your villain. What outdated thinking are you fighting?

• Loom's villain: time-suck meetings. Their message: "Async video is a better way to communicate."
• CloudZero's villain: unpredictable cloud billing. Their message: "Measure cloud costs by unit economics."

2. Sell the win. What's the one thing your buyer wants most?

• Copyhackers: "Become the most profitable person in the room"
• CXL: "Learn marketing from the top 1%"

Look at all your features and benefits. What do they ladder up to? What's the deepest thing your customer wants? That's your flagship message.

2️⃣ The Right Balance

Here's the eternal debate: Do buyers care about themselves or do they love our product?

The answer? Both.

But most companies pick one side and ignore the other. You end up either feature-heavy or benefit-heavy. Neither works alone.

Use the messaging spectrum to find the right balance:

Map your messaging across this spectrum. Where are you overloaded? Where are you empty?

Example: Time tracking software

• Feature: Automated time categorization
• Action: Track time across apps automatically
• Benefit: Know exactly where your team's time is going
• Gain: Make data-driven decisions about workload
• Outcome: Optimize team workflows
• Result: Save time

Most B2B messaging lives on the left (features) or tries to jump straight to the right (results) without the middle. The middle is where meaning lives.

Here's the key: infuse customer insight into your spectrum.

Don't guess what matters. Talk to customers. Pull from sales calls. Mine support tickets.

One example Diane shared? A demand planning and forecasting software for consumer brands came to her with messaging on the extremes - "Free your team," "Move with confidence," "Fast, actionable insights."

So she talked to their customers and found out what was actually happening: People were spending 3-5 hours every single week uploading and downloading spreadsheets, pulling data from five different tools, then manually aggregating it all just to get one report.

The actual value? The platform consolidated all data sources in one place. It pulled every warehouse and supply chain system into one dashboard, giving them a real-time view of sales and inventory without the CSV uploads or tool-jumping.

That's the right balance. Feature + what it does for you + the specific pain it solves.

3️⃣ Your Buyers' Framing

Here's what most people miss: 78% of B2B buyers shortlist only three vendors for demos. And 54% start with a category search.

Your buyers are already framing the problem in their head before they find you.

Your messaging needs to match their reality. Not your internal view of the product.

Here are the 5 stages of awareness (from Eugene Schwartz):

Most of your traffic is probably problem aware or solution aware. But most homepages are written for product aware buyers.

How to match your messaging to awareness stage:

Problem aware: Highlight the problem. Empathize. Show how your solution solves that pain.

• Shield - "You've got the content. Now get the data."
• Kondo - "LinkedIn's inbox is sh*t, Get Kondo instead."

Solution aware: Position yourself in the category. Show how you deliver results. Demonstrate proof.

• Paddle - "The Merchant of Record for digital products"

Product aware: Differentiate from alternatives. Prove it works for people like them. Heavy social proof.

• Fathom - "A Google Analytics alternative that's simple and privacy-first"
• Clay - "Every Artist Has a Medium. GTM Has Clay."

Match the message to where they are. Not where you want them to be.

What to Do Next

Here are 3 things to work on this week…

1. Find your flagship message. Ask: What's the ONE thing we want to be known for? Write it down. Test it.
2. Map your messaging spectrum. List your features. Then map them through action → benefit → gain → outcome. Fill in the gaps.
3. Check your framing. What stage of awareness are most of your buyers in? Does your homepage match that reality?

Most copy problems are messaging problems in disguise. Fix the messaging first.

If you’re still reading this: go audit your homepage right now using Diane's messaging spectrum.

Where does your copy actually live?

Try filling in the gaps and reply back - I want to hear what you find.

– Dave

P.S. Diane’s talk was great I won’t lie but the best part was hanging out as humans! She’s awesome and we went for a nice long walk with a crew and then had a “cheeky pump” (she taught me about the cheeky pump) before Day 2 of Drive 2025.

She’s coming back to Drive this year too and we’re going bigger and better and more beautiful with the venue in Stowe, VT. Put your name on the wait list now right here.