This article comes from Tim Pollard’s insightful talk at our Chicago 2024 Sales Enablement Summit. Check out his full presentation and our wealth of OnDemand resources.

Let’s talk about messaging. More specifically, let’s talk about why so many sales teams struggle to tell their story in a way that actually wins deals.

It’s not just a minor issue—it’s a major problem. As solutions become more complex, customers give us less and less time, and distractions pile up, delivering a compelling message has never been harder. 

Virtual meetings make it worse. Attention spans are shrinking. Buyers are more overwhelmed than ever. And when messaging goes wrong, it costs you deals—deals you should be winning.

But here’s the good news: this isn’t just a problem. It’s an opportunity.

I’d argue that messaging is the most underappreciated lever in sales enablement. Getting it right can dramatically improve your win rates in ways very few other initiatives can.

And the best part? Messaging isn’t some innate talent—it can be learned.

Let’s break it down into three simple parts:

  1. What’s going wrong with messaging today?
  2. How do you fix it?
  3. What kind of results can you expect when you do?

Where sales messaging goes wrong

There’s a principle in storytelling that comes from Tolstoy’s Anna Karenina: “Happy families are all alike; every unhappy family is unhappy in its own way.”

Sales messaging is exactly the same. Sales conversations fail for countless reasons. But when they succeed, it’s for a small number of consistent and predictable reasons.

So, what are the ways messaging typically goes wrong? Broadly, they fall into two buckets:

  1. Message design (what you say) – the actual content of the story you’re telling.
  2. Message delivery (how you say it) – how effectively you execute that conversation.

Let’s dig into these.

The three biggest messaging mistakes

1. Too much information

We cram way too much into our sales decks and pitches.

It happens for good reasons. We want to be thorough. We want to cover every angle, every feature, every benefit. But the result? Cognitive overload.

How many times have you been in a presentation where you checked out by slide 10—knowing there were still 40 more to go? Buyers experience the same thing.

The reality is, the human brain has limited bandwidth, especially in virtual settings. Overloading prospects with information makes them disengage. If they disengage, the deal is already slipping away.

2. An unclear value proposition

After a sales conversation, a buyer should walk away knowing two simple things:

  • What problem of mine are you solving?
  • Why do you solve it better than anyone else?

Yet most messaging buries these answers under a mountain of slides, jargon, and details that don’t matter. If the buyer can’t immediately articulate the value, you’ve lost them.

3. No logical narrative flow

Messaging often lacks a clear, logical story. Without it, buyers can’t follow the conversation, let alone retell it later when they have to convince their colleagues.

Think about reading Lord of the Rings out of order—it would be impossible to follow. Yet that’s exactly what we do when we present jumbled, incoherent messages to prospects.

The most overlooked sales problem: Retellability

Here’s the real kicker: sales are won and lost in a meeting you don’t attend.

Your buyer isn’t the sole decision-maker. After your sales call, they have to sell your solution internally to their team. And that’s where most deals fall apart.

If your messaging isn’t crystal clear, if it’s not easily retellable, your champion won’t be able to effectively pitch it in the next internal meeting.

So the real test of your messaging isn’t whether it sounded great when you presented it. It’s whether your buyer can retell your story later, without you in the room.

This means you need a retellability strategy—a way to ensure your message survives the second meeting.

How to fix your sales messaging

Let’s dive into the seven hallmarks of a great sales message:

1. Simplicity and clarity

Great messaging is crisp, clean, and simple. It’s not about saying everything—it’s about saying the right things.

Every great sales message should fit on four panels or less. If you need more than that, your message isn’t disciplined enough.

2. Rooted in the customer’s problem

Buyers don’t care about your solution until they fully understand their problem.

Lead with the problem. Linger on it. Spend a third of your conversation here before you even mention your product.

3. Framed around big ideas, not features

Buyers don’t remember lists—they remember big ideas.

Instead of listing features, frame your value proposition around 2-3 core insights that drive action.

Value proposition template
Craft clear and compelling statements that communicate the benefits of their products or services.
Sales Enablement CollectiveJames Shaw

4. Engages both logic and emotion

Facts alone don’t persuade. Stories and visuals make ideas memorable.

Example: Instead of saying, “The Toyota Tundra can tow 8,000 pounds,” show a picture of it towing the space shuttle. That sticks.