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He was so excited about his idea.

The email would go to, well, everybody. It would be divided into four equal sections, each featuring one of our product categories. We would list the manufacturers in each category and link them to our website.

Before I throw him completely under the bus, you need to know something about my former boss.

He was an incredible salesman. Energetic, charismatic, and no one knew our products better than he did. He could talk to a customer for five minutes and know exactly which product mattered, which objection needed answering, and which detail would close the sale.

You also need to understand that the production industry was in the middle of a messy transition from tape to digital. Some customers were investing in solid-state workflows. Others were searching for professional-grade tape as shortages disrupted supply chains. Everyone was trying to figure out what came next.

So from his perspective, the idea made sense. Show everyone everything. Let them choose what mattered.

But I knew the email would fail.

I had recently run a layout test. One version gave every product equal weight. Another was built around a single featured item with three smaller related products.

The single featured item won. By a lot.

I didn’t know how to calculate statistical significance yet. But I knew I was onto something, and the email he wanted to send was going in the wrong direction.

When everything is important, nothing is important.

Most people approach their inbox the way I approach a Whitman’s chocolate sampler box. They open it, poke around for a few seconds, and hope to find a caramel.

That’s how email works. A quick glance of three or four seconds before they move on to the next message.

If someone gives you three seconds of attention, a hero image can grab them. A clear recommendation can grab them.

Four equally sized images usually won’t.

My boss thought customers wanted choices. I knew they wanted direction.

The campaign was a disaster.

If memory serves, it didn’t generate a single sale. I wish I could tell you there was some hidden victory, like it generated a bunch of traffic. Nope. Or that it sparked useful conversations with customers. Not that either.

It was exactly what I expected: four equally important pieces of information that nobody knew what to do with.

At the time, I was frustrated because I had already run the test and seen the results. Larger featured products outperformed evenly weighted layouts.

What I didn’t appreciate yet was that I was making my own version of the same mistake.

I understood that customers needed direction. But I didn’t realize that my boss did too.

I treated the conversation like the data should speak for itself. I wanted him to look at the results, connect the dots, and arrive at the same conclusion I had.

But bosses are audiences too.

And smart audiences still need help knowing which information matters. My boss was one of the best salespeople I’ve ever worked with. But sales conversations and emails are not the same thing.

A salesperson can answer questions. A salesperson can adjust in real time and steer the conversation toward what matters most.

An email gets a few seconds. And hopefully, someone finds the caramel.

I’ll make other campaigns that fail. I’ll adjust, correct course, and move on. But I remember this one because it taught me that persuasion isn’t about adding information. It’s about helping people see what matters first.

Sometimes that means helping a customer find the caramel. 

And sometimes, it means helping your boss do the same.