Five Questions: A Framework For Brand Strategy

In a recent post, "Data needs your honesty", I talked about my experience helping Royal Caribbean shape the brand’s strategy during a pivotal period in their growth. I’ve since been asked about the process, or framework I use for strategy development.

The truth is, I don’t really have a formalized process, per se, but I do have a handful of questions, whose answers have consistently done a good job of informing or shaping strategic direction. While simple and straightforward, they carry a lot of weight. And every time I’ve been tempted to skip one, I’ve always felt it later.

1. What does your brand or product actually do?

Not the mission statement. Not the positioning line. Not the language everyone nods at in meetings. What does it actually do in someone’s life? When you strip it down, most brands usually do one or more of these things, like:

Save time, Reduce risk, Signal status, Deliver access, or Entertain

If you can’t easily describe what you do in plain language, you don’t have a messaging problem. You have a clarity issue. For Royal Caribbean, we had to admit something that sounds obvious now: we weren’t in the cruise business. We were in the vacation business. Until that clicked, the brand was optimizing all the wrong things.

2. Why is that valuable?

This is where strategy quietly breaks. Teams describe what they do and assume the value is self-evident. It never is. In the mind of the consumer, value only exists in comparison to something else. Saving time matters if time feels scarce. Luxury matters when perceptions are important. Convenience matters if the alternative feels inconvenient.

You always have to ask: Valuable compared to what? Valuable for whom? Valuable in what moment? If you can’t explain the cost of choosing something else, your value proposition needs some work.

3. Is this unique to you, or are you one of many?

This question has the tendency to bruise egos. Most leadership teams believe their brands are meaningfully different. Sometimes they are. Often they’re incrementally better in ways customers barely notice. We had the data to prove we were “better” on food, entertainment, and activities. But it didn’t move the needle. Being slightly better within a category (cruising) with low interest or relevancy doesn’t promote growth. Uniqueness only matters when it is valued.

4. If there are others, are they better?

(Or more trusted? Or more established? Or simply more familiar?)

This is where honesty gets expensive. You may not be objectively worse. But perceptually? Culturally? Historically? Familiarity can provide a formidable advantage. Sometimes the competitor isn’t better. They’re just better known. And that matters more than we like to admit. When leaders answer this question defensively, strategy starts protecting pride instead of pursuing progress.

5. Are prospects even aware?

You can be valuable. You can be differentiated. You can be objectively superior. None of it matters if people don’t know you exist. Or if they misunderstand what you are. Awareness isn’t vanity. It’s oxygen. But awareness in the wrong frame can trap you. The cruise industry had awareness. What it lacked was relevance in the everyday vacation conversation. And that distinction changed everything.

Why These Questions Matter

None of these questions are complicated. But answering them honestly is. Because once you do, familiar narratives begin fall apart. You may realize:

You’re not as differentiated as you thought.
Your value isn’t as urgent as you assumed.
Your competition isn’t who you’ve been fighting.
You’ve been optimizing inside the wrong things

This can be uncomfortable. But it’s also freeing. In my experience, clarity usually shows up right after discomfort. With experience, direction becomes obvious. It may not be what you expected, or wanted, but you can see it. And it’s real.

The Link Back to Data

Here’s the part that’s harder to explain. As I ask these five questions, I’m not doing it in a vacuum. I’m usually already sitting with the data. Cross-tabs that no one has summarized yet.
 And as I'm reading, these questions are continually running quietly in the background, as if a guide.

What does this actually tell me about what we do?
 Is that really valuable, or do people just say so? 
If we’re truly “better,” why isn’t that translating?
 Where are people hesitating?
 What are they not saying?

Data leaves clues. But when you’re too busy looking to confirm what you already believe, you’ll miss them. When you’re willing to challenge yourself, you’ll start to notice what others skim past. That’s how strategy actually forms. Not after the data. But from within. And once you see it, you’ll understand.

Data needs your honesty.

But it also needs your curiosity. And that part is human.