I'm going through this right now on a client's website redesign. I presented 32 different homepage messages, grouped by audience, pain points, value, and other themes. Nobody came in saying the same thing. There were places where people intersected, but everyone was on different parts of the spectrum.
I use this exercise with B2B software teams reviewing website messaging before testing it with buyers. The current example is an ongoing redesign at an established privacy-software company.
That's why I want people to compare their answers before we choose the message. First understand what the team thinks matters. Then find out how buyers perceive those things.
Ask the leaders before choosing the headline
A useful starting exercise is to ask five leaders who should choose the company, why, and what evidence supports their answer. Five is a practical prompt, not a requirement or the number of participants in the current workshop.
In the redesign I'm working on, we used 32 messages to make the discussion concrete. Grouping them by audience, pain points, and value gave people something specific to react to. Their opinions differed, and the discussion also showed where they intersected.
The discussion included how we position AI in the product and how hard to lean into it. Should we declare a specific category in the headline, let people infer it, or explain it elsewhere? We also debated how many calls to action to include and what belonged above the fold.
We also discussed the paths different segments of our ideal customer profile should take through the site. How much belongs in the navigation? Should those paths be labeled with product names or with the jobs buyers are trying to get done?
Those decisions bring the positioning discussion onto the page. What do we lead with? What do we explain next? What do we ask someone to do before they scroll?
In the September 3, 2026 discussion, we agreed the first screen needed to make clear what the company does, who it serves, and what the visitor should do next. The disagreement was how to achieve that: how much to say, which message to lead with, and how the design should support it.
One tension was between buyers looking for an immediate solution to a familiar problem and those evaluating a broader product offering. An AI-led story had to be considered alongside the needs of buyers trying to understand the basic solution. The final headline and navigation were still open decisions.
Agreement inside the company is only part of the work
What interests me about this exercise is seeing what people on our side view as important. Once we've identified those priorities, we need to understand how the buyers perceive them.
That's where I see value in tools such as Wynter and in talking directly with prospects. The question I want to take to buyers is whether the things we think matter actually mean something to them. That buyer research is the next step; the redesign is still underway.
Don't turn the exercise into a vote for the best-sounding line
The current discussion has shown me where people differ. The next question is what those differences mean for the buyer. A message winning internal support doesn't establish how a prospect will interpret it.
Where this breaks
This exercise exposes internal priorities. It doesn't establish that a buyer shares them or that positioning caused a channel problem. If a founder is still figuring out who buys the product, internal message selection can't replace that discovery.
Questions leaders ask
What if everyone gives a different answer?
That's what I'm seeing in this redesign. Nobody came in saying the same thing. The discussion became useful when we could see both the differences and the places where people intersected.
Does everyone need to agree before we talk to buyers?
In the current exercise, the differing opinions are part of what we need to understand. I'd take the important differences into buyer research rather than treat an internal vote as the final answer.
Have you tested these messages with Wynter?
The work I've described so far is the internal review. Buyer-validation results aren't available for this account yet.
Did the exercise improve conversion?
The redesign is still underway. I don't have that result yet.
Look at the messages behind the discussion
Bring the messages your team is debating to our first conversation.