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Doing the work

Everyone has an opinion on our new messaging and nobody can settle the argument. How do I test it instead?

Stop reviewing messaging internally, because the most senior opinion wins and none of you are the buyer. Put the actual page or email in front of twenty five to thirty people who match your ICP and ask five plain questions: what do you think this does, who is it for, what is different, what would make you take a call, what is unclear. Test it section by section so you learn which line is broken rather than that the page as a whole scores six out of ten. Then triangulate with recorded sales calls, because the sentence a prospect repeats back to a colleague is the one that works, and you did not write it, they did.

Go deeper

4 resources, 4 link-checked.

📄 Article
✓ Link checked Free Intermediate

The actual method: which five dimensions to score, the open questions that get useful answers, and why you test section by section instead of judging a whole page. Laja's claim that a third to half of your messaging is not landing is a good reason to start.

What is Message Testing in Marketing and How To Do It

From Wynter by Peep Laja 13 min read

  • Assume 30 to 50 percent of your messaging is not landing with the audience at all.
  • Test five components: clarity, relevance, value, differentiation, and brand.
  • Score each on a 1 to 5 Likert scale plus open-ended questions, so you get the why alongside the rating.
  • Done manually, one message test takes a week or two, which is why most teams skip it.
Open wynter.com
📰 Newsletter
✓ Link checked Free Intermediate

Three real startup homepages taken apart, showing the whole chain from positioning statement to messaging to the actual sentence on the page. Seeing the translation fail in someone else's copy is the fastest way to spot it in yours.

Positioning & messaging teardown, with Anthony Pierri

From MKT1 Newsletter by Emily Kramer and Anthony Pierri 20 min read

  • Even startups that write a perfect positioning statement lose it by the time it reaches the site.
  • Point the homepage hero at your primary audience and route other ICPs to audience-specific pages.
  • The fastest way for a sales-tech company to sound like everyone else is to lead with increasing revenue.
  • New way positioning is the hardest of the four product types, because you have to build problem, solution and product awareness at once.
Open newsletter.mkt1.co
📄 Article
✓ Link checked Free Beginner

The interviewing craft, not the theory: how to open so people feel safe being blunt, how to use five whys past the polite answer, and why you let the buyer talk ninety percent of the time.

How to Conduct Win-Loss Interviews: Step-By-Step Guide

From Klue 14 min read

  • Follow the 90/10 rule in a win-loss interview: the buyer should be speaking 90 percent of the time.
  • Plan for 30 minutes but block an hour, and prepare 20 to 30 questions knowing you will use 10 to 15.
  • Uses a D.E.P.T.H. structure (details, engaged, personal, trust, high impact) plus five-whys laddering to get past the first answer.
  • 41 percent of win-loss programs are now owned by product marketing (2025 Win-Loss Trend Report).
Open klue.com

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The same ground, at another level

How positioning and messaging reads from a different seat.

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The same ground, over in Understand your customers, our Starting Up track.

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