Your New PMM Gave You the Messaging, But It Doesn't Sound Like You
A Founder's Honest Checklist - Pt.3

As a founder, you followed the checklist, crossed the Ts, dotted the Is and did a perfect handoff. You pulled the sales calls, flagged the customers who did not convert, told your new hired PMM which positioning ideas you had already tried. S/he took all of it seriously, asked good questions, and came back with new messaging. Now, the copy reads clean nothing in it is technically wrong but you still do not want to publish it

The obvious conclusion would be that the hire did not understand what you want or cannot deliver. Fourteen years doing product marketing taught me that this conclusion is usually wrong, and expensive to be wrong about, because "the messaging isn't working" is actually describing one of three different problems, and only one of them is something a new hire can be blamed for.

First: Separate the Three Problems Called “Messaging” 

When founders say, “The messaging isn't working,” they are describing one of three completely different failures.

1. Positioning problem

You do not yet have a sharp answer to: Why should this specific customer choose us instead of the most likely alternative?

You may know what the product does, the category, have a list of benefits. However, can you identify the reason that materially changes the buying decision? No amount of better wording fixes this.

2. Hierarchy problem

You know why customers buy, but is it leading the message or buries under five other points fighting for the same attention. Your homepage has five benefits receiving equal weight and the strongest proof appears halfway down the page, this makes it a hierarchy and execution problem. A good PMM should be able to help structure and articulate your offerings better here.

3. Language problem

Now you have right argument and structure but the language sounds like someone else.

Let’s say, the copy says: Accelerate transformation with a seamless, intelligent platform, when in sales calls, you would naturally say: Get routine contract questions out of Legal's queue without losing control over the answers. Same offering but very different signals. This is the language problem. It can be fixed, but only after the first two are reasonably clear. The mistake is treating all three as “copy feedback.”

Here is what all three look like on the same homepage, before we get into how to test for them yourself.

One Example. Same Product, Three Different Problems: Imagine a contract-software company. Its homepage says: "Streamline your contract lifecycle with an AI-powered platform that increases efficiency, reduces risk, and empowers teams to move faster." The founder hates it. But why?

Positioning problem: The company cannot say which of those benefits actually drives purchases, the competitors say almost exactly the same thing. However, the fix is not another headline.

Hierarchy problem: The company knows something important that the customers are buying because business teams can resolve routine issues themselves while Legal controls the approved playbook. But the homepage barely mentions it. The fix is to reorganize the hierarchy around that insight.

Language problem: The page already communicates that distinction clearly, but says: Empower distributed stakeholders with governed contracting intelligence. The founder says: Let the business answer repeat contract questions without giving up Legal control. It is the same strategic idea but wrong language. Three similar feelings. Three different fixes.

The 15-Minute Test to Identify Where the Issue Lies

Open a blank document, do not look at your current homepage, answer these five questions in plain language.

Question 1: What was your best customer doing before they bought you?

Not their industry or persona but the pain point that you are seeking to address. For example:

Weak: Managing contracts inefficiently.

Useful: Every non-standard contract question went to Legal, so sales reps waited two or three days for answers to issues Legal had already resolved dozens of times before.  The second answer contains something a PMM can work with.

Question 2: What happened that made the old way unacceptable?

Customers rarely buy because your product exists. Something changed that made them outgrow their old ways/software and created a need to be out in the market to fill the gap. Usually, sales calls have these reasons. Write down the event that caused action.

Question 3: What did they seriously consider instead?

Do not write only your named competitors. The alternative might have been spreadsheet, build internally, make the current vendor work or even do nothing for a foreseeable amount of time. Positioning becomes much easier once you know what you are actually replacing.

Question 4: Why did they choose you?

Write one sentence. Not five reasons, not your feature list, not “better service.”

Complete this: They chose us over ______ because ______.

If your answer is something like because we are easier to use, more flexible, and provide better support, you probably do not have the answer yet. If your answer is something concrete like because their sales team could handle repeat contract questions without waiting for Legal, while Legal still controlled the approved answers, now you have something.

Question 5: What evidence proves it?

A useful message has somewhere to go after the claim. Can it be supported with any customer example, usage data, implementation time, a before-and-after workflow, a specific result, a reason your architecture enables it, or a quote from a customer?

If you cannot prove the difference, you may have a slogan rather than positioning.

How to Read Your Results

If Questions 1–4 were difficult to answer, your next step would be customer and market work. If Questions 1–4 were easy, but your current copy barely reflects the answers, you probably have a hierarchy problem. If the copy communicates those answers accurately but still sounds foreign, you probably have a language problem. That simple distinction can save you another expensive rewrite.

If you want a faster, second way to confirm a positioning problem specifically, run this next.

The Fastest Way to Check the Claim Itself: Take the paragraph doing the most work on your new homepage. Delete your company name. Ask whether two or three direct competitors could publish the exact same paragraph without changing anything that matters. If yes, you are not looking at differentiated messaging, you are looking at a category description with your logo on it, and that is true no matter how well it is written.

Checklist: Signs the Claim Itself Is the Problem

• You cannot point to one reason that matters more than the others, only a list

• Different people on your team give different answers about why customers actually buy

• The new hire's early questions about what makes you different were hard to answer

• The copy accurately describes what you do without making anyone feel like they should care

Once the claim and hierarchy are solid, here is what points specifically at a language problem instead.

Five Signs to Identify Language Problem

Founders can overcorrect here and blame themselves for everything, but sometimes the PMM do miss to capture the tone and effect of the positioning. Signs the PMM actually has a language problem:

• A reason you know you win on disappeared or got flattened into something generic

• The page gives your strongest point the same weight as five weaker ones

• You can name the exact idea that got buried or lost, not just a feeling

• Multiple people, independently, flag the same specific gap

Once you know which layer is actually stuck, here is how to fix it.

How to Make Sure the PMM Gets the Messaging Right.

A.      Stop Giving PMMs “Brand Voice” Adjectives

A reason competent work comes back sounding generic is that most voice briefs are nearly useless. The bad copy would usually say: Confident but not arrogant, professional but approachable, intelligent but human, bold, clear, conversational. Almost every B2B company wants some variation of this.

Give the writer language rules instead.

For example:

We do:

• use concrete operational examples;

• name the person doing the work;

• prefer ordinary verbs;

• explain exactly what changes;

• make narrow claims we can defend;

• allow technical detail when it increases credibility.

We do not:

• use “unlock,” “reimagine,” “revolutionize,” or “transform” without saying what actually changes;

• describe ourselves as innovative;

• call every capability “AI-powered” when the AI is not the reason to buy;

• use rhetorical questions in every section;

• make claims like “10x” without evidence;

• write as though the reader is excited about our category.

Now the PMM has constraints that creates voice.

B.      A Better Way to Explain “Sound Like Us”

What actually works is contrast. Write one sentence you would say to a customer, and one sentence in the same spirit you would never say, for example:

Not us: Transform your contracting process with an intelligent platform that empowers teams to move faster.

More like us: Let teams handle routine contract questions without sending every one of them to Legal.

Then explain why: We prefer concrete workflows to abstract benefits. We name who is doing the work and avoid inflated language. We want the reader to see the operational change immediately. You have now given the PMM a reusable rule instead of a preference. Do these three or four times and you have the beginnings of a real voice system.

C.     Do Not Ask for Another Rewrite Until Something Has Changed

This is the rule I wish more teams followed. A new draft should receive new information or a new decision, otherwise you are asking the PMM to roll the dice again. Bad revision request would be something like: Can we try another direction?

Useful revision request: I reviewed our last six wins. Four explicitly mentioned avoiding a lengthy implementation. We have been treating implementation speed as secondary, but the evidence suggests it belongs much higher in the message. Please revise the page around that. Now the next draft has a reason to be better.

D.     Your Comment History Is a Diagnostic Tool

If you are already six revisions deep, do this before commissioning revision seven. Export every comment you have made on the copy and put them into three buckets:

D.1 Evidence. Customers do not use this term, this claim is not true, this misses the reason we won the customer, buyers compare us with X, not Y.

D.2 Direction. Lead with this idea, this benefit is secondary or move this proof higher or explain the workflow before the feature.

D.3. Preference. Punchier, warmer, more premium, more energy, not quite us.

If most of your comments fall into evidence, the writer may not have enough access to the business. If most fall into direction, you may need stronger message architecture. If most fall into preference, you probably need to define your voice more concretely. If the comments contradict one another from round to round, the problem may be upstream of the copy entirely. That exercise alone can tell you why the project is stuck.

Good PMMs Do More Than Polish Words

None of this means founders should write everything themselves. It is tempting, once you see this, to conclude the hire was a waste and start writing everything yourself again. That overcorrects. A good hire still brings something a founder rarely has: distance from material you are too close to, judgment about what to cut, and the skill to make a real claim memorable once it exists. The miss was expecting them to supply a claim that was never handed to them, no matter how thorough the Day-One handoff otherwise was.

Stuck Between Layers? Let's Talk. If you have run this diagnostic and are still not sure whether you are looking at a claim problem, a structure problem, or a voice problem, I take on a limited number of engagements each month specifically to sort this out.

Frequently Asked Questions

We did the full Day-One handoff from earlier in this series. How can the claim still be unclear?

A handoff gives a new hire raw material, not a finished conclusion. Call recordings and near-loss customers are inputs to the five-question test above, not a substitute for actually running it. Sometimes the claim only becomes obvious once someone sits down and answers those five questions directly instead of trusting it will emerge on its own from the source material.

What if my team gives genuinely different answers to why customers buy?

That is common and worth taking seriously rather than smoothing over. Look for a pattern by customer type or use case before assuming everyone should converge on one answer. You may be running more than one real buying story at once, which is itself useful to know before writing a single homepage for all of them.

Is it fair to ask my PMM to also do the customer research this needs?

Sometimes, if you scope it that way on purpose. There is a real difference between "help me express positioning we already have" and "help me find out why customers actually buy," and both are legitimate engagements. The problem is only when one gets bought while the other gets silently expected.

How do I build a voice reference without a big brand document?

Collect four or five examples of your own past writing that felt unmistakably right, plus a couple that felt wrong, and say specifically why for each. That handful of real examples, with reasons attached, is more useful to a writer than a page of adjectives.

How do I know whether I have a positioning problem or a copy problem?

Ask three recent customers why they chose you and what they considered instead. If their answers reveal a consistent reason that your current copy fails to communicate, you probably have an execution problem.

If their answers are all over the place—or you have no idea what they will say—you need to investigate the positioning first.

What if I cannot talk to customers before rewriting the site?

Use the evidence you already have. Review sales calls, CRM notes, lost-deal reasons, implementation calls, support tickets, customer emails, demo questions, and objections. You are looking for repeated evidence of why people act, what they compare, and what they value.

What should I do if the copy is strategically right but still sounds generic?

Build a language brief. Collect examples of how your company naturally communicates when it is at its best. Identify recurring sentence patterns, vocabulary, degree of technical detail, claim style, humor, and words you deliberately avoid.

Give the writer examples and rules, not adjectives.

Where, exactly, is the message breaking—positioning, hierarchy, or language?

That is the question I help founders and product teams answer before they spend another round of budget fixing the wrong problem.