Insights

Your message was written by people who have never had to say it.

Why won't my sales team use the messaging we built? Usually because it was authored at an altitude where it never had to survive a live conversation.

Russell ScherwinSeptember 8, 2026Five minute read

A leadership team spends real money and real time on messaging. The work is careful, it is well argued, everybody in the room signs off. Six months later the field is not using it, and the diagnosis in the building is that the sellers are undisciplined, or that enablement did not push hard enough.

That diagnosis is almost always wrong, and it is expensive, because it sends you back to do the same thing again with more conviction.

Five altitudes

There is a stack inside every company, and go-to-market runs the whole height of it. Executive strategy and where the money goes. Cross-functional alignment between marketing, product and sales. The manager operating rhythm, which is what actually gets inspected week to week. Individual opportunity execution, deal by deal. And at the bottom, the actual words spoken to a buyer.

Almost everyone who advises you stops somewhere in that stack, and each stopping point has its own failure mode. Strategy people frequently never reach field behavior, so they cannot tell you whether what they designed is sayable. Trainers often do not know whether the underlying strategy or message is right, so they teach people to execute something that may not be worth executing. Enablement people can become custodians of someone else's process, which is a real job and is not the same job as authoring.

None of that is incompetence. It is range. And a message authored entirely at the top of the stack has never met the only constraint that finally matters, which is whether a person can say it out loud to a stranger who is deciding whether to keep listening.

What the bottom of the stack tells you that the top cannot

I spend weeks at a time coaching sellers and customer success people against their own live deals. That is bought as coaching and it is coaching. It is also the best diagnostic instrument I have ever used.

When you sit with a cohort every week, you are not hearing about the business, you are watching it. You hear the same objection arrive in three different accounts, framed three different ways. You hear which sentence in the approved messaging nobody uses, and then you hear the sentence they invented to replace it, which is often better and which nobody upstairs has ever heard. You find out that two of your own offerings are being positioned against each other by accident, in the field, by people trying to be helpful.

The recommendations that come out of that are not cleverer than the ones a strategist would make from the top. They are built out of what is actually happening, which is why they tend to get acted on. A leadership team can argue with an opinion. It is much harder to argue with what its own people said last Tuesday.

This is not an argument for working bottom up

Some of the best work I have done ran the other way: a diagnosis at the leadership level that drove all the way down into what a seller says in a first meeting. Both directions work. What does not work is either end on its own.

A strategy that never reaches field behavior is a document. Field behavior with no strategy behind it is activity. The gap between the two is where most go-to-market money is lost, and from either end alone it is invisible, because from the top a strategy that is wrong and a strategy that is not being executed look identical, and from the bottom every problem looks like a messaging problem.

The test

Take the last strategic decision your leadership team made about how you go to market. A new segment. A repositioning. A change to what you lead with.

Now ask three sellers what changed in their first meeting because of it. Not what they know about it, and not whether they agree with it. What they say differently.

If nothing changed, the decision has not happened yet. It has been made and it has not been executed, and those two states look the same on a slide and completely different in a quarter.

What to do instead

Build the message with the people who have to say it, in your buyer's terminology rather than in your own, and test it in a live conversation before it is printed anywhere. The people who own the position have to be in the room, because a position their product leader did not help write is one he will correct in his own meetings without telling anybody. And somebody in that room has to have said this kind of thing to an actual buyer, recently, and had it not work.

That is slower than writing it upstairs and sending it down. It is considerably faster than doing it twice.

Building the message with your cross-functional leadership team, in your buyer's language, so the field can actually run it. Conversational Messaging →

Russell Scherwin runs B2B Tracks. He works with leadership teams on the distance between the go-to-market strategy they agreed on and the conversation their buyer actually has: the story, the conversation the field can run, and the management system that keeps both alive. He has grown an application business from $2.6M to $14.1M, a distribution business from $45M to $77M as business unit executive, and a commerce business from $324M to $394M as CMO.

Ask three of your sellers what changed in their first meeting.

Whatever they tell you is the real state of your messaging, and it is the conversation I would rather have than a general one.

Start a conversation
Why Won't Our Sales Team Use Our Messaging? | B2B Tracks