When Your Messaging Stops Working, It’s Usually Not a Messaging Problem

The thing I’ve heard most from clients who needed messaging support is a mix of small irritations. It’s rare that they know what the problem is or even that it’s key messaging that is causing the friction. 

The most common signals I see that tell me the frustration is due to messaging are things like:

• “People don’t fully get what we do.”

• “The team has to constantly explain ___ and ___.”

• “We keep hearing that people go to the website and don’t know what to do next.”

• Conversations drift in directions you didn’t intend.

• Prospective clients expect something adjacent to what you actually offer.

• You have to repeat clarification during sales and intake conversations.

• It’s difficult to succinctly summarize the business without oversimplifying or launching into a long explanation.

They have to constantly correct people about what their business does (and by people, we’re talking customers and prospects). 

Are you noticing that you have to explain yourself more and more?

You may be tempted to treat this as a communication issue. Looking into refreshing the website, but most often people go in and change copy. The thing is, key messaging is a piece of brand positioning. It’s not just copy or basic communication. It’s about strategically communicating the key messaging consistently across channels, and understanding the user journey to ensure the key messages reach people at the right time. 

Why messaging problems show up later than the real change

Businesses change internally before they change externally. 

Things shift over time, including external communications and messaging. This breaks the underlying foundation that made clarity possible. This is why it’s not one big moment or sign that messaging is off. It’s more that things drift as businesses grow, and as that piles up the strategy behind your messaging has been silently broken. 

And this makes sense, as the work evolves you need to update messaging. Language usually stabilizes around what’s already known, not what’s still forming. So you end up with a mashup of copy that once fit well and updates that compile over time.

Eventually, the mismatch becomes noticeable but not to you. It’s that you begin to experience more and more friction with your audience.

Why fixing copy too early doesn’t help

As mentioned above, the most common instinct is to keep editing. And usually it’s done piecemeal, as you get feedback and see the tensions… you want to fix them. While this sometimes helps momentarily, it actually compounds the challenge: things have already shifted and now they’re shifting more, ad hoc. 

You’ll notice this show up as:

• drafts that sound fine but don’t quite land

• multiple versions that all feel “almost right”, but none actually fit (and you can’t say exactly why)

• small tweaks that don’t change how people respond

It looks like a writing issue, but it’s actually a clarity issue.

How this connects

By the time messaging stops working, there’s already been:

• decision fatigue

• prioritization friction

• pressure coming from the drive to grow

These are all signals that the business has crossed into a more complex phase, and the way it’s being understood hasn’t fully updated yet. Both externally and internally. 

Messaging is often the last place this becomes obvious, because it sits downstream of everything else. And when it gets to the point where it’s obvious, the founder feels exhausted and really unhappy with the site. Most times the topic comes up it’s something they want to avoid because there is just no clear answer and they’re over trying to fix it to no avail. 

What actually helps 

Before you find the right key messaging and can let the language settle, something else needs attention. Strategy. I know, that’s a very annoying word because it’s thrown around so often it’s lost all meaning. What I specifically mean by using it here is taking the time to look at the landscape and make some decisions.

It’s about:

• Understanding your current context

• Identifying what has changed and why

• Identifying what has not changed, and why

• Looking at what you know so far about where you’re headed, and

• Noting what decisions are outstanding

When those things become clear, the words will follow with much less effort. And more importantly, you can begin to make decisions based on your real context—strategically!

Not because you found better copy or redesigned the website, but because there’s finally something stable for the copy to point to. And across channels, you can ensure that your copy is strategically fitting together to serve the way your audience is getting to know you.

This is how you go from “nobody can really tell what we do” to “our website is really helping people see the value we bring.” 

And it’s important to note

This isn’t a branding failure. Businesses grow, that’s usually the goal. And growth means change. This is expected and is usually a sign that you’ve grown and gained insights and evolved things based on those learnings. These are good things! 

Unfortunately, it can feel like a bad thing. Especially if you’ve invested time and resources to address how you present the business. Isn’t it fun when a sign of maturity somehow makes you think you’ve messed up?! 

Let’s set the record straight, if you’re facing this issue it’s most likely because your business is working and it has simply evolved faster than its language. A challenge that is expected and can definitely be addressed. 

Though, trying to force alignment at the surface level won’t work. This is going to be more about looking at things holistically and allowing clarity to emerge so you can decide how to address this from a grounded and context-aware place.

If this is where you are

Don’t fret! If you’re frustrated with how your business is coming across, or you’re starting to notice that people are finding it challenging to see what you’re doing… it’s worth pausing before you reach for a quick fix. This is usually where people tend to squeeze it in while it’s never a priority. 

I strongly recommend not jumping into action right away. When messaging stops working, it’s inviting a deeper look. Not about how you sound.

This means looking at your bigger picture to see how what you’re communicating speaks to what you’ve actually built (in its current state). Brand positioning often gets treated as something that is purely creative (as in visual and content). This is a mistake that often costs a lot of time and money (and energy). 

Brand position is business planning. It must be a part of your business strategy. The way you express your brand absolutely requires creative work and expertise to carry out. But that work must be built on a solid foundation, and that means brand positioning that is part of a business strategy. 

If all of this makes your eye start to cross, or you’ve already tried to address messaging issues multiple times to no avail… I’m always happy to hop on a call (no charge and no selling). I’ll want to hear what you’re facing so I can share strategic insights that will help you figure out your next steps. 

Just keep in mind that I only offer consulting for clients I am currently advising. This is because I have found that consulting without advising leads to creating work that does not outlast me. And I can’t sleep well doing things that way. 

What I can do though, is help you see what your options are and what each would look like in practice. Knowing your goals, needs, and constraints means I can tell you what I would consider and what I would do in your situation. Usually, it’s the most simple answer!

You do not have to overhaul or commit to some six month long agency contract. You just need to orient towards the context that matters so you can clearly communicate the value you bring. And sometimes, a fresh POV can help you see that.