What Is a Brand Messaging Problem — and How Do You Know You Have One?
A brand messaging problem exists when the language your business uses to attract, convert, and serve customers no longer reflects what you actually do, who you do it for, or what makes you different. Signs include: it takes multiple conversations to close deals, your sales team has created their own materials, and your messaging hasn’t changed despite significant business changes.
“I think I have a brand messaging problem, but I’m not sure”
When I ask business owners I meet with to “show me on the content doll where it hurts,” more than half the time, that’s what they tell me.
My brand messaging is all wrong.
I think.
Yeah, my gut says it’s messaging.
… but I don’t know.
If this is how you’re feeling, I know it sucks.
You’re the authority of what you’ve built. In fact, you are likely the business: your vision, your voice, your ideas are the engine of the language you use to sell what you do.
So, when you start feeling new pains in your business — less excitement, reduced lead flow, more objections, more pushback — you might wonder if the language you’re relying on is the problem.
But is it?
Sometimes, yes, you do have a messaging problem: it’s outdated, it’s self-obsessed, etc. It’s time for you to make a change. Then there are cases where your messaging isn’t the problem at all. Instead, your messaging is adjacent to the real issue: a gap inside your business that you haven’t named yet, or you’re not willing to look at.
How do you tell the difference? This is the question you need to answer before you take action. Overhauling your brand messaging — even if it is the right move — can quickly become a very costly wild goose chase if you don’t figure out what’s actually going on.
So that’s what we’re going to talk about today: how you know when you’ve actually got a messaging problem, and when brand messaging is an accidental scapegoat for something else happening inside your company.
You have a brand messaging problem if…
Let’s start with the obvious stuff.
These are the symptoms I see that make me immediately smash the “brand messaging problem” button for a company:
- Your brand messaging has always been a problem, if you’re being honest. You can capture attention and attract referrals, but it usually takes a conversation or two to get someone to truly “catch the vision” of what it is you do or sell. Historically, you’ve considered that a symptom of the complexity of what you do, or just how the game works. But that’s not how it should be.
- You or your sales reps have a bank of their own content (decks, one-sheeters, etc.) they’ve created that (they believe) better explains your products and services. Why? Because what already exists on your website or in other marketing materials don’t get the job done. The thing is, you may not even know they’re doing this. You might have to ask. Sales reps often feel like islands-of-one, where they need to fend for themselves to hit their numbers.
- On the service delivery side, your people are chaffing. From their perspective, what’s being told or sold to prospects is out of whack with what is actually true of the product or service in some (or many) ways. So, their job feels harder than it should be.
- You’ve made big changes to your business, but “you’ll get to messaging later when you have more time.” When I say big changes, I mean internal (leadership shake-ups, new/different products, new/different target customers) and external (economic shifts, industry changes). When big changes happen, it’s sometimes easier to keep moving, but you’re going to pay for the lack of change in your messaging.
- You’re intentionally gate-keeping your “secret sauce.” Maybe you’re worried about competitors. Maybe you’re worried about people taking your processes and doing it themselves. Doesn’t matter: we live in a world where that kind of gate-keeping is costing you more than it’s protecting you.
- You haven’t touched your messaging in 2+ years. Think about where you were in your business two years ago. Think about where the world was two years ago. If your messaging is still the same today, that means you’re still communicating to the world in a way that’s tone-deaf to where you are now.
In the heat of the moment — when you’ve got a team that’s strapped for time and you’ve got “more important stuff to do” — messaging work doesn’t feel mission critical. These types of brand messaging problems, however, are like the worst kind of compounding interest for your business.
By the time you finally look at changing your messaging, you’ve got a bigger problem than when you started.
You don’t have a brand messaging problem if…
Now, this is where things can get a bit tricky and (occasionally) downright uncomfortable. I’ve worked on messaging projects over the past 15 years for a ton of different industries: SaaS, financial services, DoD contractors, manufacturing, home services, healthcare, private equity, ad tech, medtech, business consulting services, and many more.
Across all of those projects, I’ve noticed a weird, almost counter-intuitive pattern.
When messaging is actually the problem, everyone acts like it’s the worst kind of homework. So it’s hard to get folks to make it a priority outside of super obvious circumstances like a product launch. They just want “the right words” to appear.
On the other hand, when messaging is being looked at as “the problem,” but it isn’t, there’s a strange, sudden urgency that appears to slash-and-burn all the words, because new messaging is being looked at as a silver bullet. Then conversations about deeper problems are deprioritized.
Some of the most common examples I see of that are:
- Internally, you’re not aligned at the right level of who your ideal customers are and/or the priority order of who is the most important among those profiles.
- While you’ve got “enough” of the details baked out, you haven’t made certain fundamental decisions about a new product or service that any good messaging strategist would want (e.g., processes, outcomes, expectations). But you’re expecting “good, high-level messaging” to either make the value clear or tell a compelling enough story where the lack of those details isn’t a problem.
- Either at a company level or a product or service level, you’re communicating in a way that is aspirational, rather than reflective of reality.
- You’re solving for imagined problems or questions you want your buyers to have rather than the real ones they do have.
- You can’t tell me what problems your ideal customers have right now, in their words, without doing research or “speaking from instinct.”
Yes, these are problems where messaging can and should be part of the solution.
But messaging is like a mirror. It’s only going to reflect back to you what’s already true. So, if you’ve got in-house dysfunction (lack of alignment around ideal customers, vague ideas about products or services, etc.), that’s all your messaging will show you.
Messaging can’t solve those types of business problems. You can only work on messaging once you’ve done the real problem-solving first.
Ask yourself the right questions
Before you decide your messaging needs to be rebuilt, get more specific about what feels broken.
Are people confused by what you do? Are the wrong buyers showing up? Is sales explaining around the website? Did the business change while the words stayed the same?
That’s messaging.
But if the real issue is an unclear offer, internal disagreement, or a version of the business you wish were true but haven’t built yet, don’t ask the words to do work the business hasn’t done.
Better messaging can sharpen reality for your buyers.
It can’t invent it, and it can’t make an unclear business clear.
The sooner you know which problem you actually have, the less time, money, and energy you’ll waste trying to rewrite your way out of something that needs a bigger decision.


