How to Learn from Brand Management Mistakes and Move Forward
Brand management mistakes can be costly, but they also offer valuable lessons. This article explores key insights from industry experts on how to learn from these missteps and move forward. Discover practical strategies to align brand perception, prioritize clear messaging, and maintain authenticity in your branding efforts.
- Align Brand Perception with Customer Reality
- Serve the Right Customers to Build Brand
- Prioritize Clear Messaging Over Visual Appeal
- Maintain Brand Authenticity and Distinctiveness
- Integrate Brand Materials for Consistent Growth
- Balance Familiarity and Evolution in Rebranding
- Research Existing Customers Before Brand Changes
- Ensure Consistent Messaging Across All Platforms
- Embrace Strategic Specialization in Brand Positioning
- Allow Brand Flexibility for Meaningful Growth
- Build Trust Through Consistent Delivery
Align Brand Perception with Customer Reality
The single greatest mistake I ever made in managing a brand was failing to account for the gulf between how we believed the brand was perceived and how it was in reality received. At an earlier organization, we did a rebrand that featured a sexy new look and feel and messaging that focused on innovation and coolness. Offscreen, the rebrand just felt right for our product roadmap and company values. But when we launched publicly, we learned — slowly then all at once — that our customers didn't see us the way we saw ourselves. The language was aspirational, not descriptive. It was a bold design, if not especially usable. And the customer feedback, while indirect, was loud and clear: engagement went down, conversion decreased and customer service began receiving questions no one had ever asked.
The lesson went along these lines: brand is not what you say it is — it's what your customers believe it is. We'd been so wrapped up in re-imagining the brand from the inside out, that we had neglected to move the customer with us. Brand isn't a pitch deck or a press release. It's the culmination of all these microinteractions, from website load time to the way a support email is worded, and when you change it without having an intimate knowledge of your audience's emotional connection to it, you risk breaking trust.
Ever since, I have made it a rule to never pursue or lead a brand shift without first mapping the customer journey — not just functionally, but emotionally. At RedAwning, as we started experimenting with new value propositions and content formats, we combined every change with user testing and journey mapping. One small but significant impact was altering our pre-arrival emails from being solely instructional to more welcoming and experience-based. Bookings simply rose; customer reviews grew warmer and more personal. That shift began with humility—admitting a prior mistake and being prepared to listen more closely.
Serve the Right Customers to Build Brand
One of the most costly brand mistakes we made early on, and a mistake I see other businesses repeat, was selling to the wrong customer.
When you're starting, it's tempting to say yes to everyone. You want the revenue and the growth. But you don't see right away how one wrong customer can erode your brand from the inside.
However, we learned that not every dollar is worth it. Some clients cost more than they give financially, emotionally, operationally, and reputationally. They drain the team, leave misaligned reviews, fail to get results (because they were never the right fit) and refer no one.
We now ask a simple question before every deal: Will this customer multiply or sabotage our business?
We look at five R's:
* Revenue (yes, important)
* Results (can we deliver for them?)
* Referrals (are they influential?)
* Renewals (will they stay?)
* Reputation (will they enhance or damage it?)
The brand isn't just built through what you say; it's built through who you serve.
Since learning that, we've introduced a stricter client selection process. We treat red flags seriously. If someone is in a hurry, overly controlling, or asking for something out of scope, we politely walk away. We'd rather preserve our brand than sacrifice it for short-term cash.
When we do onboard someone who turns out to be a mismatch, we don't hesitate to part ways early. Protecting the brand is always more important than pleasing the wrong person.
Most importantly, we only take feedback from qualified sources. If most clients are thrilled and one person is out of alignment, we know the real issue—the wrong client, not the wrong product.
In brand management, protection is everything. Don't build your business on shaky foundations. Serve the right people, and your brand will speak for itself.
Prioritize Clear Messaging Over Visual Appeal
One of the biggest brand management mistakes I made early on with Oswin Hyde was focusing too much on aesthetics and not enough on clarity. We had a beautiful website, well-shot visuals, and premium packaging—but our messaging lacked precision. Customers appreciated the look, but they didn't always understand why Oswin Hyde was different or what problem we solved for them.
The Lesson:
A brand is not just how it looks—it's how it communicates value. If your messaging doesn't immediately connect with your audience's needs, even the most polished visuals won't convert. We learned that clarity, not cleverness, wins.
What We Changed:
We revised our website copy, product descriptions, and even packaging inserts to speak directly to the customer's lifestyle, values, and needs. We also incorporated crosslinked storytelling—tying in the meaning behind our leather craftsmanship, the durability of our pieces, and how they serve as timeless accessories for modern life. Blogs were optimized for SEO and utility, not just brand tone.
Moving Forward:
Now, every branding decision—from email flows to product pages—starts with one question:
"Will this make our value unmistakably clear to the customer?"
That shift helped increase conversion rates and reduced bounce rates significantly.
Lesson learned: clarity builds trust. Never sacrifice that for style alone.
Explore how our refined approach shows up across products at oswinhyde.com.
Maintain Brand Authenticity and Distinctiveness
I once allowed a brand to become excessively polite.
It was a client in the wellness space. They had a beautiful product and a strong mission, but their brand voice was raw, real, and slightly defiant. It was working effectively. However, somewhere between scaling up and attempting to "appeal to more people," we softened it. We cleaned up the tone and neutralized the edges.
Engagement dropped. The copy lost its bite. People stopped sharing posts.
We hadn't improved the brand; we had diluted it.
That was the lesson. In brand management, the instinct to smooth things over often kills the very thing people loved in the first place. You think you're broadening appeal, but you're actually losing clarity.
Moving forward, I intentionally build tension into the brand. If something feels too safe, we push until it doesn't. Brands should polarize a little. If you're never making someone uncomfortable, you're probably not being clear.
Polish is not the point. Precision is.
Integrate Brand Materials for Consistent Growth
I started a global branding and digital marketing firm 23 years ago. My first job was in brand management at Procter & Gamble, and applying B2C lessons to my B2B business, I learned that brand materials must be integrated; they cannot be created in a vacuum. The inability to control and manage brand campaign materials can lead to inconsistency, slow brand growth, confusion, and random brand materials floating all over the place.
I recommend NOT spending money on things like fancy brochures, letterhead, business cards, etc. Until you know your business is launched, I would say to put your budget into things that help fill your pipeline with customers. Getting your URL and a website up and running is key. I created online stationery for proposals and invoices, ordered my cards online, and made downloadable materials as leave-behinds for people looking for more information to help me find clients more quickly. I know other business owners who spent thousands of dollars on these things and found it was a waste of money. Your story will evolve as you find your market; you need to look professional and have a website to be taken seriously, but embossed paper with watermarks and heavy card stock is not going to accelerate your sales cycle. Find those reference customers quickly, use them to get testimonials and referrals. There is plenty of time later to dress things up!
Balance Familiarity and Evolution in Rebranding
One mistake we made was trying to change too many things at once during a rebrand. In the process, we lost some of the familiarity that made people feel connected to our brand in the first place. The lesson was clear: evolving a brand works best when you keep the core steady and build around it. Moving forward, I focused on clarity before change, determining what stays, what shifts, and why it matters. That approach made everything feel more intentional and less disruptive.
Research Existing Customers Before Brand Changes
Early on, we helped a client rebrand without properly researching their existing customer base. We created a sleek, modern identity that tested well with focus groups but alienated their loyal, traditional customer base—sales dropped 30% in three months. The lesson: never change brand direction without understanding why current customers chose you originally. Now we always conduct "brand archaeology"—analyzing what draws existing customers before making changes. This approach has helped us evolve brands successfully while maintaining customer loyalty.
Ensure Consistent Messaging Across All Platforms
In the beginning, I didn't fully grasp the crucial importance of maintaining consistent messaging across all platforms.
We launched a campaign at Estorytellers that looked fantastic on paper, but it didn't quite match the tone of our website and social media. The outcome? Confused customers and a dip in engagement. This experience really drove home the importance of having a clear and consistent brand voice everywhere. From that point on, I made it a priority to ensure that every piece of content—be it a blog post, social media update, or email—told the same story and reflected our core values. This consistency has been instrumental in building stronger trust and a more defined identity.
Remember, your brand is more than just a logo or a catchy slogan; it's the impression people have every time they interact with you. Maintaining that consistent feeling is absolutely essential.
Embrace Strategic Specialization in Brand Positioning
Early in my journey, I made a classic brand management mistake that many entrepreneurs fall into: trying to be everything to everyone. When I started my first 3PL in that vacant morgue (yes, an actual morgue!), I was desperate for business and positioned our services as a one-size-fits-all solution for any eCommerce company that came knocking.
The results were predictably disastrous. We took on clients whose needs didn't match our capabilities, creating frustration on both sides. Our messaging became diluted, our operations stretched thin, and our team confused about our core identity. We were working harder but accomplishing less.
The pivotal moment came when we lost a major client because they didn't feel we truly understood their specific industry challenges. That wake-up call taught me perhaps the most valuable lesson in brand positioning: the power of strategic specialization.
I completely revamped our approach, focusing first on the tabletop board game niche - something we genuinely understood well. We refined our messaging, operations, and team expertise around serving that specific community. Almost immediately, our conversion rates improved, client satisfaction increased, and word-of-mouth referrals multiplied.
This lesson profoundly shaped how we built Fulfill.com. Instead of trying to match every business with any 3PL, we developed sophisticated matching algorithms that consider dozens of factors - from product dimensions to geographic requirements - ensuring truly compatible partnerships. We prioritize depth of compatibility over breadth of options.
The logistics industry is incredibly diverse, with specialized needs across verticals. What works for apparel fulfillment can be disastrous for food products or hazardous materials. By embracing specialization rather than generalization, we've helped thousands of businesses find their perfect fulfillment fit, creating lasting partnerships rather than temporary arrangements.
Remember, in brand positioning, clarity beats volume every time. Your strongest brand message is one that confidently declares not just who you serve, but who you don't.
Allow Brand Flexibility for Meaningful Growth
Early in OutSail's journey, I was proud of how focused our brand was. We had a clean message—"We help mid-market HR teams select new software"—and we stuck to it with discipline. Every piece of marketing, every sales call, and every website headline reinforced that positioning. We wanted to be known for one thing and known for it clearly.
The problem was that clarity slowly became rigidity.
I remember one prospective client in particular—a global manufacturer—who reached out asking if we could help them evaluate not just software, but their entire HR service model. They wanted to understand what to insource, what to outsource, where their team had gaps, and how technology could support a redesigned HR function. It was a big, valuable project, but it didn't fall neatly inside the brand lines I had drawn. So, I politely declined.
A few months later, I learned that they'd hired another firm. Not only did that firm complete the service model analysis, but they used it as a jumping-off point for a multi-year advisory engagement that spanned systems, processes, integrations—you name it. Watching that play out was the wake-up call. By saying no in the name of brand clarity, I hadn't just passed on short-term revenue—I'd missed a chance to build new competencies and deepen our value proposition.
That moment taught me that branding shouldn't be a set of guardrails so tight that they box out meaningful growth. Our messaging still needs to be focused, but it can't be so narrow that it blinds us to real opportunities. Since then, I've tried to be more open to adjacent use cases and emerging client needs, especially if they align with where we can add value. We still lead with our core offering, but we also give prospects a clearer picture of the full range of ways we can help—both today and where we're heading.
The result is a brand that still feels coherent, but no longer overly rigid. We've gained new clients, expanded our services, and turned more one-time buyers into long-term partners—all by learning when to loosen the reins just a little.
Build Trust Through Consistent Delivery
If I had to say that we did something wrong when I first started leading EVhype, it would be the fact that we overpromised and under-delivered our product. We released a feature on EVhype with great fanfare and had high hopes for it - we just didn't realize how challenging taking it to market would be. The result was unhappy customers and negative reviews that damaged our reputation in the short term.
The takeaway is that brand trust is earned through consistency and reliability. I applied this lesson moving forward, emphasizing transparency with our clients. One of the things we're focusing on now is sharing honestly and openly about what we can deliver and ensuring everything is functioning properly before we publicize our work.
Today, our brand reputation is built on fulfilling our promises, and now customers know that when we say we will do something, we follow through.
