🚀 How to Make Your Brand Soar Where Others Faceplanted 🔥

Part Seven of 'Oops, We Made It Worse' (Part 7 of 7 Part Series)

Mark S. Carroll ✅

May 13, 2025

Top of the Series: 🧯 Oops, We Made It Worse (Part 1)

Previous: 🐯 Mascot Madness: When Sports Teams Go Way Too Far 😱

🧯 Oops, We Made It Worse (Part 7)– The Anti-Playbook

A field-tested guide to spotting dysfunction, dodging disasters, and building smarter from the ashes of branding failure

Introduction: This Is Not Just Satire—It’s Survival Training

Let’s be honest—there’s something deeply satisfying about watching a branding fail combust in real time. Whether it’s a soda that tastes like cucumber regret, a mascot that haunts dreams, or a logo that screams “We didn’t run this by anyone under 40,” the comedy practically writes itself.

But here's the thing: this series was never just about pointing and laughing.

It was always about pointing and learning.

Because beneath every hilarious misfire is something a lot more serious—a moment where someone, somewhere, could’ve said, “Maybe let’s not.” A slide that could’ve been cut. A stakeholder who could’ve asked one more question. A junior team member who had the right instinct but didn’t feel safe enough to challenge the room.

Each of the branding disasters we covered in this series is a real-world parable. Not of stupidity, but of unexamined assumptions, organizational dysfunction, and that all-too-common enemy: the echo chamber of leadership ego. The more outlandish the story, the more invisible (and common) the root cause usually is.

So yes, this has been satire. But it’s also been a field guide. A diagnostic tool. A cautionary tale told in six punchlines and a punch list.

And now, in this final entry, we’re not just rolling the highlight reel—we’re handing you the Anti-Playbook:

The 🚩 Red Flags to watch for
The 🔍 questions to ask before someone prints the T-shirts
The 💄🔥 cultural patterns that turn good ideas into dumpster fires
And the 🧰 repeatable moves that help you build branding that sticks—for the right reasons

Because if the only thing you got from this series was a laugh, you missed the deeper lesson.

But if you’ve been quietly asking yourself, “Could we be doing any of this without realizing it?”—you’re in the right place.

👉 And if you’re hungry for more than just branding wisdom—if you're ready to rethink how teams communicate, make decisions, and stop stepping on the same rakes—then keep your eyes peeled for my upcoming book, Collaborate Better. It’s the full playbook for turning silos into synergy, broken meetings into momentum, and team chaos into clarity.

In other words, it’s how to stop making it worse—together.

Let’s pull the pin on these mistakes—and build smarter from the fallout.
Ready to dive in?

We were aiming for a mascot that inspires team spirit. We landed somewhere between a fever dream and a cease-and-desist

🧯 Section 1: They Didn’t See It Coming—But You Can

🚩 Red Flags That Signal an “Oops” in Progress

The most catastrophic brand disasters rarely start with someone yelling, “Let’s make something terrible!” No one sets out to create a drink that tastes like sadness, slap a haunted meatball on their team logo, or name a new SUV after a war crime. These flops don’t happen because people are evil. They happen because systems are broken, incentives are misaligned, and most of all—the red flags were waving long before the fire started.

In this section, we’ll walk through the five early warning signs that almost guarantee a branding faceplant—unless you catch them first. Every example here is drawn from this very series. These aren’t hypotheticals. They happened. Publicly. Loudly. And at great cost.

The good news? They didn’t see it coming. But you still can.

❌ 1. 🚫🙊 No One Spoke Up

Symptom: Dissent is absent or punished. Everyone nods. The loudest voice wins.

Example: Pepsi’s Kendall Jenner ad or Pepsi Ice Cucumber—branding decisions so disconnected from reality that it’s hard to imagine a single person in the room actually believing this was a good idea. And yet… it happened. Because no one challenged the premise.

Root Cause: Psychological safety was missing. When people fear being labeled “difficult,” “negative,” or “not a team player,” they stay silent—and bad ideas slip through on a wave of polite approval.

Solution:

Build feedback-friendly cultures where pushback is welcomed, not weaponized
Ask: “What’s something about this that could land wrong?” instead of “Any feedback?”
🛡️Make it safe for someone—anyone—to raise their hand and say, “This feels… off.”

🙈 2. 🧏‍♂️📉 They Skipped the Audience Check

Symptom: Assumptions made. Personas ignored. Messaging built for the mirror, not the market.

Example: From Branded Lies to tone-deaf heritage rebrands, we saw companies whitewash their pasts, misrepresent their customers, and fumble cultural cues—all while congratulating themselves on being “bold.”

Root Cause: Internal bias. Teams drank their own Kool-Aid, mistook internal consensus for public validation, and forgot that your brand is not what you say it is—it’s what your audience says it is.

Solution:

🧪 Validate with real users, not creative directors with opinions and a latte
Bring actual personas into early development, not just as a final checkbox
Remember: if it doesn’t resonate outside the bubble, it doesn’t land at all

🐘 3. 👔 Top-Down Ego Override (The HiPPO Problem)

Symptom: The highest-paid person steamrolls better ideas. “Vision” replaces validation & can be the largest elephant in the room.

Example: Elon Musk’s Cybertruck window smash, “non-marketing” rebrands, or ambitious pivots that ignore actual market data—all red flags of leadership choosing performance theater over process.

Root Cause: A power imbalance where feedback is interpreted as insubordination, and brainstorming is treated as a loyalty test.

Solution:

📥 Use structured intake funnels (like those in Collaborate Better) that force stakeholder input to be weighed alongside data
Defer to the best insight—not the biggest title
Ask: “If this weren’t their idea, would we still be doing it?”

🫥 4. 😐👌 “It’s Fine” Culture

Symptom: No one rocks the boat. Bad ideas survive by being just tolerable enough.

Example: Mascot Madness—when a sports team (or a cereal brand, or a fast food chain) unveils a baffling, nightmare-inducing character and everyone wonders who approved it. The truth? Everyone did. Passively.

Root Cause: The slow erosion of standards. When mediocrity isn’t challenged, it accumulates like lint in a dryer—and eventually catches fire.

Solution:

Normalize feedback as part of the process, not an attack
Create “bravery incentives” for early-stage critique
💬 Reward curiosity, not compliance. The best marketing question? “What are we not seeing?”

🏁 5. ⏩🚧 The Org Thought Speed Was Strategy

Symptom: Launch before validation. Urgency beats insight.

Example: Crystal Pepsi. Orbitz. New Coke. DeLorean. Cybertruck again. A recurring theme across Overhyped Cars and What Were They Drinking?!—the idea hits shelves before it hits a test group.

Root Cause: Pressure to deliver “something big” overtakes the discipline of delivering something smart. The launch becomes the goal—not the outcome.

Solution:

🔁 Embrace test-learn cycles (MVPs, pilots, soft launches) over “big bang” reveals
Treat deadlines as checkpoints, not finish lines
Remember: You’re not behind if you’re iterating. You’re ahead if you’re learning.

🧯 Final Thought: Fire Drills Start with Smoke

Every single disaster we’ve profiled started with a subtle signal—ignored. The key to smarter branding isn’t genius. It’s vigilance. The Anti-Playbook works when you use it upstream—before the CMO’s nephew is in the mascot suit, before the cans are printed, before your team is trending on Twitter for all the wrong reasons.

Catch the smoke early, and you won’t need the extinguisher later.

Up next? We break down the deeper causes behind these red flags—and how to build systems that stop failure before it finds the group chat.

🎯 Branding Blunder Self-Check Polls (Personal Insight)

What’s Your Biggest Branding Sin (Be Honest)?

🙈 Skipped the user test because “we already knew”
💡 Fell in love with a clever idea that solved nothing
👂 Ignored feedback because the deadline was looming
🧼 Let the HiPPO have their way because… politics
🤷 I have never sinned (and we all hate you just a little)

The product’s a disaster, but the deck is 🔥

🧯 Section 2: Behind the Laughs—Systemic Failures in Disguise

🔍 The Real Reasons These Things Keep Happening

On the surface, branding disasters look like someone just had a bad idea and ran with it. But if that were the whole story, they wouldn’t happen so often—or with so much budget behind them. The truth is more uncomfortable: these aren’t one-off flukes. They’re the predictable outcomes of broken systems.

And the worst part? Most of those systems look like they’re working—until launch day proves otherwise.

Let’s peel back the banana-scented curtain—a little artificial, a little overripe—and see what’s really driving these fiascos.

🧱🫣 1. Silos Make Dumb Decisions Look Smart (Until Launch Day)

Symptom: Everyone agrees—but only because they’re all from the same department, speaking the same language, with the same blind spots.
Outcome: Internal consensus feels like confidence. Until it crashes into the outside world.

Example Context: That brilliant ad campaign cooked up in the marketing echo chamber—only no one invited customer support, legal, or the person who actually talks to users.

Systemic Failure: Siloed departments don’t challenge each other’s assumptions. They amplify them.

Solution:

📌 Use the rule of Right People, Right Conversation, Right Time
🎯 Involve cross-functional stakeholders early—not as “reviewers,” but as co-creators
🧠 Gut check: “Have we pressure-tested this idea with someone who might hate it?”

Reminder: If the only people in the room look and think like you, it’s not a review—it’s a rehearsal.

📅🤖 2. When Collaboration Is a Checkbox, Not a Practice

Symptom: Meetings are scheduled, boxes are ticked, Slack is pinged—but no one’s truly aligned.
Outcome: Faux-collaboration gives everyone plausible deniability. And no one owns the outcome.

Example Context: Everyone attends the rebrand kickoff call. No one says anything hard. A week later, the logo drops and everyone’s surprised it sucks.

Systemic Failure: Collaboration without psychological safety is just cosplay. It looks like teamwork, but it feels like surveillance.

Solution:

🧭 Build a feedback loop that includes dissent, iteration, and actual risk-taking
👂 Encourage questions like “What feels wrong?” or “Who are we leaving out?”
🫶 Create space where junior voices aren’t just heard—they’re invited first

Insight: If your collaboration process can’t handle a little turbulence, it’s not designed for lift-off. It’s designed for quiet failure.

💄🔥 3. Branding Without Redevelopment = Lipstick on a Dumpster Fire

Symptom: The logo changed. The slogan’s snappy. But nothing inside the org has evolved.
Outcome: The rebrand collapses under scrutiny—and becomes a case study in performative transformation.

Example Context: Think of companies that change their visual identity while the customer experience, product relevance, or internal culture remains broken (looking at you, Facebook > Meta).

Systemic Failure: Rebranding is used as a shortcut for reinvention—because fixing culture, leadership, or customer trust takes longer than swapping fonts.

Solution:

🧱 Reference the Collapse & Rebuild Framework
- 🔁 Replace what’s broken
- 🔧 Restructure how the org works
- 🌱 Redevelop what it offers
- 📣 Then rebrand
🔎 Ask: What problem are we solving with this rebrand—and is a new logo actually the answer?

Truth Bomb: If the inside of the house still smells like smoke, don’t just repaint the door.

🧯 Final Word: These Aren’t Isolated Incidents—They’re Systemic Signals

If your team is seeing the same mistakes again and again, it’s not a coincidence. It’s an unaddressed pattern. Behind every headline-making misstep is a set of hidden fractures in how teams communicate, test ideas, and share power.

The solution isn’t more process. It’s better design—of how we collaborate, how we validate, and how we listen before we launch.

Coming up next? The Anti-Playbook Principles—ten field-tested rules to keep your brand off the next fail compilation reel and squarely in the category of “They actually got this right.”

🔥 Red Flag Radar Polls (Smarter Teams Start Here)

Which Red Flag Are You Most Guilty of Overlooking?

🚨 Nobody speaks up in meetings
🧏 Skipped real user input
👑 Visionary override (a.k.a. HiPPO attack)
😐 “It’s fine” energy from everyone
⏩ Speed over validation

🧯 Section 3: The Anti-Playbook – 10 Principles to Build By (Not Burn By)

🧰 Your Toolkit to Lead Smarter and Fail Less

By now, we’ve dragged enough brand corpses out of the wreckage to recognize a pattern. When disaster strikes, it’s rarely due to a lack of creativity—it’s because creativity wasn’t balanced by courage, structure, or self-awareness.

So here it is: the Anti-Playbook. Ten principles forged in the smoke and glitter of campaigns gone wrong, designed not to stifle boldness—but to protect it from becoming a punchline.

These aren’t best practices. They’re non-negotiables.

🎯 1. Know Your Audience Like You Know Your Password

If your audience is “everyone,” your message is “no one.”
Research like you’re building trust, not just selling stuff. Treat personas like living, breathing humans—not demographic checkboxes in a deck.

If you wouldn't say it to your audience, don’t write it for them.

🧪 2. Test Ideas Early—Even If It Bruises Your Ego

If it hasn’t been tested, it’s not a launch—it’s a gamble.
A little embarrassment in a focus group beats public shame at scale. Remember: “They just don’t get it” is not a valid user insight.

Pain now prevents pain later.

😐 3. Don’t Ship “Meh” and Hope the Tagline Fixes It

Branding isn’t polish—it’s promise. If the product doesn’t back it up, even the catchiest slogan becomes a customer complaint.

You can’t out-brand mediocrity. (And yes, we’ve tried.)

⏳ 4. Never Confuse Urgency with Strategy

Deadlines are not reasons. Ship fast if it's right—not just because the quarter's ending and someone needs a win.

The road to regret is paved with “we had to ship something.”

😶‍🌫️ 5. Assume Someone’s Too Scared to Tell You the Truth—Go Find Them

Silence is not consensus. Ask the intern. Ask the quiet designer. Ask the person who looks like they swallowed a wasp in the planning meeting.

You’re not looking for feedback. You’re looking for friction.

🏗️ 6. Design Your Feedback Culture on Purpose, Not Default

If feedback only shows up during post-mortems and annual reviews, it’s already too late. Create rituals where truth is expected, safe, and useful.

A culture that can't course-correct can't grow.

🗣️ 7. Elevate Dissent—Especially from Your Quietest Contributors

If the loudest person always wins, your brand loses. Make it a rule: if everyone agrees too fast, pause and investigate.

Dissent isn't derailment—it’s design improvement.

🧼 8. Use HiPPO-Repellent: Visible Intake Process + Transparent Priorities

When the Highest Paid Person’s Opinion starts steering the ship, the iceberg isn’t far. Process is how you tame ego without killing vision.

Democracy with deadlines > Dictatorship with design creds.

🧊 9. Kill Cool Ideas That Solve No Real Problem

No matter how slick, viral, or award-worthy it seems—if it doesn’t align to a real need, it’s just aesthetic vaporware.

Not every clever idea deserves a budget line.

📛 10. If You Wouldn’t Want It on Your Own Résumé, Don’t Brand It

Gut check: if this flops, do you still want to be associated with it?
If the answer’s anything less than “hell yes,” it’s a no.

If it makes your portfolio cringe in advance—walk away.

It’s ugly, dangerous, and unstable—but it launched on time

💡 Last Final Thought: This Is the Anti-Playbook, Not the Anti-Vision

🧯 Laugh, Learn, Lead Better

Let’s be real: it’s fun to roast a branding failure. There’s a guilty pleasure in watching a campaign unravel in public, or a mascot emerge from the uncanny valley with jazz hands and dead eyes.

But this series wasn’t just for the roast—it was for the rebuild.

Every one of these case studies, cautionary tales, and creative catastrophes carried a deeper message: these mistakes are avoidable. They happen when teams lose sight of who they’re serving, skip the hard questions, or let process rot behind the scenes of performance.

We laughed—but only because we saw the truth beneath the glitter and gasoline.
And we learned—because each “oops” is really a map showing where not to step.

Now it’s your turn to lead better.

Lead the brainstorm. Lead the process redesign. Lead the moment where someone says, “Should we… maybe rethink this?”

And if you want more tools like this—the funny ones with sharp edges, the strategic ones with heart, and the practical ones disguised as punchlines—subscribe to Collaborate with Mark on Substack. This series is just one slice of the larger mission: helping real humans build unstoppable teams that don’t just survive collaboration—they thrive in it.

🔥 Coming next week:

Grifted: Success That Survives the Scam – A Practical Field Guide to Business Betrayal.
We’re diving into the most infamous business cons—from Enron to Theranos—to uncover how the smartest people got fooled, what they missed, and how you can spot a scam before you sign the dotted line.

Because the next big fraud isn’t coming—it’s already here.
Let’s make sure you’re not the one left holding the invoice.

Here’s how you can keep the fire (and the wisdom) spreading:

❤️ Like this post if it made you nod, laugh, or rethink something
💬 Comment with your favorite (or most painful) branding “oops” moment
📣 Share with a friend, team, or leader who could use a laugh and a better strategy

Because great brands aren’t built by accident.
And mediocre ones don’t burn down by accident, either.

Let’s keep building better—together.
And next week? Let’s grift-proof your game.