đ How to Make Your Brand Soar Where Others Faceplanted đ„
Part Seven of 'Oops, We Made It Worse' (Part 7 of 7 Part Series)
Top of the Series: đ§Ż Oops, We Made It Worse (Part 1)
Previous: đŻ Mascot Madness: When Sports Teams Go Way Too Far đ±
đ§Ż Oops, We Made It Worse (Part 7)â 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 SatireâItâs Survival Training
Letâs be honestâthereâs something deeply satisfying about watching a branding fail combust in real time. Whether itâs a soda that tastes like cucumber regret, a mascot that haunts dreams, or a logo that screams âWe didnât run this by anyone under 40,â 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 seriousâa moment where someone, somewhere, couldâve said, âMaybe letâs not.â A slide that couldâve been cut. A stakeholder who couldâve asked one more question. A junior team member who had the right instinct but didnât 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 itâs 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, weâre not just rolling the highlight reelâweâre handing you the Anti-Playbook:
The đ© Red Flags to watch for
The đ questions to ask before someone prints the T-shirts
The đđ„ cultural patterns that turn good ideas into dumpster fires
And the đ§° repeatable moves that help you build branding that sticksâfor the right reasons
Because if the only thing you got from this series was a laugh, you missed the deeper lesson.
But if youâve been quietly asking yourself, âCould we be doing any of this without realizing it?ââyouâre in the right place.
đ And if youâre hungry for more than just branding wisdomâif you're ready to rethink how teams communicate, make decisions, and stop stepping on the same rakesâthen keep your eyes peeled for my upcoming book, Collaborate Better. Itâs the full playbook for turning silos into synergy, broken meetings into momentum, and team chaos into clarity.
In other words, itâs how to stop making it worseâtogether.
Letâs pull the pin on these mistakesâand build smarter from the fallout.
Ready to dive in?

đ§Ż Section 1: They Didnât See It ComingâBut You Can
đ© Red Flags That Signal an âOopsâ in Progress
The most catastrophic brand disasters rarely start with someone yelling, âLetâs make something terrible!â 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 donât happen because people are evil. They happen because systems are broken, incentives are misaligned, and most of allâthe red flags were waving long before the fire started.
In this section, weâll walk through the five early warning signs that almost guarantee a branding faceplantâunless you catch them first. Every example here is drawn from this very series. These arenât hypotheticals. They happened. Publicly. Loudly. And at great cost.
The good news? They didnât see it coming. But you still can.
â 1. đ«đ No One Spoke Up
Symptom: Dissent is absent or punished. Everyone nods. The loudest voice wins.
Example: Pepsiâs Kendall Jenner ad or Pepsi Ice Cucumberâbranding decisions so disconnected from reality that itâs 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 âdifficult,â ânegative,â or ânot a team player,â they stay silentâand bad ideas slip through on a wave of polite approval.
Solution:
Build feedback-friendly cultures where pushback is welcomed, not weaponized
Ask: âWhatâs something about this that could land wrong?â instead of âAny feedback?â
đĄïžMake it safe for someoneâanyoneâto raise their hand and say, âThis feels⊠off.â
đ 2. đ§ââïžđ 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 cuesâall while congratulating themselves on being âbold.â
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 isâitâs what your audience says it is.
Solution:
đ§Ș 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 doesnât resonate outside the bubble, it doesnât land at all
đ 3. đ Top-Down Ego Override (The HiPPO Problem)
Symptom: The highest-paid person steamrolls better ideas. âVisionâ replaces validation & can be the largest elephant in the room.
Example: Elon Muskâs Cybertruck window smash, ânon-marketingâ rebrands, or ambitious pivots that ignore actual market dataâall 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:
đ„ Use structured intake funnels (like those in Collaborate Better) that force stakeholder input to be weighed alongside data
Defer to the best insightânot the biggest title
Ask: âIf this werenât their idea, would we still be doing it?â
đ«„ 4. đđ âItâs Fineâ Culture
Symptom: No one rocks the boat. Bad ideas survive by being just tolerable enough.
Example: Mascot Madnessâwhen 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 isnât challenged, it accumulates like lint in a dryerâand eventually catches fire.
Solution:
Normalize feedback as part of the process, not an attack
Create âbravery incentivesâ for early-stage critique
đŹ Reward curiosity, not compliance. The best marketing question? âWhat are we not seeing?â
đ 5. â©đ§ 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?!âthe idea hits shelves before it hits a test group.
Root Cause: Pressure to deliver âsomething bigâ overtakes the discipline of delivering something smart. The launch becomes the goalânot the outcome.
Solution:
đ Embrace test-learn cycles (MVPs, pilots, soft launches) over âbig bangâ reveals
Treat deadlines as checkpoints, not finish lines
Remember: Youâre not behind if youâre iterating. Youâre ahead if youâre learning.
đ§Ż Final Thought: Fire Drills Start with Smoke
Every single disaster weâve profiled started with a subtle signalâignored. The key to smarter branding isnât genius. Itâs vigilance. The Anti-Playbook works when you use it upstreamâbefore the CMOâs 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 wonât need the extinguisher later.
Up next? We break down the deeper causes behind these red flagsâand how to build systems that stop failure before it finds the group chat.
đŻ Branding Blunder Self-Check Polls (Personal Insight)
Whatâs Your Biggest Branding Sin (Be Honest)?
đ Skipped the user test because âwe already knewâ
đĄ Fell in love with a clever idea that solved nothing
đ Ignored feedback because the deadline was looming
đ§Œ Let the HiPPO have their way because⊠politics
đ€· I have never sinned (and we all hate you just a little)
đ§Ż Section 2: Behind the LaughsâSystemic Failures in Disguise
đ 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 wouldnât happen so oftenâor with so much budget behind them. The truth is more uncomfortable: these arenât one-off flukes. Theyâre the predictable outcomes of broken systems.
And the worst part? Most of those systems look like theyâre workingâuntil launch day proves otherwise.
Letâs peel back the banana-scented curtainâa little artificial, a little overripeâand see whatâs really driving these fiascos.
đ§±đ«Ł 1. Silos Make Dumb Decisions Look Smart (Until Launch Day)
Symptom: Everyone agreesâbut only because theyâre 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 chamberâonly no one invited customer support, legal, or the person who actually talks to users.
Systemic Failure: Siloed departments donât challenge each otherâs assumptions. They amplify them.
Solution:
đ Use the rule of Right People, Right Conversation, Right Time
đŻ Involve cross-functional stakeholders earlyânot as âreviewers,â but as co-creators
đ§ Gut check: âHave we pressure-tested this idea with someone who might hate it?â
Reminder: If the only people in the room look and think like you, itâs not a reviewâitâs a rehearsal.
đ
đ€ 2. When Collaboration Is a Checkbox, Not a Practice
Symptom: Meetings are scheduled, boxes are ticked, Slack is pingedâbut no oneâs 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 everyoneâs surprised it sucks.
Systemic Failure: Collaboration without psychological safety is just cosplay. It looks like teamwork, but it feels like surveillance.
Solution:
đ§ Build a feedback loop that includes dissent, iteration, and actual risk-taking
đ Encourage questions like âWhat feels wrong?â or âWho are we leaving out?â
đ«¶ Create space where junior voices arenât just heardâtheyâre invited first
Insight: If your collaboration process canât handle a little turbulence, itâs not designed for lift-off. Itâs designed for quiet failure.
đđ„ 3. Branding Without Redevelopment = Lipstick on a Dumpster Fire
Symptom: The logo changed. The sloganâs snappy. But nothing inside the org has evolved.
Outcome: The rebrand collapses under scrutinyâand 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 reinventionâbecause fixing culture, leadership, or customer trust takes longer than swapping fonts.
Solution:
đ§± Reference the Collapse & Rebuild Framework
đ Replace whatâs broken
đ§ Restructure how the org works
đ± Redevelop what it offers
đŁ Then rebrand
đ Ask: What problem are we solving with this rebrandâand is a new logo actually the answer?
Truth Bomb: If the inside of the house still smells like smoke, donât just repaint the door.
đ§Ż Final Word: These Arenât Isolated IncidentsâTheyâre Systemic Signals
If your team is seeing the same mistakes again and again, itâs not a coincidence. Itâs 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 isnât more process. Itâs better designâof how we collaborate, how we validate, and how we listen before we launch.
Coming up next? The Anti-Playbook Principlesâten field-tested rules to keep your brand off the next fail compilation reel and squarely in the category of âThey actually got this right.â
đ„ Red Flag Radar Polls (Smarter Teams Start Here)
Which Red Flag Are You Most Guilty of Overlooking?
đš Nobody speaks up in meetings
đ§ Skipped real user input
đ Visionary override (a.k.a. HiPPO attack)
đ âItâs fineâ energy from everyone
â© Speed over validation
đ§Ż Section 3: The Anti-Playbook â 10 Principles to Build By (Not Burn By)
đ§° Your Toolkit to Lead Smarter and Fail Less
By now, weâve dragged enough brand corpses out of the wreckage to recognize a pattern. When disaster strikes, itâs rarely due to a lack of creativityâitâs because creativity wasnât 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 boldnessâbut to protect it from becoming a punchline.
These arenât best practices. Theyâre non-negotiables.
đŻ 1. Know Your Audience Like You Know Your Password
If your audience is âeveryone,â your message is âno one.â
Research like youâre building trust, not just selling stuff. Treat personas like living, breathing humansânot demographic checkboxes in a deck.
If you wouldn't say it to your audience, donât write it for them.
đ§Ș 2. Test Ideas EarlyâEven If It Bruises Your Ego
If it hasnât been tested, itâs not a launchâitâs a gamble.
A little embarrassment in a focus group beats public shame at scale. Remember: âThey just donât get itâ is not a valid user insight.
Pain now prevents pain later.
đ 3. Donât Ship âMehâ and Hope the Tagline Fixes It
Branding isnât polishâitâs promise. If the product doesnât back it up, even the catchiest slogan becomes a customer complaint.
You canât out-brand mediocrity. (And yes, weâve tried.)
âł 4. Never Confuse Urgency with Strategy
Deadlines are not reasons. Ship fast if it's rightânot just because the quarter's ending and someone needs a win.
The road to regret is paved with âwe had to ship something.â
đ¶âđ«ïž 5. Assume Someoneâs Too Scared to Tell You the TruthâGo 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.
Youâre not looking for feedback. Youâre looking for friction.
đïž 6. Design Your Feedback Culture on Purpose, Not Default
If feedback only shows up during post-mortems and annual reviews, itâs already too late. Create rituals where truth is expected, safe, and useful.
A culture that can't course-correct can't grow.
đŁïž 7. Elevate DissentâEspecially 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 derailmentâitâs design improvement.
đ§Œ 8. Use HiPPO-Repellent: Visible Intake Process + Transparent Priorities
When the Highest Paid Personâs Opinion starts steering the ship, the iceberg isnât far. Process is how you tame ego without killing vision.
Democracy with deadlines > Dictatorship with design creds.
đ§ 9. Kill Cool Ideas That Solve No Real Problem
No matter how slick, viral, or award-worthy it seemsâif it doesnât align to a real need, itâs just aesthetic vaporware.
Not every clever idea deserves a budget line.
đ 10. If You Wouldnât Want It on Your Own RĂ©sumĂ©, Donât Brand It
Gut check: if this flops, do you still want to be associated with it?
If the answerâs anything less than âhell yes,â itâs a no.
If it makes your portfolio cringe in advanceâwalk away.
đĄ Last Final Thought: This Is the Anti-Playbook, Not the Anti-Vision
đ§Ż Laugh, Learn, Lead Better
Letâs be real: itâs fun to roast a branding failure. Thereâs 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 wasnât just for the roastâit 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 theyâre serving, skip the hard questions, or let process rot behind the scenes of performance.
We laughedâbut only because we saw the truth beneath the glitter and gasoline.
And we learnedâbecause each âoopsâ is really a map showing where not to step.
Now itâs your turn to lead better.
Lead the brainstorm. Lead the process redesign. Lead the moment where someone says, âShould we⊠maybe rethink this?â
And if you want more tools like thisâthe funny ones with sharp edges, the strategic ones with heart, and the practical ones disguised as punchlinesâsubscribe to Collaborate with Mark on Substack. This series is just one slice of the larger mission: helping real humans build unstoppable teams that donât just survive collaborationâthey thrive in it.
đ„ Coming next week:
Grifted: Success That Survives the Scam â A Practical Field Guide to Business Betrayal.
Weâre diving into the most infamous business consâfrom Enron to Theranosâto 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 isnât comingâitâs already here.
Letâs make sure youâre not the one left holding the invoice.
Hereâs how you can keep the fire (and the wisdom) spreading:
â€ïž Like this post if it made you nod, laugh, or rethink something
đŹ Comment with your favorite (or most painful) branding âoopsâ moment
đŁ Share with a friend, team, or leader who could use a laugh and a better strategy
Because great brands arenât built by accident.
And mediocre ones donât burn down by accident, either.
Letâs keep building betterâtogether.
And next week? Letâs grift-proof your game.




đ§ Collaboratorâs Poll Expansion
âWhich of these do you think would most improve your teamâs creative process right now?
đ§Ș Real user feedback early
đ§ Braver collaboration culture
đŁïž Mandatory dissent from junior voices
đ Ruthless idea pruning
đŹ Space to ask â...what are we missing?ââ
â (Encourage replies with a why or story.)