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“THAT’S A GREAT QUESTION”

BRAND STRATEGY
MARCH 2025

A Guide to Asking Better
Branding Questions

If you’ve spent more than 10 minutes listening to business podcasts, you’ve heard it. The rhythmic ritual that occurs when a host lobs even the most pedestrian question at their guest:

“So... what made you start your company?”

‍Thoughtful pause

“Wow, that’s a GREAT question.”

This, frankly irksome, verbal tic has become the thought-leadership equivalent of saying “bless you” after a sneeze - an automatic response that’s lost all meaning.

In the land of branding, your questions determine your destiny. Ask mediocre questions, get mediocre brands. Ask revolutionary questions, spark revolutions.

Why “Great Questions” Are Usually Terrible

Most so-called “great questions” in branding are simply variations of:

What’s your USP?
Who’s your target audience?
What’s your brand story?

These aren’t bad questions by definition, they’re just so often answered with autopilot thinking. Everyone has a USP. Everyone has a story. Everyone has a vague notion of who their audience is. What these questions fail to do is interrogate assumptions, challenge conventions, or provoke actual clarity.

Branding legend Marty Neumeier argues that “a brand is not what you say it is, it’s what they say it is.” That means our job isn’t just to articulate, it’s to explore, test, and reframe. Questions are how we get there.

“What can we claim that no competitor would dare to?”

The Revolutionary’s Questioning Toolkit

Want to build a revolutionary brand? Start by asking questions that make you uncomfortable. Here are few that don't show up in Top 10 listicles.


Reframed Fundamentals

Even “standard” questions can become revolutionary if asked with more precision. These questions still explore positioning, audience, and narrative, but they do so in a way that cuts deeper.
Instead of: What’s our USP?
Try: What can we claim that no competitor would dare to? What are we not that everyone else is pretending to be?
Instead of: Who’s our target audience?
Try: If we could only serve 100 customers this year, who would be on the list, and who wouldn’t?
Instead of: What’s our brand story?
Try: What story do our customers already tell themselves that we can amplify instead of overwrite?

Sacred Cow Slayers

These questions challenge the unspoken rules and untouchable norms of your category, they help expose the comfortable myths your brand might be living under.
  • “What industry best practice is actually holding everyone back?”
  • “If we deliberately did the opposite of our top competitor, what would break, and what might thrive?”
  • “Which customer needs are we ignoring because they’re inconvenient, expensive, or don’t scale easily?”
  • “What assumptions about quality, price, or value are we too afraid to challenge?”
  • “What’s something we believe is ‘mandatory’ that no one has ever actually tested?”
  • “If our industry had to start over with zero history, what wouldn’t be rebuilt?”
  • “What’s the most overrated metric we’re still optimising for, and why?”
  • “Is our strategy merely a goal in disguise? Are we confusing aspirations with actionable plans?”

Discomfort Provokers

These questions shine a light on vulnerabilities and tensions, what we’re avoiding, what scares us, and what could transform us if we dared to confront it.
  • “What would we do if we had to charge 10x our current price tomorrow?”
  • “If our biggest weakness became our central story, how would that shift our brand identity?”
  • “If our top three competitors disappeared overnight, would our customers miss us?”
  • “What would it look like if we tried to kill our own product with a better one?”
  • “What do we pretend isn’t broken because fixing it would be politically risky?”
  • “Where are we being cowardly in our communication, and why”
  • “What part of our brand promise keeps us up at night, because we can’t yet fully deliver on it?”
  • “Are we overestimating our uniqueness? Could our perceived differentiators be easily replicated?”

Future Forgers

These questions push us past the present and into the next era, where unmet needs, cultural shifts, and emerging expectations live.
  • “What new problem will our customers face in five years that we could start solving now?”
  • “What belief about our industry will seem laughable in a decade?”
  • “If we launched today, what assumptions would we abandon from day one?”
  • “What will our customers expect by default in the near future that feels premium today?”
  • “If AI or automation ate 90% of our category, what would be left that’s still truly human?”
  • “What emerging cultural shift are we ignoring because it doesn’t ‘fit’ our current brand?”
  • “What version of our brand would Gen Alpha fall in love with, and why?”
  • “How can we create a strategy that not only meets current demands but also sets new industry standards?”

How to Tell If Your Question Is Actually Great

Creates discomfort

If no one shifts in their seat, it’s too safe.

Evades pre-packaged thinking

If the answer sounds like it came from a brand deck, go deeper.

Demands specificity

“We want to be authentic” is not specific. “We will never use stock photography again” is.

Reveals assumptions

Good questions expose invisible constraints. Great ones dissolve them.

Shifts the energy in the room

When someone puts down their phone or mutters “huh, that’s interesting,” you’re close.

When and How to Use These Questions

Different phases of brand development call for different types of questions. Here’s a framework:

Brand Stage:
Primary Focus:
Use These Questions:
Startup / Pre-launch
Clarity & Positioning
Sacred Cow Slayers
Future Forgers
Growth / Scaling
Differentiation & Focus
Reframed Fundamentals
Discomfort Provokers
Rebrand / Maturity
Relevance & Reinvention
Future Forgers
Discomfort Provokers
Reframed Fundamentals

Internal Stakeholder Dynamics

Not every room is ready for revolution. Here’s how to navigate tough rooms:

With leadership teams:

Frame questions as strategic risk mitigation. “What assumptions are we betting millions on?”

With creative teams:

Use questions to unlock emotional or human truths. “What’s the story we’re afraid to tell?”

With product teams:

Tie questions to user needs and roadmap implications. “What feature do we keep avoiding and why?”

“What would make us unmistakable at a glance, even without a logo?”

What Today’s Brand Leaders Say

Byron Sharp (How Brands Grow):

Brands must build distinctive mental availability. Your questions should focus not just on being different, but on becoming memorable in repeatable ways. “What would make us unmistakable at a glance, even without a logo?”

April Dunford (Obviously Awesome):

Positioning isn’t found, it’s constructed. Good questions help you reframe your market context. “What category do we really belong in that no one’s noticed yet?”

Marty Neumeier (The Brand Gap):

A brand is a gut feeling. Clarity beats cleverness. “What do we want our customer to feel at the moment of decision?”

Debbie Millman (Design Matters):

Branding is meaning-making. It’s cultural, emotional, and narrative. “What meaning are we creating, and who needs it most right now?”

Final Word

In branding, the questions you ask matter more than the templates you fill out. Don’t aim for polite nods or podcast flattery. Aim for confusion, discomfort, and revelation. That’s when real brand strategy begins.

When we hear someone say “That’s a great question,” our goal isn’t to bask in the praise, but to recognise we’ve cracked open something that might just change everything.

Your advantage starts with a better question. Start your Revolution.

Dan Matthews, Thinkable

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