The Importance of Asking Why Not?

In our recent bi-monthly LinkedIn newsletter we received a lot of interest and feedback. In that newsletter, we emphasized the importance in marketing and branding of asking the question Why? That got me thinking about a few other key questions… like Why not?

Some of the best ideas don’t start with a pitch or a premise. They start with a pause, or a skeptical, raised eyebrow. The concept of ‘Why not?’ shouldn’t be taken as a rebuttal or a confrontation. In brainstorming sessions, it’s always meant as a thoughtful challenge to the status quo.

The simple question: Why not? is as important as it’s counterpart Why?

Unlike Why, which seeks to understand, Why not? seeks to expand. It allows us to open doors we didn’t know were closed or, dare I say, even existed. It pushes us to question the rules we take for granted. It helps brands go beyond expectation and bridge into relevancy. Now that’s exciting.

Challenging the norm is a good thing.

Whenever a new brand manager comes into a brand, I get excited. There’s nothing like a fresh pair of eyes and a new perspective on a brand that’s been worked on by the same team. A brand manager only has that fresh, almost naïve perspective once, and it’s during the first three months of taking over a brand.

Out of necessity, every brand develops unwritten rules and internal assumptions. These create creative boundaries. Add market conventions and conventional wisdom into the mix and the end result often becomes sameness. And while some of these assumptions are valid, many are simply habits. Habits that go unquestioned because “that’s how it’s always been done.”

Remember the terrible twos? Some of us don’t…but the Whys and Why nots were the only questions we asked!

Asking Why not? doesn’t just poke at norms. It forces us to examine whether they still serve the brand. Why not show vulnerability in a financial brand?
Why not bring humour to healthcare?
Why not simplify where everyone else over-explains?

Asking Why not? isn’t about disruption for disruption’s sake, it’s about staying relevant. And if the market has changed, and it has… then shouldn’t our assumptions change too?

Progress comes from pushback

I believe that the biggest creative breakthroughs come from challenging small constraints.

I always think about the Dove’s Real Beauty campaign. I like to assume that campaign was grounded in the question: Why not show women the way they actually are? That simple challenge reshaped an entire category. This wasn’t a small gesture to appease a certain demographic profile. It was a perspective shift. It moved the conversation away from what the product was, to what the product was meant for. In doing so, it reshaped the brand and its relevance.

Reframe the risk

In marketing, we often treat risk as something to minimize or avoid. But there’s another side to risk and it’s the risk of irrelevance. The risk of sounding like everyone else. Of being easily ignored.

We need to ask ourselves: What’s the risk of staying the same? Or worse, what’s the cost of playing it safe?

Ensure a fresh perspective

When used in brainstorms or strategy sessions, Why not? invites input even when we don’t have all the answers yet. It welcomes different viewpoints. It makes space for questions that don’t have immediate answers but just might lead to better ones.That doesn’t mean we’re tossing the strategy out the window. It means we’re holding it up to the light. True relevance isn’t about fitting in. It’s about showing up with clarity, confidence, and curiosity. Why not? is the first step in getting there.