The power of "why": Strategic questioning for business clarity

Nearly 70% of business projects fail, not because of a lack of data, but because we fail to ask the right questions.

"Strategic questioning isn't about slowing down; it's how you accelerate clarity and meaningful action," said brand strategist Kathy Guzman Galloway during an episode of the "Insightful Inspiration" podcast, hosted by Owner & Chief Insight Seeker Isabelle Landreville from Sylvestre & Co.  

Their conversation examined the hidden cost of skipping purposeful questioning and provided practical guidance for achieving clearer, more impactful research strategy outcomes.

Why strategic questions matter more than speed

Business leaders often feel the pressure to act fast, but according to Landreville, rushing into projects without asking strategic questions leads to misaligned goals and wasted resources.

"Sometimes clients think I'm slowing them down," she said, "but I'm actually helping them move faster by ensuring we start in the right direction."

Galloway, a former brand manager in high-pressure corporate environments, agreed.

"It's hard to convince leaders to pause because everyone demands results now," Galloway said. "But when you take the time to ask the right questions upfront, you're not slowing down, you're accelerating clarity and meaningful action."

The cost of not asking "why"

At the core of strategic questioning lies one simple, powerful tool: asking "why." Although straightforward, this question can uncover misaligned objectives or faulty assumptions that drive projects off course.

"'Why creates clarity," Galloway said. "It pushes clients beyond surface-level goals or trendy buzzwords to connect with deeper business priorities."

It also challenges businesses to confront uncomfortable truths.

"Resistance to the 'why' often means there's no clear purpose behind the project," said Galloway. "And without purpose, you'll always end up asking the wrong questions."

Actionable steps toward research strategy clarity

Both offered practical approaches to implement strategic questioning in your research process. These techniques help create clarity while building a foundation for meaningful results.

Begin with a learning plan

Instead of commissioning broad, resource-intensive research, Galloway suggests first crafting a structured learning plan to prioritize objectives.

"You don't need massive studies or endless interviews when your goals are clear," she said. "Start small, stay focused, and it'll save both time and money."

Turn data into stories

Data is valuable, but it's the story behind the numbers that drives impact. Isabelle emphasized that asking meaningful questions upfront allows researchers to craft narratives that resonate.

"If we skip this step, we're reduced to reporting raw data, which holds little strategic value," she said.

Ask diverse "whys" for cultural brand insights

Purposeful questioning becomes even more important when engaging diverse audiences for brand insights. Galloway highlighted how deep questioning uncovered a key insight at Frito-Lay.

"Hispanic mothers prioritized their families' happiness over their own, while general-market mothers focused on balancing everyone's needs. Without strategic questions, we wouldn't have uncovered these differences."

Understanding cultural nuances is equally critical in regions like Quebec and English Canada.

Build collaborative alignment

Effective research relies on alignment between strategists and researchers.

"We're not here to direct research methods, our role is to clarify the strategic goals, so researchers can work with precision. When we align on the endpoint, everything else falls into place."

Create brave spaces for honest dialogue

And finally, don't shy away from challenging conversations. Look for "brave spaces" where uncomfortable questions are encouraged.

"True insights aren't born of protection," she said. "They come from courage and candor."

Clarity is the best shortcut

Both Galloway and Landreville stressed that strategic questioning is not a luxury but a necessity for modern enterprises. While it may feel like a delay, it’s not taking the time to ask the right questions ultimately streamlines the business process, saves costs, and delivers meaningful results.

Don't underestimate the power of starting with "why." It might just be the most valuable investment your research strategy can make.

Strategic questioning is the art of research strategy

At Sylvestre & Co., we blend cultural intelligence with strategic inquiry to help organizations find clarity before action. Our senior researchers work with clients to articulate the essential questions that reveal underlying business needs and cultural nuances.

Looking to build strategic clarity into your research strategy process? If so, it might be time to talk. Our team specializes in creating frameworks for purposeful questioning that respect both organizational goals and human complexity.

Insightful Inspiration features conversations with thought leaders in research, strategy, and cultural understanding. Listen to the full episode with Kathy Guzman Galloway on our website, where 50 years of human-centered expertise in brand insights comes to life.

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