At Six06, we believe the best strategies don’t start with answers—they start with questions. Strategic consultancies worth working with are question-generating machines.

Design Thinking is built on this principle. As IDEO’s Tim Brown puts it: “If you think as a leader you can and should have all the answers, then you’re both wrong and significantly constraining the capacity of the organization to be creative. The best leaders are not coming up with answers, they are coming up with great questions.”

With that in mind, here are 55 questions we often ask in our work with clients. They’re not exhaustive, but they show the kind of inquiry that creates clarity.

Brand & Identity

• What are our reasons to exist in this market?

• What is our mission, purpose, and position?

• What values define us?

• What is the emotional resonance behind our brand today? What do we want it to be?

• How do we evoke those emotions in customers and employees?

• How do we inspire action among audiences?

• Is our intent clear? Is our brand relatable?

• Which brand architecture model best represents us?

• How should our master brand and sub-brands cohere?

• What is our rallying cry?

• What makes us memorable?

• How do we achieve cohesion across messages, tone, and design?

• What does our current logo say about us? What story should it tell?

• How can we evolve our visual system—colors, typography, imagery—while maintaining accessibility and compliance?

• Which brand assets will have the greatest impact if refreshed first?

Audience & Market

• Who is our target audience? Where are they? What do they believe in?

• How is our industry changing or evolving?

• Who are our competitors?

• What truly differentiates us from them?

• How can we be better—not just different?

• What proof points (RTBs) will resonate most with customers?

• How can we structure offerings or messages to align with audience needs?

Digital Experience

• What problems should our website solve?

• Which pages drive the most traffic, leads, and engagement?

• What analytics and tagging are in place—and what’s missing?

• What do users need? What do they want? What frustrates them?

• What’s the hardest part about using our site?

• What do users wish the site could do?

• What actions do we want them to take?

• What are our content pillars?

• What should the sitemap look like?

• What taxonomies and labels should we use?

• What’s our CTA strategy?

• Do we have data-modeling requirements?

• How should the homepage feel? The subpages?

• Which technologies will deliver the richest experience?

• What integrations are required (CRM, ERP, marketing tools)?

• Which social channels need to be embedded?

• How does our SEO strategy affect design and development?

• What’s our approach to landing pages?

• How do we balance immediate lead-gen with long-term brand building?

Ask, Then Design

This isn’t a checklist to run through once. It’s a mindset. Asking the right questions—again and again—is how organizations uncover clarity and design solutions that matter.

During pivotal moments—M&A, growth plateaus, leadership changes, digital transformation—the stakes are too high for assumptions. You don’t need all the answers. You need the courage to ask the right questions, and the discipline to follow where they lead.

Ask, and see where the questions take you.