To Get to the Right Solution, Ask the Right Questions—Here are 55 of Them

To Get to the Right Solution, Ask the Right Questions—Here are 55 of Them

Creative agencies—at least the ones worth working with—are question-generating machines.

This is because design thinking is driven by questions, and coming up with the right questions—and even a bunch of the wrong ones—is imperative to understanding the problem that needs solved, and coming up with the right solution for that problem.   

“If you think as a leader you can and should have all the answers,” says IDEO CEO Tim Brown, “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 Tim’s words in mind, here are fifty-five questions we ask at some point during the work we do with clients.

It’s by no means an exhaustive list, but these questions will get you started down the path of understanding. 




  1. What are our reasons to exist in this market?
  2. What is our mission, purpose, and position?
  3. What are our values?
  4. What is the emotional resonance behind our brand right now? What do we want it to be? 
  5. How do we evoke those emotions?
  6. How do we use our brand to inspire action amongst our current and prospective audiences?
  7. Is our brand’s intent clear?
  8. Is our brand relatable?
  9. Which brand architecture model best represents us? 
  10. How should our masterbrand and sub-brands cohere?  
  11. What is our brand’s rallying cry?
  12. How do our brand messages differ from one another? How are they the same?
  13. How do our RTBs (reasons to believe) get expressed throughout each of the sub-brands? 
  14. What will make us memorable? 
  15. How do we achieve brand cohesion?
  16. How does our tone change throughout each of the sub-brands? 


Identity Design


  1. What does our current logo say about us? What do we wish it said? 
  2. What’s the meaning behind the logo design? What story does the logo tell?
  3. Is our font unique? 
  4. Do we stand out for all the right reasons? If not, how can we? 
  5. What choices should we make regarding color, composition, typography, photography, and illustrations? 
  6. What are the rules for print and digital expressions? 
  7. How can we evolve the color palette?
  8. Is our design system accessible and compliant? Does it take users with special needs into account? 
  9. What collateral needs attending to immediately? 
  10. What collateral will have the highest impact? 




  1. Who is our target audience, where are they, and what do they believe in?
  2. How do we see the industry changing or evolving?
  3. Who are our competitors?
  4. What differentiates us from our competitors?
  5. How can we be better than our competitors?




  1. What problem(s) does our website need to solve?
  2. What current web pages drive the most traffic, leads, and user engagement?
  3. What analytics and tagging are currently in place? What needs to be?
  4. What do our users need? 
  5. What do our users want to do? What are they trying to find? Where do they get hung up? What frustrates them?
  6. What’s the hardest part about using the website? 
  7. What do users wish the website could do?
  8. What action do we want users to take?
  9. What are our content pillars?
  10. What should the sitemap look like? 
  11. What labels should we use?
  12. What taxonomies should we use?
  13. What is our CTA strategy? 
  14. Are there any data-modeling requirements?
  15. What are the needs of landing pages?
  16. What does the homepage look like? What does it feel like?  
  17. How do the subpages look and feel?
  18. Which front-end technology should we use? 
  19. Which front-end technology will give us the richest web experience? 
  20. Which code repository should we use for version control and collaboration?
  21. What tech integrations do we require? 
  22. Which social channels need to be integrated? 
  23. Which digital marketing strategies need to be considered?
  24. How does the SEO strategy impact the development process? 


See where the questions take you


As I mentioned before, this is by no means an exhaustive list, but it should give you the stimulus you need to come up with your own questions. Keep an open mind and remember that all questions are good questions. Be creative. Be fearless. Be diligent. 

Ask the questions that no one else will so you can design solutions that no one else has. 

Ask, and see where these questions take you.  

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