Great Questions Lead to Great Design

By Jason Robb

Jason Robb is a designer, consultant, writer, and speaker. He believes great design can make people happy. Coincidentally, he organizes the UX Book Club Boston to encourage healthy discussion about design, and smiles a lot.

Creating a great design is a challenging endeavor.  In my progression as a designer, I’ve found at least one way to make it easier: start by asking the questions that reveal important constraints. Without constraints a designer cannot operate, but if you don’t ask the right questions, small issues can lead to big problems down the line. Here’s a typical set of questions I use to sift out the constraints within a design project.

Always start with why

The highest level question a person can answer is “why” (as Simon Sinek, author of “Start With Why” explained in his 2009 TED Talk). As soon as I hit a roadblock when designing an interface, I ask myself, “Why are we designing this?” If I can’t answer why a page should be designed, then asking how it should be designed or what it should look like is irrelevant.

When in doubt, retreat to the high ground of asking “why.” Once you’ve answered why, you can safely dive deeper into the problem.

Who are you working with and who will influence the design?

Before the first pixel is pushed, understanding where I stand in the organization is critical for me to do my job effectively. I always ask “who will I be working with, and who will have influence on the work we do?” Along with that is usually a sketch of the relationships between myself, my client, and everyone else involved in the process. Understanding these relationships allows me to tailor my design documentation appropriately (wireframes, site maps, and user flows are examples of design documentation).  For example, if my wireframes are eventually going to land on an engineer’s desk, I’ll be sure to include notes in the margin about what databases we’ll need access to, or other equally nerdy things that enable them to do their jobs.

Where is the design being used?

I spend a great deal of my time focusing on where the end users are going to be using the product or service I’m designing. One of the best way to gain that understanding is through Contextual Design methods.  These include visiting the user in the location where they use a product. That way, I gain an understanding of which parts of the product are most relevant in the context of their environment.

Unfortunately, I don’t always have access to the end users. When that’s the case, I try to mitigate the risks of being blind to what end users are experiencing by asking the business and engineers questions about the users. They can act as a proxy for their customers, though I always take their input with a grain of salt.

What hidden assumptions are present in your design?

In his article Design Lesson 1 of 1, Andy Rutledge defines a few common design principles revealing a slew of questions behind each one. Examining rounded corners, he writes:

“A sharp or round corner is not its shape. It is an explanation of character and personality. What are you trying to say with your corners and why? And do you need corners and the structures they inhabit at all?”

Andy illustrates that the design decision to make a corner rounded or sharp can be backed up by sound judgement. Notice how he punctuates one of his questions with “why?”  He knows that the questioning doesn’t end once you get to the pixel-level in graphic design. In fact, I’d say it becomes even more rigorous and detailed as you delve into your design.

Stop asking questions and work with what you have

In closing, the more questions you ask, the better your chances will be to uncover useful information to inform your design decisions. Of course, the flip side is also true: it’s just as vital to know when to stop asking questions and make progress on your design. As Theodore Roosevelt said “Do what you can, with what you have, where you are.”

In every project, beginning with a framework of key questions will make your job a little easier. To recap the questions that I recommend:

  1. Start with why: If you can’t answer why, you are missing information—find it.
  2. Find out who is going to influence your work: Tailor your design documentation to best help your team.
  3. Gain empathy for your users: Soak up their natural environment and usage patterns. Empathy is worth its weight in gold.
  4. Assume your design is wrong: Poking holes in your design and exposing its weaknesses is a great way to make the design stronger.

What questions do you regularly ask your clients and customers? What questions have you forgotten to ask that later came back to haunt you? Post them in the comments section; we want to hear your questions and the answers you’ve found.

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  • Megan Grocki

    Great post Jason!

    There is no substitute for asking great questions. I always try to sniff out anything emotional in their responses and then say “tell more more about that” and then sit back for a wild ride of active listening.

    Looking forward to seeing other techniques, examples of great questions and comments.

  • Jason Robb

    “sniff out anything emotional” —good call! It’s the fuzzy stuff that’s an early indicator of hidden constraints. If someone has a hard time explaining something without saying “I feel” that’s a good reason to pry a little until it’s more easily understood in concrete words.

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