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Unpacking Design Problems

Jordan Moore

The answer is at the bottom of the article

The best puzzles are the ones that demand more of you. When the answer appears obvious, but you second guess yourself. When you know there’s more to it than meets the eye.

Nob Yoshigahara’s infamous number tree puzzle is certainly one of my personal favourites for just these reasons. It gives you a set of information and asks, What do you make of this?

Puzzles are a great tool for strengthening mental muscles that can help unpack design problems. They push you to adopt a different mindset and perspective, challenge assumptions, study intently, and look closely. Like a puzzle, difficult design problems evoke that same moment of epiphany when you peel back the layers to find hidden truths.

But design challenges are not quite as easy as puzzles, which have the answers hidden in plain sight. With puzzles, all the pieces are available to you: You just need to put it together. With design problems, you need to find the pieces first, then put everything together.

This can be daunting, but there are methods, tactics, and techniques you can reach for to help facilitate these discoveries.

First principles

Although used heavily in the field of physics, Aristotle’s method of reasoning known as “first principles” originated as a means for organic reasoning (as opposed to looking at analogies, which are often riddled with errors).

When applied to design problems, you start with an observation, such as a requirement in a project brief. Then you ask why until you arrive at the most basic understanding of the truth of the problem. This provides a solid foundation to build upon.

First principles force you to look at the problem without using other people’s preconceived ideas and attempts on how to solve it. When you use this approach, you automatically generate new value. It’s certainly cognitively more intense, but in my experience it produces more original and valuable results.

What happens if you arrive at the same conclusion others have already reached? Is this method a waste of time?

Mike Bithell, an independent game developer, sums this up nicely:

“Oftentimes, when trying to reinvent the wheel, you end up with a wheel. But there is a nice moment of ‘huh, I guess that’s why people just use wheels’… that process of justifying the standard is satisfying, if massively wasteful. Still. Cool wheel.”

For a good example of first principles in action, try this Wikipedia experiment. Click on the first non-parenthesized link in any random article and follow the chain. It will lead you down a path toward the most basic understanding of any concept. Strangely, approximately 80% of articles deconstructed in this manner bring you back to the Wikipedia article about philosophy.

Question everything

“Judge a man by his questions rather than by his answers.”


A design problem is only as difficult as the questions you ask of it.

Good questions don’t necessarily lead to definitive answers, but rather further questions. The amount of additional questions tends to correlate with the value hidden within the problem. If a question is easily snuffed out and the conversation cut short, it might not be as provocative as you originally suspected.

Some good starting points for exploratory questioning are:

  • Why is this a problem?
  • What makes you believe this is true?
  • What is your biggest challenge?
  • Who does this well?
  • What question did I not ask that would be valuable to know?

Feel free to use why liberally. Why is like a jackhammer for drilling through a problem’s layers. Why is flexible enough to get to the basic fundamentals (see: first principles), but can also be used to dig deeper into the problem you’re facing.

Sometimes, the best follow-up question is no question at all. A tactical silence can encourage your client to fill in the gap and reveal additional knowledge that might have otherwise been overlooked.

Collaborative understanding

Your strength as a product designer is determined by your ability to provide valuable solutions that address your client’s business goals and objectives. This can only be achieved if you deeply understand the original problem.

I find it beneficial to collaborate intensely with the client to define the problem(s) you’re going to address. Don’t take the version defined in the brief as the be all, end all. Explore it completely, break it down to first principles, build it back up, and communicate the problem back to the client.

This demonstrates your understanding of your client’s problems, your ability to grapple with problems, and your client’s understanding of their own problems. It creates a good starting point, and it’s the perfect time to demonstrate exactly how you’re going to test assumptions and measure success.

“A design lives and dies by its designer’s understanding of the problem. Understand the problem.”

Jared Erondu

A few more back-pocket methods

There are always more ways to test your solutions.

For example, Occam’s Razor is a mental model that suggests that the simplest solution — the path of least resistance — tends to be the right one. Although it isn’t always indicative of the truth, it’s a good technique to help avoid assumptions and analogies.

It’s also worth implementing techniques that help remove biases and ensure objectivity. One of my particular favourites is “steelmanning,” or building the strongest possible counter-argument to your solution. Adopting both for- and against-mindsets as you pursue a solution is hugely valuable; it not only produces a better solution, but arms you with a defence against the alternative.

The path to delivering value in product design isn’t through shiny user interfaces. Like a good puzzle, it lies in your ability to approach the problem from an inquisitive perspective, assemble the pieces of information you need, explore fundamentals and truths, and build back up to the definitive solution.

No one said it would be easy.

Answer: 12