tap tap is this thing on? Welcome to the first email edition of matthewstrom.com. Thanks for joining me in this weird experiment in publishing and distribution.

This essay was inspired by Richard Feynman's concept of "The Pleasure of Finding Things Out." I'd highly recommend reading Feynman's writing on science (not the autobiographical stuff) if you're interested in asking better questions .

Before, after, and/or while reading this, please put on Stereolab's "Freestyle Dumpling." It's a newly-reissued outtake from their 1996 album Emperor Tomato Ketchup.

And now, on with the essay.

The Role of Doubt in Design

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At a recent happy hour, I struck up a conversation with a product manager. I told him I was a product designer, and he asked "one of the good ones, or one of the bad ones?" A designer on his team — a "bad one" — asked too many questions. Questions like "Why are we building this now?" "Are we sure this is the right problem to solve?" "Why don't we approach the problem in a different way?"

I immediately recognized this type of designer, because sometimes, that's exactly who I am. A question machine. A doubter.

While it’s important to acknowledge uncertainty, doubt isn't always the right mindset. Sometimes it’s ok to ask questions, but most times, it's your job to have answers. So how do you know when — and more importantly, how — to express doubt?

Don't be a question machine

It’s hard to know when it’s appropriate to express your doubts. Here are a few questions that help might help:

1. Are there lots of unknowns? If you've already gathered lots of data, research, or understanding, your colleagues will expect you to have answers.
2. Is there time to explore? If you need to move fast, it might be better to go with your gut feelings.
3. Is there a lot at stake? Sometimes, being wrong isn't that bad. If the stakes are low, just ship the dang thing.

If there are a lot of unknowns, if you have time and energy, and if there's a lot to be gained, doubt can be a powerful tool. But even when it's appropriate to doubt, be careful not to fall into the role of a question machine. Expressing doubt with question after question can come across the wrong way: at worst, your doubt might be taken personally, especially if you question someone else’s decision or idea. Instead, try to doubt constructively.

Constructive doubt creates curiosity. It compels exploration. It’s easy to tell if you’re on the right path: constructive doubt means you don’t care who’s right.

How to doubt constructively

Use the Socratic method

The Socratic method is a form of constructive dialogue pioneered by (you guessed it) Socrates. Socrates was fond of insisting that he knew nothing. When asked a question, he would often answer indirectly, in the form of another question. Socrates’ questions were constructive: they would guide the original question-asker to the right answer.

When formulating your own questions, focus on where your doubt can be most constructive.

Make sure your questions come from a sincere curiosity. Avoid these kinds of questions:

• A leading question that suggests a particular answer or contains information the inquisitor seeks to have confirmed
• A suggestive question that implies that a certain answer should be given in response
• A loaded question that contains a controversial assumption
• A question based on a false dichotomy — that is, assuming there are only two answers (yes or no) when there, in fact, are many more

Use the Scientific method

Building on Socrates’ philosophy of knowing nothing, scientists in the 13th, 14th, and 15th centuries formulated processes of making and investigating observations about the world. What we today call the scientific method is really a whole family of ideas, each based on the following structure:

1. Ask a question \ Just as in the Socratic method, a good question is the first step to constructive doubt.
2. Make a hypothesis \ A hypothesis is a guess that can be proven true or false.
3. Test your hypothesis \ Commit to proving your hypothesis either true or false.
4. Repeat steps 2 & 3

While this process seems completely obvious to us now, it sparked a revolution in early modern science. The major innovation was the inclusion of hypotheses and tests; it isn’t enough to simply ask questions.

Here’s how to apply the scientific method to design: before asking a question, formulate a plan to answer the question. Then, explain the plan. For instance, instead of asking "Why are we building this right now?" pick your favorite prioritization framework and offer to help the team organize their roadmap.

Stay curious

It's easy to question others' ideas and plans, and I often express doubt at the wrong time. But as Richard Feynman¹ said, doubt is the key to progress:

"It is imperative in science to doubt. To make progress in understanding we must remain modest and allow that we do not know. You investigate for curiosity ... it is not that you are finding out the truth, but that you are finding out that this or that is more or less likely."
— Richard Feynman, The Relation of Science and Religion

Doubting is good! At its best, doubt doesn’t increase uncertainty, or cast an idea in a negative light. It's a way to express curiosity. Curiosity leads to understanding. That's the key. The more we can contribute to the collective curiosity of our peers, the more we can be seen as the "good" designers.

As usual, a very heartfelt thanks to Josh Petersel for reviewing a draft of this essay