Designer Journeys 🗺️

Sometimes it’s a little better to travel than to arrive.

Robert Pirsig, Zen and the Art of Motorcycle Maintenance

I interview a lot of designers in the course of any given week. Less than half have taken the usual path to becoming a designer. Most took a more meandering route, stumbling upon design through some random, happy accident, with little formal training.

Personally, I landed solidly in the “happy accident” cohort. I started studying computer science, convinced that was my path*. And I never considered becoming a designer until long after I was already doing design work.

In the years since, I’ve worked in a variety of roles — from consultant, to product designer, to leading design teams, to hiring designers. No matter the specific role, you start to realize that you’re always designing. You might move on from designing interfaces to designing the high-level strategies. Or, as a manager, you become focused on designing the environment for your team to create great products. The tools you use from the toolkit may vary — perhaps you design using words and influence rather than pixels — but the same design process and thinking applies.

Working on the Design Ops team at Automattic, the designers we hire are our users. We can map the journey, and design their experience, just as we would for users of our products.

As we’ve run journey mapping exercises with our designers, we’ve look for:

  • What are the pain points? There are always the obvious ones that everyone knows and agrees on — but what about the ones we’ve gotten used to and don’t see as clearly anymore? What about new ones that have emerged as the org has grown and changed?
  • How does the experience differ for veterans, who have been around for several years (or more), from those who have joined in the last year? Do people have different mental models? Different pain points? Do they use tools differently?
  • What moments stand out as particularly meaningful, either positive or negative? Which moments do people remember, even after they’ve been with the company for years? What are the turning points?
  • Who are the outliers? Who is succeeding in areas that others are struggling? What can you learn from them?

Think of it as a high-level retrospective: What is the experience of being a designer at your company? How does it affect the quality of your product, and the business impact your designers can have?

*Fortunately I got distracted by this interesting little department called Cognitive Science. 🙂

By Brie Anne Demkiw

Designer hiring lead @ Automattic. Work in progress. Because it's there.


I bumbled into design (and particularly web design) after failing at, or attaining only middling success in, a variety of other creative/professional fields. (And before that I failed at service jobs.)

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