When Progress Feels Like Success

A note on milestones

There's a question I always liked asking other designers when talking about work.

How did you know you were making progress?

The answer was usually a description of some flavour of a design process—the difference in approaches within our field can be quite interesting. There's always something to learn or, better yet, steal to make my execution of the Unsexy Middle Bits more effective.

Then there was my favourite follow-up.

How did you know you were successful?

There was a look, a pause, and the answer, tinged with disbelief.

"We launched?"

Earlier this year, I spent a large chunk of my time interviewing product designer candidates. Screening calls feel like ticking off a checklist during an awkward first dance, so why not just chat design instead?

I asked my questions and, almost without fail, the success definition for a lot of the projects I heard about was "the launch". And a few seconds of awkward silence afterwards.

One last difficult conversation, a final round of revisions, a handover to engineering makes progress look and feel like success. Time and budgets make milestones matter more than solved problems.

I wrote the opening paragraph of this note when the lockdown first started. I stopped when I realised how much of my work doesn't have a success metric—its only outcome is a concluded contract or a closed ticket. And I realised the question I so liked isn't fair.

"What did you want to know from the customers who'd used it?"