Up the hill Backwards

I wrote in June about my early experience leading a remote team and the experimental tool I borrowed from behavioral economics to help foster the growth of my teammates. The ‘tool’ is a set of four questions I ask every two weeks during one-on-one sessions each designer.

  • How do you think you’re doing the last two weeks?
  • What’s the thing you’re most proud of last two weeks?
  • What’s something you’d like to improve on in the next two weeks?
  • What do you want your role to look like one year from now?

The questions help frame our conversations and provide a baseline by which the designers can measure their progress. If they look back and see several disappointing periods it can provide motivation. If they look back and feel good about their progress then they’re on the right track. If they’ve gotten ahead, but feel burnout coming on they can slow down to a nice renewable pace.

The first iteration contained just the first three questions. After the first month I realized those three questions alone did not provide enough context for them to zoom out—to imagine a line between where they were one year ago and where they want to be one year from now. The line needed to point somewhere tangible.

The fourth question was added to provide that context. It confronts them with their future on a regular basis and gets them thinking about their direction.

The first few times I asked the question the answers were inconsistent. It can be answered in a variety of ways, in just a few words, or with a very detailed picture. I needed a way to normalize everyone’s answers.

Around the same time I participated in a design exercise where someone suggested we use Amazon’s procedure for kicking off a project by first writing its press release. They call it “working backwards“. By imaging the announcement before building anything they make certain promises to themselves and their users. They end up with a rubric to test their concepts against. Does this UI live up to the promise? Does the concept appeal to their audience?

How does that translate to career development?

Instead of asking the generic question “What do you want your role to look like one year from now?” we added structure to the question by drafting formal job descriptions for the aspirational role they would like to have one year from now. They spent a few weeks drafting and then we discussed the results. After a few iterations we have a nice set of documents that paint clear pictures of the future.

By imagining a future and putting work into formalizing their vision, they’ve given themselves a trail of breadcrumbs toward becoming a better designer, project lead, or manager.

Now all they have to do is work backwards.



By Rick Banister

Designer at Automattic