Design Sprinting While Remote Working

One of my favorite designers who speak to the importance of craft in design is my Automattic colleague, Kjell Reigstad. He recently shared an illustration that he made out of hundreds of tiny little arrows. It reminded me a bit of something I shared on the topic of leadership a few years ago while working with John Donahoe and Dane Howard:

This little video describes the challenge that a leader has in “aligning” the folks in their organization to point generally in the same direction. When that happens, then everything starts to move. It’s really hard to make that happen, so it’s important that a leader spend more time “storylistening” than storytelling.

That ties into a convo I had with another Automattic colleague today, Filippo di Trapani, who pointed out a recent challenge in working with a large group of folks in a design sprint. Note that Automattic is a completely remote company — so we’re talking “100% online, design sprint.”

The usually very observant Filippo pointed out that the way he ran the sprint on Day One involved asking people to provide their thoughts on little virtual stickies in a shared online space. He then proceeded to read out each of the items … and he noted that it felt a little awkward because the entire team sort of receded in their level of engagement.

But on Day Two, Filippo shared how another of our Automattic colleagues, Brie Anne Demkiw, took a different approach than he did when she took leadership of the group.

What was different? According to Filippo, Brie asked each of the people who filled out a sticky to read them out loud. And then while each person read their sticky out loud, everyone else started to define categories in which each sticky could be moved to — while the reader was in the act of reading. 

What does that mean? It means that by Brie’s shifting to “arrow listening” mode quickly, it enabled the entire team to gather around and find ways to listen better to the individual arrow. And in doing so, it meant that after each arrow shared their stickies and handed off to the next arrow, that reciprocity could also occur as the session progressed. It turns out that while a sticky was being read, the other participants (literally “arrows” 🙂 ) were urging the sticky-reader to put their sticky into the categories they were collectively pointing towards.

How can I use this technique in my own work? Instead of getting stuck in your own “blah blah blah” as a leader, do the work of listening to what’s out there. You might find out something new and important that you’ve missed. And if you are in a well-designed, online collaborative environment you might find a faster way to … real collaboration with real co-investment. Imagine that!

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