Cap Watkins, Design Lead at Etsy, didn't set out to be a manager. He never imagined himself taking 12 talented designers under his wing, managing expectations, workflows, processes, and design collaboration. But, as it turns out – Cap is actually loving it.

Cap, who once studied creative writing, pivoted into the intersection of startups and design early on in his career. The scrappiness, he says, has made him better at what he does. He's planted roots at Formspring, a global social network for Q&A conversation, as well as Zoosk, an online dating service that uses big data and algorithmic patterns to identify potential suitors. Cap also spent time at Amazon, before making the switch to Etsy, where he dug his heels into usability and organizational operations.

Today, we're talking with Cap about Etsy, 2014’s prestigious Cooper-Hewitt Smithsonian National Design Award recipient, about showing the "messy" underbelly of your design work, celebrating failure within culture, and why design leaders need to do more than poke holes – they need to learn how to ask better questions.

Talk to Cap on Twitter as @Cap, and Tweet us with your favorite takeaway from the show at @BrandFever and #OnBranding.