How Squarespace’s Chief Creative Officer Emboldens His Team

David Lee aspires to “keep people slightly out of their comfort zones.”

How Squarespace’s Chief Creative Officer Emboldens His Team
David Lee, Chief Creative Officer at Squarespace [Photo: Celine Grouard for Fast Company]

David Lee is on a mission to inspire the millions of users of the website-building platform Squarespace to communicate more effectively and creatively online. Here’s how he pushes the company toward bold product design and award-winning marketing campaigns:

The Team Is Supreme

Lee is less interested in hiring superstars than in creating highly collaborative groups. “The team dynamic and chemistry is actually more important than pure, raw talent,” he said at the Fast Company Innovation Festival in November. “On paper, some people might seem like the perfect fit in your organization. But if you place them in a certain context, it completely backfires. You need people who feel compelled to work together, but who can still push each other.”

Be A Shrink

If you truly want to inspire people, you have to be more of a psychologist than a taskmaster. “Leadership is all about understanding people—learning what makes every member of your team tick. It’s fine and dandy to set a North Star that anyone can march to, but ultimately people are unique. Some want to be inspired, some need tough love. Your job is to pull on all these levers to find the best ways to get your team to do the best work of their lives.”

Make Them Sweat

Success should be measured less by what you’ve done and more by what you want to do in the future. “It’s my job to keep people slightly out of their comfort zones—to push them beyond what they think they’re able to achieve. There’s this delicate balance of setting milestones for people to hit and celebrating them, but then making sure to set the next milestone the next day.”