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Why Deadlines Are Arbitrary and Meaningless

Anthony Casalena, founder and CEO of Squarespace, says that deadlines, at their worst, compromise design quality and burn people out.

Anthony Casalena, founder and CEO of Squarespace, the well-funded ($78.5 million) and well-known (Super Bowl ad) maker of website-building tools and software, shared the company's story this week in First Round Review, the online magazine for the VC firm First Round Capital.

For my money, the most surprising and refreshing takeaway was his flexible philosophy around deadlines.

"If we don't think we can deliver something phenomenal by a certain date, we'll just change the deadline," he says. "We tend to see a lot of deadlines as arbitrary and meaningless. At their worst, they compromise design quality and burn people out so much that they stop having good, creative ideas. Sprinting is not our core differentiator."

Reinforcing the Flexibiilty With Culture

This is a pleasingly contrarian take on the "fail fast" mantra, touted and successfully implemented by Aaron Levie, cofounder of Box, among countless others. 

While there are many arguments to be made for "iterating" as quickly as possible, and promptly getting your so-called "minimum viable" prototypes (MVPs) in front of would-be customers for early-stage feedback, there are some founders and aspirants who err on the side of building their initial prototypes a little too hastily. 

Of course, the fine line between slow-baked perfectionism and deadline-driven efficiency is one that all companies--and the individuals therein--have to navigate. And to be certain, the need for speed can often vary from project to project, or even depending on an organization's seasonal priorities. 

When it comes to Casalena's flexible-deadline philosophies, it's important to point out that he and Squarespace, which was founded in 2004 and now has 273 employees, have built a culture to support it--a workplace that has meshed and balanced the design world's aesthetic priorities with the software world's iteration priorities.

How do you build a culture like that? By hiring the right people.

Specifically, by hiring people who share your priorities when it comes to delivering, as Casalena puts it, "something phenomenal." In the First Round Review, Casalena lists three qualities that help him realize a candidate is an excellent long-term fit. One of the three is:

  • Has the right cultural mindset. "You want to all be fighting for the same thing. For example, at Squarespace we all have a similar aesthetic and are wired with a design-focused mindset," he says.

Casalena's two other hiring pointers also speak to "fighting for the same thing" and sharing an aesthetic sensibility. 

  • Understands your definition of "good enough." "I know I've hired the right person when I'm the one needing to pull them back from perfection," he says. "If I'm the one saying 90 percent is good enough so we can get it out there sooner, that’s about right."
  • Is committed to the same outcome as you. "This isn't just about the financial outcome, either," he says. "It's about the actual physical outcome, even the physical suffering it takes to make things good. You want to hire people who hold themselves and the products they build to the same expectations."

Those three bullet points on hiring--and Casalena's ability to execute on them--are surely a big reason why he can encourage flexibility around deadlines.

He's recruited a team--and built a company--that won't let a flexible-deadline culture preclude its productivity or commitment to delivering "something phenomenal." 

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