They usually say something like, “The page you are looking for does not exist.” But at the time, the team was really focused on developing a funny, unique voice for MailChimp. So they decided to call it an “oops” moment and started brainstorming funny ways to communicate that idea. Pretty soon, someone had designed a page showing a pregnancy test with a positive sign. Everyone thought this was hilarious—right up until Kiefer Lee took it to her CEO. “Absolutely not,” he told her. Looking back, she’s glad he killed it.

