Before Cortana, before Siri, before Alexa, even before smart interactive voice response (IVR) systems, there was Microsoft’s Office Assistant, one of the first widely deployed digital assistants that shipped as part of Microsoft Office in 1997. You might remember this feature better as the animated paper clip Clippy, even though Microsoft insists its (his? her?) official name is ClippIt. Doesn’t ring a bell? How about this: “It looks like you’re writing a letter.” 

Even though Microsoft officially retired Clippy in April 2011, the character continuously resurfaces as a meme in the cultural zeitgeist. Exhibit A: the back of Microsoft Cloud Developer Advocate Chloe Condon’s business card, which served as an inspiration for this video:

In this episode, a16z Board Partner and longtime Microsoft executive Steven Sinofsky shares his personal remembrances, lore, and archival footage of Clippy with a16z Operating Partner Frank Chen. Along the way, they discuss:

  • What problem the newly formed Microsoft Office team was trying to solve
  • Which Stanford University and Microsoft Research ideas informed the design of the feature
  • How the project was approved, what size team worked on it, and what BillG thought of it (warning: f-bomb ahead!)
  • What user testing the team did on both the look-and-feel of the feature, as well as the cast of characters that ended up in the gallery (including a sternly worded letter from the Microsoft Japan office objecting to 4-fingered characters)
  • How advice from legendary Disney animators led to the assistants having a stage to “perform” on
  • How the feature got launched and marketed, and early reactions from users and reviewers
  • Clippy’s cameo on Conan O’Brien’s late night show during the government antitrust case
  • How the team went too far with their templates and demos, ultimately resulting in the letter-writing meme  
  • Clippy’s elaborate retirement party in San Francisco, complete with a press release and a blues song (which you’ll hear in the video)
  • The nature of risk-taking in software development
  • What Clippy tells us about the future of digital assistants which are increasingly pervasive in the landscape with smart speakers, chatbots, and other social helpers

Enjoy watching the full arc of Clippy’s life from prototype to retirement to cultural meme.

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