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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 “It looks like you’re writing a letter”?

Even though Microsoft officially retired Clippy in April 2020, the character continuously resurfaces as a meme in the zeitgeist. Try to see an assortment. Or check out Microsoft Cloud Developer Advocate Chloe Condon’s business card in her tweet (one of our inspirations for making this history):

In this episode, a16z Board Partner and longtime Microsoft executive Steven Sinofsky shares his personal remembrances of Clippy with a16z Operating Partner Frank Chen. They discuss these and many more vignettes from the history of
– What problem the newly formed Microsoft Office team was trying to
– Which Stanford University and Microsoft Research ideas informed the design of the
– How the project was approved, what size team worked on it, and what BillG thought of it ( 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 (dolphins! geniuses not named Einstein! leprechauns!):
– How a pair of legendary Disney animators inspired the “stage” the characters perform
– How the feature got launched and marketed, and early reactions from users and
– How Clippy got an elaborate real-world retirement party in San Francisco, complete with a blues
– Watch Clippy featured on Conan O’Brien’s late night TV
– What Clippy can tell us about the future of digital
– The nature of risk-taking in software product

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

***
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