The Life and Death of Clippy
The Life and Death of Clippy
Tomorrow night, at 6:30PM, Dean Hachamovitch will come by Postlight and talk about his work over several decades at Microsoft. You’re invited! These talks are a great opportunity to learn about how software is made at scale, and we encourage people to ask a lot of questions.
Dean did many things while at Microsoft but one of the things he’s best known for is killing “Clippy,” the little animated bot that helped you use Microsoft Office. Here is a screenshot of a typical, totally genuine Clippy interaction:

Clippy was just one manifestation of the “conversational interface”/“intelligent agent concept in action,” but it was also the most widely-deployed.
Software is just too hard for humans, went the thinking. It’s too complex! Everyone went away and thought about that. They probably went to a number of retreats. Perhaps tired of bad coffee and unwanted backrubs, they came up with the only obvious solution: If software is too complicated, we need more software to serve as a guide!
In retrospect the strategy could have been “simplify the software” but do you want to go to war with the WordArt people? Hell no. Let’s animate a paperclip. Ignoring that Clippy freaked the women out:
Most of the women thought the characters were too male and that they were leering at them. So we’re sitting in a conference room. There’s me and, I think, like, 11 or 12 guys, and we’re going through the results, and they said, ‘I don’t see it. I just don’t know what they’re talking about.’ And I said, ‘Guys, guys, look, I’m a woman, and I’m going to tell you, these animated characters are male-looking.
Once unleashed in Office 97, Clippy was…not beloved. It was of course not always easy to make him go away, nor was the user ever sure that he was truly, actually blocked from popping up (this pattern would repeat with real, living men on Twitter). There were other creatures, like a wizard or a dog, Einstein or Shakespeare, but Clippy was the default, and came in for the heat. Dean can tell us more.
Clippy has a legacy: Microsoft has embraced him as a kind of tacky anti-marketing, and they trot him out from time to time with a wink.
when Windows 10 was announced. Ironic erotic fiction (NSFW) has been published—

The basic approach that Microsoft was using — trying to make something chatty to manage the complexity— is enjoying a resurgence. This article, “The Future of Conversational UI Belongs to Hybrid Interfaces,” popped up in various feeds over the weekend and explains where chatty, conversational interfaces are today.
Each message has the potential to be a mini application. It might be just an application that displays text, a photo, or alternatively presents an interface for something more complex in the constrained environment of a message cell. There is an unlimited set of opportunities to create bite size applications like a photo carousel, media players, mini games, inventory items, in-messaging payments, and many others.
It’s the same complexity and form fields as back in 1997, but over a network, and with consumer transactions as the goal. I guess the assumption is that humans now understand how to use software, and the big problem is that they’re not buying enough. So we need bots.
March 15 @ Postlight: Come see the man who killed Clippy
Dean Hachamovitch is one of the most influential human beings who ever served time in the software industry. He served as Corporate Vice President of Internet Explorer at Microsoft — and oversaw the launch of IE9. Under Dean’s management, Microsoft helped millions of people experience a secure, private, responsive, cross-platform, and standards-based Web.

That responsibility was earned: Before IE, starting in 1990, Dean led the development of several versions of Word and Office on both Windows and Mac. AutoCorrect? Dean. Automated formatting? Dean. Clippy? NOT Dean. His team was the one that killed Clippy in 2007. RIP.
Dean is a modest person and does not enjoy being promoted, but the truth is he’s had as much of an impact on culture and software as nearly anyone alive. He has graciously agreed to speak about his work at Microsoft, building software at a huge, global scale before anyone knew what that meant — and, if we are very lucky, he might do his Ballmer impersonation.
At Postlight’s offices in NYC.
Today’s Links
- Today’s variety of religious experience: Daesun Jinrihoe.
- Today’s old-school Unix fortune: “Nobody can be as agreeable as an uninvited guest.”
- Today’s North Korean slogan: “Let us put an end to the anti-DPRK hostile policy of the U.S., the source of confrontation and escalation of tension!”
- Today’s JavaScript library: Apostrophe — CMS with content editing and essential services.
- Today’s Creative Commons media link: ImageBase — Collection of free photos.
- Today’s freely available programming book: JAAS in Action.
- Today’s public data set: Our World in Data.
- Today’s religion: Neoshamanism.
- Today’s React component: jreact — React on server-side Java (with Rhino or Nashorn).
About Postlight
POSTLIGHT is a growing web agency in New York City. We build great things for the web and mobile. Check us out. Thanks!