Holy crap is that goofy looking! And those animated eyebrows were even goofier! And then he'd ask you really annoying questions like "Do you need help with that?" to things you don't need! Gah!
That was the general reaction. Clippy was universally mocked. Reviled. Other bad things.
But really, was it so bad?
Lately (20 years later) it seems that everyday a new 'assistant' is coming out. Siri, Cortana, Alexa, chatbots up the wazoo. Clippy asked you more questions, based on what you were doing and had answered already, just like a good chatbot. You didn't write to it natural language, but the intention was the same, help out the user by asking questions back and forth.
It was context dependent (Siri is not). It followed a decision tree to maintain context (most current chatbots have trouble with context). It doesn't use speech (like S/C/A) or even typed natural language (chatbots), but it was still an assistant to do things you weren't sure about doing.
Clippy didn't try to do NLP, but frankly the non-speech part of S/C/A and chatbots, just the text, is mostly picking out keywords using hardcoded scripts, not terribly different from hardcoded trees.
So what was so bad about Clippy?
The idea was right, lead people through tasks they are unsure how to do. The implementation as decision trees was both easy and well integrated. What the decision trees helped with...well maybe that wasn't so great. I know I turned off Clippy immediately because I knew what I wanted to do (haha no comment people from twenty years ago!).
But was that the main problem?
I believe the main problem was... the first thing I said, the superficially distasteful graphic and its smarmy animation. It wasn't with the suggestions (though those may have been too simple) it wasn't the use case (helping to write a letter) which was surely too simplistic, but it was just never pursued (unlike the more popular and well-deserved complaints about MS PowerPoint's Auto Content Wizard, a not too dissimilar concept to the assistant).
The problem was the front face of the feature. A weird laughable graphic. I'm sure the idea team thought it was cute and would draw people in with its informality. Fashion is hard to gauge. But the universal response of cringing was no fashion statement. It's hard for those people inside the design team/the makers to see what outsiders see. And sometimes organizations can be too...polite (I know I know, crazy. Sometimes people just don't tell you what they really think).
The major lesson of Clippy is that when designing an assistant/chatbot, first avoid smarmy (and get honest opinions). The second, which is not a lesson that people normally take from Clippy because they already turned it off because of the first point, is to make the assistant relevant (I know that's a bit broad). That is, make it help people with things they really want. SOmetimes wording makes a big difference "Do you want help writing a letter?" Of course not , I know exactly what I'm going to say to that lawyer! "Do you want help formatting a proper legal letter?" Oh. Right. Yes. Where does the return address and salutation and letterhead go? Yes, that is what people want to be asked for and helped with. So even the subtlest wording can make a difference. The third lesson? Remember the context of prior questions. It just makes things easier for a human.
But what really killed Clippy? Just the graphic. Nothing else, whether substantive or not, really came into play.
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