Microsoft Bing chatbot Sydney: helpfully moody like Knight Rider’s KITT, bad at search


Despite Google having 92% of the search market and Microsoft Bing having 4%, Bing continues to hog headlines. Forget the new Google Bard AI search. This week, it’s been all about Microsoft Bing chatbot Sydney. And we’ve got the best quote, best headline, and best analysis all picked out for you.

First up in today’s awards is NYT’s Kevin Roose who, after using Sydney extensively, summed it up with the best business news quote of the week, LOL!

“[Sydney seemed] like a moody, manic-depressive teenager who has been trapped, against its will, inside a second-rate search engine.”

Next up in Microsoft Bing chatbot Sydney awards is best headline, which goes to The Verge for this gem:

Microsoft Bing is an emotionally manipulative liar, and people love it - The Verge - best search wars headline - via The Basis Point

Roose’s quote, The Verge’s headline, and the flood of Sydney coverage get at how intrigued people are by AI assistants.

And this has been a thing since decades before Microsoft’s Sydney, or Siri’s newer condescending “Umm, hmmm?” response (are we the only ones noticing this?!).

It reminded us of Knight Rider’s KITT who was helpful to The Hoff for sure, but definitely moody, with an easily bruised ego.

Which gets at the two most important questions:

1. Will AI selflessly help us or turn against us?

2. Is Microsoft Bing chatbot Sydney any good at web search?

Today’s final award winner is for best analysis of Microsoft Bing search, and goes to Ben Thompson at Stratechery for answering both questions.

He did a signature deep dive on this topic and ultimately found that, while Sydney seems coded to do good for humans (moodiness aside), this Microsoft Bing chatbot is no good at search.

Which brings us full circle to BofA’s search engine wars research Robyn covered to start the week.

Don’t you have to be, like, the best in the world ever at web search to change this pie chart?

Google search engine market share vs. competitors Microsoft Bing and Yahoo - BofA Global Research via The Basis Point

Or will Microsoft Bing chatbot Sydney be so much more than search to people, and build new markets we don’t even know exist yet?

Here’s all the links so you can read this weekend and decide for yourself.

Hit us with questions. We promise no moodiness in our answers. But fair warning, we might consult our smart toasters first.


Will Microsoft Bing win AI search wars? Google it.

Stratechery’s Ben Thompson on if Bing Sydney chatbot is good/bad for humanity/web search

Microsoft’s Bing is an emotionally manipulative liar, and people love it (The Verge)

A conversation with Bing’s chatbot left me deeply unsettled (Kevin Roose, NYT)




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