Ghost of Clippy-past

Cortana has some great functionality crippled by an obsolete, out-of-date set of concerns generated, perhaps, by Windows 8. Cortana wouldn’t be terribly out of place in 2010, but today?
A few days ago, Windows bamboozled me. A little pop-up appeared (grr, and stole focus): “If you tell me which teams you like – or don’t – I can tell you how they are doing”. My third thought(*1) was “who is this message from?!”
I’m just guessing it’s from Cortana, if so it seems like the Cortana team is for some reason resurrecting the worst of Clippy… (*2)
Thanks to daily interaction with Google, Amazon, Facebook, Siri, etc, a modern user will interpret “Ask me anything” on a device differently than they would have in 2010.
disablesearchIf your plumber has to google every step of a basic repair job for you, you’re going to try another plumber next time. You don’t hire an accountant on the basis that they “know the URL for TurboTax”.
When someone says “ask me anything”, the response “you can look that up on the web” quickly becomes a contradiction of the original statement.
Eventually, it feels like they lied.
That’s the current presentation of Cortana.

Sometimes Cortana presents you with a card that says
Cortana can do so much more! ^
I was genuinely excited for this, so I clicked it. There’s no great reveal. Just the blank “Ask me anything” UI.

pizzastoreWhen you get search results: the term “Best Match” gives the impression that the results are ordered, which makes the ordering, if there is any, feel random, weird … confusing. My search for “pizza” is greeted with “(search the web for) domino’s pizza greece” as a “best match”. (Screenshot from Store)

This critical, core, search UI is also one of the most retro pieces of tech in the Windows ecosystem, it would seem incomplete on a Windows 7 Phone. You can’t reorder the sections or the cards, you can’t right click to provide feedback that a result is inappropriate. The key/button/swipe you use for “back” everywhere else does nothing in Cortana (except maybe cause it to close).

I’ll give just one more example of how this UI is failing the product.

I was trying to launch “Putty”, an app installed on my PC.  I hit start and typed “Putty”.


I’m not sure why for this app it thinks that a web search is the best call, but hey. I’m not sure why “Putty” isn’t the first thing listed under Apps, but hey. Lets move past that.

It turns out that you can narrow down your searches by typing a keyword, so you can explicitly search the web with web: putty, or search for a folder with folder: putty, an installed app with app: putty. (Note:  other screenshots are from full-screen Start, apparently the results are different in menu mode…)


What if I want to search the Windows Store, generally branded as just “Store” throughout the UI?store: putty


It turns out that they’re apps, so that’s the keyword you need. How does Cortana reinforce this?


Cortana could be salvaged. I believe that, in order, its issues are: verbiage, authenticity and inconsistency. It’s OK, feature wise; it feels very dumb when you try to ask it questions – but that’s back to the wordcraft issues – it’s a search engine, not an AI.

There’s also a lack of feedback-based training: it doesn’t learn, so you go thru the same sequences of expect-like clippy q/a sequences to do what should otherwise be simple things.

*1 First thought: “What have I done to give my computer the impression I have *any* interest in /sport/ of any kind?”, second thought: “If you’re going to tell me how they’re doing whether I like them or not, why do you need my input in the first place?

*2 These toasts are optional, but (a) the option is now on by default, (b) the only ones I’ve seen so far read as desperate pleas for you to stop using <insert browser here> and please, please, try Cortana and Edge!

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