They have this incredible knack for integrating new features into their software that backfire, often in an effort to promote their other software.
They are always trying to copy Apple's awful proprietary model -- like how if you buy songs in the iTunes store, suddenly you need iTunes for everything, and you're buying an iPhone instead of a Droid, and.... you know. It's Apple everything.
But Microsoft lacks Apple's slick simplicity and overall user-friendliness. iTunes, iPhones, etc delivers on what users want, so they're willing to go Apple for everything. The word "innovation" seems to be paired with the brand "Apple" a lot, and for good reasons, but a lot of Apple's success isn't really about being new and fancy. It's about consistently satisfying their users' basic needs. (And much, much better marketing than Microsoft, but that's a story for another post.)
It's about asking a simple question: what does your end user WANT?
I mean that literally. Ask them, and then listen.
Marketing works this way, now more than ever. It used to be about making up a product and then finding the right narrative to sell it. It's become increasingly more fashionable (and more efficient) to just listen to people tell you what they want. Then you give that to them and they keep coming back.
As soon as you try a ploy that benefits YOU, and not your customer, you're on thin ice. Better make sure that new feature is AMAZEBALLS.
But this is what Microsoft actually tends to deliver:
The new Outlook for Mac! Now with MSN Messenger integration, for all your contacts on MSN Messenger!
Right? Who gives a f*#&?! Why don't you just link it to my old AIM account?
Because of this new feature, here's what happens. You get an email, and Outlook inserts the name of the contact in place of the 'From' email address. This is pretty standard, but actually kind of a pain if you want to know exactly where an email is coming from.
In my line of work, for example, I sometimes need to check that an email is coming from an '@mit.edu' address. Occasionally students from other universities email me about our programs or scholarships, or to ask for advising. That's not actually what MIT pays me to do, so...
I used to hover over the contact name to see the email address. Simple. Works in GMail! Google: good at ensuring that the delivery of basic is not impacted by the innovation of fancy.
In the new Outlook, if you hover over the contact name (which Outlook renders regardless of whether or not that person is a contact or even an actual person (see the above Sri Lankan spam as a perfect example)), you get a pop-up window that still just shows you the contact name... along with an MSN Messenger status.
Since I don't have that program, nor am I considering using it, the pop-up window just delivers this default message: "Presence Unknown."
For every email, every 'contact,' every time. "Presence Unknown." What does that even mean? Is this some kind of po-mo existentialist poetry? Outlook has decided that this is more important information than the email address of the person who emailed me.
How long do you think it took me to figure out what "Presence Unknown" means? Google it, and you find yourself in a lot of forums full of angry Outlook users demanding to know where their email is coming from.
To see the actual email address, I need to "double hover." Guess how long that took me to figure out.
The moral of the story? I despise Outlook. I am writing a boring blog post just to whine about how stupid Microsoft is for wasting my time figuring this crap out. And for slowing me down every time I need to look at an email address. (Also: can't copy/paste that little yellow box! For that, you need to open the contact or forward the email -- more clicks, more time wasted.)
Frustration! And for what? Because they tried to get all fancy in a very self-serving way, and wound up obstructing a simple, basic function that I require of my email software.
You can't sell fancy if you can't deliver on basic.
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