Microsoft Keyboard favorites key assignment

So i’m trying to set up a hotkey assignment on my Microsoft Keyboard Elite for Bluetooth (that’s what it’s called).  I want to assign hotkey 5 to open Windows Live Writer, an excellent program for blogging (I’m using it now to write this post).    I hit the “5” key, which is unassigned, and the installed Microsoft keyboard software helpfully pops up a dialog to allow me to choose the program to assign it to:

But when I hit Browse… what pops up is a generic file chooser sotensibly to give us the ultimate power to browse off into the bowels of our computers and choose any file we like: 

 

Even I, a technology veteran, am shocked at the thoughtlessness of this UI failure.   What I wanted to do was assign Favorites hotkey “5” to run Windows L ive Writer, and now Microsoft was asking me to navigate the file structure of my computer to find the binary executable program to do it.    This is so wrong on so many levels. 

For starters, Microsoft has broken the metaphor.   The conceptual model the user has in his head is of a “favorite” keyboard key is:  press key, run program.    By asking the user to involve the physical file system browser,  we have invoked a set of completely different and unrelated models.  The filesystem is a containment hierarchy of drives, folders, and items.  The identification of a specific program within the filesystem is another foreign model, more the domain of software writers and geeks, wherein the user must correctly identify which item in a specific folder is the correct Windows executable program.

How could Microsoft fix this?    By simply providing a pre-populated list of the likely and sensible choices for an application that might be one of my favorites.    I had recently installed Windows Live Writer.   I had run Windows Live Writer many times over the past few days since installing it.   I had pinned it to the Windows taskbar, which, for those of you not familiar with Windows 7, is the equivalent of marking it a heavy favorite since the taskbar’s primary purpose is enabling the quick launch of an application.    

Recommendations

Here are a few specific ways Microsoft could easily improve this interface.

• Provide a list of installed applications and enable the user to choose from them.   Enable the users to sort by name, installation date, or last access.
• Allow the user to choose applications refererenced by desktop shortcuts, pinned Start menu items, or Windows taskbar items. 
• Allow the user to choose applications that are currently running.

Conclusion

This failure, while it’s only on a specialized Microsoft keyboard, typifies the issues at the center of Microsoft’s failure to connect with people.    Microsoft’s software is often highly functionally oriented, emphasizing capabilities over tasks.   While at the end of the day, capability is king, in a commoditized market it is wise to continue to evolve.   Companies like Google and Apple get it;  it remains to be seen how quickly Microsoft can turn the battleship before it takes significant damage.