Nick Wingfield has a Windows 8 story in the New York times that provides a pretty good summary of everything we’ve heard on the tech blogs over the past few months. This passage from Fresh Windows, but Where’s the Start Button? stood out for me:

Many of the familiar signposts from PCs of yore are gone in Microsoft’s new software, Windows 8, like the Start button for getting to programs and the drop-down menus that list their functions.

It took Mr. McCarthy several minutes just to figure out how to compose an e-mail message in Windows 8, which has a stripped-down look and on-screen buttons that at times resemble the runic assembly instructions for Ikea furniture.

“It made me feel like the biggest amateur computer user ever,” said Mr. McCarthy, 59, a copywriter in New York.

If your software makes users feel stupid, you’re in big trouble. Quotes like Mr. McCarthy’s is a manifestation of the age-old legacy software dilemma that Microsoft faces with Windows: do you scrap the thing and start over, or evolve what’s already there? Microsoft chose to start over, and we’re about to see if the gamble is going to pay off for them.

My money is on the argument that Joel Spolsky made in April 2000 in Things You Should Never Do, Part I:

When you throw away code¹ and start from scratch, you are throwing away all that knowledge. All those collected bug fixes. Years of programming work.

You are throwing away your market leadership. You are giving a gift of two or three years to your competitors, and believe me, that is a long time in software years.

You are wasting an outlandish amount of money writing code that already exists.

Or to bring it closer to design (and users) — as I argued in The Data-Pixel Approach To Improving User Experience:

The main problem with big redesigns is that, even though objectively the UX might have been improved, users are often left confused about what has happened and are unable to find their way. In most cases, making “steady, relentless, incremental progress” on a website (to borrow a phrase from John Gruber) is much more desirable. With this approach, users are pulled gently into a better experience, as opposed to being thrown into the deep end and forced to sink or swim.

I think we’re going to see a lot of sinking in the coming weeks…