Hotmail redesign: Too hot to handle?

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By Ina Fried
Staff Writer, CNET News.com
May 7, 2007 4:00 AM PST

MOUNTAIN VIEW, Calif.--Microsoft had been tinkering with Windows Live Mail for months, but testers still weren't happy.

The program was too slow to load, too different and, well, just not like the old Hotmail it was intended to replace.

It was a painful realization for the more than 100 managers and developers on the project. In banking on a snazzy Web 2.0 application to try to catch up to rivals Yahoo and Google, Microsoft had dramatically overshot its audience.

But Mike Schackwitz, one of the program managers on the mail redesign, had an idea.

Months earlier, a small team had started working on a second version of Windows Live Mail. At first, it was just a very limited program designed for people whose browsers wouldn't run the new program. But in recent weeks, the team had decided to add a few tricks to it and turn it into a "classic" version that felt more like the old Hotmail.

What if that version was the new Hotmail, or at least the default option for most people, Schackwitz thought.

In October, he approached a few colleagues with the idea. Although such a move would be counterintuitive, key leaders on the project quickly realized that he was right. Bowing to its users, and despite grumblings from the developers, Microsoft shifted much of the team away from the "full" version and onto classic.

On Monday, Microsoft took the beta tag off the Hotmail redesign, and its classic mode took center stage. The full version with its Outlook-like look and feel is still there for those who want it, but it's not the default interface.

The change was hard on many levels. It pushed the product behind schedule. It meant less time spent on the fancier Web 2.0 client that competes most directly with Gmail and Yahoo's new mail program. And it raised the question of whether Hotmail will ever move beyond its reputation as the Web mail program for the technologically challenged.

The legacy problem
It's a situation Microsoft has often faced in other parts of its business, particularly Windows. It has a tougher time making radical shifts, even necessary ones, because it has a large user base it can't afford to leave behind.

Special report
Hotmail's new address

An overhaul is the cornerstone of Microsoft's plan to win fans to its Windows Live services. See CNET News.com's Ina Fried's original report.

While Microsoft was building out the classic mode, Yahoo was adding other features, most recently building instant messaging directly into the new mail program. Google was refining its integration of chat, as well as building ties between Gmail and its online spreadsheets-and-documents program.

The shift to make classic mode the view most users will see was also painful from a morale perspective.

"A lot of the team felt dejected at this point," product planner Richard Sim acknowledged.

But the move was clearly necessary. Despite months of work, the main version of Windows Live Mail was still way too slow for many users' taste. It was particularly slow over dial-up connections, still used by roughly a third of Hotmail users, particularly outside the United States.

Microsoft had designed Windows Live Mail to feel more like a desktop program than a traditional Web page. To do so, however, such Web applications have to download a significant chunk of code before they can open a single message. Classic mode, which loads like a traditional Web page, doesn't allow things like drag-and-drop editing, but it feels much faster on a slow connection.

Classic mode wasn't the only bitter pill the development team had to swallow. Even in the full version, it turned out that many customers still wanted to select messages using check boxes rather than a mouse click or keyboard shortcut, much to the dismay of Microsoft's programmers.

"They were digging in their heels," Sim said.

Another popular feature in desktop e-mail programs is the "reading pane" that shows the top of an e-mail before it is opened.

But Sim's sister was among the significant group of Web mail customers who didn't want it. "It makes me feel vulnerable if I have this preview pane," Sim said she told him. The preview pane is still there in full mode, though Microsoft no longer opens the first message automatically in it.

Even changing the Hotmail name proved to be too much of a shift. What was once Windows Live Mail is now Windows Live Hotmail, a reflection of the fact that much of the venerable Web mail program has remained.

Microsoft also is holding back from quickly forcing its users onto the new version. Although those who sign up for Hotmail will automatically be taken to Windows Live Hotmail, existing users will still have to opt in, though Microsoft does hope to move all users over in a period of months.

Next page: Engine overhaul

The Match.com effect

If you open Windows Live Hotmail and notice that your first message doesn't automatically open in the preview pane, you can blame Match.com.

Initially, Microsoft figured people would like to see their first message. But, it turns out that many people don't necessarily want their co-workers or anyone else to see that Victoria's Secret special offer or the update from their online-dating service.

"They hated the fact that when you launched the product, it would automatically select the first message in the reading pane," program manager Ellie Powers-Boyle said. "They thought it was an invasion of their privacy."

Product planner Richard Sim said feedback was echoed loudly when he did field tests where he went to watch people in their homes to see how they used their e-mail.

"No. 1, I was just surprised that so many people use Match.com," Sim said. "When we were there, and the first message would show up in the reading pane, and it would be a Match.com e-mail, and they would get really embarrassed, we took that to heart."

--Ina Fried