Hotmail redesign: Too hot to handle?
Microsoft embarks in a years' long redesign of its Web mail program only to find most of its users like things the way they are.
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
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.
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.
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
Images
Just a basic version at the start, "classic" mode has become the default for the redesigned e-mail program.
May 7, 2007
As Microsoft gets set to launch its revamped Web mail service, here's a peek at how its look evolved.
May 7, 2007
Microsoft's Mike Schackwitz works under the hood on the veteran Hotmail service.April 26, 2006
Related stories
Microsoft still trying to answer Google's wake-up call
Yahoo opens up e-mail APIs to outsiders
Yahoo Mail to offer unlimited storage
Microsoft sticks with Hotmail name
Hotmail's replacement is going Dutch
Microsoft to bring Hotmail onto the desktop
Windows Live beta is delivered
News from around the Web
Windows Live Hotmail to debut Monday
Microsoft's Hotmail brand will live on
Thousands fall for Hotmail prank
Yahoo blows roof off e-mail storage
Google ratchets up Gmail storage
Gmail opens its doors to the world
Maybe you should back up your own e-mail
Credits
Editors: Anne Dujmovic, Mike Ricciuti
Design: Andrew Ballagh
Production: Jessica Kashiwabara
(continued from previous page)
The redesign effort, even its more ambitious aspects, is not a total wash, however.
Both the classic and full modes sit atop a far more modern engine, the internal part of the mail system. With Hotmail, Microsoft was at the end of its development rope. Every new feature basically had to be "hacked" into the code.
The new code can support multiple interfaces, not just Hotmail's classic and full modes, and can support sending mail information to other Microsoft properties as well as potentially to third parties.
Already, Microsoft has said it will use the new mail engine to power Office Live mail accounts as well as a new Windows Live @ Edu effort, in which Microsoft is trying to get universities and public-school systems to allow it to power their mail.
December 1997
Microsoft acquires Hotmail and its 8 million users.
December 1998
Hotmail tops 30 million users.
December 1999
Hotmail hits 52 million users.
April 2004
Google announces Gmail.
July 2005
Microsoft demos improved Hotmail (code-named Kahuna) at a conference for financial analysts. It starts public testing of the product.
September 2005
Yahoo launches a limited U.S. beta of its improved Yahoo Mail service with features like drag-and-drop organization and a built-in RSS reader.
November 2005
Microsoft announces Windows Live, including plans to rename Hotmail as Windows Live Mail.
October 2006
Amid pushback from users, "classic" mode is made the default for the revamped Hotmail.
November 2006
Windows Live Mail drops its beta tag in the Netherlands but remains in testing in the United States and elsewhere.
February 2007
Microsoft announces that a Web mail initiative called Windows Live Hotmail.
May 2007
Windows Live Hotmail loses its beta tag worldwide.
For those who really want a more Outlook-like experience, Microsoft has another option: Outlook. Microsoft plans to make available in a couple of weeks a new test version of its Outlook connector software that will enable anyone with a copy of Outlook 2003 or Outlook 2007 to use the software to access Windows Live Hotmail messages and contacts.
Microsoft also plans to offer a separate Windows program, Windows Live Mail, which is similar to the Windows Live Mail desktop program that the company has been testing. That software, set to run on Windows XP and Windows Vista, is designed to work with Hotmail as well as e-mail accounts from rivals. It will feature contextual advertising tied to the contents of users' e-mail, though users will be able to turn off the "active search" feature.
Windows Live Mail will be one of Microsoft's first desktop programs to include advertising, though the company is
Kevin Doerr, the Windows Live general manager in charge of the redesign, likens Microsoft's lesson of going too far with the Hotmail redesign to that of
"Even in software, you can go broke underestimating how little change people want to experience," Doerr said.
Microsoft isn't alone in its challenges trying to get Web mail right. Yahoo's redesigned mail is still in beta, as is Google's Gmail. Yahoo plans to drop the beta moniker in the coming months, while Google would not say just when it will move out of beta.
Yahoo has also found that some users want to use check boxes, adding back the boxes in its most recent test version, which is being rolled out to current users.
"We thought it would be a natural enough experience for users that they would be able to drag and drop, and use keyboard shortcuts," Yahoo spokeswoman Karen Mahon said. "The feedback we heard from our users is, they were lost without the check boxes, so we put them back."
In some ways, Microsoft's failures worked to its advantage. Few workers would have been excited by the prospect of building a new mail engine rather than leaving the interface largely unchanged. It might have also proved a tougher sell to get the resources needed for a ground-up rewrite.
Even Sim, who joined the Hotmail effort in August 2004, said it might have been a tougher sell for him, had he known how much would have to stay the same.
"I came thinking I would change the way people would communicate online," Sim said.
Indeed, that's the same draw Gmail product manager Keith Coleman sees in his job. "It's really exciting to do that because you can change the way people's lives work," he said. "The risk, of course, is something like what it sounds like Hotmail is seeing. If you take too big a leap, people get lost."
The Hotmail team believes that, despite taking a circuitous route, it has found a happy medium. But it doesn't plan on staying in the realm of the comfortable forever.
"That doesn't mean you shouldn't continue pushing," Doerr said. "It means you need to understand that and honor that and figure out a way to transition them from where they are today to where they should be."
No forwarding allowed
What will now become the primary interface for hundreds of millions of Web mail users was originally designed as a fallback.
The first version of what is now Windows Live Hotmail's default "classic" view was rushed out to offer a better option than what some beta users were getting--an error message saying the new Hotmail didn't work with their browser.
"We just shipped immediately anything we could ship," program manager Ellie Powers-Boyle said. "You could view mail. You could send mail. You couldn't forward mail because we didn't have time to add that button."
Not too much later, Microsoft decided that it needed not only something for older browsers, but also an option for those who didn't want as radical a makeover as the new Web 2.0-style mail program.
Months later, it decided that there were more of those people than those who wanted the new version. The company shifted the bulk of its engineers to work on the classic mode, completing its transformation from Hotmail's stepchild to its poster child.
And, yes, the Forward button works just fine.
--Ina Fried
Images
Just a basic version at the start, "classic" mode has become the default for the redesigned e-mail program.
May 7, 2007
As Microsoft gets set to launch its revamped Web mail service, here's a peek at how its look evolved.
May 7, 2007
Microsoft's Mike Schackwitz works under the hood on the veteran Hotmail service.April 26, 2006
Related stories
Microsoft still trying to answer Google's wake-up call
Yahoo opens up e-mail APIs to outsiders
Yahoo Mail to offer unlimited storage
Microsoft sticks with Hotmail name
Hotmail's replacement is going Dutch
Microsoft to bring Hotmail onto the desktop
Windows Live beta is delivered
News from around the Web
Windows Live Hotmail to debut Monday
Microsoft's Hotmail brand will live on
Thousands fall for Hotmail prank
Yahoo blows roof off e-mail storage
Google ratchets up Gmail storage
Gmail opens its doors to the world
Maybe you should back up your own e-mail
Credits
Editors: Anne Dujmovic, Mike Ricciuti
Design: Andrew Ballagh
Production: Jessica Kashiwabara
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
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.
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.
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
Images
Just a basic version at the start, "classic" mode has become the default for the redesigned e-mail program.
May 7, 2007
As Microsoft gets set to launch its revamped Web mail service, here's a peek at how its look evolved.
May 7, 2007
Microsoft's Mike Schackwitz works under the hood on the veteran Hotmail service.April 26, 2006
Related stories
Microsoft still trying to answer Google's wake-up call
Yahoo opens up e-mail APIs to outsiders
Yahoo Mail to offer unlimited storage
Microsoft sticks with Hotmail name
Hotmail's replacement is going Dutch
Microsoft to bring Hotmail onto the desktop
Windows Live beta is delivered
News from around the Web
Windows Live Hotmail to debut Monday
Microsoft's Hotmail brand will live on
Thousands fall for Hotmail prank
Yahoo blows roof off e-mail storage
Google ratchets up Gmail storage
Gmail opens its doors to the world
Maybe you should back up your own e-mail
Credits
Editors: Anne Dujmovic, Mike Ricciuti
Design: Andrew Ballagh
Production: Jessica Kashiwabara
(continued from previous page)
The redesign effort, even its more ambitious aspects, is not a total wash, however.
Both the classic and full modes sit atop a far more modern engine, the internal part of the mail system. With Hotmail, Microsoft was at the end of its development rope. Every new feature basically had to be "hacked" into the code.
The new code can support multiple interfaces, not just Hotmail's classic and full modes, and can support sending mail information to other Microsoft properties as well as potentially to third parties.
Already, Microsoft has said it will use the new mail engine to power Office Live mail accounts as well as a new Windows Live @ Edu effort, in which Microsoft is trying to get universities and public-school systems to allow it to power their mail.
December 1997
Microsoft acquires Hotmail and its 8 million users.
December 1998
Hotmail tops 30 million users.
December 1999
Hotmail hits 52 million users.
April 2004
Google announces Gmail.
July 2005
Microsoft demos improved Hotmail (code-named Kahuna) at a conference for financial analysts. It starts public testing of the product.
September 2005
Yahoo launches a limited U.S. beta of its improved Yahoo Mail service with features like drag-and-drop organization and a built-in RSS reader.
November 2005
Microsoft announces Windows Live, including plans to rename Hotmail as Windows Live Mail.
October 2006
Amid pushback from users, "classic" mode is made the default for the revamped Hotmail.
November 2006
Windows Live Mail drops its beta tag in the Netherlands but remains in testing in the United States and elsewhere.
February 2007
Microsoft announces that a Web mail initiative called Windows Live Hotmail.
May 2007
Windows Live Hotmail loses its beta tag worldwide.
For those who really want a more Outlook-like experience, Microsoft has another option: Outlook. Microsoft plans to make available in a couple of weeks a new test version of its Outlook connector software that will enable anyone with a copy of Outlook 2003 or Outlook 2007 to use the software to access Windows Live Hotmail messages and contacts.
Microsoft also plans to offer a separate Windows program, Windows Live Mail, which is similar to the Windows Live Mail desktop program that the company has been testing. That software, set to run on Windows XP and Windows Vista, is designed to work with Hotmail as well as e-mail accounts from rivals. It will feature contextual advertising tied to the contents of users' e-mail, though users will be able to turn off the "active search" feature.
Windows Live Mail will be one of Microsoft's first desktop programs to include advertising, though the company is
Kevin Doerr, the Windows Live general manager in charge of the redesign, likens Microsoft's lesson of going too far with the Hotmail redesign to that of
"Even in software, you can go broke underestimating how little change people want to experience," Doerr said.
Microsoft isn't alone in its challenges trying to get Web mail right. Yahoo's redesigned mail is still in beta, as is Google's Gmail. Yahoo plans to drop the beta moniker in the coming months, while Google would not say just when it will move out of beta.
Yahoo has also found that some users want to use check boxes, adding back the boxes in its most recent test version, which is being rolled out to current users.
"We thought it would be a natural enough experience for users that they would be able to drag and drop, and use keyboard shortcuts," Yahoo spokeswoman Karen Mahon said. "The feedback we heard from our users is, they were lost without the check boxes, so we put them back."
In some ways, Microsoft's failures worked to its advantage. Few workers would have been excited by the prospect of building a new mail engine rather than leaving the interface largely unchanged. It might have also proved a tougher sell to get the resources needed for a ground-up rewrite.
Even Sim, who joined the Hotmail effort in August 2004, said it might have been a tougher sell for him, had he known how much would have to stay the same.
"I came thinking I would change the way people would communicate online," Sim said.
Indeed, that's the same draw Gmail product manager Keith Coleman sees in his job. "It's really exciting to do that because you can change the way people's lives work," he said. "The risk, of course, is something like what it sounds like Hotmail is seeing. If you take too big a leap, people get lost."
The Hotmail team believes that, despite taking a circuitous route, it has found a happy medium. But it doesn't plan on staying in the realm of the comfortable forever.
"That doesn't mean you shouldn't continue pushing," Doerr said. "It means you need to understand that and honor that and figure out a way to transition them from where they are today to where they should be."
No forwarding allowed
What will now become the primary interface for hundreds of millions of Web mail users was originally designed as a fallback.
The first version of what is now Windows Live Hotmail's default "classic" view was rushed out to offer a better option than what some beta users were getting--an error message saying the new Hotmail didn't work with their browser.
"We just shipped immediately anything we could ship," program manager Ellie Powers-Boyle said. "You could view mail. You could send mail. You couldn't forward mail because we didn't have time to add that button."
Not too much later, Microsoft decided that it needed not only something for older browsers, but also an option for those who didn't want as radical a makeover as the new Web 2.0-style mail program.
Months later, it decided that there were more of those people than those who wanted the new version. The company shifted the bulk of its engineers to work on the classic mode, completing its transformation from Hotmail's stepchild to its poster child.
And, yes, the Forward button works just fine.
--Ina Fried
Images
Just a basic version at the start, "classic" mode has become the default for the redesigned e-mail program.
May 7, 2007
As Microsoft gets set to launch its revamped Web mail service, here's a peek at how its look evolved.
May 7, 2007
Microsoft's Mike Schackwitz works under the hood on the veteran Hotmail service.April 26, 2006
Related stories
Microsoft still trying to answer Google's wake-up call
Yahoo opens up e-mail APIs to outsiders
Yahoo Mail to offer unlimited storage
Microsoft sticks with Hotmail name
Hotmail's replacement is going Dutch
Microsoft to bring Hotmail onto the desktop
Windows Live beta is delivered
News from around the Web
Windows Live Hotmail to debut Monday
Microsoft's Hotmail brand will live on
Thousands fall for Hotmail prank
Yahoo blows roof off e-mail storage
Google ratchets up Gmail storage
Gmail opens its doors to the world
Maybe you should back up your own e-mail
Credits
Editors: Anne Dujmovic, Mike Ricciuti
Design: Andrew Ballagh
Production: Jessica Kashiwabara