Windows Phone will only sync with cloud-based data sources like Exchange, Windows Live, and Google/Gmail, so those who are still using Outlook as a hub for their personal information are going to have to move their data to the cloud. This isn't a bad thing. In fact, it's an opportunity to jump into the 21st century and make your data more resilient and accessible.
Around the globe, companies of all sizes are evaluating various cloud computing solutions related to email and personal information management, communications, document management and data storage and even PC management. I've written a lot about cloud computing in business, and will no doubt continue to do so as the industry evolves. But what I'd like to focus on today is more personal in nature. And that is what I see as a pressing need for individuals to move their most often-used data--email, contacts address book, schedules, especially, and, eventually, important documents and photos, among other things--into the cloud.
The reasons for doing so vary, but at a high level, this is really about not tying your data to a particular PC, as we've done for the past few decades. That PC could be lost or stolen, or could suffer a hard drive failure or other catastrophe, and if you haven't backed up, or backed up recently--and studies suggest you've done neither--then that one copy of your important data is gone forever. (People who do make proper backups are either wired that way or got the religion after suffering from a major disaster; I fall into the latter camp.)
But it's not just about backing up. A PC is also a physical thing, and can be in only one place at a time. If you're out and about, you should be able to have up-to-the-second access to your data from a smart phone, or another PC, even that PC is a public PC in an Internet caf? or library. By freeing your data from the PC silo, you're ensuring that you can access the data at any time, from anywhere.
In the past, we bridged that gap with sync software that would funnel PC-based data to devices when they were connected with a cable of some kind. Changes made on the device could be synced back to the master data store when the connection was reestablished. This weird offline/online interchange is both old-fashioned and inefficient, and has been neatly replaced by far more elegant over the air solutions that occur in real time.
More specifically, a coming generation of solutions will simply assume your data is available only online. The first step in this direction is Windows Phone 7, which dispenses with PC-to-device sync for email, contacts, and calendar data, relying instead on cloud-based data sources like Exchange, Windows Live, Google/Gmail and others. Windows Phone does utilize the PC for digital media sync only--using Microsoft's Zune PC software as the sole conduit--but one gets the idea that even this is temporary. And while it's not perfect, Windows Phone can even automatically copy pictures taken with the phone's camera to online services like Windows Live and Facebook, eliminating another reason why portable devices like phones and cameras were traditionally used with PCs for sync purposes.
It is Windows Phone that touched off the idea for this article: In writing about Windows Phone's cloud-based email, contacts, and calendar sync requirements, I've received a number of emails from people who are still syncing data from a PC master data store--usually Outlook, but sometimes even more old school applications like Palm Desktop--with their devices. And they're wondering, sometimes frantically, whether they can continue doing so if they move to Windows Phone. They cannot. And while this is frightening to some of these people, I believe it should be viewed as both an opportunity and a reason to do the right thing, and untether that data from the PC desktop, moving it into the cloud.
In such a scenario, a modern, PC-based client like Outlook could still be used to manage your email, contacts, and calendar. The difference is that the actual data is stored in the cloud, and Outlook is an end-point for that data, and not the receptacle. In this way, Outlook will work just as Windows Phone will: You can view, edit, and add data at any time, and any changes you make will be replicated, up to the master copy of the data in the cloud. And changes made anywhere will occur, in near real-time, in the master copy, and in any connected client.
While I can't cover every possible permutation of cloud data storage, there are certainly some basics, most importantly, the aforementioned email, contacts, and calendar management. And a look at which account types Windows Phone syncs with is instructive. These include:
Windows Live. You will always have at least a single primary Windows Live account that ties your Windows Live ID to the phone, opening up access to your Windows Live (Hotmail)-based email, contacts, and calendar, your Messenger Social feeds (which will populate the What's new lists in the Pictures and People hubs), integration with Windows Live SkyDrive and Photos, and, if you have them, your Zune Social and Xbox Live accounts too. You can also optionally have additional secondary Windows Live accounts that can sync email, contacts, and/or calendar.
Outlook. This misnamed account type actually works with Exchange, Outlook Web Access, Exchange Online, and any other Exchange ActiveSync (EAS)-based accounts (including Gmail/Google Calendar and, sometime soon, Windows Live) and provides access to email, contacts, and calendar synching.
Yahoo! Mail. This account type is for email only and uses the IMAP prototype to synchronize with your server-based email. (IMAP works much like EAS except that it's email-only; you can't sync contacts or calendar using IMAP or this account type.)
Google. This account type utilizes EAS under the hood to connect with Google's Gmail, Contacts, and Google Calendar services. It works identically to the Outlook account type, but is of course Google specific and is much easier to configure.
IMAP and POP3 email. Via the "Other account" and "Advanced Setup" options, you can also configure other email-only account types: IMAP and POP3. IMAP is the more sophisticated of the two, and lets you work with server-based (i.e. cloud-based) data on the phone, which is desirable. But both only support email, not contacts or calendars.
(Note that Windows Phone supports multiple email, contacts, and calendar sources. However, it can work only with the primary calendar in any given calendar source. So you will need to consolidate multiple calendars on a single calendar source--like Google Calendar--or simply understand that second calendars will not be synced to the device.)
If you're looking to move or copy data out of a PC-based application so that you can get it into the cloud, you're going to need to do three things: Choose a cloud-based service provider, export the data into formats that the provider understands, and then import the data into the provider.
When it comes to choosing a provider, I recommend Google, which offers excellent email and contacts capabilities through Gmail and calendaring through Google Calendar. The Google solutions are free, and top-notch, better than even the paid competition. Alternatively, you could go with Windows Live: It's also high quality, but has web-based graphical ads unless you pay, and is not quite as efficient as Google. (But what the heck, you need a Windows Live account for Windows Phone anyway.)
Gmail/Google and Windows Live are it for the free services that offer email, contacts, and calendar. You could, of course, also use Exchange but there are at least two potential problems with this approach. First, it's not free. Second, if you're getting Exchange access through work, I recommend not using that account to consolidate your personal information. Your work and personal data should be separate, and besides, what happens if you get cut off from your work data for some reason?
Since Outlook appears to be the number one data silo in use, and the one I can actually test, I'm going to focus on that. But if you're using something else, you'll want to at least understand which formats to export to. These formats are different for each of the supported data types.
I do not recommend exporting/importing email. If you really need to copy or move your old email messages (and, perhaps, folder structure) up to the cloud, you should load your old account and new account side-by-side in either Outlook (if you have that) or Windows Live Mail (which is free) and then drag and drop messages from account to account. This process is time consuming and can error out, so move only small batches of messages at a time. It's tedious, but you only have to do it once. That is, if you do it: It may not be worth bothering.
For contacts, you will need to export to CSV (comma separated values; a text format). Outlook supports two forms of CSV, DOS and Windows, the difference being that each is encoded differently. (DOS uses an ASCII character set while Windows uses ANSI.) According to Microsoft, "the largest difference between ASCII and ANSI are the upper 128 characters; the lower 128 characters are the same. The upper 128 characters are often referred to as extended characters. ASCII extended characters include line draw characters while ANSI extended characters include international characters and publishing symbols." Long story short, try Windows first. If you get a lot of garbled garbage when you import later on, wipe out the contacts (in the cloud), export in DOS format, and try again.
For calendar, the exporting steps are different for Google Calendar and Windows Live Calendar. If you're going the Google route, the CSV format is again your friend: Outlook can export a calendar in this format and Google Calendar can import it. (You'll find this interface in File, Options, Advanced, Export.)
To export from Outlook to Windows Live Calendar, you need to use a different export format (iCalendar) and a different set of steps, as Windows Live Calendar cannot import CSV. To do this, navigate to the calendar you wish to export and then choose File, Save Calendar. In the Save As windows, click More Options to specify the date ranges you wish to export.
Once you've exported your relevant data, you can import it into your cloud service of choice.
To import contacts to Gmail, navigate to Contacts and then click Import Contacts. Gmail supports CSV importing from "Outlook, Outlook Express, Yahoo! Mail, Hotmail, Eudora and some other apps," according to Google. (And vCard importing from Mac OS X's Address Book app.)
To import contacts to Hotmail, it's Options, More Options, Importing Contacts. Hotmail's contacts import functionality is more user-centric and supports explicit services like Facebook, Gmail, AOL Mail, and so on, as well as Outlook. That latter option requires you to have previously exported your contacts as a CSV file, just like Gmail does.
Whichever route you go, you will almost certainly have to edit and clean up the imported contacts. As with any other similar transition, this can be time consuming but is a one-time deal. It's worth doing, and getting it right.
To import calendar data into Google Calendar, navigate to Settings, Calendar Settings, Calendars, and then click the Import Calendar link.
To import (ICS/iCalendar) calendar data into Windows Live Calendar, click Subscribe and then choose "Import from an ICS file."
Once you've detached your email, contacts, and calendar from a local application and gotten it up into the cloud, you can of course "reconnect" with it using Windows applications like Outlook or Windows Live Mail, if you prefer to do things that way: Both offer some degree of interconnectivity with Google/Gmail and Windows Live. If you go the Windows Live route, you're all set. Both Outlook and Windows Live Mail will connect automatically to email, contacts, and calendar data from that service.
If you're using Google, things are a bit more complex. Gmail is not a problem: Both Outlook and Windows Live Mail can connect seamlessly to Google's email solution. But if you want to access your Google-based contacts and calendar from the desktop, you're in for a bit of trouble.
Google offers a handy Google Calendar Sync utility for Outlook users, but it only works with primary calendars, and is currently incompatible with Outlook 2010 (It works with both Outlook 2003 and 2007). But the company doesn't offer any way to sync Google-based contacts with Outlook. So you could export them from Google Contacts (in Gmail) manually and import them into Outlook. But this is a one-time deal, and future changes won't be synced between Google Contacts and Outlook.
To export Google Contacts, click More Actions and then Export. Choose Outlook CSV as the format.
Of course, email, contacts, and calendar are just the beginning. Eventually, we'll need to figure out seamless ways to store other documents, media (music, photos, and videos), and other data files in the cloud. We're not quite there yet.
In the interim, there are some interesting scenarios around syncing data like this between PCs--see my article Sync It. Sync It Good for more information. PC to PC sync isn't as "perfect" as cloud sync, but it at least prevents the data silo issue somewhat. (On the other hand, if every one of your PCs is in the same physical location, and that location suffers some catastrophe like a fire or theft, this set up will be of little help.)
There are online backup services, too. None of the big players--Microsoft, Google--offer anything seamless that work across all data types, and Microsoft in particular has shown no interest at all in opening up a free or paid storage service of any actual use. (SkyDrive is purposefully limited to prevent people from actually dumping data there in volume.) Third parties are interesting, but unknown, and pricing and storage allotments continue to fluctuate in the right directions, but it's unclear where this is all heading and which of these services, if any, will emerge as legitimate contenders for the future.
We'll get there. In the meantime, backup and then backup again. Move backups off-site, to your parent's house, or to a bank deposit box, or to wherever you feel they'll be safe. Replicate you important data between PCs as much as possible to ensure redundancy. And keep an eye on the tech news, to see what's happening with cloud-based sync and backup services. We're in a time of transition, and this stuff is only going to get more powerful, easier to use, and less expensive.