I really appreciate well-produced synchronization, because I’ve experienced firsthand how difficult it is to get right. It seems that software developers can never quite agree on how to organize contact information, so everyone’s databases are different. For a long time, for instance, one of the major makers of financial management software didn’t even create city, state and ZIP/postal code fields, opting instead for an address field where all of that information was run together, making the data very difficult to parse.

So I’ve been pleasantly surprised with Snow Leopard’s “sync with Google” function, especially because I have a fairly large address book, and most of its entries have photos associated with them, something that very few sync solutions even try to support.

With a little planning, you can easily sync your address book with Google. Here are some tips — some of which are also applicable to other synchronization systems, such as the one available for synchronizing data between Google and Thunderbird’s Address Book on a PC.

1. Clean up your contacts. It’s easy to get sloppy about how we enter information, so it’s worth looking through your Address Book to make sure that your data is accurate and well-formatted. Putting first names and middle initials together in the first name field can produce amusing results, as can forgetting to check the “company” box for such entries — I had one card titled “Daily, Web Worker”! I also discovered a bunch of messed-up entries that had apparently been caused by previous experiments with sync software and services. One such service must have been European, because I found lots of entries where the postal code preceded the city, as is standard in France, but which isn’t correct in North America or the UK. Be careful with international phone numbers, too. If you don’t precede country codes with the plus (+) sign, some programs will try to format the numbers in North American format.
2. Back up your data! At the least, use Address Book’s Export function, and save a backup in Address Book Archive format. If you want added safety, use a program like Address Book to CSV Exporter to save your data in CSV format, which can be read by lots of other programs.
3. If possible, don’t try to sync two sources with different data, at least for an initial synchronization. You’ll get best results if you can clean up your data in the Mac Address Book, and completely erase all your contacts in Google. However, if that’s not possible, the charmingly named Conflict Resolver will spring into action during the sync, and give you the choice of which records to keep.

Once you’re ready, enter your account information into Address Book’s Preferences. Go to Accounts, check the “Synchronize with Google” option, click “Configure,” and enter your Gmail or Google Apps email address and password. That’s really all there is to it. I’ve found that you need to be logged out of the Google web interface for the sync to start. You might also need to make a change to your Mac Address Book in order for the sync program to become active, but once it begins, the process is surprisingly fast.

The Mac-to-Google sync system does have limitations. It can sync with one Gmail or Google Apps account at a time, and although it offers sync with Yahoo Mail’s contact lists, I’ve never been able to get Yahoo sync to work. Sync is also available with Apple’s MobileMe service, but I haven’t tried that.

All in all, I’m quite pleased with the results, and am happy that I can have immediate access to my contact information in several different places. As far as I’m concerned, one can never have too many backups of this vital data.

How do you keep your contact data synchronized?

Is It Worth It?

I’m generally not in a hurry to rush out and buy the latest and greatest OS. It’s always worth reading the reviews, and following reports of bugs. In this case, it’s been a while since Snow Leopard came out, and there’s already been a .1 maintenance release that seems to have dealt with most of its known issues.

Snow Leopard is, by all accounts, not that heavy on new features, but it’s also relatively inexpensive. Most of its advantages are under the hood, with 64-bit processing and better memory management. But one feature caught my eye: the ability to synchronize the Address Book (including pictures) with Gmail or Google Apps — a feature that’s been around for a while, but which, for some reason, was previously only available to iPhone users.

Can Your Hardware Handle It?

This is an important consideration. Windows, in particular, is notorious for increasing its memory and disk space requirements with every release. And with computer prices falling all the time, it’s often tempting to just buy a new computer with the new OS pre-installed. But I decided that my Mac could work with the upgrade.

Is Your Software Compatible?

Planning for an upgrade made me realize just how much outdated and unnecessary software I had accumulated on my hard drive. Luckily, a couple of sites have compiled lists of what works, and what doesn’t, under Snow Leopard. I looked at several of them; I found this one particularly useful. It even has an application called SnowChecker that can be used to find what programs you have, and display information about their compatibility.

When you discover programs that are listed as incompatible, you can either find an upgrade (sometimes a beta version), switch to an alternative app that is compatible, or decide that you don’t need the functionality it provides.

Do You Have Backups of Everything, In Case Something Goes Wrong?

When preparing for major upgrades, I probably spend more time making sure that all of my data is backed up than I do anything else. Of course, I use the OS’s built-in tools like Time Machine, and I store multiple copies of customer data on an external drive, in the cloud through Dropbox, on my smartphone through Missing Sync, and on my company’s development server (which itself gets backed up). But it never hurts to make manual backups of really irreplaceable data, so — for example — I made backups of my address book in VCF, CSV and Address Book Archive format. You might think that I’m overdoing it, but I felt that the time was definitely worth taking after learning of Sidekick’s data loss and an apparent bug in OS X relating to guest accounts that could cause it to lose data. As Kevin over at jkOnTheRun says: “Services fail…what are you doing about it?”

Do You Have the Time to Plan and Execute the Upgrade?

Of course, doing all of this takes time, which is why I prefer to undertake projects like this after business hours. Even if it means missing a beautiful fall weekend. That way, I don’t have to interact with clients or put out fires, and being offline for a while won’t make a difference. I picked up a couple of good books at my local college bookstore where I bought Snow Leopard, and got to page 50 of Terry Pratchett’s “Nation” while waiting for the installation, so it was time well spent!

So far, I have been extremely pleased with how much faster many of the programs I use run under Snow Leopard, especially those that are available in 64-bit mode. And I’m happy with many of the OS’s new features. So for me, the time spent has definitely been worth it.

Have you upgraded to the latest operating system? How has it worked for you?

First, I started using social networks like LinkedIn and Facebook heavily. As a result, my address book ballooned from a few hundred contacts to over 1,100. The additional contacts were all people I knew, but I hadn’t seen many of them for a long time — being able to see photos makes it much easier to find the right contact. Second, I switched to a Mac as my main machine, and I started using the Mac OS X Address Book. It’s a very well-designed application, and it makes adding pictures to contacts incredibly easy.

Just open the Address Book to the appropriate contact. You don’t need to click the edit button. Then, use your web browser to find a photo you want to use as that person’s image, from a web site like Facebook or LinkedIn. In the browser, click on the image, hold your mouse button down, and drag the image to the Address Book. Let go of the mouse when you’ve dragged the image to the pale-grey square immediately to the left of the person’s name. A green circle with a white plus sign in it will appear when you’re in the right place. You may then crop the image as you wish. I like to crop tightly so that the person’s face is easily recognizable in the small space provided.

Most other address books have a way to attach photos to contacts, including the address books for online services like Gmail. Unfortunately, I haven’t found any others that allow easy drag-and-drop of images like the Mac Address Book does.

There are programs that allow one to sync pictures between Facebook and the Address Book; I haven’t tried them, as I prefer to select my own images.

Finding images of your contacts is generally easy. Use an image search in your favorite search engine. Social networks like Facebook and LinkedIn, and sites like Twitter, encourage people to post pictures of themselves. I sometimes don’t like the pictures that people select, though; I prefer headshots that actually look like the person! For that reason, I’m not thrilled about cartoon avatars, either, unless the caricature is really good.

I suspect that more and more people have growing address books. If you want people to remember you, post picture of yourself that can easily be added to address books.

Do you add images to your contact list? Do you post headshots that can easily be imported?

My friends forwarded the invitations to me. They were dated yesterday, and the headers indicated that the messages were from Facebook servers. There have been recent reports of phishing scams aimed at Facebook users, though, so I changed my Facebook password, even though I don’t have any evidence that my account has been compromised.

But then I started thinking about all of the places that could potentially have access to my address book. My “master” address list is in the Mac Address Book app, but it’s synced to my web-based Google Apps contact list, and to the Thunderbird address book on my PC laptop. It’s also synced to my Palm Treo smartphone.

I’m pretty careful about passwords, and I respect the privacy of the folks in my address book. But I’m always trying new services, and it seems like everyone wants their site to have a social component. So the list of places that might have access to my address book is appallingly long.

• Adium
• AirSet
• AOL/AIM/Netscape
• Biznik
• Blogger
• Chi.mp
• Delver
• Digsby
• Dropbox
• Dropcard
• eBuddy
• eWallet
• Facebook
• Flickr
• FriendFeed
• Ginx
• Gist
• GizaPage
• Gizmo5
• Glide
• Gmail
• Goodreads
• Googaby
• Google Apps
• identi.ca
• LastPass
• LibraryThing
• LinkedIn
• Live.com/MSN
• LiveJournal
• Mikogo
• Mozy
• Mundu
• MySpace
• net4mac
• Ning
• OperaMail
• Skype
• SocialMinder
• Soocial
• Sprint
• ThinkFree
• Time & Chaos
• Trillian
• Twitter
• TypePad
• Ulteo
• ViaTalk
• VoxOx
• Xmarks
• Yahoo
• Yuuguu
• Zoho

Now, most of these places have clear privacy policies, and I’m sure none of them would knowingly leak their users’ data. But let’s face it, security breaches are common these days, from national governments to banks to credit card companies. So with a list that long, how can I figure out where the breach might be?

Social networks need to provide tools that let individual users track how our data is being used. Gmail, for example, has an “Activity on this account” page (accessible from the bottom of the main screen) that shows when and how the account was accessed, and from which IP address. Facebook and other social networks need to make similar information available.

In the meantime, some elementary steps will keep your data, and your contacts’ data, more secure.

• Use anti-virus, anti-malware and firewall software.
• Make hard-copy and off-site backups.
• Change your system, network, email and web site passwords frequently, and make them difficult. (Use the “generate password” function included in most password storage programs.)
• Keep track of social web sites to which you have given access to your address book data. Be extra vigilant about changing passwords for these sites, and if you aren’t using them anymore, delete your accounts.
• Check which applications have access to your social networking accounts, like Facebook and LinkedIn. Delete any applications that you aren’t using.

Has are you keeping your address book secure?

Image by stock.xchng user xaila.

I’ve decided to only sync my calendar between Google and my iPhone, which after one false start now works well. I didn’t bother syncing contacts. Why? Because nowadays when I need to find someone, the last place I seem to look is in my usually-outdated contacts application.

Sure, I have some contacts in my desktop address book which I sync back to Google with Spanning Sync. Mostly immediate family, doctors, school contacts, etc. Those few people I really need to call when out and about. Every work contact is in our organization’s CRM and is accessible through the Salesforce iPhone app. The rest of my life is either in Facebook, Twitter or LinkedIn where the contacts themselves make sure their own data is up-to-date. All are easily accessible from my iPhone.

When I leaf through my desktop address book there are so many out-of-date entries, I often wonder why I bothered putting them there to begin with. I know there’s Plaxo for keeping an address book updated, but that utility comes with its own set of problems.

Let’s hear how other web workers handle their contacts.

Has your local address book been shoved aside in favor of web-based tools? Do you worry about the accuracy of contact data on your phone or desktop? How do you keep it all up-to-date and in sync?

The latest to join the fray is Cellity’s Address Book 2.0, launched earlier this month, at the LeWeb’08 conference in Paris. The service promises to centralize and synchronize a user’s communication points from sources as diverse as Outlook, Twitter, cellphones and social networks.

The service provides a single view of all your contact information, from their various origins,  then presents the user with various communication tasks that can be invoked for each contact – sending email, SMS, conference calls, status messages and other activities. Interestingly, even if the link to the origin service is severed, Cellity maintains its own copy of contacts from that source.

Like many similar contact aggregation services, services like Twitter and Facebook are plumbed into Cellity’s by entering your account details for those services – something I’m becoming very uncomfortable with as startups building on those networks begin to proliferate. Not only are you handing off your credentials to others, but contact points for hundreds, if not thousands, of your valued relationships – an issue explored more fully by Pamela just over a month ago.

I’m beginning to think the current approach of aggregating contact from various services and then making them viewable on multiple platforms is not enough…no service can support every device, every social network and every contact source. Even the mighty Google sees Contacts as no more than an adjunct feature of email, rather than a valuable stand-alone service that can service many other applications.

Perhaps we need a WordPress-like approach to this problem space…

• A freely available open-source service along the lines of WordPress.org or laconi.ca that users and organisations can deploy on their own servers to host their own contact information -  based on open-standards like FOAF, SyncML and vCard/hCard – this could be as simple as a web page embedded with microformatted contact information and suitable permissions.
• A freemium hosted equivalent (such as identi.ca or WordPress.com) for less-sophisticated users to host their contact information on public servers.
• Address books are simply the connections, relationships and permissions between those contact hosts.
• Encourage developer communities to provide plugins and support for analytics, phones, social networks, desktop address books etc.

We’ve seen how open source blogging platforms have evolved quickly to support almost every niche – perhaps harnessing the same structures can help bring about the mythical Address Book 2.0.

In the intervening period, we’ve seen companies such as Plaxo and Facebook seek to evolve themselves into the position of defacto social address books, but even such powerful companies have only offered uneven ‘hacks’ for integration with our email, cellphone and IM contact books.

Apple’s Mobile Me service has attempted to provide some of the ‘glue’ to connect these silos of contact data, but at a great price…and of course tied to the Mac universe. It’s also telling that Gmail still lacks a useful API to it’s Contacts data – perhaps data that should really be a standalone application? This has left an opening for companies such as Soocial…

Founded in Amsterdam, by Stefan Fountain, Soocial provide hooks into existing services and a modicum of interoperability between them. Currently the service enables users to draw contact data from…

• Gmail
• Highrise
• Facebook
• OSX’s Address Book
• A number of mobile handsets

It’s an impressive (though again uneven) list of contact sources, notably support for what appears to be a broad range of handsets,though, some like the Facebook application don’t offer true synchronization or access to contact data within that service.

I can’t help but thinking what’s really needed is a master web-based address book, with a standards-based API that any device or application can draw contact information and synchronise with. Perhaps this is the space that Soocial hopes to occupy – or indeed upcoming services such as CloudContacts.

Soocial’s Fountain has such faith in the utility of his service, that he has generously extended a limited number of invitations to Web Worker Daily’s readership, as part of Soocial’s (currently private) beta trial.

Head on over to http://www.soocial.com/web-worker-daily to pickup your invitation and put Soocial through its paces.

For starters, have an incomplete address in your contacts?  PostCheck will find the ZIP code if you have city and state.  And vice versa, if you have a ZIP with no city and State, PostCheck will find it for you.  Additionally, PostCheck will take your address and conform them to the USPS’ exacting standards for addresses.

The program is a mere $10 and is available on PostCheck’s homepage.