What Seems Like A Fundamental Flaw in Microsoft Outlook Social Connector

I’ve been obsessed with the notion of email as the ultimate social network for a while.  I wrote a post in 2007 titled Social Networks In Obvious Places that catalyzed me to thing harder about this as an investor.  I eventually decided that the email address is the ultimate reference id for one’s current online identity and that it was ludicrous to ignore this notion. This ultimately led to my investment in Gist in 2009. 

Today, there are a number of folks approaching different parts of the problem.  I believe the underlying data architecture and approach is critically important, as email resides in many different data stores and move through many different systems.  In addition, there are numerous other applications that use email as the key reference id independent of username (LinkedIn, Twitter, and Facebook come immediately to mind, but there are thousands of others.)  There is no question in my mind that the web (or the cloud if you like) is your friend in this scenario.

This morning, I noticed that Microsoft had released a beta of Microsoft Outlook Social Connector for Outlook 2010, 2007, and 2003.  I’m running Outlook 2007 on my desktop at home so without thinking too hard I downloaded it, installed it, restarted Outlook, downloaded the LinkedIn connector (the only one available for 2007), restarted Outlook again, and started cranking through email.  I liked the Email Connector window that appears at the bottom of my Inbox view, but I noticed that none of the LinkedIn data seemed to be appearing for my specific contacts.  I didn’t think much of this and figured Outlook was doing something magical in the background (since various info from my Inbox and Calendar started appearing in this view.)  I noticed a few things I didn’t like, such as the every calendar item taking up two lines in the display because the second line was an invite.ics file, but I figured that was just beta stuff.  After an hour or so, I had to jump in my car and head to Denver for a board meeting. 

Once I got into AT&T cell phone range (about ten minutes from my house) I swiped left on my iPhone and typed in the last name for a CEO of a company I’m on the board of.  I noticed that I had two entries for him.  This was strange because I’m meticulous about keeping my address book clean and deduped.  The first entry didn’t have his phone number.  That was really strange since I call him regularly.  The second entry did and looked like the correct record.  I called him, but something was bugging me.

After we talked, I did this again to call another person.  Same issue.  This time I noticed a picture with the little LinkedIn logo on the first entry, but again no phone number.  The second entry didn’t have the LinkedIn picture, but had the correct phone number (and full entry).  By this point I’d figured out what had happened.  I called Amy, told her to shut down my computer at home (I usually leave it on during the day) just in case my new friend the Outlook Social Connector could be stopped before it imported my entire LinkedIn file as new contact records.

I was annoyed throughout the day that I’d munged up my address book.  Tonight, when I got home, I hopped on another board call.  I fired up my computer, uninstalled the Outlook Social Connector, and then spent a few minutes poking around in Outlook contacts trying to find an easy way to delete all the new records.  I fought my way through a few different Outlook contact views and couldn’t figure out how to get the records to consistently appear.  If I searched by name, all the dupes came up.  But if I went into a list view, no such luck – only the correct record appeared and the new LinkedIn ones were no where to be found.  I manually started scrolling through my address book on my iPhone while on the call but by the time I got through the B’s I realized this was an idiotic way to do this and there must be a better way.

A few minutes later it occurred to me that Outlook might have created a new “subfolder” in the contacts view and put all the LinkedIn ones there.  Lo and behold it did and all I needed to do to get rid of the 1800 new contact records was to delete the LinkedIn folder.  Done.  After some happy iPhone syncing they are all gone from my iPhone also.

The decision to take this approach at a data level is beyond comprehension to me.  Almost 100% of the duplicate LinkedIn contacts shared the same email address as my Outlook address records.  I didn’t want a NEW contact record for each LinkedIn one, I wanted them to be “magically attached” to my existing contact record.  So – when I look up Brad Feld, I don’t get the “Brad Feld” Outlook contact record and the “Brad Feld” LinkedIn contact record.  They are both [email protected] – that’s all I want.

So – be forewarned – unless you want to gunk up your address book with duplicates, don’t install the current beta of Microsoft Outlook Social Connector.  Maybe I did something wrong, or have a weird configuration of Outlook 2007, but I simply did a straight install.  Maybe Microsoft will fix this in the next version, but it definitely doesn’t seem ready for prime time, especially on live data.

  • For my money (and I actually coughed up the 30 bucks for the premium version) Xobni does this best. Gives you facebook and linked in info. The only problem is that it does not integrate that data in your outlook contact files. I have written to linked in about this. But you can't beat the info it gives you

  • You know, when you wrote last year that you didn't know why you kept using MS for mail, and I suggested it might be Stockholm Syndrome? I was guessing you liked that because you retweeted it.

    Well, at the end of the year (end of the decade) I decided to stop having sympathy for my captor. As of Jan. 1 I'm all in Gmail, and life is good. The last vestige of M$ has been removed from my daily life.

    Ahhhh. Freedom.

  • I've moved almost completely to Gmail as well. The only thing I don't like about Gmail is that you can't easily copy/paste a screen shot into it, though I have seen a dedicated app that does that. Also, if you set up contacts syncing with the iPhone you don't have to worry any more about the local address book. In my world it's all in the cloud.

    I really like the direction Google is going with their office suite. I almost never open Word unless it's a document with track changes enabled like a contract. Same for Excel.

  • This has been a perennial problem for Outlook since early years. It also happens sometimes when you sync a new phone to outlook – though usually to calendar items not contacts. I was using the new MyPhone service on a phone, used it to transfer over all my contacts to my new phone – only to have it dupe them all to my computer the first time I synced up. Is pattern recognition REALLY that hard? I think not. It's just lazy programming on the Outlook dev team's part.

  • I have my contacts synced up with both Google and Facebook and I'm regretting both decisions. Google occasionally drops people while Facebook adds tons of dupes. I'm not sure why contact syncing is so hard, but I've not seen anyone manage to get this right. I really want this functionality, but I wouldn't recommend it to anyone. It's way too early for them to be releasing this stuff. It should be labeled early alpha at best.

  • I, like the other participants in this discussion, have gone "all in" with Gmail. I've taken it a step further however and shunned MS altogether. I'm proud to say that I have become a Apple convert. I encourage you to join me.

  • Dave Millman

    You've been able to paste images into Gmail for many months now.

  • Raffaele Sgherri

    You did right, I suppose, as I do have the same issue. The same applies for Outlook 2010 and a feature that adds a new contact for EVERY mail you send or reply to. Fortunately, this one can be deactivated 😉

  • I will go one step further and say that your ultimate social network – the "core" network is your contact list on your phone.

  • JFreeston

    I considered downloading Microsoft Outlook Social Connector yesterday morning. Glad that I didn't pull the trigger on it yet : )

    On another note, I've been a power user of Salesforce.com for years and they just announced that they are offering 100 companies the chance to beta test its collaboration software Chatter – a kind of Facebook for businesses. Very interesting. I wonder if Rally Software or other Colorado-based companies are a part of this beta test?


  • Yup, e-mail is a mess. I recently did some mud wrestling with Outlook and concluded:

    (1) Outlook can too easily get 'confused'.

    (2) Store everything important about e-mail outside of Outlook. E.g., 'export' your 'contacts folder' to a text file and 'import' later if necessary.

    (3) Outlook keeps nearly all its data in 'personal folders files' (PST), and can 'manage' those. E.g., if Outlook corrupts its 'current' PST file, then might restore one from backup, etc.

  • I think there are two issues A how closely your Linked In and Outlook addresses match and B how your sync software is set up; I use Outlook 2010 with Exchange and sync to Windows Mobile and Blackberry and while I have a LinkedIn contacts folder, it hasn't been synced to either of my phones. Your iPhone is syncing all your contact folders; as few people on Linked In share phone numbers you will have a contact with just name, photo and email – when the Facebook connector comes along you'll get all the numbers people share. But if someone shares only their switchboard number and you have their direct dial, what would you want the OSC to do?

    If Microsoft had gone the other route, of changing information in your main contacts, people would be furious; equally no-one would want to say yes or no to changes for every single contact – so a separate contact folder and data union actually seems a sensible approach. Does your sync provider allow you to choose what contact folders you sync?

  • PSTs are the worst file format in the world; modern Outlook is designed to work well with Exchange and to use the offline cache mode (OST files, which are far more robust). it's time for PST to die – and for all the companies that force employees to create PSTs by removing mail after 30 days to cough up for the storage to allow people to mine one of their best sources of information and networking whatever mail client you use.

  • While I can absolutely choose which folders I can sync on my phone, I don’t think this is the issue.  The flaw is more fundamental – I do not WANT separate contact records for each data provider.  If you take this to its logically conclusion and include LinkedIn, Facebook, Twitter, and any other data services that OSC will support, I now have N contact records (at least four).  This is a terrible architectural approach (although it appears to be the one that OSC takes.)Gist solves this by consolidating all of the data in the cloud.  You get a combined record on the email address pivot.  They are intelligent about how they deal with multiple fields (e.g. different phone numbers, URLs, company names) from the different systems and this is dealt with automagically.  I believe Xobni takes a similar approach, but on a local data store instead of in the cloud (although I’m not as close to their technical approach).  Of course, Google will be doing this entirely in the cloud.

  • I so agree.  It’s amazing how many people still have their mail store in a PST.  However, while OST’s are much better, the data structure underlying the OST file has some real issues as evidenced by OSC.

  • I don’t know who is in the beta test although I’m surprised they are only rolling it out to 100 beta tester companies.  That smells strange to me.

  • I enjoyed your article very much. Thank you.

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