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Hi, I’m Brad Feld, a managing director at the Foundry Group who lives in Boulder, Colorado. I invest in software and Internet companies around the US, run marathons and read a lot.

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What Seems Like A Fundamental Flaw in Microsoft Outlook Social Connector

Comments (19)

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 brad@feld.com – 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.

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