UPDATED – I am all out of invites. If I get more, I will work my way down the list of people in order of comment timestamp.

Overall, I do agree that email inboxes do contain a lot of interesting data about people and how frequently they communicate over email and potentially IM if a vendor offers both products in an integrated fashion. That being said, I don’t see how any of the top web email providers (Microsoft, Yahoo, and Google) can use this email information to build new social networking products. There is, however, an opportunity to use that data to power other people’s applications.

What additional value would I get in using one of these systems over Facebook, MySpace, or my current social network of choice? Details on these products are sketchy at best. However, almost any social networking product worth its salt has a contact importer. Once a user imports his/her contacts, he or she can then determine who from that subset of people he/she would like to invite. Is having a machine prompt to do this for personal social networking of great value? I can see the utility of this auto-population or auto-discovery in a work context (Xobni does do a good job of showing me my own correspondence patterns and I can imagine many things you could build on top of that data – the work use case is different as I think work communication patterns tend to be more dynamic than personal ones). Nothing I’ve heard in the limited details that have come out gives me reason to think that they’re on to something bigger.

I’d also say that if “powering up” this network requires me to create a new profile page, it’s a non-started. I’m out of that business for now unless or until I see a really great application that’s worth the time.

Webmail inboxes are a mess – I have yet to use an email product that has an even decent address book. All of the email address book offerings from the Big 3 email providers feel really dated. For example, the Gmail address book does not do a very good job of de-duplicating contacts. I have folks in my address book who have multiple entries and I’m not interested in going through to manually de-duplicate them; I’m counting on a machine to do that for me.

The larger point here is that I don’t know how you can build a really good, effective social networking product on top of email if you don’t do something to put some good, quality structure around the data. Social networking services who are sucking up email addresses to match a user’s inbox with their database of contacts don’t have the same problem – you just throw away the ones that don’t match (or allow a user to invite them). It’s a very different situation if you want to build a whole new social network product with email as the foundation.

Cross-functional collaboration is not easy inside of large companies – This is a fairly obvious point, but big companies are notorious for having internal challenges when it comes to cross-product collaboration. When one of the products in question is email, I don’t imagine that will be an easy conversation – nobody wants to play around with an interface that touches tens or hundreds of millions worldwide.

Think about the refresh cycles for webmail systems. How often do Gmail, Yahoo Mail, or Hotmal get updated? Not that often, and I have to think that touching those interfaces requires a lot of signoff and a strong conviction that the proposed changes will positively impact a wide number of people. Otherwise, you might end up with angry users. I have a hard time seeing any of these companies acting aggressively with one of their web crown jewels.

The end game ought to be to make this information available to other services and make mail the data platform, not build new applications. Sadly, I don’t think that’s a very interesting business to be in – I don’t know how you re-establish yourself as a major player in social networking by simply providing the data layer that powers other applications.

So what’s next? Well, I think what’s next (and by far most interesting) is some concept of the “strength” of a connection. Specifically, today I can see a lot of my friends’ social networks, but I have no idea for the relative strength of connections. Sure, if I see Person A knows Person B, I can always make an offline inquiry to see if that connection is strong or weak. But very soon I think we are going to have tools like Xobni that profile communications patterns and surface that information both to end users and to other applications. And it won’t be just social networking and community applications that benefit. Enterprise applications (collaboration tools, CRM tools, HR/recruiting systems, etc) will all benefit from having access to some of this information. We’ll call this contextual “strength” Phase III.

Phase III is really interesting to me because I think it has to be a largely machine-driven approach. Communication patterns are too dynamic for any user to bother continually updating “strength” of connections. Also, as Xobni has shown me, if you are a power emailer you’re likely to be surprised by who shows up as ranking highly. There’s no reason the same can’t be done for IM. I’m not sure that I’m going to turn my phone logs over to some 3rd party analytics company, but IM and email would be a pretty decent picture of what I do and with whom I communicate. Passive profiling of communications patterns is going to be really interesting and I think will expose really interesting information about the nature of communications. I think Xobni is on to something really cool and big as it’s delivering value to me today (even though I have to use it in Outlook) and I can see a path to a lot more value in the future.
As an aside, I think this is the best shot that Google, Microsoft, and Yahoo have to wedge their way back into social networking relevance. They already own the message stream and have the data they need to get a sense for who knows whom. It will be interesting to see whether they choose to open this information up and let other applications take advantage of it or whether they use it for the bedrock of their own auto-generated social networks.

• The interface is quick – The Gmail interface is really snappy. It loads quickly and refreshes automatically. As is the case with most Google products, speed is clearly a high priority and it works really well.
• I can process/triage messages very quickly – Once you master the key keyboard shortcuts (j,k,x,n, and p are the crucial keyboard shortcuts to master in my opinion), it’s really easy to blast through a bunch of messages in your inbox and quickly triage them or otherwise mark them for future reading/evaluation.
• Search trumps foldering once you make the big leap – I am an active labeler in Gmail, but I’ve gotten lazy/sloppy with some of my labels over timer. The key “ah ha” moment in most Gmail user’s evolution is the moment in which the light bulb goes off and you realize that search is a more powerful navigation paradigm for email than foldering. It’s a leap of faith until you make the change.

One thing worth noting about the three things that I like most about Gmail – they only really matter if you are in a position where you need to manage (read, write, retrieve, and share) large amounts of email. If you don’t get a lot of email, most of these features and benefits don’t buy you much. In fact, you probably would not even bother mastering these things if you are not a power emailer.

The subject of to whom Gmail-like interfaces appeal is a subject for its own post. For the purposes of this post, we’ll just say that things like Gmail are designed for expert power users and have a high bar to adoption. However, once you adopt, it’s hard to switch.
After trying to go back to Outlook as my every day mail client, I’m finding it to be a very difficult adjustment. There are 3 things that stand out after a few days of non-Gmail email existence:

1. I miss keyboard shortcuts – a lot. After being out of the Outlook experience for over two years, I find the keyboard shortcuts to be a bit slow. Also, with the myriad number of formatting and presentation options that Outlook offers, it’s hard for me to actually remember all of the keyboard shortcuts at my disposal. The relatively short list of Gmail shortcuts that I can use really do the trick and allow me to get my work done quickly.

2. The Outlook client feels really slow. The time spent selecting messages, opening them, waiting for them to open, and then closing them and moving on to the next message just feels a lot slower in Outlook. I don’t know whether it’s because I’m less familiar with the interface or if there is something else at work. It just feels like it requires more keystrokes and work to get through my email using Outlook.

3. Working offline is not as big of a bang as I had thought originally. Now that I have a broadband access card for my laptop, there is relatively little time when I cannot be online if need be. Suddenly the ability to use my mail client offline is of less value as I find myself offline with declining frequency.

At the end of the day, I think that has big implications for folks who are building apps that plug into Outlook. Sure, not everyone in the world who uses email will switch from Outlook to Gmail. However, I know a lot of power email users who are moving away from Outlook and adopting Gmail. Given that so many of these interesting email products target power users, I am curious to hear how they will deliver their solutions to the (relatively) closed environments that we find in webmail. Greasemonkey scripts? Biz dev deals to get access to the platform? Lobbying hard for more opennes and APIs? I’m sure they’re all thinking about this stuff and what it means for their businesses.

As always, comments are welcome.

I’m not always the fastest on email (that title goes to my friends who work in venture capital), but I do try to be consistent in the time window for my responses. I tend to work under the theory that being consistent is the next best thing to being fast. My biggest concern is making sure that I do my best to get back to people in the time window that’s consistent with previous interactions.

Right now, the only two lenses through which I can interact with my mailbox are the traditional LIFV (last in first visible) approach or by the use of folders/labels. Neither one of those approaches gives me any sense as to the messages that really require my attention.

As email has become a more important communications tool, I’ve seen most of the big pain points get attacked. For me, spam is a non-issue; I still get spam but not so much that it can’t be managed. I also have tools that allow me to search through my email pretty effectively and retrieve messages where I’m looking for specific messages or keywords. The last big mountain to tackle is relevance. Relevance is hard to tackle because it means many different things to other people and unlike spam and search, the mark to hit is not a quantifiable goal (make all messages searchable, achieve a 99.99% spam capture rate, etc).

I’ve seen a lot of people talk about building more relevance into email. A lot of times it takes the flavor of “we’ll look at your inbox, your calendar, your task list, etc and magically divine relevance based on those factors.” That strikes me as a hard approach to pull of, partly because those are incomplete sources of data (for example there are people who I speak to on the phone a lot and when I get email from them it’s pretty important – you might not pick that up if you just look at my inbox and calendar) and for another reason I’ll get to later.

More than anything, I want an email analytics product that’s smart enough to do exception reporting and help me view my email through the lens of messages that are “out of bounds” in terms of the time it’s taken for me to reply.

To build a good analytics product, you need to have parameters that can be measured. For websites is page views, visitor activity via logs, etc. For feeds its distribution, readership, and clickbacks. You get the picture. Email has the same characteristics. You can see volume of communication, direction of communications, time between receipt and reply, time of day when I’m most active on email etc. Simply put, there are definitely enough parameters to build a statistical profile of my mail usage habits. If you focus just on power emailers, you’ll certainly have enough data to make things work better.
There are two things that cause wrenches in this whole plan. One is just simply the problem with out-of-bounds events. Say, for example, I got an email from Bill Gates. He and I haven’t exchanged emails before. But if he found fit to email me, I’d say that’s pretty important. Any system that relies on historical communications patterns has the danger of missing these types of events. The same can be said of emails from any new person, famous or not.

Second, I use webmail almost exclusively. If I used a desktop product, I’m sure you could deliver a product like this as a simple toolbar or plug-in. How will you make it work in a webmail environment (sorry, Greasemonkey scripts don’t count – that’s too high-end of a solution).

The only folks I’ve heard working on this problem recently are the guys at Xobni. I haven’t seen their product but I hope it moves the ball forward when it becomes available.