A Light at the End of the Scheduling Hell Tunnel?

I’ve been planning to write about calendaring for several months now, but time, ahem, keeps getting away from me.  I’m pleased to see that this area is now the focus of some innovative start ups and getting some attention from the likes of Esther Dyson.  She interviews Yori Nelken, who is working on launching TimeBridge, early next year.  But there are existing offerings I have yet to check out, including Trumba, which appears to play in the social software space.  Stay tuned in the coming weeks as I explore the possibilities and offerings, and attempt to answer the question: why must I spend half my life finding a time to meet? 

If scheduling meetings doesn’t frustrate you to the point of laughter or near rage, you’re either a zen master or you don’t get out enough. As Clay Shirky said at CTC 2005, enterprise collaboration systems are great for companies that don’t have customers, contractors, or suppliers.  At MediaLive, we run Lotus Notes, and wherever I’ve worked under a Notes regime (here and at previous companies) the calendar has been the only feature implemented to distinguish Notes from a bloated email program.  It’s not that it’s not valuable; when I used to manage a team of up to 25 people, I insisted everyone use the Notes Calendar religiously so that I could avoid spending hours a week moving meetings to accommodate team members who “didn’t get the memo.” But since it doesn’t work outside our group, it’s currently ameliorating only about 25% of my scheduling hell.  My own recent attempt to schedule a time to meet with John Battelle, chair of Web 2.0, Gina Blaber, conference director at O’Reilly Media, and Marco Pardi, our VP of sales, resulted in an email thread 25 messages long during which, at one point, we believed ourselves to have found a common time, only to discover that in the time it took to confirm everyone else for that slot, it had then been otherwise spoken for on John’s calendar. Back to the drawing board.

And this was for a meeting of only four (admittedly quite busy) people. Throw in a few more and it gets exponentially worse. We’ve all had these experiences, and it’s my theory that we all accept this as a problem technology cannot and will not solve for us, for a couple of reasons.  One, interoperability.  Duh.  Two, loss of control.  We assume that any system that came close to solving this problem would remove the cushion between “us” and “everyone else,” allowing those we don’t want to meet with to know that we do, in fact, have the time to see them, and simply choose not to, or simply provide a degree of transparency into our lives that we are uncomfortable with (“Sorry, David can’t make that time, he’s got an appointment with his sex therapist then.”) 

The third reason we seem to accept this state of affairs is that we assume the problem is too complex to address in any meaningful way.  As with so many other collaborative technologies, if the solution only partly works, eventually users will revert to the old fashioned way, and the value drops to zero.  Esther Dyson talks a bit about the levels of complexity inherent in this challenge, including the observation that

Most scheduling involves other people and external constraints - the schedules of people more important, external events such as conference time tables, financial quarters and customers’ activities, availability of resources. Some of these constraints are visible; some aren’t. More important, there’s an invisible hierarchy to the constraints, and it is all very, very dynamic.

As Yori Nelken says, “Scheduling meetings is a negotiation, not an invitation.”  This awareness of the social context of the task is, I believe, the ray of hope that this generation of solutions will provide real benefit.