We have looked at Calendaring many times (such as in our round-up of 10 players). In our own work, we have started working with both Tungle and Doodle. To understand more about why this market is strategically interesting, we recently spoke with Yori Nelken, CEO of Timebridge (see our previous coverage here).

Missing in Action: Native Mobile Interface

What has held up adoption, in our opinion, is the lack of native mobile interfaces. This is a problem in other markets as well (as we cover here in relation to Basecamp). In the real world, many of the people who matter are out and about, meeting people face to face. Perhaps developers, who spend most of their day coding at a desk, miss the nuances of this use case. Many developers point out that there are too many mobile devices with different standards.

These sound like bad excuses. You could cover the lion's share of the market with native interfaces for iPhone, Android and Blackberry; the rest can follow later. As a developer, you need to test for usability on all three. Solicit beta users who are fans of each type. Don't rely on the one device that you use and that your fellow coders happen to love.

Timebridge caught our attention for using SMS intelligently, allowing us to ping a reminder just before a meeting. This is a smart use of the lowest common denominator that all mobile devices support.

The sync between Blackberry (my device) and calendars for Outlook, Google (my calendar) and iCal works just fine at a technical level, at least one way. One problem is that these calendars get "polluted" easily with a lot of team calendars. Google Calendar does not feel like my calendar. Third-party apps can access Google Calendar very easily. Google has done a great job there, but it makes the calendar so crowded that it becomes useless.

That is easily fixed by changing some settings. But even then, I never consult my schedule. I rely on the calendar in my BlackBerry, which is always with me, even when I am far from any desktop or Internet access.

The sync has to be two-way, then. When I change something in my BlackBerry calendar, it should reflect in my Google calendar, so that any scheduling app that accesses my Google calendar will see the updated real calendar. This does not appear to be available yet.

But my colleagues use iPhone and Android phones, and I have no idea what the people who I schedule external meetings with use. To earn serious adoption, a scheduling and calendaring system has to offer: (1) an effective lowest-common-denominator way to interface (SMS and/or email), and (2) a native interface for leading smartphones.

Two Modes: Sharing and Polling

People generally schedule two types of meetings. Gross simplification alert!

  1. Sharing, when one individual, who is much in demand, sets the schedule.
    Our very own Marshall Kirkpatrick uses Tungle in this way. A lot of startups want to speak with him. If he wants to talk to them back, he simply says, "Here is my calendar, figure out what works for you." Yori created Timebridge when he was an Entrepreneur-in-Residence at the Mayfield Fund, and he has interviewed a lot of the assistants who schedule meetings for VCs (another species that many people want to get on their calendar). Yes, when you have 2% of funds under management, you can afford to have an assistant schedule your meetings! For less wealthy "influentials," the sharing mode of a calendaring service is ideal.
  2. Poll, when many peers need to negotiate a time.
    Perhaps you are starting a new project and need input from several people. You control the scheduling but cannot simply say, "This is when we'll all meet." Herding cats is hard. I have used Doodle for this purpose, and it is effective (though like all of these services, it's missing native Blackberry support).

Timebridge claims to offer both modes. For company use, this is essential because both use cases are common.

Don't Just Schedule: Launch the Meeting

What really impressed me when I first saw Timebridge was that it automatically launched a screen-sharing service. This is a great way for the meeting controller to show presentations and demos or just the agenda and objectives. (It was interesting to learn that this was a re-skinned version of DimDim, a company we have covered before and put in our 2008 Best Of Enterprise list.)

Timebridge can also automatically connect to FreeConference.com, a service we use all the time.

So, if you are at a desktop, you would join using screen-sharing. If not, you would use the telephone bridge.

This is an important next step. It is not just about "When can we meet?" but also about the subsequent question, "Where and how do we meet."

Missing in action? Skype. It would be neat if the calendaring system would either automatically launch an existing Skype chat room or create one for all of the participants.

Make Meetings More Productive? Really?

Here is the nightmare scenario: third-party calendaring becomes so ubiquitous and effective that we spend a lot more time in unproductive meetings.

Timebridge has set for itself the noble mission of making meetings more productive. Its tagline is "Make meetings great!"

I remain skeptical. That is an art, a management art. It all depends on who is driving the meeting. Yori agrees but says that by instilling best practices, the average will improve. He may be right. The basics are well known. For each meeting you need:

  • One objective,
  • An agenda,
  • Agreed actions.

But this moves us into new territory. This is the world of project management systems. In a heterogenous world, each participant may be using a different system. There is no point in having "objectives" and "actions" in Timebridge if participants monitor and manage that sort of thing in Basecamp or (getting back to the mobile issue) on their BlackBerry or iPhone.

One area where Yori convinced me that simple changes could mean a lot was in starting meetings on time. The time suck of waiting 15 minutes for Mr. Dilly and Ms. Dally to show up on a call causes a lot of teeth-grinding. Sending SMS reminders helps, but how else to change late arrival habits is unclear.

Why Microsoft Exchange Is Threatened by Third-Party Calendaring

In ye olden days, a company standardized on either Lotus Notes (IBM) or Microsoft Exchange. Notes is still very much around, despite its venerable age, but Yori told us that it rarely shows up. Most users are on Outlook and Exchange, with an increasing number on Gmail and Google Calendar.

With everyone on the same calendar system, scheduling meetings is easy. Why stick with Outlook and Exchange when Gmail is cheaper and more Web-native? The reason for many of the folks in enterprise IT who make these decisions is that calendaring is easy if everyone uses the same system.

Third-party calendaring vendors such as Timebridge, Doodle and Tungle live in a heterogeneous world where you do not know what calendar anyone is using. Increasingly, it comes down to three: Outlook, Google and iCal. Yes, these are from the big three: Microsoft, Google and Apple.

Calendaring is a side issue for Apple. But it is critical in the bruising battle between Microsoft and Google for dominance of the office market.

With Outlook email unlinked from calendaring, Google is in better shape to win over big accounts to Gmail. (And once on Gmail, other apps tend to follow.)