How to Hate Scheduling Meetings Less

generic CALENDAR dates month planning time year
There are few social contracts I hate making more than establishing a meeting time. It takes me, on average, about four back-and-forth e-mails to set up a simple appointment with a technology company exec who's dying to see me. It takes a lot more for those who are not. I know I'm not alone in hating this process, since there are whole companies that have started up to solve it.

The two main companies I'm going to look at here all share a concept for scheduling meetings that's much more agreeable than the standard e-mail dialog of, "Can you meet Monday at 2pm? No? How about Tuesday 9am? No? How about any time in 2015? No? Up yours."

The idea is this: You give the person or people you want to meet with a bunch of different times via the scheduling Web site, and then these people select their best time or times. The applications juggle the times that people select and once everyone's chimed in, they lock down the best spot in your calendar and send out confirmations.

I fell in love with TimeBridge when I first saw it in 2006. It's been improved and tweaked since then, but the meeting scheduling part of it is still much the same: You let a small downloadable app tap in your calendar (Outlook or iCal, or Google calendar without a download), and then when you want to set up a meeting, you can select up to five blocks of time you know you're available, and send out an invitation. The app then works through the best times for everyone to find a good time to meet. (See my recent review.)

One of the cool things about TimeBridge is that you can select the same block of time for multiple meetings that are still being scheduled, and that block of time will remain available for all the meetings until someone claims it.

TimeBridge also has online conference services and a cool iPhone app (which isn't out yet). It also now does neat things like automatically ping your attendees right before a meeting is about to start, or if they're late, after it already has.

A competitive app, Tungle, has a few tricks up its sleeve (review). For one, instead of selecting up to five meeting times as you do with TimeBridge, in Tungle you can select swaths of time, including big ranges like 2pm to 5pm, even if the meeting you want to have is only 30 minutes long. Also, Tungle doesn't throw a bunch of placeholder entries into your calendar while it's waiting for respondents to give you their meeting votes.

Tungle has a better experience for Outlook users, but TimeBridge is a better business and it has a more well-rounded service.

But with both products, there's a risk that the people you're sending invitations to won't play ball. I've had people who get the messages that these apps send out just ignore the instructions that come with them, and email me back with a note saying what time they want to meet. That defeats the purpose, but the fault is not the people I'm talking to, it's the app developers, for making e-mail forms that are unclear.

There's another, super-simple meeting scheduler as well, called Doodle. It's also a schedule voting system, and its Web page is ridiculously simple to use. Too simple, I think. It's really a polling system that just happens to have a few options for selecting dates. It also has an Outlook plug-in, but it's not nearly as useful as Tungle's or TimeBridge's.

Speaking of Outlook, users of that e-mail and calendaring system may complain to me that they already have a group scheduling feature in the app. They do -- but only sort of. First of all, Outlook does not work well for scheduling with people outside of your organization. Second, even when you want to set up a meeting with people in your company and have access to their calendars' free and busy times, all you can do is select a single time that looks like is open. You can't give your respondents options.

Nobody likes being boxed in to a meeting just because it looks like they have a free hour on their schedule. The schedule voting apps discussed in this column are far more respectful to the time pressures and preferences of the people getting the messages. I'd like to see more people use them.
By Rafe Needleman