Self-Documenting Software, Email Folksonomies, & the Trouble with Outlook

For some time now I’ve been using Caelo’s NEO Pro overlay for Outlook email. It has been, in a word, a lifesaver. Here are just some of the things I’m fond of:

• Integrated search (far better than relying on an all-purpose outside search tool, like GD)
• “Active” mail (don’t ask, but it’s great)
• Smarter bulk mail handling
• Automatic correspondent foldering
• Multi-index model (the same message can be in multiple folders)
• Better to-do management

The upshot: I can now deal in relatively panic-free fashion with my usual two thousand mail messages a month (yep, that’s the number) much better than I ever could have under vanilla Outlook.

There are two issues though. First, NEO, unlike, say, Flickr, is not self-documenting. You don’t simply start using it and immediately get the richness of the product, or at least get enough of the richness to make you say “Whoa”. Matter of fact, with its somewhat unusual tab-centric interface a more typical reaction is “Huh?” That’s a problem, of course, and I’m sure it has limited uptake for the product.

The second issue is that some features just aren’t well documented. Case in point: Categories. Caelo has a neat feature where you can tag emails much like the way you tag images in Flickr. While the program does some nice autonomous foldering — by date, by correspondent, etc. — you can also layer tags (as many as you want) onto a message. Those can be made up on the fly, or you can choose from a drop-down list of the tags you have used in the past.

It’s a nice feature, but it has literally taken me a year to realize that it was there. I’m a reasonably savvy email user, so having taken me that long almost certainly means that some people never get around to tagging at all.

To be fair, you’re never going to tag every message that comes in. Instead, it is more useful to tag stuff that represents active projects, things that you’re working on, or things you think you’ll need to see in context. For example, I’m working on a couple of projects that cleave along multiple dimensions — people, technologies, location, etc. — and I’m multi-dimensionally tagging crucial emails accordingly. Darn handy.

And there two obvious enhancements:

1. Autonomous tagging. Why not have the program guess, based on a combination of content, context, and prior tagging, how I’m likely to tag a new message? After all, that is a hell of a lot easier to do from an email message than from a photo.
2. Shared tags. Why not allow people to tag things in organizations and in groups and let people “subscribe” to relevant tagged emails? That way I could, in effect, have selected access to your inbox without having to be on some massive distribution list. Put another way, it would give me more fine-grained client-side control over email.

As you will have guessed, I’ve been spending more time looking at the email market — I think that Outlook is a host into which you could introduce a thriving opportunistic infection, one that rides along happily for a long time. Along the way, I’ve run into some intriguing related research.

There is, for example, working being done on auto-detection of to-dos and tasks from messages, which is quite slick. There is also interesting work being done on email activity management, in essence figuring out which messages conceptually have to do with one another and grouping them accordingly. Most of this may never see daylight, but that is not the same thing as saying that email couldn’t be much improved from its current incarnation.

Related posts:

1. Dealing with Email Overload: Managing Email
2. Why RSS and IM Won’t Replace Email, But ….
3. The Message is the Software
4. Disposable email
5. The Trouble with Software as a Service (Part I)