It’s the question I dreaded getting from my boss or my coworker. It’s the question behind every status report. It comes up at the water cooler, the coffee stand, the happy hour, and the company picnic.

It’s such a common question, you’d think I’d have an answer prepared. Sometimes I do. But when you work on multiple projects at the same time, it’s hard to have the current status of each at the top of your mind and the tip of your tongue. So if it’s more than a casual question from a coworker, boss, or client, it could take me a little while to poke around my email and files to figure out where things stand.

Though I’d been advising businesses on how to manage information effectively, my own information was a bit of a mess. You know the old saying: The cobbler’s children have no shoes.

If the most important thing I do is work on projects, and the most common question I get asked is, “How’s it going?” I ought to organize my work by project. Then I’d have the information at hand.

It sounds obvious, doesn’t it? But it’s surprisingly had to do that in practice.

Your tools are working against you

Now I’m going to pick on Microsoft for a moment, because it’s a big target and it’s easy to do.

Look at the the top-level organization structure in Microsoft Outlook. There are four items: Mail, Calendar, Contacts, and Tasks.

Microsoft Outlook organizes information by type: Email, Contacts, Tasks, etc.

Now look at the top-level organization structure in Microsoft Windows 7. There are four items: Documents, Music, Pictures, and Videos.

Windows 7 has libraries that organize information by type: Documents, Pictures, Music, Video

By default, Microsoft organizes information by what it is, not by what it’s for.

This is convenient for people that make software products. Their applications probably work with a specific kind of information, and they know right where to look for it. Microsoft Word saves to the Documents folder by default, iTunes uses the Music folder, and so on.

But it’s not very convenient for you, if what you do every day is work on projects. In fact, if you accept the defaults these tools suggest, you’ll scatter your project information everywhere. The images you created in PhotoShop will get saved to Pictures, but the PowerPoint presentation you created with the pictures will get saved to the Documents folder. The people you need to send the presentation to are in your Contacts in Outlook, and the message you sent with the attached presentation is stored in the Mail folder.

All of these items are related to a single project, but you’d need to look in four different places to piece everything together. When a coworker drops by your desk to tell you that the boss has bad case of red-eye in the photo on slide 12, you’ve got to retrace your steps.

This isn’t merely a Microsoft issue. Apple’s OS X also categorizes by type, with Documents, Images, and Movies at its top level. Web applications do this, too. A quick look at Gmail’s top categories shows: Mail, Calendar, Documents, Photos, etc.

Gmail also organizes information by type: Mail, Documents, Photos, etc.

Most of the software industry has decided to organize information by content type. But this strategy doesn’t align with the way most of us approach our work.

If you want it done right…

In relaxed circumstances, you might never notice this mismatch. But in a fast-paced work environment, with multiple active projects to manage, it becomes a source of constant friction. And it’s the reason why questions like “How’s that project going?” can take so much time to figure out.

If you want to get a handle on your information, you’ll have to take charge of organizing it yourself.

Related posts

1. Expanding your project context
2. Establish your project context