I remember when Google first began giving out invitations to its “beta” web mail service, Gmail. Back in 2004, techies and pundits predicted that it would mean the end of email as we know it. We could forget about the hassle of email folders and simply search for everything we needed. Google would make sure that access to our information was as fast and accurate as its search results for the general web.

Are email folders obsolete? Or are they still useful in the age of search engines?

Gmail’s search features were fast and accurate, certainly far better than anything than the competition had at the time. But was that enough? Could search alone really do everything a business user needed? I doubted it, but I wasn’t in a position to test it at the time.

After I co-founded Infovark, I could put that claim to the test. We signed up for Google Apps in 2008 and I decided to forgo using folders and rely only on search. (Gmail calls its organization scheme “labels” but they serve the same function as folders.)

My experiment lasted almost three years. Here’s what I discovered.

Conversation View

Conversation view is easily the most popular feature of Gmail. It’s now been adopted by most other email applications. Conversation view automatically groups messages by subject, so it can sometimes fill the void left by abandoning folders. But the reliance on the subject heading can cause trouble if:

1. You have coworkers that tinker with the subject lines of their messages, breaking a conversation into several smaller, disjointed threads.
2. You have coworkers that hijack or resurrect old email conversations because they’re too lazy to start a new message chain.
3. Since conversations drift over time, the collapsed conversation view might have a subject heading that is increasingly irrelevant to the topic being discussed. This can make it much harder to figure out what’s going on unless you read the entire chain. And it makes searching for a particularly important email buried in the middle of a long conversation quite difficult.

None of these things detract from the usefulness of Conversation View itself. After all, most of the time, it does exactly what you want: highlight a chain of messages and make it easy to see the start and end of a thread while avoiding all the junk in the middle.

But it doesn’t quite replace a folder or a label because email subjects are often too granular a way of looking at messages. Sometimes I want a higher-level grouping, to consolidate multiple conversations into the same mental bucket.

I also discovered that I didn’t like to be at the mercy of my fellow collaborators. If they changed the subject line or changed the topic of the thread, I’d have no good way of assigning a message to the right bucket on my side. It works well enough when you have a small team with similar email habits, but all it takes is one or two folks to throw your inbox into disarray.

Living in the moment

Without folders there’s no easy way to pull messages out of the stream of email into a separate area. This has the effect of highlighting the importance of “now” in conversations. Normally, this wasn’t a big deal for me in our small company because the volume of email is generally pretty low.

But when things get busy, I found myself scrolling up and down, moving between pages to find the last few conversations on a particular subject. I noticed it particularly when I got back from business trips or vacations, when I really wanted to sort messages into piles and deal with all the marketing or finance messages in a batch, rather than address each one by one.

It also meant that we would ask each other for status updates more often, even when nothing interesting had happened. What folks were really asking for was a message to get moved to the top of their inbox so that they could keep the issue top of mind. It was easier to ask for an update than to try a dig through the messages from last Wednesday.

The end of history

What really spelled the end of my “search only” experiment was trying to dig up the contracts for our Dell computer leases. (Hence the three years from the start of my experiment.) There were several email conversations where we discussed the specs of the equipment, provided financial documents, arranged for shipping, etc.

I knew roughly when these conversations occurred, but had no idea exactly which words to type into the search box to get the messages I wanted. I could guess that “Dell” and “laptop” and “lease” might bring me results, but what if we hadn’t used those exact words? Or what if those words hadn’t ranked very highly in a chain of messages where we’d talked about computer purchases?

Even if I’d been consistent about using the right terms that would allow me to search and retrieve these messages, what about the folks I was talking to? What if the developers talked about their “machines” or “rigs” or the sales reps used the term “financing options”?

As with subject lines, I was at the mercy of the folks I was corresponding with. If they’d written good, descriptive messages with clear subjects and common terms I’d have no trouble retrieving the emails I needed. But if they hadn’t, I was stuck.

Since I needed to renew my lease and make a few equipment changes, I really needed to see all the stuff from our previous lease. And through search alone, there was no way for me to be sure that I was getting it all.

Conclusion

After that experience, I started using Google’s labels to group and organize messages, much like I’d used folders in Outlook to do the same. Having that extra bit of context around my email conversations makes all the difference in the world when it comes to keeping track of particular topics.

I admit that it took me roughly three years (at a very small company without much email traffic) before the pain got so great I had to put an end to my experiment. And that’s why I think that many people believe you can get away with search alone: If you’re dealing with small volumes of information, without much history, and have little need to consider the broader context, you can get by without organizing things.

But that situation is the exception, not the rule. Unless you’ve recently started a new job, purchased a new computer, or set up a new company email system, you’ll likely find that none of those conditions hold. It might take a few months or a few years, but you’ll eventually feel the pinch like I did.

When I finally decided I’d had enough, sorting all my messages into buckets was really painful. And I think a lot of people fall into that trap — they’ve avoided organizing their work for so long, believing those who tell them it isn’t necessary — that when they do feel the need to get organized, it becomes this huge, monstrous task. So they suffer with a system that they’ve outgrown.

“Outgrown” is the operative word here. You can get by with search alone at the start, but if that’s your only strategy for locating what you need, you’ll eventually reach the limits of what it can do. There is no silver bullet when it comes to keeping up with your stuff.

A final note about Gmail and Google Apps

Google has done a lot to entrench the idea that search is the best way to get the information you need. Their Gmail marketing page touts “no more folders, filing, or fumbling” as the number one benefit. Yet folks at Google must know that search alone doesn’t cut it.

Several years ago, they introduced labels, a concept similar to tagging. In May 2011 they added the ability to “nest” labels inside each other, which now makes them capable of mirroring the classic folders-in-folders structure familiar to Windows, Macintosh, and Linux users everywhere. And when I opened my Gmail earlier today, I was greeted with no fewer than five different ways to organize my inbox.

Inbox, inbox, how do I organize thee? Let me count the ways...

When the biggest and best search company on the planet spends considerable engineering effort to sort and categorize your inbox more effectively, it’s a pretty good hint that search alone as a strategy can take you only so far. Beyond that, you’ll need more than one tool in your toolbox — or inbox.

Related posts

1. How to name your files, folders and email
2. Locating Stuff: Folders vs. Search
3. Infovark Templates: Email
4. Inverting the Inbox