One of the more interesting hacks at Yahoo! Hack Day last week was a game that challenged the notion of tagging.

How effective is tagging for recall? Can you remember what you tagged any given item? This question gets right to an important issue.

del.icio.us was invented as a type of bookmark manager. Joshua Schachter needed a way to save web pages, and the tag format seemed like a better metaphor than folders for recalling things.

When I first heard about del.icio.us from Jon Udell, my initial reaction to the idea of a bookmark manager was very negative. That reaction was clearly related to this question, as I was sure then and just as sure today that my mother will never organize her web pages with tags.

(Actually, that’s a risky statement. My mother is so organized that she can locate my primary school grade reports as quickly as she can find her most recent ATM receipt. She may actually become a super tagger some day.)

The act of tagging for the purpose of saving items for later is not for everyone. It is perhaps only necessary for a small group of people in specific circumstances. Bradley Horowitz’s influencer pyramid is a great visualization of how tagging can add value for the rest of us. At the top is the person who makes extra effort to evaluate, filter, categorize and socialize things. This is the person everyone who wants something socialized on the Internet needs to talk to.

In my mind, tags are hugely valuable. They expose important meta data at an abstraction level that was previously hidden in the Internet user interface. They are connective tissue allowing data sources to talk to each other in meaningful ways. And human-edited tags can balance the inaccuracies of machine automation that happens in any indexing exercise.

What’s missing from the tagging world is automatic learning. People shouldn’t have to find the ’save’ button, click it, fill in tags, and hit save. My browser history says a lot about what interests me. The time I spend on a page says a lot about what I value. Any social activities I initiate or receive can inform a machine what the world around me thinks about.

The influencer is clearly willing to work harder to ensure information flows through the Internet in sensible ways, but everyone else will need something more personal to happen as a result of tagging to warrant the amount of effort to do it.

The introduction of tagging into the Internet user interface was a key step in the evolution of the medium, but the process of adding and collecting tag information needs to evolve before the effects of the tags will reach their true potential.

Last week’s Yahoo! Hack Day was, as usual, an eyeopener. In addition to the creative hacks, I was hugely impressed that the co-founder of the company and CFO among several other key executives spent an uninterrupted afternoon watching and then judging all the hacks.

Photo: Yodel Anecdotal

The only other model for bridging the gap between top brass and ground troops that I’ve seen work successfully was at IDG when founder Pat McGovern conducted his annual handshake around the world during the holidays. He meets with every single employee of the company (2k plus), shakes hands, chats for a few minutes and, if available, hands the employee his or her bonus. He remembers impressive details from previous conversations and clearly challenges himself to make a tangible connection with each person’s contribution.

Everyone admits that it creates awkward moments, but the effort is appreciated by all and wins him both loyalty and credibility across the whole company.

At Hack Day, I expected Jerry Yang and Sue Decker to spend much of their time on their phones while engineers were working their hardest to impress the crowds. Admittedly, I didn’t make it through the whole afternoon undistracted, but the judges were engaged in every presentation that I did see. No doubt they were paying attention and learning things that will impact their future decision-making.

There’s always the question of whether the hackers are motivated more by peers or by bosses. In either case, the 90-second demo format is the closest thing software development has to the clean and jerk. I’m not sure I’d call it chest-thumping exactly, but don’t believe for a second that every hacker doesn’t hope to beat his colleagues with the better hack.