Work should not suck. Tools used by millions of people for 8 hours a day or more should not frusturate them and insult their intelligence. Unfortunately, most enterprise tools are sold for their ability to prevent the biggest idiots in an organization from causing the smallest dent to shareholder value. Expecting such tools to support leaps of creativity and innovation then, is a fool’s errand that many CTOs are stuck with. Fiasco-prevention and serendipitous value discovery are mutually contradictory design goals. Most of them realize this.

On the other side of the pond is the cornucopia of excellent and most usable web apps. They’ve got cool tools that ease the flow of creative thought; innovative technologies that enable new forms of value creation; collaboration tools that harness collective intelligence. Yet, they struggle to make a dent in the enterprise, where no one is even looking for some of the game-changing functionality some of them offer.

Bridging these worlds is the enterprise underground - the people who bring consumer & small business apps into the enterprise, like one might sneak an unconnected, but fun, friend into a party. They sign up for Basecamp accounts with their corporate card; set up a google group for their team; some even install and run wiki software on their desktops.

What are the members of the enterprise underground like? From my anecdotal experience, their defining trait is curiosity. They run the span from individuals with genuine insight into how a social technology can help change their organizations culture for the better, to novelty-seeking enthusiasts who want to bring every “cool” tool into work. But they are all curious. They are also often impatient and action-oriented. If they want to do X and they know that there’s MakeXr.com out there, they will simply signup and start using it. They don’t necessarily want to make trouble. Most are just trying to make work suck less for themselves and their teams. That is not to say that their behavior is tolerated by corporate IT. Far from it.

But increasingly, enterprises are becoming enlightened about the social web and the benefit of adopting these tools. In his most recent column, Jakob Nielsen discloses his finding that underground deployments of social software have far better success rates than top-down, CEO approved ones. This ties in with my personal experience. My hope is that the enterprise, it’s underground and the social web can co-exist. This, and the 2 blog posts that follow, are my ideas on how we can make it happen.

Coming soon:

• Part 2: Designing web apps for the enterprise underground
• Part 3: How corporate IT can embrace the enterprise underground