I have never found documentation to be an enjoyable part of software development, but rather a nuisance and hassle. Why? Two reasons.

First - my experience with larger organizations is that documentation requirements often bury great ideas by sucking up resources that should be spent prototyping, and always being a step behind the latest ideas and solutions flowing between the minds of the people involved in a project.

Second - Word, Power Point and Visio, the most commonly used tools for software documentation, are not agile tools. I’m not saying they aren’t good tools, I’m saying they are not suitable for an agile, collaborative software development process.

Enter startup mode. Purchasing applications for an office of less than 10, on a startup budget, led me to put the company on Google Apps earlier in the year - despite the beta status (and the beta bugs). It was free, and it gave us email, calendar, storage, docs and spreadsheets all for free (it’s now $50 per user per year as of last month - still a bargain).

Little did I realize at the time, but the decision to move to Google Apps would start a change in my perspective on documentation. What used to be a chore that chased the development process; started to transition to a task that lead the development process. But Google did not do it alone. The ability to collaborate on docs and spreadsheets in real time from multiple locations - with fellow employees and contractors - was awesome, but it is still difficult to communicate software architecture using just docs and spreadsheets.

That changed sometime in May when I was making some changes to my basement remodel diagram on Gliffy, and noticed that they added the ability to collaborate. Fast forward to today - at one point half the ScribeStorm employees (plus one contractor) were online, working on a number of documents together, in real time, between five different locations. And the beauty is, it not only works, but everyone involved is excited it works and doing what we all wished we had done on dozens of projects in the past - quickly gather everyone’s ideas and build clarity and focus on the project, early.