I'm part of a small team of four, and I'm the unofficial team lead (I'm lead in all but title, basically). We've largely been a "cowboy" environment, with no architecture or structure and everyone doing their own thing. Previously, our production deployments would be every few months without being on a set schedule, as things were added/removed to the task list of each developer. Recently, our CIO (semi-technical but not really a programmer) decided we will do deployments every three weeks; because of this I instantly thought that adopting an iterative development process (not necessarily full-blown Agile/XP, which would be a huge thing to convince everyone else to do) would go a long way towards helping manage expectations properly so there isn't this far-fetched idea that any new feature will be done in three weeks.

IMO the biggest hurdle is that we don't have ANY kind of development approach in place right now (among other things like no CI or automated tests whatsoever). We don't even use Waterfall, we use "Tell Developer X to do a task, expect him to do everything and get it done".

Are there any pointers that would help me start to ease us towards an iterative approach and A) Get the other developers on board with it and B) Get management to understand how iterative works? So far my idea involves trying to set up a CI server and get our build process automated (it takes about 10-20 minutes right now to simply build the application to put it on our development server), since pushing tests and/or TDD will be met with a LOT of resistance at this point, and constantly force us to break larger projects into smaller chunks that could be done iteratively in a three-week cycle; my only concern is that, unless I'm misunderstanding, an agile/iterative process may or may not release the software (depending on the project scope you might have "working" software after three weeks, but there isn't enough of it that works to let users make use of it), while I think the expectation here from management is that there will always be something "ready to go" in three weeks, and that disconnect could cause problems.

On that note, is there any literature or references that explains the agile/iterative approach from a business standpoint? Everything I've seen only focuses on the developers, how to do it, but nothing seems to describe it from the perspective of actually getting the buy-in from the businesspeople.