First and foremost, we approached this project out of a necessity to better organize the ever growing mountain of information and resources that our site provides our users. We were very cognizant of the fact that if we embarked on this path, we had to carefully consider how to balance our playful image with our powerful product. MailChimp helps 600,000 people send 40 million emails a day–that’s a serious business.

A few months ago we redesigned 37signals.com — our main site. I want to share with you a few iterations and permutations I created along the way. I’ll also give a little insight into the discussions we had about each design: what we saved for the next version and what we axed because it wasn’t working.

The short story is that pair programming doesn’t work for me as the main way of developing software.  I can pair program for a day, or maybe a week, especially if we’re focused on a particular problem.  But after that?  I’m done.  Toast.  I don’t want to see anyone, talk to anyone, and I need at least a couple of days in a cave until I’m fit for human company again. 

For new initiatives a product manager typically starts by writing an internal press release announcing the finished product. The target audience for the press release are the new/updated product's customers, which can be retail customers or internal users of a tool or technology. Internal press releases are centered around the customer problem, how current solutions (internal or external) fail, and how the new product will blow away existing solutions.

At the UIE Web App Masters Tour in Minneapolis MN, 37signals founder, Jason Fried described how 37signals solves design problems and collaborates by showing four days worth of chat transcripts about an ongoing redesign project at the company.

Go from brainstorm to sketches to HTML to coding
Here's the process we use to Get Real:

I'm interested in what questions y'all ask clients at the beginning of the design portion of a project. Do you lead a design discovery exercises or do you just send them a list of questions?

The secret to creativity is curiosity.

One of the things that terrifies me most about a new project is the starting point. How is the content laid out? What colors do I pick? Once things like that are decided, it becomes significantly easier to continue design, but it’s the blank page where I spend the most time.

To that end, I often start by choosing type. I don’t need to worry about colors or layout or anything else… just the right typefaces that support the art direction.

Of particular interest is their handling of key words and links and the relationship between on and offline versions.