Suppose you're the product manager for an internal enterprise web application that has 2000 users and 7 developers. You have a list of 350 future features, each ranging from 5 to 150 developer days of work.
How do you choose what features to work on, and how do you run the release process?
Here's what I'm thinking: (skip if boring)
Release Process. Work on several features at once, release each individually when it's ready. The other option (what we've been doing up to this point) is to pick out a certain set of features, designate them as "a release", and release them all at once (announcing via mass email).
The advantage of a shorter release process is that we can release features as soon as we finish development. The advantage of a bigger process is that it's easier to organize.
Feature Prioritization. Put all the future features in a spreadsheet with columns for feature, description, comments, estimate, benefit, (your) estimate, (your) benefit. Give copies to 2 senior engineers, the other senior project manager and yourself.
The engineers estimate all the features (how precisely? consulting each other?). To determine benefit, everyone allocates points (total = 10 * [number of future features]) among the future features (without consulting each other?), compare scores and average (?).
Another potential strategy here is to just rank each feature on an absolute (say) 1-100 scale. Having an absolute ranking is nice because it makes prioritizing as our feature list changes easier (we don't want to have to redistribute points every time someone proposes a new feature).
What's your strategy? Do any books / websites attack the problem at this level of detail?