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Home/ Questions/Q 79005
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Asked: May 10, 20262026-05-10T21:04:39+00:00 2026-05-10T21:04:39+00:00

Suppose you’re the product manager for an internal enterprise web application that has 2000

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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?

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  1. 2026-05-10T21:04:39+00:00Added an answer on May 10, 2026 at 9:04 pm

    There’s a great book that helps cover this topic called Agile Estimating and Planning by Mike Cohn. It has some great ways to estimate and plan releases. Including a planning game called planning poker where the engineering team gets together with cards to estaimate user stories. Each engineer plays a card 1,2,3,5,8,13 face down. The high and low card explains and you do it again. After 1 or 2 repeats there is generally convergence on the same estimate.

    There’s also Beyond Software Architecture: Creating and Sustaining Winning Solutions by Luke Hohmann which might help with some of the product management related pieces and the reasoning to use to prioritization. I have not yet read the book but I went to a talk by Luke Hohmann where he covered the subjects of his book and I can’t wait to read it.

    Also I would recommend reading books on various Agile Development processes such as Scrum, Crystal Clear, and XP. There’s Agile Project Management with Scrum by Ken Schwaber and Crystal Clear: A Human-Powered Methodology for Small Teams by Alistair Cockburn. Also Extreme Programming Explained: Embrace Change (2nd Edition) by Kent Beck and Cynthia Andres.

    As for feature prioritization, that is generally done by the stakeholders. You need to work on the features that address the needs of your stakeholders, which, as Luke Hohmann points out, includes the system architecture.

    However, one of the most important things is to make sure that you have agreement on the software development process from the team. If you force a process and the team doesn’t believe in, then it will not work.

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