Decide what Format we're going to use for the Organization Roadmap

[flyingzumwalt]

The two most important sections of our next Quarterly Roadmap Update will be to

1. Review the Q3 Roadmap & Milestones
2. Define the Q4 Roadmap & Milestones

In order to prepare for this, we should decide in advance how we are going to display those Roadmaps to ourselves and our audiences. The full details of the Org Roadmap and its structure won't be clear until we've stabilized and implemented the new PM Model (see Milestone 1), but I think it's time to start thinking about what the final result -- the Org Roadmap and its subsidiary Project Roadmaps -- will look like.

To get us started, I generated a sample Org Roadmap in PR #176 using @haadcode's roadmap-generator. This gives a compelling glimpse of what a roadmap could look like.

Please share your ideas, misgivings, confusions, etc.

Things to Consider

The Roadmap should frame our planning discussions. If we have the right format for our Roadmaps, this gives us a valuable frame for conducting planning discussions. For example, as we build up milestones and set delivery dates during the Roadmap Update, we can generate drafts of the Roadmap and see if it looks right to us.

The Roadmap is our main tool for accountability. If your work isn't on the roadmap, there's no way for your peers to see your progress and there's no way for them to hold you accountable for following through on your commitments. In fact, if your work is not visible on the roadmap, your work might not be visible to anyone. That's a recipe for miscommunication and loss of trust.

The Roadmap is something our audiences need to rely on. The roadmap is basically a list of promises that we're making to our audiences. Making clear promises and delivering on them is GREAT, but over-promising and falling short of your deadlines is NOT GREAT. Likewise, making vague promises without clear dates doesn't do anybody much good.

I'm especially curious to hear feedback from PMs and Product Leads on this. @whyrusleeping @diasdavid @haadcode @em-ly @RichardLitt @jbenet

related to #135

[flyingzumwalt]

We've settled on using a waffle board like https://waffle.io/ipfs/roadmaps plus updates to the ROADMAP.md in ipfs/ipfs