Recently, my team at Etsy and I have been doing some roadmap planning for next year. First, we made a huge list of ideas and pain points we could address, then bucketed them, then gave them some prioritization. We honed and crafted our plan until we had a short, achievable list of what we think are impactful to-dos for our team in 2014.
Then we started to put our product ideas onto a Gantt chart (on an actual chalkboard, no less). We estimated how long things would take, how many people we’d need to complete stuff, who those people could potentially be, etc. We got to the end of that process and wound up with a chart that looked something like this:
Whenever we’d talk about a project, someone would say “Oh, that’s a simple one, we can knock that out in a couple...