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I want to do a Small Batches episode on planning & roadmapping in software development. Every company I’ve worked creates a quarterly roadmap at the beginning of the year which is invalidated or reworked constantly to the point where it doesn’t make sense. Who are some great people to talk to about mapping the desire for quarterly/yearly development schedules onto the dynamics of software development?
It's something I help organizations with. Happy to chat about the different approaches we take. The "marketing spiel" I use to explain it is like this:
A good roadmap is dynamic and provides opportunities to change directions. The objective is to get to deliver the highest value in the most effective way. Think of our service like Waze. Through our knowledge and experience, the client can learn of obstacles up ahead and make a decision to take a different path. We may also recommend additional routes and stops along the way, creating opportunities to add value while meeting the primary objective
Try there @syedhussainchi. Here's a video from my business partner on the topic. There's a bunch of references to source material in there https://www.youtube.com/watch?v=Vr_5sPtm9Ic I'd also double down on Bryan's suggestion of following John Cutler as he Tweets very frequently on the topic.