I don't do estimates. I put anchor dates months in advance, and track progress with the different teams through weeklies. Project planning that breaks tasks do

I don't do estimates. I put anchor dates months in advance, and track progress with the different teams through weeklies. Project planning that breaks tasks down into granular dates just begs everyone to disrespect it once dates inevitably start slipping. Don't do that, just keep an eye on the important dates and give your teams the headroom to work. In your case I'd set strategic goals for the year to align with the business, then plan anchor dates (such as key releases) on a month or two month level for the entire year, then work back dependency and tech roadmap from there. Also keep some capacity in reserve. Plan your yearly goals conservatively but your anchor dates a bit more aggressively. Then once the plan is in place, keep track through weeklies or something unobtrusive like that.