How many roadmaps are the result of rushed, big-batch planning efforts? Lots.
You've got four weeks at the end of the year (or ten days at the end of the quarter) to get it right. Quick! Quick! Imagine the amount of money invested this way. And the dollars wasted because of premature convergence. I bet it is billions of dollars.
The flip side is playing whack-a-mole…doing whatever is hot at the moment. Who needs a stinkin’ roadmap or strategy anyway? This is costly as well.
A much better approach is more continuous roadmapping. What does that look like? Say our bets take, on average, six weeks to put in motion. To have a year's worth of work "ready", we'd need eight bets on the board.
Only two of our bets—the single item in Up Next, and the single item in In Progress—need detail. I prefer outcome-oriented one-pagers that leave room for creative solutions. We do some discovery and research with our team on the item in Up Next. Six of the bets are high-level options in an Ideas/Options stage. When we finish something, we pull in the next item from Up Next (and pick the next idea/option to start thinking about).
The important point here is that we try to keep this board filled at all times with eight cards. Eight cards! That's manageable. As new information becomes available, we swap in cards as necessary.
My agile friends are grumbling about a "year's worth of planned work!" I don't see it that way. That would be the case if the work was all committed and promised. Instead, I see this a current snapshot of where the team imagines the product is going. We avoid the rush to "fill" the roadmap at the most inopportune times.
But what if we change our strategy each year?
At least you'll be able to discuss the delta between your current mental model, and the new mental model.
But 8 items seems too few!
Forget estimation. What has happened in the past? I see teams pack their roadmaps like they're playing Tetris, only to discover—over and over—that they "don't get to things". And do that over and over. Stop the charade!
No seriously, our team releases like 25 features a year!
Try to go up a level and think beyond features. What are the actual missions?
What would it take for you to have an always up-to-date roadmap?