Weasling, wishful thinking and why roadmaps need focus
The main risk with long-term pursuits is that we humans love to lie to ourselves. We are pathological optimists. "We're behind schedule, but if we pick up pace in the second half, we can still make it..."
Roadmaps are at the heart of long-term planning. They are an intricate network that connects the strategic level with the actual work. A roadmap is a yardstick to counter-balance our optimism; hard numbers versus feelings.
Roadmaps should be timelined, outcome-based, hierarchical, unified, centralized, versioned, and focused. They are not trivial to build.
Each of these traits is fascinating to discuss in its own right, but today I'd like to talk about the last in that list.
Why do roadmaps need to be focused?
Roadmaps are often visualized as Gantt charts and will look something like this:
The horizontal axis is the timeline; the vertical axis represents the scope. The bars are the time-scope allocation. Note that only two of the sides of the Iron Triangle are represented. We see what we will do and when, but there's a blindspot on Resources. Tasks can be linked, indicated by arrows. If task B has to wait for task A to be completed, B depends on A.
A famous feature of the Gantt chart is that red line: the critical path. The critical path is the longest chain of dependencies in the plan. It's critical for a simple reason.
If any other tasks are late, the plan is merely under pressure. We can handle that. If one of the tasks on the critical path starts slipping, however, the deadline is in danger. In most organizations, going over budget is better than missing a deadline.
So, project managers get obsessed with the critical path. If we see it slipping, we'll allocate more resources.
Those who've read The Mythical Man-Month already see the issue with this approach. In knowledge work, allocating more resources to a task will make it even later!
But there's another, more hidden, side-effect.
Allocating more resources in software product environments doesn't mean hiring more developers. It often means taking them from task B and having them work on task D. This is where that blindspot on Resources comes into play. How do we know if that new catch-up plan is feasible? Good old gut feeling! Pathological optimists, remember?
We are starting a fire to put out a fire.
Not only is the critical path behind schedule now but so is the other path. Before we know it, the roles reverse, and the path we've neglected has become the longest one. We have a new critical path, and we still miss the deadline!
That's why "80% done" is so dangerous. It gives us the feeling that we've got that path under control. If you've ever seen a team churning out features and still missing the deadline: that's what's happening. We lie to ourselves. We feel we're making loads of progress, but most work is still unfinished. It sneaks up on us.
A focused roadmap addresses this. Instead of trying to tackle multiple tasks at the same time, we'll install a Work In Progress limit of 1. A focused roadmap is a Gantt chart without non-critical paths. We serialize the work rather than parallelize it.
This gives us the tools to plan effectively.
When an item starts to slip, there's no temptation to weasel. We can only allocate more resources at the expense of another item. If Task A starts slipping, we can postpone B and cut scope in F. It forces tough decisions. That's a good thing.
When our designer is vital for task E but needs time off in that period, we can easily swap roadmap items without worrying about unforeseen impacts on non-critical paths.
Expediting a particular roadmap item becomes trivial. "We'll do the Sharepoint integration first and push the calendar redesign to March".
Unfocused roadmaps make it easy to lie to ourselves. They invite wishful thinking. We can spend an hour reshuffling a plan in Jira and somehow solve a resource problem without adding more resources. I've lost count of how many times I've fallen into that trap.
Since lying to ourselves is the biggest risk in long-term planning, we need a tool that forces tough decisions and leaves no room for weaseling.
A focused roadmap is just the thing.