Delivering on long term roadmap: myth or reality?

When we plan a roadmap several quarters or a whole year ahead what are our expectations (and those of the leadership team)? Frequently the implicit and subconscious expectation is that everything will get done. After all if we use good scoping techniques we should be able to hit every deadline. Right?

Not quite. We might choose to extend the scope of some projects. We might remove some projects and add others, with different scoping, all due to market demand. And what about that quick marketing change that’s so needed but wasn’t planned for or an internal tools improvement that will shave off 20% of operational costs from your account management team? If our plans are too rigid we won’t be able to react to the outside changes and might miss good business opportunities.

Another reason why it’s typical to underdeliver on the roadmap is the one-sided variability in planned dates. A team that’s already pushing hard will almost never deliver projects ahead of time (but will sometimes run over the original plan). So whatever variability there is will add up and will eventually mean that a project or two won’t get done.

A good way to look at long term roadmapping is the same way as any other goal setting exercise. OKRs and EOS, two popular organizational methodologies, are both heavy on settings goals and both say that you should aim at about 80% achievement. Because if you hit 100% of your goals they weren’t ambitious enough and you didn’t push yourself (or your org) hard enough.

However, let’s not walk away from this thinking that roadmap planning is useless. On the contrary, we should deliberately plan roadmaps that are a (reasonable) stretch and push ourselves to deliver as much as possible. Like we do with all other goals.