This post is a continuation of the Agile Strategy post.

So, how do we get into the right frame of mind for roadmapping?

You must embrace the Tao of Planning.

There are two conflicting principles behind roadmapping: you must keep thinking out of the box while keeping work deliverable. Neither of these principles is difficult in isolation. The challenge is the keep them in balance and to make sure that the whole team is included.

For my team, we struggle to find group times when we can do some big thinking. The challenge is not the thinking – it’s the TEAM aspect of working on strategy together. Our sprint planning needs to focus on the “keeping work deliverable” objective; consequently, there is precious little time in planning to have big ideas. To make the meeting duration manageable, planning meetings should have a tactical focus. Unfortunately, that leaves a strategy gap.

So, where does a team go to dream?

I wish I had a clear answer to this problem. Ideally, sprint review meetings should extend into deep thinking about where things could go. Strategy during Review is a natural extension because a review mindset should be forward looking. Reviews help us think about how we’re going to use what we delivered and the audience should bring external perspectives. If we could do this then it would be very empowering and exciting during review.

That’s why it’s important to celebrate, play, reflect and pause. All work and no play leaves a team that makes very dull products

Note: the Agile decorations that I use are: Sprint Planning (commits that plan) -> Stand-up (daily sync meeting -> Review (demo/sprint close) -> Retrospective / Hats (team feedback, improvement).