Memento Roadmap

A story about a colleague, that approached me for coaching on how to create a roadmap. One, in which she actually remembered the details of the roadmap before it happend.

Session one

Initially, I wanted to figure out a couple of things:

Those last two questions I left her with. The former prompting her to reevaluate her assumptions about how fixed the scopes are. The latter to locate the highest priorities and plan accordingly.

Session two

A bit later, she had come to more clarity about what she wanted to achieve and asked for another round.

She lost herself in a very detailed explanation of the first of four factors that she wanted to achieve and how this would be accomplished and what steps needed to be taken and how to allocate those to the right people and...

Maximal detail mode. Depth first traversal of a work tree.

I had to re-focus her on the big picture so she wouldn't end up with a detailed task plan/gantt chart that would fall to pieces upon contact with reality.

By reflex, I decided to do a Remembering the future exercise with her.

“Imagine it's Christmas Eve. All the gift unwrapping and eating is done and you get to sit back, relax and think about the accomplishment of the past six months. Tell me what you're celebrating? What's the thing you achieved?”

Now we were talking about high-level outcomes, about the things to be proud of at the end of the project. And in the process, one of the initial four factors even turned out to not be important at all! The roadmap already got easier to complete.

“Ok, now think back. It's still Christmas Eve and you remember that just in the last few weeks the final steps were completed to actually deliver on time. Tell me about those last two, three things that happened.”

Results from work streams, adoption numbers, clear & tangible outcomes. I jotted those down on stickies to put at the right end of the roadmap, the 6-months mark.

“Now, go all the way back, to six months before. Remember, at the start of this very successful project, those first, crucial steps. The ones that got you going and gave you the energy to keep going. The moment when you knew this was off to a great start. What were those first tasks you completed?”

Now it's about individual tasks, first small milestones. Those that are already clearly visible now. I noted those down and put them all the way to the left, into month 1.

I then encouraged her to fill in the space between the two bordering colums of stickies. Before I left her, we quickly discussed the different nature of the existing stickes, actions in the short term, outcomes in the long term. Somewhere in between there needs to be a switch from one to the other and the close you get to that turning point the more abstract, fuzzy the roadmap items need to become.

Just like when planning a road trip: You probably know the first few turns to get to the highway. You're probably also clear about the address you want to end up going to. The steps between become more and more unclear, to the point where they are just a general direction, then become more tangible as you get to the highway exit closest to your target.

She happily filled in the rest of the roadmap and already ran it by her manager.