You cannot use a waterfall up-front plan to become agile. What I do is apply Mike Rother's "Improvement Kata" Start by assessing the current condition. Where are we now? What are the impediments? What are the business problems that keep the executives up at night? 1/5
We then (collaboratively) come up with a definition of "awesome." Where would we like to be? Most importantly, what's an indication we should look for that tells us we're moving in the right direction? Could be a metric, could be something qualitative. 2/5
Then, working collaboratively with the execs, we come up with an experiment that we hope will move that indicator in the right direction. Not all the way, but just a bit. We then run the experiment and see what happened and adjust. Repeat. 3/5
This is an Agile process, not an up-front plan. Inspect and adapt. Try something. Analyze it. Make and adjustment. Repeat. A "transition roadmap" is nothing but a waterfall up-front plan. I don't see how you can use a waterfall approach to become agile, though. 4/5
You need to become agile by being agile. 5/5
