Reseting and experimenting: under-rated

I was in a week-long training on Agile Development.  I spent a weekend thinking about it and something totally struck me: when a project stutters then going back to square one and restarting is the right thing to do.  After all, if one goes down the wrong path then it makes no sense to continue progressing.

This can be further extended to starting projects on an experimental basis knowing that it may fail.  Sometimes people are hesitant to do something until they are certain it is the right thing to do.  The problem is that often we don’t know if something is worth doing until after we have tried it. 

Companies take risk all the time. They experiment, start projects and happily cancel them when their bet doesn’t pay off.  Very few people remember Apple Newton, its first handheld platform that it experimented with for a decade until finally giving up in 1998.  It’s hugely successful iPhone would never have happened without that risk-taking. 

Now the question is, how should we extend that attitude to municipalities? Specifically, what are some areas Milton can experiment with, knowing that it’s experimenting?  How should Milton communicate that to the residents so a failed experiment is seen as a success (since it teaches something)?