For those of you who have implemented Scrum in your organizations, what were your biggest obstacles and if you did overcome them, how?
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We implemented Agile (set of SCRUM - management and XP - engineering practice) in an environment that was waterfall with large projects in an environment that was heavily integrated. The waterfall police were everywhere. As you can imagine, many projects failed. Having done Agile at a previous employer, we received permission to trial agile for the project.
Internal to the team, we used the Agile practice. Externally, we wrapped the agile practices with waterfall processes meaning primarily reporting. Thus, we looked from the outside like a waterfall project. However, there was a big difference, internally we were using agile and consequently we delivered, on time, within budget with high quality.
The critical success factors were embedded coaches (Iteration Manager Coach, Dev Lead Coach, Test Lead Coach and a Solution Analyst Coach). Securing commitment from dependent system in advance (required that we look ahead to identify depend systems and the work required from those systems) was a must in a heavily integrated environment. Prior to starting, we immersed the technical and business members of the team in an agile boot camp. This ensured that the key players (product owner and technical team) knew there roles and could execute effectively. Finally, the wrapping of the project with waterfall reporting enabled us to tie into all the existing reporting structure in the enterprise.
The net result is that the company is now moving waterfall projects to agile. This is all possible only because we have been able to deliver high quality software at a sustainable pace.
I have been running Scrum in several projects. The biggest problem, as I see it, is that not everybody in the organization is into the process. Everybody needs to be committed. Not only the team of developers. Often the managers are the persons that initialize the process and expect that things will change to the better without them doing anything.
My suggestion is that you run a workshop with the whole organization so everybody knows how the process works. Not only the developers. It's essential that you have a person that is really into the process. A person that can answer questions the team and organization have. A mentor.
Being agile is about welcoming change. You should not let the process gets in the way of sense. Do things that works for your organization, but you should try out the whole process before throwing something out.