All things being equal, everyone is on board with Scrum from the CTO to the janitor, and your company is functional (as opposed to dysfunctional) as all get out. There are two major challenges I see every team face to a greater or lesser degree, sooner or later. The first is simply MVP. I won’t go into the whole Skateboard through sports car metaphor, (which is awesome but not my point) I mean just simply building one slice through the application or data process or whatever it is you are going to build. One slice through it to provide some value to the end user, to the customer, so they can get something right now which you will then iterate on and incrementally build out for them until it is everything they ever dreamed of. This is a very hard transition for many teams to make in my experience. They want to design everything up front and deliver it all in a big bang and often cannot really imagine what delivering the skateboard would look like or why the customer would want it. Once they finally get it (and this happens only by doing it for the first time), it becomes a great revelation, a new way of thinking and doing that they never want to return from ever again. Once they are on the other side of this monumental change they cannot imagine ever doing it the old “big bang” way again.
The other major challenge is user centered thinking, taking the actual view of the customer of whatever they are building. This is in every sense one of the harder shifts to make in everything from how to write user stories, to simply how to look at everything they are doing from the standpoint of who they are doing it for. This is a seismic shift! It is not an easy thing to do. I often refer to it as the “broken brain” moment where new synaptic connections form and people look like dogs who have just heard a baffling sound with their heads cocked to the side. I once worked with a very large team (6 teams working together actually) on a process redesign. There was a moment where they actually turned as a group from thinking about things from their company’s point of view to the point of view of a user of the process and it was like a silent “whumph!” where everyone collectively and suddenly realized the implication of what their actions as a company meant for a user of their process. It was a revelation.
I love these two moment of realization. I live for them when working with new teams, and once they get these two things, suddenly, you have a real scrum team, one that is in tune with the Agile principles. A team that is in tune with their users, and once there you can never go back.