There are a couple of challenges that you will encounter or have to overcome when it comes to DevOps. The challenge we mostly see when working with customers involves issues in the communication between teams. This stems from the issue that silos are in fact not busted, but every silo simply develops their own set of DevOps practices and carries on.

Communication is key when starting with DevOps. It is easy to say that Dev and Ops need to get closer together. In practice, this is not a simple task at all. Communication does not just mean getting people to talk to each other and to collaborate. It also means agreeing on tools to use, development philosophies to follow, and so on.

Another challenge that is commonly encountered—not only due to a lack of communication—is a lack of consistent tooling. If every team does what they want and deploys the tool they want, silos continue to exist.

The result of this will be utter chaos. If the tool landscape is too fragmented, there is too much velocity lost simply through friction. Also, someone needs to look after all the tools. Patching and maintenance, setting up new team projects, and enabling teams to deliver great services would be some of their tasks.