Scrum as a framework is simple to understand and can be challenging to implement well, but it is easy to implement the structures. What is difficult with many teams is instilling and living by the values and the principles of the Agile Manifesto and the Scrum values. What is hardest, what is truly challenging is helping a company culture to change from one of command and control to one of empowering teams to work it out for themselves and to align with customers and the business on their own. What is hardest in Scrum is not scrum itself but the culture around Scrum teams. Teams get it quickly and are aided or impeded in their journey by management and corporate culture and whether or not they are truly on board with the values and principles which can fly in the face of how things have “always been done around here” and challenge micro-managers and command and control minded people at every level of an organization.
It is the very idea of a corporation that needs to change: how one is run most successfully, why one is run at all, what values and principles does the company possess as a whole? That is the biggest challenge of Scrum. Companies embrace values and principles either implicitly or explicitly. They may not be (in fact they often are not) the ones they have outlined as aspirational in their employee handbooks or signage. I find cultures to fall into one or another main category, trust or fear. Trust is at the heart of any Agile company. Fear is at the heart of any command and control culture. How do you migrate from one to the other? You hire for trust, you promote trust, you trust yourself, by which I mean you demonstrate trust yourself and you are trusting. I do believe that people can change, but I do not believe that companies can often change them. In those cases you may truly need to hire and fire your way into a culture of trust, a culture that supports Agility. I think you can try to educate, try to coach and encourage, but at the end of the day if you cannot change your culture, you will have to change your people. You will have to find the right people to build the explicit culture you desire. Scrum cannot help you with that, it can only start to reveal the problem. That is the hardest thing about Scrum.