1. Not focusing on Culture
Adopting Agile at an organizational level is something that will take a long time, bring about change throughout every level of the organization, face many difficulties, and require a great deal of experimentation and learning. In order for all of these to be possible it is not enough for an organization to simply adopt the practices of one of the many Agile frameworks that are currently available. This will lead to (maybe) some short term successes and some initial enthusiasm, but it will not setup the organization to sustain their Agile adoption over the long term. In order to really get a transformation to stick, the entire organization must experience a cultural shift that will encourage, support, and enable a focus on learning, failing, inspection, adaption, and continuous improvement. With the right culture in place, it will not matter what frameworks or practices the organization tries to adopt because they will be comfortable with trying many different things, continuing to focus on improving, and sustaining improvements over the long term.
2. Too much too fast
Scrum! DevOps! SAFe! Kanban! Continuous Delivery! With so many different buzz words floating around the Agile sphere, it can be easy for companies to get excited and bite off more than they can chew. Every organization is different in their readiness to adopt Agile and need to carefully consider many factors when deciding how to start their journey. Smaller organizations or teams, such as start ups or the IT department of a larger company may be able to immediately start practicing Scrum. On the other hand, larger organizations that have traditionally worked in a waterfall fashion or that are in heavily regulated industries will find it difficult to make the big changes that accompany a framework such as Scrum and they may get discouraged or quit altogether if they run into problems early on
3. Lack of support from leadership
As my colleague Russ Wetmore wrote in his article "Transitioning to Agile: An Evolving Exercise" (link to: https://blogs.mindtree.com/transition-to-agile-an-evolving-exercise), turf wars will always pop up during an Agile transformation and there will always be early failures as organizations are finding their way. When this happens, leadership teams will often start to worry about their ROI if they have not fully bought into the idea of agile and they revert to old ways of working after an early failure. When the top level leadership is fully invested, they will understand that there will be many changes and that there will be bumps along the way. Teams will fail early and often as they become comfortable with new ways of working and as they embrace a mindset of continuous improvement. By knowing that their leadership is supporting them, teams will be more quick to embrace the transformation and feel more comfortable experimenting and finding new ways to improve.
4. Unrealistic expectations
Too often organizations get excited about the time to market and quality gains that they will gain by adopting Agile, but they rarely fully understand what it will take to actually get these benefits or how long it will take to get them . Typically they will decide to adopt Scrum and then expect to see results within a few months. In addition, without a proper understanding of concepts such as MVP, User Stories, and backlog prioritization they may not understand that they will not necessarily be getting every single thing they want, but that focus will be placed on whatever will add the most value. These misaligned expectations will lead to a great deal of frustration for everyone involved. When these issues pop up, team members and leaders will eventually stray from the Agile principles in an effort to get everything they think they need done complete or they will consider their Agile journey to be a failure before it has even had a chance to really take off. Before any Agile adoption takes place, everyone that will be involved needs to be on the same page about what can be expected and when it can be expected.
5. Miscommunication throughout the organization
Everyone fears change, especially when they are not sure how they will be affected by it. When a company is undergoing an Agile transformation there will be lots and lots of change. With all this change occurring many people in key roles will be unsure of what their new place will be in an Agile organization and they will worry that they will no longer be necessary or that they will be unable to learn to work and succeed in this new environment. With these fears in mind, many people will be reluctant to embrace the Agile transformation and may even actively work to block its success in order to preserve their position in the way that they are comfortable with. By properly communicating not only the benefits that an Agile transformation will provide, but also how everyone's role will fit into the transformation can help to mitigate some of the fears that people will be building up in their minds and help them become more comfortable with the idea of change.
6. Lack of adequate training
One of the primary aspects of Agile is collaboration. This collaboration will take place between everyone, even people and departments within an organization that have never traditionally been involved in IT. This is a big shift for many organizations that have never worked this way before and too many times, organizations think they can one or two of their project managers to take a Scrum Master class and then have them teach the rest of the team. In order to have the whole team buy in everyone should go through training to be familiar with the principles and practices that they will be employing. In addition to training, teams and organizations can benefit greatly by investing in Agile coaching from an experienced professional who will be able to guide the team through many of the obstacles that they will run into as they start their Agile journey.