The first problem you may encounter is an absence of a common vision on what is needed in terms of digital transformation for your organization. That’s why there’s so much talk about buy-in in the organizations. Another blocker can be a lack of an up-to-date strategic view. Resistance to change, lack of digital skills are other social issues most likely you will have to overcome. Data silos and systems incompatibility are the major technical issues that should be taken into consideration in advance by the software company you partner with.