In gathering requirements for a new Salesforce implementation, schedule a session with the executive sponsors to gauge among other things, the ‘culture’ of the organization. Focus on the aspects of culture when it comes to adopting new systems and the formal and informal means by which users get trained in using new systems
Culture is how things get done, what behaviors are rewarded or frowned upon in the organization. While a single Q&A session with an executive sponsor is not sufficient to get a complete picture of the culture, it’s a good start. Effective senior executives give thought to this aspect when it comes to their teams, so should have well thought through ideas on the subject.
There are a number of areas you should be touching upon with the executive sponsors; here are questions that focus on the adoption of the system