The first and obvious place to initiate a change management risk assessment is with an examination of your organizations alter heritage. Register now to get the more details about risk management.
There's absolutely not any prescriptive way of doing so, but I would suggest looking at all job debriefing and wrap-up reports, I'd look closely at benefits realization, change effects, what worked and what did not and why with regard to the views and opinions of those directly involved with the attempted implementations.
I would also pay especially close attention to the opinions and views of those directly affected by the initiatives – these people working on the frontline.
Present assessments of organizational openness can and should incorporate an organizational assessment against programmers and project management, business process and change management maturity models.
This doesn't have to be a protracted exercise but may be undertaken quickly and informally. The purpose at this stage is simply to immediately invent some reasonably good reference points and to evaluate your organization's realistic and reasonable capacity in each of these regions.
A structured and detailed assessment of organizational culture benefits realization, and impact assessment is addressed as an integral part of the programmers based change model and methodology that I recommend.
I came up against this challenge when trying to argue the case for taking a more people-focused approach to change projects.
It became clear to me in working with public sector organizations that most projects failed to deliver the planned benefits because the complexity of what they were trying to achieve was not within the capability of the organization to cope with yet another change initiative.