One thing that managers generally does not like is staff that does not “fall in line” and create issues for them that they have to deal with. I would therefor not mention for example having emailed VP:s about issues or highlighting bypass functionality in systems (if your previous job description did not include to highlight this).

From a managers perspective in the example, they are trying to run an operation of good support. They have to comply with different laws and have a solution “that works”. They may not appreciate that someone in the staff highlights “flaws”. If someone highlight flaws of this type anyways:

1) if highlighted by a staff member may have to be addressed. In particular from a staff member that emails VPs. Some point in time, possibly after a difficult process, legal may have ticked this off. The manager may not be happy to have to revisit this question again.

2) It may be difficult to address for the manager (request new support services software? Get an opinion from legal? - may be a large project)

3) disrupts the main goal of the manager of providing good support services.