Are Staff & Management satisfied with response times?
Are issues usually resolved without needing to address them multiple times?
Are issues being auto-remediated without manual intervention?
Data Centre Infrastructure
Do systems adequately support the required applications?
Are the Hardware and Operating System in a vendor-supported state?
Are capacity thresholds (RAM, CPU, HDD) known, and are they acceptable?
Is there a replacement plan for aging components?
Are there systems that should be considered that will provide additional productivity?
Is DR being tested? Does backup & DR meet requirements?
Have all data sources been considered?
Is there a defined Recovery Time Objective (the duration at which DR failover should happen) and Recovery Point Objective (the period of data loss in a DR scenario)?
Is security being addressed through a cadence, not just point in time?
What security technologies are in place?
Are adequate security policies in place?
Does the organization have a defined Security Position?
Do they need one?
Are security audits requested/required?
Is data easily & securely accessible?
Does the right balance of technology tools exist? (sufficient but not overwhelming)
Is there a hardware refresh cycle in place?
Are the Operating systems currently supported by the vendor?
User Adoption & Training
Are staff highly proficient with the applications they use daily?
Is there a plan for ongoing professional development as it relates to technology?
Has management gained end-user feedback on the level of IT adoption?
Collaboration & Telephony
Are ISP & Telephony contract renewal dates known?
Are the current systems efficient for communications?
Do capabilities exist that would provide productivity gains?
Is modern collaboration understood?
Is application performance meeting expectations?
Are end of life & upgrade timelines known?
Is workflow automation being leveraged adequately?
Are other lines of business applications meeting expectations?