1. How is IT increasing speed, cost, and quality of delivery?
What to look for: Is IT moving to an Agile Scrum development model? Is it using Continuous Integration and Continuous Delivery processes? Is IT using hackathons to accelerate learning within IT? Is it using a Dev/Ops model to increase quality of deliverables? Is IT pushing to cloud and subscription-based models to reduce and avoid large CapEx expenditures?
2. How is IT building talent?
Does IT have a strategic and focused plan to build IT talent? Is there a formal mentoring plan? Is it using peer programming to accelerate learning? Is IT attending external conferences and training? For Salesforce learning, is it using Trailhead, and how many badges has it earned?
3. What are IT's key success metrics? KPIs?
Does IT have a dashboard of key success metrics that it tracks? If so, what are the trends of those metrics — flat, down, or up? Do those metrics ultimately help improve the customer, partner, and employee experience? Metrics should be focused on business capabilities, not primarily on system up-time, which does not easily translate to improving the overall experience of customers. Metrics should enforce teamwork through successful, quality delivery, adoption, and usage.
A good way to create a dialogue around these questions is to set up a meeting (allot a couple of hours) with sales, sales ops and IT. Send out the questions ahead of time. Use the meeting time to review the answers. Such dialogues can be invaluable in reinforcing the importance sales places on IT, as well as challenging the IT team to up-level its strategic approach. I recommend having this dialogue on a quarterly basis. You will help create a much more strategic IT team if you do.