1) Are you pursuing Sarbanes-Oxley projects as standalone efforts, or are you weaving them into larger, enterprisewide initiatives centered on enhanced business processes, risk mitigation, business continuity, transparency, or some other strategic objective?
2) How much of your IT team's compensation is tied to meeting the needs of business units: 50%? 25%? 10%? Zero?
3) On a scale of 1 to 10, where 1 equals "total lack of trust" and 10 equals "unconditional trust," how would you rate the trust between your IT team and your business leaders?
4) As you look at your answers to No. 2 and to No. 3, do you see any correlation?
5) If the CEO fired you tomorrow, what reason would he give? And if you know the answer, does that mean the decision is fair?
6) Can everyone on your team articulate the CEO's view of the IT organization's role clearly, unambiguously, and consistently?
7) Could the CEO articulate clearly and unambiguously the mission and key priorities of you and your IT team?
8) If your CEO asked you to describe the three most-valuable contributions you've made to specific customers in the past six months, would you look forward to that conversation, or would you dread it?
9) Which is more important for you and your team today: controlling costs and cutting risks, or increasing revenue?
11) Your CEO returns from vacation and invites you to lunch and after iced tea is served tells you that during her time away, she read Nick Carr's book, Does IT Matter? She asks you, "Well, does it?" What's your answer?
12) The IT Governance Committee you helped pull together is starting to unravel because its six members can't agree on how to set priorities for projects and spending. Who's responsible for breaking the logjam--you? The CEO? The committee? The ITAA?
13) Your colleague the CFO says he's noticed some surveys showing that some companies are having the CIO report to the CFO, and he says that if you would agree to such an arrangement, the two of you might be able to ratchet down the contentiousness that's been building over the past year. Could this be a huge benefit for you, or would it be a massive step backward?
14) Oracle and SAP appear to be squaring off for a pitched battle on multiple fronts the likes of which this business hasn't seen in a while. Is this mortal combat good for you and your customers?
15) Do you want Barry Bonds to break Henry Aaron's home-run record?
16) If you're able to recruit from colleges or graduate schools, what types of backgrounds do you look for, and how is this different from the profiles you sought two or three years ago?
17) Where do you stand today on the age-old question of buy versus build?
18) Would you encourage your children to pursue careers in IT?
19) Are you concerned by the declining numbers of computer scientists, mathematicians, and physicists the United States is producing?
20) You're lying in bed, and the question "Does IT Matter?" flits through your brain. Do you get a good night's sleep?