2) How many CIOs will be reporting to you? And is that a straight-line reporting structure so that you have at your disposal an oak paddle (not an oar-type paddle, but a whipping-stick-type paddle) with holes drilled for greater acceleration? Or will you have a dotted-line structure that arms you with conflict-resolution pamphlets?
3) Who are your direct reports? How big is your staff? Your public comments today were sprinkled with stuff about visibility and transparency and such -- so who's on your team, and what are they responsible for achieving?
4) What's your plan for your first 100 days? What project will you tackle first?
5) By what metrics will your performance be judged? And by whom? And how will that measure up to the pledges we keep hearing about "the most transparent administration ever"?
6) To fix the apparently intractable IT disasters at the IRS and FBI and other places, will you consider using U.S.-based companies who happen to have (as many thousands of companies do here in 2009) employees in other countries? For example: Google, IBM, Microsoft, Hewlett-Packard, Accenture, Oracle, EMC, Cisco, Symantec, Cognizant, and many many more?
7) Will you commit up-front to cutting the $71 billion budget that the federal government somehow, some way, managed to spend on IT in 2008?
8) What, if any, oversight will Congress have over you and your team? These days, Congress is insinuating itself into every facet of the daily lives of Americans -- how will you or your "controlling auspices" be able to ward off that type of smothering assistance?
9) How would you describe the ways in which your role and that of the proposed CTO will (a) complement each other; (b) be completely distinct from one another; and (c) have to be carefully calibrated to ensure everyone on both teams is striving to reach the same goals?
10) Before you immerse yourself too deeply into some severely hairy projects that you and you alone in all the world are capable of overseeing, we must ask: have you paid all your income taxes?
Good luck, Mr. Kundra, and remember: keep your friends close but your enemies closer.