I like this CIO.com list of nine ways application developers can determine whether their CIO is "clueless" (and nine ways for CIOs to not be such). Given the rising importance of the CIO, it's critical that CIOs earn and keep the respect of their developers.
My two favorites intersect with open source, the first being that the "CIO is a technical dinosaur." PHP? MySQL? Ruby? Spring? These are the future - just look at what leading web companies deploy. If you're still gobbling down the latest bloatware from your "enterprise" vendor, you're old school and in need of a wake-up call.
The second is closely allied with the "dinosaur" comment:
The CIO gulps vendor Kool-Aid. Did you know that there are more than 34,750 registered lobbyists in Washington, D.C., for just 435 representatives and 100 senators? That's 64 lobbyists for each congressperson. I wonder how many vendor account managers there are per CIO. You are smart enough to know that vendors are trying to sell you and you won't be fooled wholesale. Yeah right. Their influence can eat away at you without you even realizing it. Be even more skeptical than you are now. Just say no.
Even better, stop listening to salespeople altogether, and start listening to code. In today's market, if you're trusting a vendor's promises that code will work, when you can easily download alternatives and see that it will work (or not), then you're a fool if you continue to slavishly allow your Oracle or Microsoft account representative to lead you around by the nose. Open source is the ultimate risk mitigation tool for the CIO.
Challenge your proprietary vendors to put their code where their mouths are. If they won't, they don't deserve your business.