One thing to think about. As I stated, the ``pointy-haired boss'' rarely consults his own IS staff. That is because he knows almost nothing about computers, and furthermore does not want to know anything about computers. In short, he aggressively pursues incompetence when it comes to computers. All he wants is for his IS staff to keep the books straight and produce reports on time, he doesn't know a thing about how they actually do this.
That does not explain why he does not consult his IS staff, though. What does explain it is the reaction of his IS staff when he asks a question. They are likely to use highly technical language that he does not understand and make him feel like an idiot.
Point: Make sure to use easily-understandable language when dealing with the PHB. If you must introduce technical details, be sure to explain them in terms of everyday things that he understands (like MONEY, the PHB knows a lot about money, since he usually came from accounting or finance). For example, rather than talking about resource requirements, you might say ``Hey, Linux runs on our current hardware, while we'd have to spend a lot more money on new computers to run Windows NT.'' If you can quantify the money, so much the better - PHB's like little charts with x dollars on the left and y dollars on the right. It's something they understand. Using buzz-words and highly technical jargon just won't cut it in PHB-land.
It doesn't matter that you have to do some creative accounting to come up with some figures (e.g., quantifying support hours saved for going with Linux vs. going with NT, then assigning a dollar figure to those support hour savings). Just make sure you can justify them.
A strategy that has worked for me is to present detailed cost and technological analysis both for the technology I personally want, and for other possible technologies that solve the same basic set of problems (e..g, Linux, Windows NT, Novell Netware). Then I present the choices to the PHB with the appearance of impartiality (unless the PHB chooses the more expensive/disliked solution, in which case all bets are off!). 9 times out of 10, when given the illusion of choice between two alternatives, one which is cost-effective and presented in a favorable light and one which is not cost-effective and which is presented in a neutral manner, the PHB will choose the ``right'' one. If, however, you try to force a technology upon the PHB, he starts looking at you sly-like wondering what you're trying to pull, and asks for a report on the alternatives. He's likely to then choose one of the alternatives.
Similarly, reject the impulse to paint the undesired alternative in an unfavorable light. It makes you look biased (which you are, but you don't want the PHB to realize this!), and the PHB is more likely to order further investigation of alternatives.