The evolution toward Pointy-Haired Bossdom is slow and often subtle. Assuming, charitably, that one starts with a lot of knowledge, the gradual slide towards that lot becoming a little can easily pass beneath one's notice. To be caught with ones facts down in public can be embarassing. The less mature PHBs will react anger.

When taking a technical proposal to a PHB whose grasp on things technical has been faded by the passing of time, what strategy is effective?

The head-on approach, particularly when it involves threat of brain removal by small hammers, is rarely effective. PHBs can become remarkably intransigent when they feel unjustly insulted.

A better approach may be one suggested by the gentle martial art Aikido: blend with your opponent before redirecting his energy. First, admit to yourself that part of what your PHB is (or was) true, and use that to align yourself with your PHB's perspective. "Yes, you are right," you say, "Perl was originally used primarily for reporting." Then gently turn your opponent. "And your concern would be valid if that were still true of Perl. However, that language has advanced from its reporting heritage, and is now used for ..." and fill in with a list of examples appropriate for your environment.

Notice the subtlety: By first agreeing with some (albeit feeble) element of truth in your PHB's position, you breach his defences by letting him know that you're on his side. By noting the validity of his concerns, you honor his (possibly misplaced) intentions. By offering new information, you open the way for him to accept your proposal.

Compare this with a more confrontational approach. "You miserable excuse for a dinosaur, any grasp of technology you had expired with vacuum tubes. Get thee gone. Take your moldy punch cards and your crusty slide rule and Get Out of The Way of Progress."

Though satisfying, such a direct approach is best left to the imagination. Therefore, take the gentle approach, and prevail.