Everybody's Talkin'

Some years ago I attended a leadership retreat put on by my company that provided participants many tools to become more effective leaders in our company: personality and leadership style surveys, role playing games, excessive drinking around a bonfire, practical jokes played on the Sensitive/Introverts during the night. One of the important things we learned was the “12 Roadblocks to Communication”. We each got a playing-card-sized list of the 12 roadblocks summarized in one or two words. I still have that card on my desk to remind me that two of the roadblocks to communication are: 5. Using logic and 12. Using humor.
I am the grandchild of college math professors, the son of a CPA. Logic was The Force in my childhood universe. I majored in Economics in college; I was trained to use logic in the face of reality: “The laws of supply and demand tell us that, assuming individual consumers act rationally,….” A clearly flawed assumption that everything else we learned was based upon. I’m the CFO at an architecture design firm, if I don’t use logic, no one will.
When the logic voices in my head have their backs turned, the humor voices take over. So if logic and humor are out, I am Marcel Marceau. If a woman at work comes to me and says, “I feel like I will never reach the top of the org chart here because there’s a glass ceiling,” my inclination is to say “that’s not true; if there were a glass ceiling, women would be on the top floor and men would be below, looking through the glass to see up your skirts.” That is a totally inappropriate response under rule 5, using logic.
For me the number one – and only – roadblock to communication is this freaking list. Someone comes in and says, “Look, I’ve got the black, knit shirt and black jacket of a designer, I keep copies of “Architectural Pretentiousness Quarterly” on my desk, I use the word “green” as a modifier in every sentence I speak, and yet I get no respect. What can I do?” Logic and humor are out. I am not even supposed to 10. Sympathize, 4. Advise, or even 9. Agree, or 6. Disagree. I’ve only gone through half the list and I don’t know what the hell other kind of response exists.
I realize none of this entry makes any sense because I am a complete failure at communication. (Please respond constructively to that in the comments.)