We’ve all sat in our share of frustrating meetings, but I can still remember the meeting that frustrated me the most. It took place in 1987 in a boardroom in Chicago. A group of automotive industry CEOs (you’d recognize most of the company names) was meeting with a pair of representatives from a social services program. I was in the room as the PR person for one of the auto parts manufacturers.

The program’s representatives were there to deliver a report to the auto folks. This group of companies had been funding the program, which took inner-city kids off the streets and turned them into employable auto technicians. The program was clearly a success. The representatives explained how much funding they had received and how many people had been trained. Quite impressive.

Then one of the auto executives posed a question: “We gave you (I don’t remember the amount) dollars, and you trained (I don’t remember the number) kids. Suppose we were to give you (twice the amount) dollars. How many kids could you train with that?”

The lead representative from the program looked over the top of his glasses and said, “I’m sorry. I don’t understand.” The executive replied, “If we gave you twice as much money, how many kids could you train?”

The representatives looked at each other with confusion. Number Two said, “I’m sorry, but I just don’t know what you’re asking us.” The auto folks exchanged glances, and the CEO of a well-known national company patiently repeated, “We gave you $(amount), and you trained (amount) students. If we give you $(twice as much), how many can you train?”

The discussion went on like that for another fifteen minutes, but the two sides never managed to find that middle ground. The CEOs left the room frustrated, and the social services folks left the room confused. They never realized that the CEOs were ready to give them the proverbial blank check. My guess is that as they drove back to their agency, they talked about the need to find funds from another source. The CEOs assumed their money wasn’t wanted, and moved on to other causes.

I’ve often regretted not intervening, but I was a green lieutenant among captains of industry, and my attempt to bridge the gap would likely have been viewed as insolent (at least judging from the number of other times I was rebuked for being insolent). Maybe that’s why always I fight so hard to help organizations find that middle ground, so they can communicate instead of confuse.