If the boss get first crack, then he’s going to set the agenda and the boundaries, and your brainstormer is immediately limited. I know of one Silicon Valley boss who eagerly launched a brainstorm saying he was looking for some great new ideas. But unfortunately he followed that enthusiasm with a room-silencing caveat: “Oh, and every new idea has to be patentable. And something we can manufacture.” In that setting, nobody is going to suggest anything even remotely “wild.” Try sending the boss out for coffee. Or doughnuts.
I once sat in on a meeting a client though was a brainstorming. Sixteen people were packed into the room. We went clockwise around the table, and each person was given two minutes to speak. It was democratic. It was painful. It was pointless. It definitely wasn’t a brainstormer.
Let’s see, do I have a materials expert, and engineer, a software guru, and the V.P. of Marketing? In brainstorming, don’t be an “expert” snob. Bring in someone from the manufacturing, who knows how to build things. Invite a customer service rep with lots of field experience. Find someone who reads a lot of science fiction. They may not have the “right” degrees, but they just might have the insight you need.