My favorite icebreakers for executives are:
1. Ask them to answer the question: What accomplishment are they most proud of? I pose the question, give them time to think, and then go around the circle listening to their answers I summarize the themes I hear. I love how their accomplishments are always impressive, and show clearly what they most value. It has the effect of leveling the playing field even when what they share is very different. Pride does that, I think.
2. Ask them what is the one thing they want to accomplish before they die/stop working/retire. Same process as above, and the answers can be breath-taking.
What about you? Are there any icebreakers you find work especially well with executives? Share!