You can look at our Chairman's submission here:
2008
and pervious years submissions here:
2007
and
2006
Of course, these are just reports of what our team did and what we felt was appropriate to report that would be of interest to the judges. Achieving the award is a matter of judgment by some human beings that are looking at quite a few incredible teams.
After not winning a Chairman's Award, we wonder, "what could we have done better or I wonder what the judges were looking for...?" which, of course, is our competitive impulse talking. After a day or so, we realize that the things that we did, mostly, were not done for awards or recognition, but rather that they were fun or it was a very positive experience for us or others and it just grows year after year. More of a function of how much energy and time we invest.
Planning for the Chairman's Award a year ahead is great for brainstorming, but in the end, your team will do what is intrinsically satisfying to yourselves while being of service to others.
Since we are not bing involved in the judging process, we can only guess how the volunteers decide on the one winner. We tell our Chairman's team, after they have written the essay and practiced their presentation, that, if the judges are truly wise, they will study what the team has done (over three years?) and make their call. The Chairman's team (or essay or presentation) does/does not win the Chairman's Award, but rather the efforts of the entire current team and those who have graduated and parents and those who have been touched by your team. However, being humans, judges will possibly be influenced by the emotional impact of our presentation and the quality of the written work.
So, looking at other entries and seeking advice is good, but in the end, you will do what you do because it is satisfying and the Charmian's just happens (or not).