Entertaining CEOs and other executives can be a tough thing. Sometimes it is tough to hold the attention of Type A personalities to entertain them. They are busy people, and some have a hard time just relaxing to enjoy the moment. Now if you are tasked with setting up a dinner and corporate after dinner entertainment, this can be a huge responsibility. If you ask one executive what he or she would like for the after dinner entertainment, you will likely get an answer. It can vary from nothing to something really out there. If you ask a group of them, you will get different answers. However, I think the best approach to picking great entertainment for corporate events is to pick something that has been proven.
I took the time to ask the event places I was calling to find out how many large corporate events they do each year. Then I asked how many callbacks they get as well as referrals to other corporate events. That gave me an insight into the entertainment. I could have just picked something my boss likes or what I like, but I needed to try and make the most amount of our management staff and executives happy to be attending the corporate party being thrown for them. You want people talking positively about the event so they will attend again next year. I have seen second year attendance drop significantly for corporate events that were not fun to attend.
The dinner does have to be great, but the corporate after dinner entertainment also has to be great. You cannot have one without the other. People will be done eating in less than an hour, so you need to keep them entertained until the event wraps up. Just doing presentations or giving awards can get boring. You need to entertain people to the point they leave enthralled, laughing and very pleased to have attended.