Peter Figen
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Having photographed a fair number of highly placed and paid executives, you really need to have a good idea of what you're going to do well before hand. Their time is extremely valuable and unless their hobby is photography, posing for photos is usually the last thing they want to do. You should be set up and have everything lit with a stand-in of similar height and clothing color before your CEO is even on the scene.
From your equipment list, I would be worried about your lighting capabilities. Well, not necessarily yours, but that of your equipment. I would do a test shot well before hand to make sure that you have enough light, especially after putting those little speedlites through softboxes or umbrellas. You may to overcome ambient light or shade your subject from any direct sunlight in order to light him how you want. You may need to rent gear to pull of your shoot, and if you do rent, you want to be able to get familiar with the rental gear before the shoot day.
About the most time I've been given in those situations is maybe fifteen minutes. The least has been about a minute. You can do a LOT in fifteen or twenty minutes, but as others have said, you have to have a plan and be prepared.
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