My current boss gave me some good advice when I first started working for him and it has served me well. He suggested that when I set up a meeting or organize travel for him I should ask myself, if I was the one going to the meeting, or on a business trip, what would I need in order to be prepared? So I do and when he has a meeting I make sure he has the agenda and any back-up materials, the location and directions if needed, the name and title of the person he is meeting, especially if he doesn't know them well, and the purpose of the meeting. Most of this information you can get in your initial phone call or email correspondence with the other party when you are organizing it. If they are not sure then they can ask their boss so both of them will be prepared to meet each other. If my boss is travelling abroad I check to see if a visa is required and make a note to remind him to bring his passport with him. I also register him with the Canadian Embassy in the country he is travelling. If they travel a lot you never know when they will be in a country that it will important for the embassy to know where they are to bring them home safely. If you look in the side bar of the blog under Travel, you will see links for useful sites to do this and get other information.
Another executive mentioned that when she is giving a presentation, she appreciates that her assistant ask herself what would she need if she was giving the presentation. Does she need time to prepare the presentation ahead of time? If so, do you have a reminder set and blocked off time for her to do so? Does the presentation have to be put on a memory stick? Do you need to organize for a laptop, projector and screen or will there be one available when she gets there? Do you need to make copies of the presentation for the participants? What time will she be presenting and when would they like her to arrive. Most places like them to be there at least 30 minutes before they present, so make sure to block that time off in the calendar as well as travel time to get there and back. Who will the audience consist of? And of course what is the location and the directions to get there? There is more to it than just putting the date in the calendar.
If something raises a question with you then make sure you get the answer. If you have set up a meeting and wonder how your boss will get there, then that is a good question to bring up with them. Are they driving or will they need a reservation for a flight or train? Will they need a hotel room? It will not only show them that you are thinking ahead, but that you have their best interests in mind. If the meeting is around lunch time and you wonder if something should be ordered in or will they take the client out for lunch and you need to make a reservation then those are good questions to ask.
Often I have looked in my boss's Sent messages and notice he has emailed someone that he would be happy to speak at their conference, but when I look in his calendar I see he is scheduled to present at another conference in a different city on the same date. This is a good thing to bring up with him or her. They will certainly thank you and it will show you are looking after them. You might also have to follow up to make sure they have emailed the other party to advise them they are no longer available.
It is always good to think ahead for your boss. You have control of their schedules and are in the best position to make these observations and bring it to their attention.
If something prompts a question - ask! If you read an email or something in their calendar doesn't seem clear - ask! If you are wondering if they might need something for the meeting - ask!
You can never ask too many questions, but having a good strategy on when to ask is good. Scheduling yourself in for weekly meetings works well. When you have a question, ask yourself if you need to ask it right now or if it can wait for your weekly meeting. When you meet with them you will have their undivided attention and can take advantage of this time and ask all the questions you need to in order to organize their travel or prepare for a meeting or whatever it is you are doing for them. Another thing you can do is try to answer your own question before bringing it to your boss. Sometimes the answer is at your fingertips and a Google search will do it. Or a colleague will have the answer, and is who your boss would have asked anyway, so you just have saved him the trouble and did it for him.
Questions, questions, questions! Whether you are asking them of yourself, your colleagues or your boss, if you don't know how to do something, it is always good to ask.