Your resume should be updated and ready to submit at all times. If it will take you longer than a few days to provide your resume to a prospective employer it isn't nearly close enough to fully prepared to be seriously considered. Your resume should be proof-read multiple times by you and someone you trust who has strong editing skills. It must be meticulously accurate. Google and fact checking will be done before, during and after the hiring process. You want to avoid any questions regarding the accuracy of the materials you create.
Cover letters should be rewritten every time and proof read three times. A common mistake is to send materials that have the name of the wrong school or refer to a position other than the one the person is seeking. I've seen it happen many times in coaching and staff searches. If you do this for an AD position you are dead in the water.
Your cover letter should not be a review of your resume. The reader already knows this information, its on your resume! Share your values, philosophy, and the vision that you have been developing – anything but what is already stated in your resume.
If you are lucky, your materials will be read for 1-2 minutes and after that time likely go into one of three piles – yes, maybe and no. You want to be in the yes pile, or the maybe pile at a minimum. No one ever moves out of the no pile. Your materials have to look great and contain impeccable grammar, spelling and punctuation. Miss on these details and you can find yourself quickly in the “no” pile.
You need to have a significant list of at least ten references. Your references should be aware of your search. And you should know or have a very good idea what they will say about you if they are called. Will they keep your search confidential? It is also helpful to explain why someone is listed on your resume. The people reading your resume don’t necessarily know why you chose someone unless you tell them. “Celebrity” references can be helpful if you know them well, but if they really don’t know you, be careful. They could hurt more than help. Again, you need to have a clear picture what the person will say when called.
So if your materials aren't ready, its time to put them together. It's your first chance to separate yourself from the competition.
I was invited to speak last year at the NACDA Convention in Orlando, Florida and present a talk entitled "Moving from the business office to the athletic director's chair." Since that talk a number of people have asked me for a copy of my comments and notes. Since these requests keep coming, I have created a multi-part series that recaps and expands on the NACDA talk. I am far from an expert, but I hope my experiences make this series valuable and thought provoking.