Before you busy yourself with the details of how to get the attention of a booking agent, it is best to take a step back and know what gets their attention in the first place. In other words, "get inside their heads" first.
Following are some important things to consider in your bid to get the attention of a booking agent.
As maddening and contradictory it sounds, a booking agent is most impressed and interested in a band/artist that is self-sustaining on the touring front. Being self-sustaining is having the ability to provide for your own (booking) needs without the help of others (e.g. agents). It doesn't mean that you don't WANT the help; it just means that you can survive without the help. In your quest to become self-sustaining, consider venues other than clubs - for example, performing arts centers, college campuses, festivals, house concerts, etc. - to string together a regional tour of 40 - 50 dates over a 6 - 9 month period or so. This not only makes you look self-sustaining; it actually allows you to be self-sustaining.
Develop a tour history for your artist in their home town and region (surrounding states) that includes the venues played, dates performed, venue capacity, attendance numbers, ticket price/cover charge, number of bands on the bill, headlining vs. opening status of your artist, etc. Gather this data for every gig your artist performs over the course of a few months. Condense the data into a presentable form that can be easily read by a booking agent. It's important to make sure this data is accurate since it will be checked.
Put together a team around your artist. This team will include you (the manager), a label (even a solid indie label with 'real' distribution will do), a reputable entertainment attorney, and an effective publicist. This team will be a good indication to the agent of the level of promotion and marketing that will be in effect during the booking process. With labels reducing their tour support budgets, having a sponsor on board providing cash and/or in-kind support will work wonders to convince the agent that adequate resources will be allocated to promotional activities.
A Video/DVD is an essential visual representation of how your artist performs live. You must be able to match your impressive data (show attendance numbers, revenue generated, etc.) with stunning visuals of your artist's show. The DVD (or YouTube video) must also illustrate how passionate the fans are during the shows. The fact that you can show footage of fans at several different shows will be even more impressive (since anyone can pack a venue full of family members at least ONCE).
Get the attention of a few artists already represented by booking agents. Referrals from existing bands make for a powerful endorsement in the eyes of booking agents. Find bands that are of a similar sound to that of your artist(s), and then make efforts to befriend them and develop a relationship that can later be leveraged to introduce your artist to the booking agent.
If you don't already have a solid team in place, shop your artist to a label that has a roster of artists that are represented by reputable booking agents. These labels will already have the ear of the booking agents and direct access through the front door. The labels will also be able to provide the booking agent with all the relevant information necessary for the agent to make an informed decision.
As often as possible, encourage mid-large size capacity venues to add your artist's information to their web site. This is most important if your artists are headlining, since booking agents browse venue websites to see which bands are headlining. The agents then use this information to chase down 'first holds' before other agents can do so.
These, while not exhaustive, are some important things for you to take into account before approaching a booking agent. Keep in mind that if you do these things correctly, an agent will approach you first. If you haven't already done most of the things mentioned above, you should think of doing them as part of a medium-term (6 - 9 months) goal as opposed to a short-term (3 - 6 months) goal.
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