Most importantly, an air-to-air photoshoot is a formation flight. So, the basics of the formation flight should be the absolute cornerstone of the briefing.
Discuss the formation positions, the airspeeds and altitudes, words/terms/comm, visual signals, etc.
MOST IMPORTANTLY, cover "what if"s -- lost sight, lost comm, formation breakout, emergencies, lead changes, over-runs/overshoots during join-up, etc. Anyone can fly airplanes close together; the men are separated from the boys when something goes wrong or doesn't go according to plan. It's up to the photo ship pilot and photographer to think through these contingencies and have a plan for them.
Ensure formation roles are firmly established. The photo ship is the flight lead -- he is responsible for clearing for the formation, maintaining airspeed and altitude parameters, talking on the radio, navigating, etc. The photo ship needs to run the initial join-up, as well as taking care of the in-flight needs of the wingman. If the aircraft are going to split prior to RTB, ensure the wingman has good NAVAIDs/instruments, and knows where they are and who they are talking to on the radio.
From there, the photographer should thoroughly brief the order of formation positions he expects to shoot. Good photographers I've worked with (Paul Bowen, Jamie Hunter, Greg Davis, Steve Davies) show up to the brief with a "shot sheet" and pictograms to give to all the flight members, both the lead (photo ship) and wingman (aircraft being photographed).
The shot list/shot sheet list the photos to be taken in chronological order. Some of the better versions of these have photo samples that show what the end product will look like. The pictogram shows an overhead view of the formation positions when the shutter is clicked, along with lines showing what will happen in any "action" sequences (breaks, etc). Each of the photos has a number or letter associated with it, so everyone involved knows who is supposed to be where.
If interested, I can post an example of both of these products.
The photographer should then brief his formation signals that he will use to make small positional changes to the other aircraft. Will it be visual signals or radio calls. If radio calls, then will the photog be on a headset or will the photo ship pilot have to relay the position changes requested by the photographer. Remember, the photographer is not running the formation, so the photog and the pilot need to have coordinated how they're going to talk to one another over the intercomm (or using visual signals if not in an intercomm-equipped aircraft).
There's tons more to think about and talk about if you want to cover all the bases, but that's the basics that need to be covered at minimum.
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