I received an inquiry several months back that read something like, "Hey, we're having a family gathering in the summer and we'd like you to photograph the full set of people". Sounds innocent enough until you discover that the invite list is just over 100.
Might be old hat for some but I looked at this as a challenge since up to that point, the largest group I've shot was about 25 people. I reached out to the internet for suggestions and there were some good ones. 'Bring a bull-horn and a step ladder' was a funny one that I remember. Turns out I didn't need the bull-horn but I definitely knew I would need the ladder.
I showed up a little early to scope out the situation and this venue had a wedding going on outside (the preferred location) and the family's event was inside. I had about 30 minutes to determine a location, set up lights, grab some test shots and get it done.
Here's the result. A few head-swaps later, I did manage to get everyone in. Phew.