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Navigation, and leading groups is the biggest thing I've overcome recently.
Most of it was mental. I still don't like leading group rides in areas I've only rode once or twice, but once I've been somewhere a few times I'm a lot more comfortable getting around and leading the group.
Buddy I ride with a lot usually takes the lead, and the rest of us work out our pecking order and follow suit. I'm usually in the front part of the group, or taking up the tail (I pack a -ton- of tools, so when our group includes newer riders or older machines, I usually take up the end in case they break down or get stuck).
Aforementioned buddy got real busy with work, I put on a lot of miles solo in the summer on the motorcycle. Won't ride alone snowmobiling, but since I was somehow deemed "most qualified" to lead, off I went.
Took a couple of times to get my confidence up, and I still find myself circling an area I want to get to, but overall I'm a lot better now.
Depends on the group a little too, there's some people I don't like riding with because we end up spending the day herding cats instead of riding.
Pic was a massive group a few years ago, close to 20 people... only 2 knew the area, and both of them are professional guides. Worked out really well.
