I've said elsewhere that I like riding on my own. You ride when you want, where you want, at the speed you want, stop when you want etc. But I also like riding in a group. There is something quite special about riding together with a bunch of mates on bikes!
Small groups are good because it's more friendly and personal. A small group of like-minded people riding at like-minded speeds etc can be a great day out - on a personal level as well as a biking level. Larger groups are enjoyable for the same sort of reasons, but also for the amount of bikes and the sheer volume of it all. In a larger group too, you will often get to meet people you may not have met before, and that's always interesting. So riding on your own is good, riding in a small group is good, and riding in a large group is good. It's all good! But each of these situations is different, and there are, I think, certain things to consider. 
Let's start with larger groups. In a larger group, usually you just kind of join in and go with the flow. Unless you are the one who has organised it, or leading it, there is usually a feeling of being "a small fish in a big pond"; so you just swim along with the rest of them! There will be a common destination, but not necessarily a common way of getting there. The route should be the same, but the way each rider travels the route may not be. And this should be taken into consideration.
In a larger group it is inevitable that the group will get split-up. If you are in town then traffic-lights will break the group up probably before anything else does. Once out on the open road, the "different ways each rider travels the route" will come into play. There will inevitably be different speeds that people will want to travel at. And it's only common-sense (and courtesy) to allow people to ride the way they want to. So the larger group will break into several smaller groups. I'll give you an example I recall of different riders in a large group.
On one occasion I joined a group I hadn't previously ridden with. The bikes (and the other bikes are always an interesting aspect of any group ride!) were mainly sportsters or sports-tourers, but with a couple of tourers and I think one smaller bike. Most were fairly new, although a couple had seen a few years. So a bit of a mix. When we took off, a couple of the guys on sports-bikes began weaving from side-to-side, warming-up the tyres like a race-bike approaching the start-line. I thought, "This looks serious!" Although I had been warned. One guy, probably reacting to my age and the mid-size bike I was riding, said to me that a couple of the guys liked to get stuck in, but not to worry about trying to keep up. They'd wait for everyone to catch up later on. Well, it wasn't long before they were way out of sight. But I did manage to keep up with the small bike and a couple of older tourers. So, very different bikes and riding styles, and it soon broke into several small groups, but it was still an enjoyable ride! Then later, as promised, everyone met at a pre-arranged destination.
There needs to be certain "catch-up" points like this along the way. Points at which those in front will pull over and wait for the others to catch up, so the group becomes one big group again. This is especially important at turn-offs, or places where people might get lost or go the wrong way. And it's only logical to become one big group again when you get to the final destination.
Smaller groups are different. Because they are smaller and more personal, it isn't as appropriate to break into smaller groups. And of course, depending on how small the group is, breaking into "smaller groups" could mean riding solo - which kind of defeats the purpose of a group ride!
The smallest "group" is, I suppose two; if you can still call that a "group"! And when you're riding with just one other person I think there has to be a certain amount of consideration given to the other rider. The first thing is to pick appropriate people to ride with. A rider on a 1000cc sports-bike is not going to enjoy riding with someone on a 250cc commuter! Similarly, someone who likes to cruise along enjoying the scenery is not going to enjoy riding with a Valentino-wanna-be! I'll give you another example.
Back in my trail-riding days we had a group of four or five guys that went riding most weekends. We all had fairly similar bikes, and we were all roughly the same age. We also rode at a similar speed. We always enjoyed riding together because of those similar riding styles, and the common type of riding we enjoyed. On a few occasions we were joined by a younger guy who's riding style was probably closer to motocross than it was to trail-riding. He'd be following us down a fire-trail, and then suddenly just take off and blast away down the trail infront of us. That was fine, he was just riding at a speed he enjoyed, but the problem was he didn't know where we were going! So we'd get to a turn off and we'd all have to stop and wait until he realised we weren't behind him. We'd see him way ahead up the track suddenly stop, look around, and then come hurtling back again. Down the next trail and he'd be off doing the same thing. He was a good-natured guy, and I think he still enjoyed his rides with us, but he probably felt a bit frustrated at times with our slower, more trail-riding-type speed. And we probably felt a bit frustrated at having to always stop and wait for him to come back to where we were going.
So, especially in a small group, I think it's important to choose appropriate people to ride with. Although, depending on the people and the occasion, certain considerations can be made.
For example, when my son-in-law got his P-plates we went riding together quite a few times. He was, of course, restricted to doing 80kph, and the 250 he was riding fell behind a lot on hills, but I still rode along with him. I wouldn't have wanted to ride like that all the time, but I accepted the limited speeds for the sake of riding with him. Later, when he graduated to a full license and a bigger bike we continued to go riding. I enjoyed those rides, because we seemed to like the same sort of rides - similar distances and similar speeds. But he's a nice guy and also very considerate, so I strongly suspect he was repaying my previous courtesy by being content to travel at a slower speed than he would normally have, so the old bloke could keep up! And this points to the general approach I take with small groups.
For some reason, when I'm riding with just one or two others, I'm often the one who has organised it or who has set the destination. So I usually lead. And that means that I am setting the speed. But in that situation I think the leader should consider the others in the group and set a speed that is suitable for all the others. If there is someone I haven't ridden with before, I usually say to them that, if they feel that I am riding faster than they are comfortable with or able to, then just to ride at their speed. I'll be watching in the mirrors to see where they are, and if they start falling behind then I'll slow down. Now, I admit that it probably doesn't happen too often that the riders following me are slower than me, but it does happen; with smaller capacity bikes, or cruisers on twisty roads etc. So by watching the mirrors the leader can still set a pace that is comfortable for everyone.
Another thing that I think is important in these small groups is to change leaders. On the sort of rides I was mentioning above, I will suggest someone else leads when there is no need for me to be infront. Such as sections where there aren't turn-offs, or when we're on the return trip etc.
Riding in groups - small or large - can be great! It usually makes for an enjoyable and often memorable time together. I reckon if you keep these few points in mind it will make your time together in a group even more enjoyable!
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