I would NOT use a light modifier in that situation. I think that you are looking for a softer light and that's what a softbox or umbrella normally does. But neither will do this under these conditions.
What makes a light soft is its size and proximity to the subject. Size alone doesn't always do this. The biggest light source there is - the sun - is a point light source because it's so far away. The softbox/umbrella WILL create a soft light if your subjects were a few meters away, but they will be a lot farther away than that. If you do use softboxes or umbrellas what in effect you've done is to make THEM point sources, but much weaker ones.
I did a shot like this a few weeks ago and I turned my AB1600's around and aimed them both at the subjects. I had one on each side of me about three meters from the camera. At that point I was about 12-15 meters from the group. I had both lights on camera stands and they were as high as I could get them. I wanted to get at least f11 out of this and I did so.
By the way what you don't want to do is to move the lights in closer. The inverse square law comes into effect then. (Yeah I know ISQL is always there, but if you don't notice any effect that's all moot.) With the lights ten meters away you will have even light from the front row to the last, with maybe a little fall off. If you were closer there would be a much greater exposure difference between the first and the last row.
The other technique I like to use is to stand on a ladder, or a big table if I can. That gives me a shooting position where I have to tilt the camera slightly forward. That changes the plane of depth of field to more closely match the angle of the subject's heads from the first row to the last. The effect is that any selected aperture will have a greater depth of field, at least as far as the subject's heads are concerned. You also get the benefit of making the subject's lift their chins, which is as simple a double chin remover as there is!
"There's never time to do it right. But there's always time to do it over."
Canon 5D, 50D; 16-35 f2.8L, 24-105 f4L IS, 50 f1.4, 100 f2.8 Macro, 70-200 f2.8L, 300mm f2.8L IS.