We've been trying some experiments liveblogging with the outliner.
For now, I think outlining doesn't add much to liveblogging. But there is an area where I am pretty sure outlining makes a big difference in a group setting, because we've done it -- in meetings.
You can try it with one other person looking over your shoulder while you outline a project you're doing together. For example, imagine you're buying a house with your spouse. Start by listing all the things you want and don't want in a house. As you list your ideas, the other person will get some too, you add them to the outline.
Pause for a moment and group them.
Start listing neighborhoods.
How much money you want to spend.
How many bedrooms. A yard? A nice view? Schools? Close to public transit?
Jump around. If your partner has an idea in one category when you're in the other, just do what they ask. It's about being fluid with your thinking.
Pretty quickly you start using the outline to organize the problem. It becomes a shared space between the two of you, and it really doesn't matter who is at the keyboard, who controls the mouse. The ideas come from both of you.
The same idea works in a larger context if you can project the outline on a screen.
It can have magical results in organizing a project that has resisted organization.
Don't make a big deal about using the outline at first. It's just being projected, maybe one or two people will start looking at it while you type. Then someone says "Move this item under the other category." They have trouble explaining so they get up and show you. Do what they ask you to do. Now they're controlling the outline by pointing to the projected image of it.
Sometimes the power of technology is less important than the communication between two human beings.
This process was possible 25 years ago. I know because we did it back then.
Give it a try.