As someone who identifies as an Anarchist, I've been on a hunt for literature that talks about leadership from an informal, even horizontal, perspective.
I found the chapters to be better than most books on the subject I'd browsed recently and so I read the whole thing, skimming the last two chapters on Organizational and Political Leadership. Overall, there's lots of good advice and the chapters give less of a shallow treatment than most books. Still, all of these books focus on formal leadership, and I suspect the audience is Outward Bound/NOLS students. This might be great, but for those of us that are out in on trips with peers and without a guide, the advice from books like this often come across as ridiculously black and white, especially when you've been in situations of crisis (small or large).
The trouble arises when nobody is really sure where the stand in relation to one another. When no one's experience is known to the group, when people expect spontaneity, confusion over what decision making process will be used if need be, and when the buck doesn't stop anywhere in particular. Now don't get me wrong, there's plenty in this book on interpersonal skills that is useful, but I still don't feel like some of the more common problems I've encountered were dealt with.
For example, you suspect most of the people in your group are homesick, but you had expectations of accomplishing something in particular. How do you bring up the subject without embarrassing others, being accusatory, etc? How do you deal with people being homesick without making it obvious?.
So ultimately, while the book has a good amount to offer (and LOTS to offer if you're a guide or some sort of formal leader), I felt like it didn't give enough treatment to the far more complex situations that arise when people get together to do a trip, when nobody really wants to plan ahead and you don't even meet some of the participants until the trip has started. What are the priorities in these instances when someone wants to bring out the best in others?
I found the 10 page chapter in Freedom of the Hills (also put out by The Mountaineers) was short, but at least acknowledged the issues I'm talking about, so it's worth a read, if you're puzzled like I am.
The biggest issue I had with the advice given (aside from the omissions mentioned above) is that too much of the advice boiled down to "don't rock the boat". The idea always seemed to be to just make it back to civilization without getting onto touchy subjects, or having to cll out really bad behavior unless necessary (though the Women in Leadership chapter was less protective of the status quo, which was nice)
I also was not a fan of the typical leftist approach to environmental issues, but beggars can't be choosers I suppose. Nothing new said here, though there is some detail given if being another Sierra Club campaigner is your bag.
At the end of the day, I'd still consider trying to buy this book used, as it is the best I've come across so far, but there's definitely a lot to be desired if non-hierarchical leadership is your area of interest.
I looked at a few books to see what they said on Leadership. I already mentioned Freedom of the Hills. The New Wilderness Handbook by Paul Petsoldt (who's often quoted in this book) was another. It wasn't as focused on leadership though, and while it's certainly a landmark book (far as I can tell), it's certainly a little old fashioned on some of the leadership stuff.