[programminggeek]

In my experience, the biggest hurdles to a truly self-organizing organization (at every level) are people and trust.

If you don't have really excellent, self-motivated people, you are going to have a lot of trouble with self-organization simply because some people need to be told what to do. People also have to be 100% bought in to the concept and don't try to create themselves management and authority roles. It really does take the right people.

Trust is probably the biggest problem. It takes a lot of trust from the people who start the business to let it run itself. It is probably easier at the start of a business than when it's big. Everybody has to have a high level of trust of everyone else, and when that trust is broken the organization probably needs to be willing to fire the person who took advantage of the system.

For many people, the hardest part would be to maintain that kind of system with ruthlessness enough to fire people who don't work well in the system. Knowing that it's not going to be for everybody and practicing that is hard.

[antinescience]

Not only trust, but honesty. It's a lot harder (I would wager almost impossible!) to operate in a flat organization without everyone being willing to both be honest and receive honest criticism.

The company I work for is about 30 folks strong and there are, for all intents and purposes, only two levels of hierarchy. It could probably sustain being completely flat, but I'd fear that it'd fall apart relatively swiftly due to people being unwilling to both bring others to task and be brought to task themselves.

Plus, there's something to be said for decision by committee severely obfuscating progress if consensus can't be easily reached.

[pfraze]

I think some service industry employers try to get around trust and employee quality by limiting the capabilities of the employees, and it's a nightmare for everyone. Often its done by software-- "sorry, the computer won't let me." It feels awful to be a part of; the lack of trust is hard not to take personally.

[fmoralesc]

This.

I'm now part of a project (it is a creative enterprise of sorts, i dont' want to make it so easily identifiable) that is trying to apply this sort of ideas in its working process. It's been growing lately, and we've had to start thinking about this sort of thing (people we don't necessarily know are interested to join us, and it's a bit of a problem in some cases to decide whether to abandon our current "flat" structure (where everyone has access to everything) and "enrollment process", or bite the bullet and take some risks with these people).