What is your experience with holacracy?

I’d add to that the sub question of whether anyone has seen — and under what circumstances — “self organising” teams work/fail.

I’ve only seen self organising teams in a flat structure fail, on count that if everyone is responsible for everything there are many things no one is responsible for. I think “bike shedding” is very much a thing. Most people will hitch their contribution to what they can understand leaving many of the hard and but vague things in the wind.

I am suspicious of these wholesale systems/solutions to the problem of organisations to a large extent. I'd argue that it is faulty thinking to even characterise something as complex as an organisation as "holocratic" or "communist", etc (one word is insufficient to capture the actual dynamics of an organization). It so happens that whenever the "system" doesn't work, it'll get blamed on the implementer for making mistakes (rather than the concept or its application). I'd say such doctrinate way of thinking is not super useful. Moreover, I believe it is best to remain sceptical and critical of people who want to float such general concepts into the world.

Organizations are highly contextual entities; they are tightly coupled to the external environment and culture. Hence, making organizations better is almost always a study in the socio-economic conditions of the organization. The place and times matter more than anything else in setting up successful policies.

When we study history, we see very few exemplary system builders. One such builder was Lee Kuan Yew, builder of modern Singapore. Another - Admiral Rickover, who built US navy's first nuclear submarine. Both of these people had a great "ways" of handling things at an organizational level, I'd say. Their system was mostly focused on: studying the specific states and ailments of the organizations, using erudition, worldly knowledge, and common sense to propose a way forward, and to commit their lives to improving the situation, and then simply keeping the course.

So coming back to your question: perhaps some ideas under the banner of holocracy could be useful/applicable to some organizations, operating under some specific socio/economic/cultural conditions. That's quite a lot of caveats because, when it comes to organisations, there is rarely a satisfying wholesale answer.

PS: I am an avid student of organizations, and am always in the search for potentially universal (or at least largely applicable) truths about organizations. The result of my attempt is my book "Turnover and Other Organizational Ailments" (Free to read on the web [1]). I have, in the book, some validated (not terribly sensational) conclusions about organizations that are supported by empirical/longitudinal studies.

[1] https://turnoverbook.com/html/book.html