Making organisation self-organizing

As part of my Bachelor’s, I had to take up an internship. There were several interesting choices, but the company I joined was especially so. What was initially five guys coding in two rooms tucked away on the last floor of an old building soon became sixty and eventually over two hundred people - one of the fastest-growing companies in Poland.
Organisational woes
I generally tried to focus on delivering projects instead of getting people organised. This was to an extent true for most of the hires, resulting in a very flat company. Soon (well, after a couple of years) it became nigh impossible to manage the situation - even mundane problems were escalated to the founders, who were all too busy dealing with them to deliver any projects or improve the company.
Holacracy to the rescue
Getting this situation sorted out required a framework. One of the true and tested solutions was getting some sort of management hierarchy in place. But maybe there was an alternative, one that could preserve the leaner approach that many in the company were fond of.
The framework that was decided upon was Holacracy - a system made famous by Zappos and later adopted by Medium. I was proud to be one of the organisation members selected for in-depth training, with the goal of this smaller group then gradually introducing more people to the idea and teaching them in turn.
The what?
The basic premise of Holacracy is to build "circles within circles" organically. Start by defining roles that map to responsibilities. Wherever more hands are needed, add people. If communication overhead grows, split off the concerned group into sub-circles. On top of that, certain core roles are defined by the Holacracy Constitution and a quite formal description of how basic meetings should be structured.
My initial assignment was the Facilitator (one of the core roles) of the Engineering circle - one that was meant to encompass all developers working on all projects that were the bread and butter of Tooploox.
How it caught on
The strategy we came up with was pretty simple - start by solving a couple of "non-client" issues that pestered developers to learn the ropes, then gradually introduce people project-by-project. Since usually client projects had some sort of SCRUM structure anyway, this did map to a holarctic sub-circle almost perfectly.
I genuinely enjoyed being a facilitator in that process. My main responsibility was running the meetings - making sure they happened, were timely and adhered to the main tenets of Holacracy. Scheduling the meetings and taking care of artefacts was a job for the Secretary. This way of setting up meetings is in my opinion one of the core strengths of the process - as long as the facilitator fits the role. One needs to be able to direct the meeting without imposing judgment on the ideas being debated - which often happens in other setups.
During the next year, I fulfilled more roles in the Engineering circle:
- Architect,
- Estimator,
- Strategy guardian.
Each corresponded to a problem that we faced and a responsibility to solve it. My last project as Strategy Guardian was to seed a new role amongst all client projects: a Shepherd - a person who was responsible for the overall health of the project. Not just delivering objectives dictated by the client, but also making sure devs enjoy working on it and the future of the project is bright. This idea felt (and still feels) unique to the perspective given by Holacracy. Even after a couple of years in different companies, I still feel that this responsibility is either piled on top of other "managerial" ones fulfilled by one person or missing entirely.
What it might become?
At one point I felt that a change was needed - I spent five years in one company, building it from the ground up. As such, everyone knew me and seemed eager to listen to my suggestions. I felt that to grow I needed to see myself in different environments.
As I left Tooploox, the dream of having a whole company working under Holacracy was still unfulfilled. From what I know it was later abandoned, but that story needs a different teller.