The concept of official initiatives came out of lessons learned from the Drupal 7 development. We learned a lot from that and in a recent blog post about Drupal initiative leads, I recognized that we need to evolve our tools, our processes, and our organizational design. Others like Nathaniel Catchpole, Larry Garfield and Gábor Hojtsy have shared some of their thoughts already. One of the things I'm most proud of is that the Drupal community is always looking to improve and reinvent itself. Evolving is an important part of our culture. Each time it will get better, but still won't be perfect.
For me, one of the biggest take-aways (but not the only one) is that for an initiative to succeed, it needs to be supported by a team. An initiative needs to carry out a technical vision, plan the work, communicate with all stakeholders, mobilize volunteers, raise funding, organize sprints, and more. It can easily be more than one person can handle -- especially if it isn't your full-time job or if your initiative is complex.
More specifically, we have learned that the most successful initiatives appear to be run by teams that are self-managed; the team members collaborate in the development of the initiative, but also share both managerial and operational responsibilities like planning, coordinating, communicating, sprint organizing and more.
Because self-managed teams are both responsible for their outcomes and in control of their decision-making process, members of a self-managing team are usually more motivated than traditional hierarchical teams. This independence and greater responsibility are important in volunteer communities. Self-managed teams also build and maintain institutional knowledge. The outcome of their work is also more easily accepted by other stakeholders (like core committers) because they have already built a lot of consensus.
If I were to be an initiative lead, I'd feel strongly about building my own team rather than being handed a team. My initial assumption was that each initiative lead would build his/her own team. In hindsight, that was a mistake. Team building is not easy. It requires a time investment that can seem to compete with technical priorities. This is an important lesson and something we can do better going forward. Before making an initiative official, we have to make sure that each initiative has a good team and the support to be successful -- either we can help create a team, provide more coaching or formal training around team building, or we shouldn't designate the initiative official until such a team has coalesced.