This is the second part of a blog post that got way too long to be just one. The first part, which details prerequisites, what Wikimedia chapters do and much more, can be found here.
So I left off at the three possible paths I see to professionalisation of a Wikimedia Chapter. Note that I don't necessarily believe that all chapters should professionalise to start with. But given that a chapter is thinking about it, here are three possible start points I can imagine.
Getting rid of administrative hurdles: The Secretary
The first direction I see is prompted by the growth of administrative burden on chapter volunteers. Whether it comes in the form of donations (lots of tax receipts and accounting to do) or members (keep lists up to date, take money in, prepare General Assemblies), or expense reports (many volunteers doing little events by themselves, sending in their train ticket and other bus ticket to be reimbursed), the administrative burden is the first one that usually becomes too heavy. It is also probably, some exceptions notwithstanding, the most boring part of running an association. When that takes too much of the volunteers time and motivation, the first thing that suffers is programs. Cool activities, outreach and such, which directly pertain to the objective of the chapter, are quickly put in second place, with an enormous guilt feeling. Not because they are not good, but often because the little administrative things have some fear factor engrained in them if you don't do them, as they are often tied with legal requirements that might threaten the survival of the chapter.
So the first option is to outsource (here, outsource means take out of the hands of volunteers to a professional) those, in way of hiring a secretary-type person. A good option might be to start with someone freelance, when the workload does not justify having someone full time. The advantages of having a secretary is that all the administrative things are then taken care of professionally, by someone who can be held accountable. The drawbacks is that a secretary usually has little potential of "growing", of becoming more than a secretary, just because it's what they do well and they don't really want to do other things. In the mid term, a secretary might not be enough to ensure the chapter runs smoothly, especially if the potential for growth is important.Note that the secretary-type job might also apply to other areas such as accounting or press relations. Those are quite easily outsourced (this time, not hired in full, but buying a few hours of someone doing this as a freelance).
Supporting members and initiatives: The Project Manager
The second option to get onto the path of hiring someone is that of hiring a Project manager. In chapters wih active members that come up with lots of ideas, one of the bottlenecks might be that those ideas never see the light of day because the logistics or program management aspect of them never gets done. We go back to the "not having time" to do things. Having someone dedicated to implementing ideas might be a good option to make sure that nothing gets forgotten and that the chapter keeps a healthy level of programmatic activities (in direct connection with the objectives of the chapter). Often, events for example, will require some things such as finding a venue, keeping a budget and such, which not all volunteers are ready/able to do. However, without this part, the events just don't happen. Having someone who has an idea of what the timetable should look like, who is able to break down tasks and assign them, is a good way to make sure that as many people as possible see their ideas implemented. It also takes the boring-stressful part of putting together real-life projects which might put off volunteers. It also helps with talking to integrated bodies (such as local institutions, or even suppliers) as this gives them a sense of organisation which might reassure them. A project manager should be comfortable working with volunteers (not always an easy thing) and take the lead on organisational aspects without taking the lead on content aspects (you want to keep your volunteers in a state where they are actually doing something). They should also be comfortable with the very difficult step of making virtual things into concrete things (a particularity of Wikimedia crowds being that they live in a very virtual world and that going "back to earth" may be a difficult step).
The advantages of having a project manager is that while not all projects might see the light of day, it is easier for the chapter to prioritize which initiatives they want to carry out by assigning one person to support the volunteers on a particular idea, rather than having only ideas implemented which have enough volunteers to be carried out. The drawbacks is that a real project manager needs projects, otherwise they get bored. They also need a strong management, which is able to give strategic directions as to which projects should be supported and which should not, in short, what the priorities are. And that kind of management takes an awful lot of time on the part of volunteers. On the longer term, the project manager could evolve into say a "program manager" overseeing a little team of project managers. However, I don't think a chapter can go on for ever with just project managers, there comes a point where more management strength is needed, which leads up to my third option.
Starting at the top: The Executive Director
The third and last option I am going to look at here is that of hiring an executive director. If a chapter is big enough (read: has the money), hiring an Executive Director is another option that they might want to consider. The idea being here that you introduce right away someone at the top of the management scheme, who will help the chapter implement its strategic decisions. Their role is then not so much to do things, but rather to have things done by building the chapter staff from scratch, addressing the right issues at the very beginning. This might be an option for chapters which come into a lot of money quickly (obviously, an executive director with the right skills will probably cost more than a secretary), or for those who are willing to invest in the future quickly. Note that I think that any hiring will mean investing in the future, but hiring an executive director right away is a way to push a chapter's volunteer body (the board, mainly) to evolve to a strategic planning role and take them away from the day-to-day business. Hiring an executive director as the first person is a tricky thing, as volunteer boards (in Wikimedia and otherwise) usually have a hard time getting away from the operational side of things.
The advantages I see in hiring an executive director is that the chain of command is easier to build on the longer term. Hiring a project manager or even a secretary, and then imposing a manager on top of them is sometimes difficult, especially when they have been working alone for long. An executive director coming in first has the advantage that they can build their team from scratch, and avoid having to "manage" people who are not ready to see someone come and tell them what to do. The drawbacks might be that an executive director as a first hire will have well... nobody to manage. This situation depends on the chapter's means of course, but it might linger until the chapter actually have the means to hire someone else. Starting off with an executive director can also be problematic if the board is not ready to let go of operations, or on the contrary suddenly gives up everything they were doing until then, which might end up in an executive director doing tasks that should be done by others (read: doing the work of a secretary and/or a project manager, among others). An efficient executive director must be empowered from the start, not an easy thing to do.
The more I think about it, the less I know which option has my preference. I've seen all implemented, with more or less success, and I am not sure if I have a preference at all. I guess a project manager might be the easiest to handle as a first hire, simply because you can always have a secretary on an hourly basis if the need really arises, and because I believe that in the end, programs should have the highest priority. This said I believe that a project manager should be hired because they're good at what they do, and not in the light of them becoming an executive director at some point. Of course, it can happen, but managing an office and managing staff and setting up an office are not the same thing, so the project manager should probably be told at the beginning that the next hire might be an executive director.
Note that all of these options are thought up to answer the question of "who should we hire first". In the longer run, if a chapter is to professionalise, I think that all of these people should be part of the staff. Along with, later on, a person specialised in PR, someone to take care of fundraising etc. (which, however, I don't think should be the first hires). Of course, there's always the fourth option, which implies not hiring anyone. I think it's particularly true for Wikimedia that not all chapters will have to professionalise, even in the long run. But I'll talk about this in another post, maybe a part III. :)