Thank you for the opportunity to be your OSMF board member these past two years. The experience has been full of teaching moments while I attempted to support this beautiful project and community. It has been an honour to meet people from around the world in this community of communities. I am thankful for all the support and efforts to make OSM a healthy, global open project. It is a testament to the passion for the project. With that, I am sharing some reflections:
Boards are often a convergence of different skills, opinions, and ‘constituencies’. As with any board and/or team, there are differences in work style, time/effort, and opinion. One thing I have learned is to try to see the ‘middle ground’ or ‘middle way’. How can we meet each other half-way? Yet, the ‘my way or the highway’ mentality is no stranger to technical communities and OSMF has it in spades.  It is evident that each of my fellow board members (past and present) truly care about OSM. There were times when we really managed to collaborate with each other. There were other times that things went awry. Some of the conversations/debates left me completely exhausted and unable to dig in more due to the sheer volume and tone of the back/forth. In some circles, this is called ‘win by wearing down the others’. We need to find ways to negotiate more, not just in the board, but in the whole community. It is not a productive or healthy use of our time and mandate.
Being a board member is a volunteer contribution. It is time that this board and the OSMF community considers how to better equip themselves to be ‘fit for the future?’ Some of my fellow board members have done ‘hero’ efforts this year to ‘keep the lights on’. The reasons for this includes personality, passion for the project, and the need to fill sheer organizational gaps. There are some blurred lines between ‘role of board’ and ‘role of board members who are on working groups’ and ‘role of the community.’  This is expected as we evolve. The adhoc and stressful approach of being a sometimes ‘operational board’ vs, as some would have it, ‘a board that just keeps the lights on’, is no longer sufficient to support the project. We need the board, working groups, advisory group, and the community to prioritize OSM in a more cohesive and coordinated way. The board should be a ‘strategic board’ rather than ‘operational’. In order to do this, we need to adjust.
Organizations are in place to provide governance, leadership, planning and strategy. OSMF, as a culture, finds these concepts often wrought with opinion which fray action. For two years, I brought up the topic of OSMF building a strategy for the community and the project. This was not welcomed due to a multitude of reasons. The main argument against this was that ‘OSMF and OSM are organic and should only act like this’. The argument continues that “OSMF is governed by the working groups.” Yet, the working groups do not often meet, collaborate, and plan across the whole project. There are no overarching OSM and OSMF project maps, product(s) map and/or community strategy. As such, some of the complex issues and root causes of problems fester and are not addressed. I’ve been involved in open organization governance for well over a decade. In other open organizations, they have made the switch to be more ‘proactive’ rather than ‘reactive’. Being “open” means considering how to be transparent, inclusive, adaptable, collaborative and community-oriented. These organizations have done this shift because it was time and because the health of the project precipitated it. I thought that the Board was the best place to work on this. This was not feasible yet given the culture and/or opinion of the board or some vocal community members.
I’ve been left with more questions than answers: How can OSM and OSMF really safeguard/improve/grow the project while being more healthy? What if the OSMF board actually functioned like a board of a large open project? What if staff were encouraged to support the large project? If the membership does not want OSMF to have staff, could we have ‘seconded’ help via the local chapters and/or corporate helpers that report to the working groups? What if we actually learned and listened to how other open projects worked to support the diversity and the strategic needs? 
The working group members are amazing. But why aren’t more people joining the working groups? Why do people despise the mailing lists? Why do people state that they would never get involved in the governance of the project? If the governance of OSMF is to be ‘strategic’ and the working groups are to be ‘operational,’ why are we not talking about the need for ‘hero efforts’ to solve issues? Why are some items never addressed? Why are we not growing working groups and local chapters to truly support the project, product set, and community? If there was a product/technical project plan/group, would it help us negotiate the various tool sets that support OSM? I’m not sure another working group is the issue here. The suggestion that OSM needs a Director of Technology is also exciting, but again, how are we planning for this type of change? It is the ‘organic’ nature that is causing us to not be coordinated and collaborative. I was super shocked at the pushback on having a community strategy and engagement plan. If there are governance and working group fires, it is because we have not been structured to truly have open governance and we have not built a healthy ecosystem to have new ideas/people engaged. Again, the people in leadership roles in board, working groups, local chapters, and events, are doing amazing efforts. But, while other open organizations are planning and supporting, OSMF is somewhat stuck.
When I asked people at SOTM if they would run for OSMF board and/or get involved in working groups, the responses were familiar: don’t want to deal with the toxic masculinity, toxic meritocracy, [insert name dynamics], gender imbalance, targeting of leaders, drama, games, ‘us vs them’ mentality, and time suck.
For the past week, I’ve been delighted by social media posts from around the world hosting OSM events. All the while, I’ve been pondering what to write here about my time as your OSMF Board member. This week the Community Map of ‘channels’ was published. This is a fantastic example of why and how OSM must shift to be more collaborative and open. There is still an unhelpful perception that the community is the ‘mailing lists’ and that decisions from the ‘community’ stem from free and open dialogue on the mailing lists. It is clear that the power centers, governance, and planning/decision-making mechanisms needs to shift to reflect how we might be a true open, global community. What do we want from the OSM community?
During the 2017 election, I filed a complaint about how I was treated. I found out that while there is a ‘etiquette guidance’, there was no recourse for me. How does this make for a healthy, inclusive environment if there are issues and no way to address them? People told me that they would never get involved in OSM/OSMF governance (board, working groups or local chapters) because this ‘implicit acceptance’ of bad and toxic behaviour. After an attempt to lobby the board for a ‘code of conduct’, I gave up this initial change request due to the lack of support. It is shocking considering how OSM/OSMF does not change yet other open organizations are working to improve community health and reduce toxic masculinity. So, instead of continuing to champion a code of conduct, I joined up with others to build the ‘example base’ and ‘dialogue’ to improve spaces for people to talk. I’ve joined up with colleagues via the Diversity mailing list and at State of the Map(s) to host conversations around inclusion, diversity and gender in OSM. This is something I will continue. 
If we want OSM and OSMF to change, then we have to find a way to broach needs together. The OSM global communities are doing amazing things, but many are not keen to get involved in governance (board, working groups, chapters) are also acqueancing (accepting the status quo). I knew that being on the board would be hard, but I tried. The OSM community of communities is incredibly inspiring. The only way to shift these dynamics is if we, collectively, help make that happen.
https://www.bustle.com/p/what-does-toxic-masculinity-look-like-how-it-can-casually-show-up-according-to-experts-18550175 and https://mozilla.github.io/maintainer-cohort/articles/week-1/leadership/
 community management research https://docs.google.com/document/d/1Lq1ZO4DhxUXv0-CiFxz0Yv8mmryD-fw0yAZZwR7U1V8/edit#heading=h.omaajijmdsh1
 https://wiki.mozilla.org/Diversity_and_Inclusion_Strategy https://wiki.mozilla.org/Diversity_and_Inclusion_for_Communities_and_Contributors
Comment from Sawan Shariar on 19 November 2019 at 06:55
Informative. Thank you so much @Heather Leson
Comment from imagico on 19 November 2019 at 20:34
Thanks for this summary and thanks for your work on the board.
Since you mention the middle way - and i am not sure if you have the buddhist concept of the Middle Way in mind here - i wanted to mention that in Buddhism, at least as far as i understand it, this concept is less a call for making compromises on practical decisions (where the compromise between two extremes in a multi-dimensional parameter space might not in any way represent moderation) and more, as it is usually phased, calls for moderation between the extremes of sensual indulgence and self-mortification or between the ideas of existence and non-existence. Translated into the world of practical community cooperation i would think this to be more a call for a middle way between self confidence (or self-conceit/arrogance in the negative extreme) and tentativeness (or self-denial in the negative extreme). Or - to use your term - a middle way between my way or the highway and treating every decision as a calculation of arithmetic means between different articulated interests.
You mentioned a Community Map of ‘channels’ which i am not aware of - could you provide a link?
Comment from Andy Allan on 20 November 2019 at 12:10
You mentioned a Community Map of ‘channels’ which i am not aware of - could you provide a link?
I suspect the map is https://openstreetmap.community/ , which is built using https://github.com/osmlab/osm-community-index
Comment from imagico on 20 November 2019 at 12:45
Thanks. There is some irony in that this is mentioned here on a communication channel that is not listed in said database. ;-)
Comment from pangoSE on 20 November 2019 at 16:33
@Heather Thanks for this summary and thanks for your work on the board. I’m sorry to hear you have had such a hard time on the board. I have been in OSM for years without hardly meeting any others physically and I have had a great experience communicating with fellow Swedish and Danish mappers online via comments and email mostly.
I am personally puzzled about the way OSM/OSMF goes about organizing their organization and infrastructure but honestly I have not felt their influence that much.
I rely on JOSM and Overpass API which has nothing to do with OSMF, but the first is supported by OSMDE judging by their website. The OSM database is practically always online (thanks for that whoever you are who keep it running!) which is the only element in my toolchain that depends on the OSMF and from what I understand OSMF does not do much direct work or policy deciding around how to organize the database/API/osm.org. Unlike Wikimedia which has a whole other organization built up and with servers, reoccurring campaigning, technical staff and server resources allocated in a very different and more centralized way.
I use Swedish governmental sources which have been released as a consequence of Wikimedia Sweden and others (not OSMF what I know) lobbying for years for Open Data (on EU level).
I map with a GPS-phone I bought for 100 SEK and I’m happy!
If you are fed up with talk and boardwork come help us in Sweden. We have loads of missing roads to draw from high quality sources (Trafikverket Roads layer), etc.
I invite you to take breaks and do as I do and go to the woods and have fun and perhaps you will forget for a while about all the things you/we have a hard time changing :) (You are very welcome in Sweden. We have thousands of natural reserves and many more kilometers of trails (see this query for all the parks https://overpass-turbo.eu/s/Ohe NB: 70 MB!)
@imagico I agree, it would be interesting to see e.g. hot spots for people writing diary entries.
Comment from skorasaurus on 23 November 2019 at 19:41
Thank you for sharing your time, energy, and talents over the years.
I agree that OSMF needs to coordinate the working groups and ensure communication with each other and plan cohesive, intentional communities and actions.
People should realize that the status of OSM over the past 5 years is the result of a lack of broad coordination or dedicated investment to anything like (paying) people to maintain infrastructure and foster communication internally and externally, for starters.
Comment from Heather Leson on 24 November 2019 at 18:41
Thanks for the comments.
PangoSE - i will continue to focus on governance changes, community engagement, and strategic growth.
I was in Sweden for holidays last summer. maybe I’ll visit again :)
Comment from Stereo on 2 December 2019 at 16:47
Thank you for all the work you’ve done for the board.
I’m wondering what you mean by ‘toxic meritocracy’ in the OSM context? The abuse you got on the mailing list about your amount of mapping back in 2017?
I’m also genuinely curious if you have examples of toxic masculinity that you can share. I must confess that it’s something I have seen elsewhere, but not much in the OSM world. It’s hard to do something about a problem that you care about but can’t see.
Comment from mikelmaron on 3 December 2019 at 12:30
Guillaume, yes, I think you can find direct abuse, and the acceptance of that from others, on the thread you mentioned https://lists.openstreetmap.org/pipermail/osmf-talk/2017-November/004382.html. You can find some explicit examples of unfair treatment and toxicity in that thread based on gender.
I’ve also heard plenty of other stories from women across OSM of both explicit and beneath the surface sexism. A public forum like this is not a great way to explore specific examples of the problem however, since it exposes people to further abuse. I understand what you’re saying that it’s hard to do something about a problem that you can’t see. If you do really want to understand more, I suggest a better start is reaching out for a direct conversation with women in OSM, and then finding good ways to surface the issues.