Software tools in volunteer organizations

America is nearing a generational shift, as more and more of the Boomer generation reaches retirement age, and more and more Gen X and Millennial start taking more of a leadership role in organizations. I’ve made a bit of a personal brand identity as one who straddles between this digital and analog world, and I’ve made a living by helping organizations move between the two. As more and more of my focus shifts away from established businesses and toward startups, non-profits, campaigns and community organizations, I’ve been spending a lot more time thinking about the tools and apps available within these spaces, how to select them, and how to get traction within them.

It’s not an easy problem to solve, and this post will likely have more questions than answers. All I can do is present a few use cases and share some thoughts.

The first political campaign that I became involved with was the 2016 Sanders campaign. I got involved with the state grassroots, we didn’t have any official support from the campaign at all, in fact, the first direct involvement that we had was during the petition-gathering process. A campaign representative came in and met with all of the various organizers that could make it to the state capitol, and we went over the process and requirements. Up into that point, all of us were operating over several dozen Facebook groups. There was one at the state level, and regional and city groups as well. Communications required crossposting events and news to about a dozen of these groups at a time.

I think a few of us recommended some distribution groups. I found a service and volunteered to setup the various lists to hand over to individual admins; another person put up the $35 to get it started. We also rolled out a Slack instance for the state, and used that extensively throughout the campaign.

Now one of the problems that I’ve seen over and over again with rolling out new tech is that there’s always a certain number of individuals that are tech-averse. More accurately, they’re risk averse. They may be more comfortable with email or text messages, or Facebook, than using Slack, Signal, or Twitter. That’s just the nature of the beast. There also seems to be a sweet spot for the size of the organization and the number of people that participate with these apps. Generally speaking, if you can’t get more than two thirds of a group membership to use a tool, then it will most likely not be useful as a public tool. This is more true the smaller the group is.

Now, there are exceptions to things that are more useful from an individual standpoint. Things like Google Drive or Trello are helpful even if you’re just using them for yourself. Other things may be impossible to roll out organically. I once tried recommending our local Democratic party executive board start using Signal instead of group text messaging, and while most everyone agreed in spirit to using it, the initiative never moved forward.

Ultimately, anything that is going to require people to install another app or create a new account is going to be met with pushback in any volunteer or service organization. Hell, that holds true for any organization. But for startups or existing orgs that are still living in the analog world, technology deployments can have a great effect on productivity.

Choosing from all of the options out there is another challenge. When I was in the enterprise space, the process usually involved gathering business requirements, doing an initial selection of vendors, and then putting together a request for proposals from vendors, compiling reports and making recommendations to an executive board. This process is no doubt familiar to people in any large organization. In smaller orgs, the decision making responsibility might fall to one technology ‘expert’, who has to make these recommendations, implement them, and ultimately provide support. The latter of those tasks is ultimately the longest and most expensive of them, and is where most of the frustration ultimately lies.

My daughter just joined the Girl Scouts, and I got an email several days ago that they were moving to Slack and Google Calendar instead of text messages and emails. I went to a leadership meeting earlier tonight and was talking with a couple of the parents while we waited for the building to open up. One of them said “I downloaded so-and-so’s Slack app like he asked, but no one was in it.”

We’ll see if this time is any different.

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