Training + organizing volunteers at scale (in a pandemic)
Ashley Williams shares lessons learned from leading some of the largest political organizing trainings of all time
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In the 2020 election cycle, an enormous number of Americans signed up online and volunteered for a campaign or political organization for the first time. How did Democratic groups recruit and retain the *tens of thousands* of volunteers needed to take on Trump?
For this week’s Campaigner, Arena’s Debra Cohen spoke with Ashley Williams, a leader who worked with two of the largest volunteer recruitment and training efforts last cycle - Organizing Together 2020 and Vote Save America - about all things organizing.
Q&A with Ashley Williams
Campaigner: You led at least one very large distributed volunteer and training program in the 2020 cycle. Can you talk about what that was like and how you all approached your work?.
Ashley Williams: I was the National Training Director for a campaign called Organizing Together 2020, which was working to build capacity in six battleground states in the lead up to Democrats having a [presidential] nominee last cycle. One of our projects was a partnership with Crooked Media’s Vote Save America to lead a training series for their volunteers as we were working in the same six states. We were really aligned, so myself and the training team at Organizing Together put on what I have now dubbed “the largest political organizing training of all time,” because I've never heard of any that have been bigger: Over the course of one month we trained 60,000 people live. The first session alone had 16,000 people live - around 10,000 on Zoom and another 6,000 via a live stream on YouTube.
When my time at Organizing Together wrapped up, I had this relationship with the folks at Vote Save America, who had all of these volunteers that had gone through the training and were chomping at the bit to stay involved. I'm not really sure if I made up a job for myself [at Vote Save America] first or if they had a vision for a community of their volunteers, but basically, I was brought on as a contractor to take the volunteers who had gone through training, really invest deeply in them, and help them become volunteer leaders.
Campaigner: That was during the early days of the pandemic, right? So this all had to be virtual?
Ashley Williams: Exactly. All of this was in the early days of COVID when all of our grand plans of traveling to do in-person work in battleground states were halted - it became clearer and clearer that that [in-person organizing] wouldn't be able to happen. We had to think of other ways to develop and test volunteers and move them up the ladder of engagement to become volunteer leaders going into GOTV season. We essentially built a volunteer community as an organizing tool where we would funnel people into shifts in the states that they had “adopted.” Folks would virtually “adopt” one of six battleground states. This model became a fairly common thing that happened especially in 2020 for groups building volunteer communities. What we did differently is that since there were two of us dedicated to building this community full-time, we leaned into improving the volunteer experience and were less focused on shifts or fundraising goals or things like that. It was really all about creating a positive experience for people who wanted to get involved, and I think that's something that we did that made it really successful.
Campaigner: Organizing Together was kind of a unique idea. Can you talk a little bit more about that program? What are some of the lessons that you think Democrats should take forward as we look to future primaries or future staff trainings?
Ashley Williams: Organizing Together 2020 was sort of an experiment to see what would happen if Democrats built up field staff for a potential nominee in advance of that nominee being chosen. The original plan was to open field offices in battleground states and train volunteers, and then basically hand them over to whoever the nominee would be.
It was a learning experience - I think the transition from Organizing Together to the actual Biden campaign didn't go as smoothly as you would've hoped it could have. I wasn't involved in those conversations, so I can't say why, but I do think the idea of hiring locally in advance of the primary and building up volunteer leaders so that you're ready once there's a nominee is really smart, and I definitely think that's something that should continue in the future. The big investment in training from Organizing Together was also worthwhile - for me training is the gateway to becoming a volunteer leader and building that confidence to know that you can jump into a campaign, even if you've never volunteered before. The investment in training was really exciting to see, and I always think that's something Democrats should keep investing in.
I was based in DC, but we were hiring people locally in the six states that we were organizing in. That's another thing that Democrats need to continue improving on - not just helicopter people in, but developing the people who are already there, even if they don't have a traditional organizing background.
Campaigner: Talk about building communities focused on the “volunteer experience.” Are there things you did that are transferable to down-ballot or statewide races?
Ashley Williams: One of the things that I really tried to do was think about what gets someone to go from donating money online to taking that next step and actually volunteering. For so many people, volunteering happens when they’re invited to do it by someone that they already know. So that feeling of having friends who are also volunteering - like “Hey I'm gonna go do this kind of scary volunteer thing. Will you come with me?” - was important. The way I looked at it with Vote Save America was that the Crooked Media hosts from Pod Save America and all their different shows served as the “friends” inviting people to show up for the first time. That gave us the advantage of having a “known” or familiar person making the initial volunteer ask.
Campaigns can and should replicate that by using trusted voices in the voters’ or volunteers’ communities. It doesn't have to be a super well-known celebrity or an influencer, but it can just be a church leader or a mom who's already organizing a book club. Having some trusted voice to be the one inviting people to volunteer for the first time is really, really important.
And then the second thing to consider is the experience that people have once they get there. I first got involved as a volunteer on the 2008 Obama campaign, which was such a joyful sort of kumbaya experience that can never be replicated. But I’ve also had some other really negative volunteer experiences where I walked in and was not acknowledged, and no one knew what was happening. So I really wanted to make sure that every interaction that we had with the volunteers was leaning into that fun and joy and really appreciating the volunteers every step of the way. That's absolutely something that can be replicated on any campaign, no matter how big or small the budget is. You can always create a culture where people feel welcomed and included and they know that they're valued.
I was really inspired by a quote that I heard from one of the directors of the office. He said that “the job of the director is to love people into doing their best work.” I really saw that as my role as the leader of this volunteer community - to love everyone into doing their best work as volunteers. I felt that if we made everyone feel so valued and so included every step of the way that when it came time to make a difficult ask of say, calling through a list of voters that have never been called before, they would do so enthusiastically.
Campaigner: Traditional campaign volunteer recruitment has often involved phone banking supporters and asking them to volunteer. It can feel sort of like a grind. There's sometimes tension between that kind of traditional organizing and distributed or relational organizing models. How do you do both at the same time?
Ashley Williams: I think it's hard. Every interaction that people have with campaign staff or volunteers is a chance to create an experience. As an organizer, you may not be able to have a one-on-one meeting with every single volunteer and make them feel valued and important, but there are little things you can do along the way before that conversation that would've even happened, where they can feel valued. Maybe you’re just telling them the details of their shift ahead of time, or you're sending training material ahead of time so they can feel more comfortable - all of those little touches help build trust and safety in the volunteer-organizer relationship. So even if a volunteer never has a direct interaction with you, they still feel like they're welcome and part of something.
To me, it's almost like thinking of it as a brand - in that every little touch means something and helps create the way people see your campaign. Even the volunteer signup forms you use are important. You can start giving people information there, you can make it feel fun and colorful, or you can ask a silly question at the end to set the tone. Every single one of those things matters. And then if you are hosting a physical field office or staging location event, it’s important to think about the experience from the moment when someone walks in the door. What is the flow of the space like? The same goes for virtual trainings: as people arrive into a Slack group or community, does it seem chaotic or is it organized?
I won't even get into all my thoughts about how some of the Slack groups were run during the 2020 campaign, but they felt so chaotic and intense at times. Sometimes a few people would have an issue and it just kind of would consume the space. Being really intentional about the space you're creating virtually or in person can help people feel comfortable and want to come back. That's how you build volunteer leaders. Then, the more volunteer leaders you have, obviously the more you can scale and remove the responsibility of work and burden on the actual campaign staff.
Campaigner: The hardest part of working in politics sometimes can be getting your foot in the door. Are there things you've observed that might help someone who's been a volunteer leader, highly involved, you really make that jump to a paid job?
Ashley Williams: A couple of things: I think number one, we did some informational sessions on different areas of campaigns with our volunteers, so I think they had a very clear and realistic understanding of what they were getting themselves into. My approach has always been to be super honest with people: letting them know that they're probably gonna make less money than they're making in other fields, that they’ll be out of a job at the end of the campaign, etc. It can be really hard. Your boss might be 10 years younger than you, and that's kind of weird. I've always been super honest with people about that, and I think those who've gone into paid roles that I’ve worked with have gone in with their eyes open and knew what they were getting into.
Many volunteers that I worked with have a community now - and many of them have kept in touch with each other and supported each other on their political journeys. That's something important for someone who's considering getting involved is finding other people who are also in the same boat of thinking about transitioning careers. Having someone to commiserate with and vent to at times is incredibly important.
I come from a very non-traditional organizing background. My background is in marketing and the music industry and totally none of this at all. (laughs) I think there’s a place for folks who are transitioning careers and maybe doing Arena programming to see if they wanna transition careers is really useful. Bringing outside experience to politics is useful - whether people have a tech background or marketing background or communications background, all of those things are so useful in this work. Bringing those other skills to it are so needed because you know, campaigns need everybody's talents brought to them. Don’t be afraid to say that you’ve done something like this before and let me offer that skill.
Campaigner: On Vote Save America, it seemed like you built up this massive trained group of people who could do a lot of different things they were asked for and you worked with different campaigns to plug them in. Are there things that campaigns did really well or that you wish that they did differently to help you plug in those volunteers?
Ashley Williams: I should say first, that I wasn't the person at Vote Save America who handled those relationships, but I did hear from the volunteer's perspective what it was like when they then tried to plug into campaigns. The most important thing for campaigns to know is to not make it hard. Don't make it hard to sign up, put the start and end times of your events everywhere. Make it clear if there's gonna be training beforehand, or if there's gonna be an interpreter. Don’t make people guess the details of an event. Some people are already nervous or scared about volunteering. They are giving you their time and that is valuable. Don't make it hard for people to sign up. Don't make it hard for people to get in the door.
I saw a lot of campaigns that were just super convoluted, where folks would apply and then they would never hear back. Maybe that’s a capacity issue on the side of the campaign, but you could also have set up something like an autoresponder that says your request has been received and we may not get back to you, but here's what to do if you don't hear back. Right? Those little touches that can be built in that make people feel like, okay, like this is actually gonna happen. I'm really gonna volunteer. Those are important. I've seen that a lot.
One of the things I'm proudest of in my own organizing work is that I've always had a really low flake rate. (The percentage of people who bail on a volunteer activity) My flake rate is usually around 20% instead of the more common 50%. The reason for that is because auto responders can allow you to use follow-up emails and so many things can totally be automated. These processes don't have to cost money. Getting people to show up is half the battle. Just really thinking through if you're a complete newbie and you're nervous and you're scared, how can an organizer or organizing director make it a really easy, seamless experience to volunteer? Once a volunteer is there, they're gonna do it. But getting there is the tricky part.
Campaigner: There’s a balance between busing in outside capacity vs. building local volunteers. As we think about the 2022 midterms do you have any thoughts about how campaigns or the larger Democratic ecosystem approach that work?
Ashley Williams: As someone who lives in New York City, I’ve always been that volunteer that takes a bus into a swing state and canvasses. On the one hand, for me, it was a life-changing, transformative experience, and I'd like to feel like I made some small amount of impact in the areas that I was volunteering in. But also, outside volunteers are never a replacement for a person in a community going or talking to other people in their own community. So [with programs like Organizing Together or Vote Save America], I think we need to do both. I think those of us who are outside of a battleground state or district should bring additional capacity to the folks who are on the ground and let the people on the ground lead.
Whether that's donating money to pay local organizers, or just asking how can we be supportive to you? Maybe it's we come and all we do is provide meals for the folks who are local, who actually should be the ones knocking doors, or maybe we come in and offer popup consulting for campaigns that don't have the capacity on the tech side or, or things like that.
Seeing ourselves as additional resources and capacity, but always knowing that the people who are in those states are the ones who should be doing the core persuasion work. It's hard. I say that as like a person who always wants to go to a swing state and knock doors. Being available when you're asked to show up, but also not assuming that you should be the ones who do it the whole time. 🇺🇸
More Highlights:
Ashley is currently the Managing Director of Iconico. She's available to connect to talk more about organizing, volunteer programs, and career transitions. Schedule a time to chat here>>
If you’re on the job hunt or hiring for the 2022 cycle head to Arena Careers - a one-stop platform for progressives looking for work and employers looking to hire - and create your profile in minutes. Get started today>>
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