Facilitating All Together Bold: Reflections on Designing, Adapting, and Engaging in a Learning Community

Crystal Shaw
Bold Ventures
Published in
10 min readJul 26, 2024

All Together Bold (ATB) emerged as an idea to respond to the need for spaces in the social sector where individuals working towards racial, cultural and financial equity could connect, discuss and question in the pursuit of learning and action. The program aimed to foster an environment where we co-created community, trust and accountability to address the influence we wield due to our proximity to wealth and power, share about and examine the guiding principles of our work, and explore the collective impact we can have by aligning our values and actions.

Since September 2023, ATB has gathered a community of practitioners dedicated to fostering a more just and equitable world. We leaned into joyful leadership; sat in collective grief; shared with one another about our money stories, identities, relationship to power and questions about doing business differently; learned from partners about reciprocity, care and healing; offered each other the grace to show up when and how we were able to; and navigated the ebbs and flows of embarking on a new program together.

One of the purposes of publishing pieces throughout the program was to extend the peer learning community beyond the cohort; to contribute to the larger conversations being had about how resources and power are distributed and utilized equitably. To this end, as the first year of the program comes to a close, we share some reflections, learnings and thoughts about what’s to come. These reflections are the outcome of a series of conversations between Crystal Shaw, Community Coordinator, and Eli Marsh, program contributor and participant.

Designing the Program

When Jessyca, the CEO and Founder of Bold Ventures, first announced All Together Bold in June of 2023, she described it as a space where individuals working towards racial, cultural, and financial equity can come together for learning, skills development, and candid conversations. Throughout our planning leading up to this announcement, we spent several hours discussing the need for community for people in the social sector. As I embarked on building Jessyca’s vision, I kept the future members at the forefront of my mind from marketing materials and pricing conversations to program design and experiences. Even decisions, like defining All Together Bold as a learning community, took many discussions to ensure that we appropriately communicated what we were building.

Although we decided on a broad target audience by extending the program to anyone committed to relationship, repair, and the redistribution of wealth, application responses indicated that people understood the intended premise of a learning community. They wanted a dedicated space to continue to wrestle with the concepts that envelope their work. It was clear that we were cultivating a group headed in the same direction with differing opinions and ideas of how to get there — which would make for rich conversations.

As I began laying the groundwork for building a community space that was loosely structured and responsive to the personality of the cohort, the program components started to come together: structured group coaching calls, free-flowing office hours, quarterly speakers, and an online community space to house it all. Besides being topic-specific, the group coaching sessions were used as connection points from curated breakout rooms designed to foster new relationships to time dedicated to crafting our community norms together. The roadmap for the group coaching calls informed the monthly themes and more malleable parts of the program. I began to ask myself questions like, “Where would this speaker best fit into our monthly themes? Would it be helpful to extend this group coaching conversation into the next office hours?”

The more organic, easygoing sibling to group coaching calls, office hours, unearthed topics from unfinished conversations, and member questions and ideas. Our quarterly speakers were selected to complement the monthly themes and incorporate emerging patterns from the cohort. The online community space housed session agendas, and recaps; our extensive resource library; a hand-picked jobs and opportunities board; and a themed online forum to continue our conversations between sessions. I curated this space to be visually cohesive, from the design elements to the content.

We began the program with Akya Windwood and Rajasvini Bhansali discussing joyful leadership inspired by their book, Leading with Joy, which discusses many of the topics that we expanded on in the coming months, such as rest, power, collaborations, and grief. From there we planned to move from intrapersonal topics like identity and power to intrapersonal topics like rest and boundaries to collectivist topics like revolutionary love and community support. Although we did not proceed as planned, it provided a flexible structure that bent to the needs and capacity of the cohort.

Shifting Along the Way

The first cohort of All Together Bold began in September of 2023, with blissful optimism and discussion of joyful leadership. I was excited to see everyone together as they openly shared their hopes for the community. The events of October 7, 2023, as well as the subsequent and continuous attacks on Gaza, shifted the tone for the world and our small community. As I waded through a wave of grief and swift education about Palestine, my thoughts turned to our community members, most of whom work in the social sector. Over the next couple of months, I spent much of my time checking in with members individually via chat and gauging interest in a collective grief session, which never came to fruition.

As it continued to be clear that global events and personal circumstances were heavily impacting our members’ capacity to show up in the group, we reached out for feedback about what would work and not moving forward. Their responses lead to many small shifts, like timing, that would hopefully allow more people to engage.

Additionally, in January we opened up our quarterly speaker series to the public with limited tickets. This felt like a natural pivot that also allowed our past members, who no longer had the capacity to commit to the full program, to participate. Interviewing Cúagilákv (Jess Housty) and Kim Hardy, co-leads of Right Relations Collaborative, about how their values guided their actions provided useful reminders as I continued to make shifts while keeping the integrity of the program.

Throughout the program, I consistently asked for feedback and the community provided me with their opinions and encouragement. Responsive shifts were possible because of the built-in feedback loops and emphasis on co-creating a space to be curious. Although this cohort of All Together Bold experienced many shifts and pivots, I attempted to focus my efforts on what would be most impactful for the community.

Facilitating and Participating

Coming into this program as a facilitator, I knew I wanted to lean into my strengths of asking questions and being present while maintaining the program’s focus on building connections and learning together. As demonstrated through the design of the program, I needed to provide a flexible structure that would bend to the members’ needs. In sessions, I made it clear that I would not be providing answers but rather cultivating a space for inquisitive conversation that would lead members to their next ‘aha’ moment. Some of the essential elements to achieve this aim included time for silent reflection before discussions, crafting a gradual progression of questions throughout the session, and remaining flexible to the group’s contributions to the conversation.

My identity as a neurodivergent, black woman heavily influences the way I facilitate community-based programs to cater to people whose brains think differently. There was no obligation to have your camera on or share with the whole group. We took scheduled breaks. I planned for potentially triggering conversations by presenting solo participation options, reaffirming consent for recording, and closing with short meditations. One-to-one breakouts were meant to build personal connections and allow members to participate in conversations, even when they were not ready to share with the whole group. All discussion questions were displayed visually, read aloud, and posted in the chat to increase accessibility. These were small actions that made a big difference in how members engaged in these vulnerable conversations.

Although I was the facilitator of ATB, I did not want to be seen as the authority figure in an imaginary hierarchy, so I vulnerably participated in all of our conversations without presenting myself as the expert. I was there to learn from everyone else as an integrated part of the community. Alongside vulnerability, transparency was another important factor in diffusing the illusion of an authority figure. I shared some of my decisions with the group, provided resources when I got ideas from outside people and institutions, and admitted when I made mistakes or had to shift in real time. I was not an expert on the topics we discussed, nor did I claim to be. I did not have it together all of the time, nor did I claim to have it together. My job was to ask the next right question while being present in my humanity. If I wanted members to be vulnerable and transparent as they explored their relationship to these sensitive topics, then I would be vulnerable and transparent in how I facilitated and participated in the group.

If I were to change anything about my experience, it would be to have a co-facilitator. I had a wonderful thought partner in Jessyca Dudley, and fantastic support from our contributor, Eli Marsh, and the rest of the Bold Ventures team, Melissa Gomez and Alysha Catalano, who helped me move forward through the shifts and pivots. I could not have done it without them, and I wish I had a co-facilitator. When I had co-facilitators in the past, I always thought it was “nice to have”, but this experience taught me that it is a “need to have” for me. They provide a unique partnership to plan the program, maintain the energy of the group, and pivot when necessary.

It was a long, joyous, and sometimes frustrating journey in facilitating the inaugural cohort of All Together Bold, and I will forever be grateful to everyone who joined. While facilitators usually offer advice at the end of reflective pieces, I prefer to glean insights from facilitator, ATB contributor, and participant, Eli Marsh.

  1. Add levity. Our work can be heavy! Create opportunities and be open to having fun and experiencing moments of joy. Let go of some of the weight to really be with and to see others.
  2. Be curious. We don’t have all of the answers. We have our perspectives, experiences, ideas and folks around us. By approaching the shape and content of the program with curiosity, it felt as though we were in it together.
  3. Be solidly grounded in the purpose of the program. Through the in-the-moment and the foretold shifts, I felt a cohesiveness that kept me connected to what I had signed up for and to those with whom I was moving through the program. The consistent expression of programmatic values contributed to being able to craft articles on brand and that weaved themes together.
  4. Lessen the unknowns while not being prescriptive. The structure that was provided calibrated my expectations and offered enough details that allowed me to feel comfortable and prepared to show up and participate. However, the built-in flexibility invited folks to co-create the experience and to show up in ways we were able.
  5. Create multiple and varied points of engagement. While there were commonalities and alignment in values that brought us all together, what we each needed and wanted from the program varied. From the onset, many types of engagement opportunities were presented, inviting us to connect one-on-one, to listen and learn, to lead discussion, and to ask for thought partnership on something specific to what we had going on. My experience was that this approach encouraged us to show up in ways that were mutually beneficial to the group and to ourselves.
  6. Value the individuals within the whole. I felt and observed how our community was centered in the design and facilitation of the program. Crystal demonstrated appreciation for community needs and interests, and for us as unique humans. We were part of the whole, and individuals participating in the experience of the whole. Her ability to honor both felt crucial to the strength and impact of the program.
  7. Extend grace. We have full lives outside of the program, and are impacted by what’s occurring in the world around us. We do the best that we can in any given moment, and sometimes are not able to fulfill a commitment in the way we intended. Extending grace to the lot of us, and to herself, Crystal embodied the vulnerability and transparency I believe the program wanted to create space for in order for us to dig into what’s required to advance justice work.
  8. Get yourself a co-facilitator. We don’t have to go at it alone. Shared leadership grants us the opportunity to enhance our creativity, distribute responsibility, and foster a richer, more dynamic learning environment.
  9. There’s a demand for values-aligned peer learning communities.

--

--

Bold Ventures
Bold Ventures

Published in Bold Ventures

News, opinion, and commentary from BOLD leaders advancing racial, cultural, and financial equity.