Challenge Circles

Magical Meetings Stories

A Magical Meeting Story from Root + River Co-Founder Justin Foster

Welcome to Magical Meetings Stories, a series where I chat with professional facilitators, meeting practitioners, leaders, and CEOs across industries about their meeting culture. We dive deep into a specific magical meeting they’ve run, including their approach to facilitation design, and their tips and tricks for running meetings people thrive in.

I spoke with Justin Foster about a monthly meeting he designed called Challenge Circle, what prompted him to come up with it, what it helps accomplish, and the future opportunities he sees for it.

Challenge Circle is Justin and Emily’s version of a mastermind group — members bring issues they’re having with the human side of branding and marketing, and the idea is that the collective intelligence of the room will come up with a solution. Justin and Emily provide recommendations but it’s more about the power of the group:

The purpose is to create more momentum and traction in branding and marketing efforts. Branding/marketing can feel so overwhelming, Justin explains, because there’s so much to do and not everyone can afford to have a team do it for them. Therefore, the mind begins to shut down and prioritize primarily off of impulse, rather than intuition or strategy. “Everybody’s trying to take care of the marketing, but what about the marketer? What about the human? Here’s what we know: If you’re burnout, tired, fatigued, overwhelmed, you make poor decisions. It’s just human nature. Like I said, you become impulsive, and you become short-term, and you become desperate sometimes, because you’re tired. So when we think about a community, it truly is a community to provide spiritual and emotional support to the humans that are doing the marketing.”

Challenge Circles are able to get people helping one another, working together and participating, either by sharing their challenge that they would like help with, or helping someone else with their challenge and learning from that.

Let’s dive into Justin’s process to see what makes these meetings magical.

Participants receive some contemplative prompts prior to the Challenge Circle, where Justin and Emily ask questions such as “What have you attempted, and why didn’t it work?” This gets them thinking in preparation to address and work through their challenges in the Challenge Circle.

Then, they always start each Challenge Circle with what Justin calls “a two-word check-in.” They ask the participants “What are you feeling right now?” Sometimes they do an intention, but generally the two-word check-in gets the meeting going.

The meetings, held Thursdays at 1PM CT for an hour, range from 8–20+ people, and Justin and Emily aim for 2–3 challenges per Challenge Circle. Everyone is encouraged to be ready to share a challenge that they’re having. The decision process of which challenges to tackle during the Challenge Circle is not democratized — participants submit a few and then Justin and Emily (acting as co-facilitators) discuss and decide which ones to tackle, live in front of the group. The goal is to see how many challenges can be addressed in that hour.

Challenge Circles go off of the belief that there are a lot of universal problems and challenges that people face (regardless of industry), and the intention behind these meetings is that once people realize they can come together and have a vigorous conversation about a challenge, it becomes much more doable. “There’s a lot more hope and a lot more enthusiasm for the possibility that it doesn’t have to be this way,” Justin says.

I asked Justin when a challenge is considered complete. He said it’s complete when there is the idea of what he calls “make it real.” “Make it real” means that the person that submitted the challenge feels satisfied, with a solution that they can go implement. The second indicator of a challenge being complete is that everyone has spent all of the conscious ideas in the room. “We don’t want to belabor it, and we’re not trying to glean every little detail. We’re trying to get to the nuggets that can be applied immediately.”

Finally, the meeting ends with a two-word check-out of how each person is feeling–similar to the way it started, with a two word check-in. “What we’re trying to do here is change people’s perspective, and the way that we know our perspective has changed is the shift in emotion. That’s why we ask a two-word check-in, two-word check-out, around what you’re feeling. If someone comes in, they’re like, ‘I’m frustrated, and I’m impatient.’ And they checkout with, ‘I feel motivated, and grateful.’ That’s progress to us.”

Unlike other meetings where an email with notes or next steps is the follow-up deliverable, Challenge Circles have a guide in the form of a graphic recording of the solution. Justin explains that as ideas start to flow from participants, patterns and principles begin to emerge. Emily creates a graphic recording of the solution that the group comes up with, and that becomes the output that can be used as a guide. Each guide is unique per challenge.

I asked Justin about any rules or protocols he had in mind when coming up with the Challenge Circle meeting idea. He cited vulnerability and being willing to be challenged. “If you have some fragility, the Challenge Circle really isn’t for you. If you don’t like feedback or you’re really sensitive, or easily offended. So you got to be willing, you’ve got to have this willingness to be challenged.”

One operational rule is that everyone speaks first before anyone else speaks twice, when discussing feedback after challenges are shared. This encourages those who may be more introverted or hesitant to speak up immediately to contribute, and helps encourage those that may typically dominate meetings to also listen.

Justin and I also discussed his process for designing this meeting. He highlighted three key elements, which also relate to his overall approach to facilitation and coaching:

Another critical aspect of the Challenge Circle meetings includes flexibility/fluidity. As discussed earlier, the goal is to get through at least 2–3 challenges but if somebody has a challenge that takes a little muscularity to get behind it, the group will take more time to brainstorm and not rush through it. “This is the key thing for us, we allow room for intuition.”

I asked Justin what he sees as future opportunities for the Challenge Circle meetings. He has a lot of ideas in mind.

There are a few tools Justin uses to create magic and connection in his meetings:

Through Challenge Circles, Justin is able to bring much-needed insight to his BeMa community, because the meetings actually work. His approach as a facilitator is to bring people together as a group and provide participants real value. “This model of collective consciousness of the room, and this awareness that we marketers all sort of have the same set of problems, really has an efficacy to it. And that’s great. I mean, we would never want anyone to spend time or treasure on something that did not bring them relief or value or insight.”

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