Over the past year or two, I’ve worked with a few family foundation clients who were either planning for or had recently undergone a transition to the second or third generation of family members. Each transition brought its own opportunities and challenges. But underneath them all sat the same questions: Who holds power? Whose voice counts? And what does it mean to steward wealth in service of a community?
With one family, the third generation already comprised the entire board by the time we came to work with them. They were wrestling with their voice and identity as the “grown-ups” now in charge. What did they want to carry forward from their parents? What did they want to leave behind? And how solid were their relationships with one another, now that those relationships had to hold up in a boardroom?
For another family, a member of the second generation had just become Board Chair while the board was also bringing on community experts as new members. Together, these shifts surfaced questions about power. Did every board member’s voice carry equal weight? Were longtime family members and newly arrived community members truly sharing authority, or only appearing to? And whose values were actually driving decisions?
And with a third family, the founders and wealth generators were just beginning to talk about inviting their adult children onto the foundation board. This raised questions for the founders about what they were willing to shift and what they wanted to hold constant. And it raised questions for their children: What is our role? When can we disagree with our parents? How do we navigate a relationship that’s suddenly both personal and professional?
Across all of these examples, it was about more than the decisions facing these families, it was about more than the decisions facing these families: it was about family dynamics, shared tensions, and emotions. Listening became core. And deep listening among family members is genuinely hard when there’s years of history in the room. When your cousin was your first boss, and still talks to you like it. When your father wasn’t present because he was working for most of your childhood. When your mother held expectations you could never quite meet, and now you carry those expectations with you into the boardroom.
This work is professional, but some of what I know I learned at home. I grew up in a conflict-averse family and didn’t learn early to name things directly or say them clearly. As an adult I’ve worked on that skill, a LOT.
One tool that has helped, particularly as I’ve grown in this work and seen recurring patterns is the use of listening or reflection circles to work through especially thorny topics and surface unspoken tensions.
This started with one client where we noticed unspoken tensions beneath the surface. I turned to a trusted colleague, Ilana Zafran Walden, who helped create the restorative justice program at NewRoot, to think through whether circles could work with families in the philanthropy space. I first encountered the practice while working at NewRoot, and returned to it as a funding partner of Truth, Racial Healing & Transformation Chicago (now Solidarity Heals), which uses circles to discuss racial differences and build communities of healing.
A listening circle is a variation on a restorative circle – a practice rooted in Indigenous and restorative justice traditions, and one that schools have increasingly used in recent years for preventing and resolving conflict. The core rules are simple:
- You speak only from your own perspective.
- You listen deeply to whoever is speaking.
- You speak only when it’s your turn.
- Your turn comes when the talking piece is passed to you.
Simple to describe and demanding in the moment. The hardest shift is listening to the person speaking instead of rehearsing what you’ll say next and then waiting until it’s your turn to speak.
I won’t share what was said in any of our circles. But I can tell you that family members voiced perspectives they’d never shared before. People recognized common experiences. Key tensions got named out loud. And nothing was “solved” in a single circle. But people felt heard, and feeling heard matters enormously to a group’s ability to work together and make hard decisions.
To be clear, the goal of this work isn’t better family dynamics for their own sake. It’s also not a replacement for individual or family therapy. It’s helping families and boards function well enough to make decisions rooted in shared values and real community needs. I measure my work less by how much smoother the family feels and more by whether the board can focus on its mission and take on the genuinely hard questions of strategy, sharing power, and shifting philanthropic practice to better center the communities it serves. That work becomes nearly impossible when unspoken grievances and old patterns quietly steer how people show up. Naming those dynamics isn’t a detour from the mission. It’s often the precondition for it.
If you want to try this in your own work, here’s a taste of what circle practice involves.
- Actually sit in a circle. This is the literal and symbolic foundation. A circle puts everyone on equal footing, keeps every face visible, and makes eye contact and connection possible. This can also happen in virtual meeting spaces by asking everyone to have their cameras on and committing to being fully present.
- Set shared agreements together. These are the norms the group establishes for how you’ll engage, listen, and speak. Ground them in shared values, if possible. A few examples: listen without interrupting, speak from your own experience, consider the impact of your words.
- Use a talking piece. Choose a small object with some meaning to the group. It passes from person to person in sequence, and only the person holding it speaks. No one is ever forced to talk – if it’s not your moment, you can pass. This one tool does two jobs at once: it gives everyone equal voice, and it keeps everyone else listening. If you’re virtual you can ask folks to bring their own personal talking piece to hold while speaking, and name whose turn it is explicitly.
- Have a facilitator (sometimes called a “circle keeper”). This person plans the circle, introduces it to participants, explains the ground rules, asks the questions, and keeps time. Just as importantly, they model active listening and hold the group to the shared agreements. If you’re doing repeat circles, you can rotate this role, but when it’s new to your group, an experienced facilitator makes a big difference.
- Hold preconferences. Ideally, the facilitator meets one-on-one with each participant beforehand to understand what they’re hoping to get out of the experience, then designs the questions accordingly.
It looks simple on paper. It’s harder in practice to hold all of these pieces together. As a facilitator, a lot can come up in a circle, and there will not be space to unpack and sift through it all in one sitting. Part of the facilitator’s job is to notice themes and patterns, help participants see them, and name ways to move forward, which is also easier said than done.
Finally, it’s truly challenging for participants to continue to practice deep listening regularly in day-to-day spaces like boardrooms or staff meetings, where we tend to return to old patterns. I highly recommend if you’re going to try this tool, you keep trying it to build the skills. Use the circle practice regularly for lighter conversations: use a circle format to debrief an article you all read together, or for the start of every group meeting just to check in and practice the skill of taking turns, listening deeply and sharing with thought.
If you’re interested in this topic, here are a few possible next steps:
- If you want training, the International Institute for Restorative Practices (IIRP) offers trainings in listening circles.
- If you’d like to hear more about a specific client example, we’ll be speaking at the Council on Michigan Foundations Conference in a session titled Reflection Circles: A Restorative Practice to Build Trust on Tuesday, October 13, 2026.
- If you’re in a role seeing some of the issues named, I’m facilitating a family philanthropy coaching cohort for staff at foundations, or anyone who works closely with families and their philanthropy vehicles. While the focus is really what the group brings, I expect generational shifts and family dynamics to be part of the conversations.
- If you want to talk about how this practice could be used at your organization, I’d love to connect – auptonlopez@ktisiscapital.com
