Preparing for Bold Leadership

watercolor pine trees

As I look back at the past few years, it’s clear that the challenges we faced as a society and as a sector have been unrelenting. It’s also been a time of great promise. Many families have shifted their philanthropic practices to respond to urgent and entrenched problems. They have taken bigger risks, leaned into trust, listened to communities, and committed to racial justice. And yet, in 2023, some of the momentum and resolve in our field started to stall or, even worse, slip away in the face of social, economic, and political pressures. To continue the pursuit of effective family philanthropy, we need our leaders to fearlessly lean into their values and make the choices that will define the course of our future.  

Last fall, the National Center for Family Philanthropy gathered more than 100 family foundation CEOs and trustees at our inaugural Leadership Retreat in Park City, Utah. Our aim was to reflect on what it means to truly lead our organizations and our sector, and to reimagine how we might lead in ways that will achieve new possibilities. As I’ve been thinking about what lies ahead in the new year, I’ve found myself returning to the conversations and lessons of our retreat. The message is clear: to make progress on issues that are critical to supporting more equitable and resilient communities, family philanthropy must go beyond tinkering at the edges of change. Specifically, to prepare to make the necessary bold choices, leaders must reflect on the seasons of their leadership, reimagine the role of family philanthropy in making change, and redefine risk and progress.  

Using a seasonality framework to reflect and learn

For philanthropy to be effective, we must honor a commitment to learning, renewal, and assessment. It is in fact, one of the essential principles of the work. Core to this commitment is assessing the seasons of our movements and cycles of leadership. Retreat speaker Carlos Saavedra, founder of the Ayni Institute, developed the seasonality framework to help leaders protect and understand the natural ebbs and flows of their time in this work. 

“Every season has an incredible power and an incredible purpose and because of that we need to understand and protect our seasons,” Saavedra shared. Seasons like spring and summer tend to be more externally focused and where the work seems to be moving and making the most progress, while fall and winter are more internally focused and may seem dormant to those outside of the organization. He argues that it’s crucial for funders to consider how these seasons impact the organizations they fund, noting that it’s most common for funders to support organizations when they are in their summers: “Summer is too late,” Saavedra said. “The real investment is to invest in the winter, because that’s the time when you can influence the most and you can generate the most resilience and health.” 

As we enter the new year, it’s vital to explore what season we are in as leaders, organizations, and movements. Are we in a summer season of growth or a quiet, restorative winter? Are our actions aligned with our season? What would we need to do to better align? What do we need to move forward into the next season? How should we use the framework as a lens to view funding priorities and partnerships?  

Reimagining the role of family philanthropy

Throughout the retreat, speakers echoed a call for philanthropy leaders to interrogate what aspects of our role have not been truly in service to our missions and what new—if uncomfortable—roles and practices might better advance our work. Namely, we must ask: what do we bring that other players don’t and what are others better positioned to do?

“The best thing we can do, as donors and funders, is move the most money with the least amount of friction,” said plenary speaker Dr. Carmen Rojas, president and CEO of the Marguerite Casey Foundation. “We should be clear in our commitments and not confuse charity for stewardship.”

Fellow speaker Jamie Allison, executive director of the Walter and Elise Haas Fund, shared three aspirational shifts for funders as they reimagine their roles: move from silos to integration, from contribution to commitment, and from symptoms to systems solutions. “Govern toward exploration, discovery, and learning; and toward trust with your partners and communities,” Allison said. “When you think about governance that way, our board meetings are less about transactions and more about relationships and learning.” 

Redefining risk and progress

Risk is everywhere, but it’s important to contextualize that risk. Philanthropy can absorb more risk than most, and it should. “Funders who are committed to racial justice should understand that there is a difference between reputational risk and material risk when it comes to possible lawsuits or political exposure,” said Rojas. She argued that philanthropy is well positioned to weather the storm of litigation and public scrutiny and that it is often our duty to do so to ensure that grantees and community members are able to continue their work.  

As leaders contextualize and redefine their understandings of risk, it is also crucial to build up a tolerance for and resilience in the face of perceived loss. Plenary speaker Stacey Abrams, former minority leader of the Georgia House of Representatives and chair of race and Black politics at Howard University, spoke about the need for leaders to not only build resilience and a capacity to accept that loss is part of progress, but to reshape what progress looks like altogether. “Philanthropy has the capacity to withstand the attacks that come, but rather than face the possibility of attack there’s a retrenchment happening,” Abrams said. “Well, if you are willing to leave before the fight, they’ve already won.” 

Ready for bold choices

For too long, the field of philanthropy has been tethered to fear, which continues to perpetuate inequity and injustice. We have the power to break out of this mold and carve a new path. Aside from some compliance restrictions, philanthropy has few rules—what we’ve been beholden to for so long are just norms. As Abrams shared, “Philanthropy is about looking over the horizon.” We must envision a different future and work actively toward it.  

“Anything becomes normal over time,” said speaker Jason Franklin, Ph.D., founder and principal of Ktisis Capital. “Can we as funders hold our impatience for change and our resolution to keep working when change doesn’t happen. That’s what’s required to take on any complex issue.” As we reflect on the seasons of our leadership, reimagine our role in making change, and redefine risk and progress, he challenged us to ask: Can we gain a deep understanding with constant learning to make sure we are keeping up with the issues at hand? Can we fund with impatience and steadfastness? Can we use our voice and networks? Can we focus on the issues that we are best positioned to work on, and let go of those that don’t resonate?  

As we resolve to continue our work, it is equally important to consider and reflect on the ideas, practices, approaches, and norms we will leave behind as it is to keep sight of what we will embrace.  

Nick Tedesco is the president and CEO of the National Center for Family Philanthropy