From Transition to Transformation: Leaning in to Support During Periods of Leadership Transition

By: Monisha Kaplila, Founder and Former Co-CEO, ProInspire, and Liz Sak, Executive Director, Cricket Island Foundation

We are in an unprecedented period of leadership transitions happening across the social sector, at the same time that organizations are navigating fundamental shifts shaped by Covid, the racial reckoning, and a fraught political environment. 

Two key patterns have emerged among leadership transitions that require us to build a different support structure for nonprofits and their leaders. First, a number of transitions in recent years have involved a new leader of color coming into the CEO role, often the first for the organization. Second, people aren’t staying in nonprofit CEO positions as long as they did before leading to an increase in transitions. These transitions are healthy and good but require organizations to build a different muscle around navigating transitions and develop organizational structures that support more frequent transitions.  All of this means funders need to think differently about how they support and sustain organizations and intermediaries need to support organizations in developing the muscles and systems needed to weather transitions successfully .

Transitions are an opportunity for organizational transformation, and we need to support them more intentionally. There are three critical ways that funders and nonprofit intermediaries can better support healthy leadership transitions:

TRANSITIONS ARE NORMAL - Normalize talking about transitions

Given power dynamics between funders and nonprofits, many nonprofit leaders are afraid to even bring up the topic of leadership transition or succession planning out of concern that their funders may withdraw or scale back funding. In fact, we have seen this happen with nonprofits in our networks. To address this, funders can create a safe space for  EDs to talk openly about these topics. A simple way to signal this is, during check-ins with grantees, funders can ask about succession planning across the organization (not just focusing on the ED role), or leadership pipeline initiatives, and ask where more capacity may be needed to support overall organizational capacity. Funders who want to build strong relationships with grantees should demonstrate that they are trustworthy on these capacity needs before expecting that a nonprofit leader will cross the power divide to broach the subject of their departure. (148)

Intermediaries can support nonprofits by highlighting emerging practices in leadership and shifting the narrative around transitions. Transitions are an important element of organizational transformation, and intermediaries can normalize talking about them as part of building strong operational infrastructure, engaging boards, and supporting staff and organizational culture. Building in conversations about leadership transition planning will strengthen an organization and ready it for the inevitable

FOCUS ON VALUES ALIGNMENT - Support organizations with building values alignment

The work needed for an organization to be ready for a healthy leadership transition happens long before an Executive Director announces their departure. It can take an organization 3-5 years to build values alignment internally to be ready for a leadership transition, particularly around racial equity and justice. This includes building a board that reflects the values and constituency of the organization and considering different leadership structures such as co-leadership. This is not fast work or work that can be shortcutted when a leader decides to depart.

Waiting until a transition is announced to consider support, which is the current norm in philanthropy, is too late. Funders can support these practices by asking questions about how Boards hold and reflect their organization’s values and can direct funding to increase staff and board capacity in these areas before a leadership transition is even on the table. Then, when a transition is considered, organizations already have the capacity to manage it without significant disruption. Funders can also support nonprofits to build strong leadership pipelines, like supporting the creation of new positions (such as Deputy Director) or opening up time and capacity in the organization to explore non-traditional leadership models (such as co-leadership). We can also more intentionally engage with organizational leadership beyond the ED.  Trust-based philanthropy lends a lot of lessons here around how general operating support and unrestricted funding helps support organizational capacity for adaptation.

This support can look like coaching, facilitation, and training for board, staff, and leadership around racial equity, so that the organization is preparing a culture that would be supportive to a future BIPOC Executive Director. The Building Movement Project’s report, Trading Glass Ceilings for Glass Cliffs highlights that “the proverbial glass cliff is an all-too-common reality for leaders of color in the nonprofit sector. Ascending to an executive position does not end a leader’s struggles with racism, and sometimes increases those challenges.”

Equipping organizations for change - all kinds of change - will make them more sustainable. Intermediaries can use their role of influence to focus on values alignment when they are engaging with organizations. For instance, during a board retreat, addressing alignment with the organization's values on equity and justice is crucial. Given the size of many nonprofits, building an internal leadership pipeline or training the board may not always be feasible for a single organization. So, intermediaries can contribute significantly by offering cohorts and fellowship programs to support leadership development.

TRANSITIONS ARE A MULTI-YEAR PROCESS - Provide multi-year general operating support and targeted support

It is clear that one of the most important roles funders can play to support healthy transitions is ensuring organizations are well-resourced. We can think about leadership transitions in terms of before, during, and after. According to Brilliant Transformation: Toward Full Flourishing in BIPOC Leadership Transitions, “the best way to support an organization making a transition to a BIPOC leader is to grant substantial, multi-year general operating funds. These funds should be easily accessible and not be conditioned upon additional requirements.”

In Cricket Island’s grantmaking program in support of leadership transitions, we give flexible support for a minimum of three years to support leadership transitions. These resources can help the outgoing ED build organizational capacity and strengthen culture before a transition, and provide resource stability for the incoming ED. Besides general operating support, funders should provide targeted support around leadership transition planning, board development, executive search and hiring, DEIAJ work, professional and personal development of the incoming director, and relationship work among staff through the transition. Decisions on how to utilize capacity building funds should be  left up to organizations rather than decided by funders who are many steps removed.

And, there is an important role for intermediaries to play here, too. Intermediaries can partner with nonprofits in planning out multi-year transition processes, including supporting CEOs, working with leadership teams and engaging with boards well in advance of transitions. Organizational sustainability matters all the time, not just when a leader is contemplating leaving. People leave, people change jobs. It’s normal, and expected, and there is no indication that the pace of leadership transitions will slow in the coming years. 

TRANSITIONS CAN BE TRANSFORMATIONAL

Transitions can be healthy, active phases in an organization’s lifecycle, but this requires that organizations develop the structures, cultures, strategies that support the nonprofit and its staff when leadership shifts. All of this means that funders and intermediaries need to think differently, and partner more closely, to shift how they support and sustain organizations to build moments of transition into opportunities for organizational transformation.

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