Navigating the Unique Challenges and Opportunities of Being a New Executive Director

SIF’s ElevatED Cohort offers support and fellowship for new-to-their role nonprofit executives

Our team noticed that many organizations in the Alumni & Nonprofit Network were in the process of transitioning between Executive Directors. We know that bringing in a new Executive Director can represent opportunities and challenges for both the organization and the new Executive Director. In May of 2023, the Alumni & Nonprofit Network brought together a group of new executive directors to see how SIF could support them and their organizations. The EDs spoke about the possibility of a peer cohort and more opportunities to connect with others in similar roles.

The Alumni & Nonprofit Network partnered with Erin Cox, a leadership, impact, and personal development coach, to form a cohort of Executive Directors in the first three years of their tenure. The cohort would enhance their leadership capacity by finding community among themselves, learning new skills, and speaking to longer-tenured EDs.

Between April and June, the nine members of the ElevatED cohort gathered five times at the SIF office from all over Eastern Massachusetts. Together, they built a community to share meals, questions, difficulties, and successes. ElevatED’s first session began with one question: What is one item that represents your leadership journey? 

Each cohort member brought an object and a story, explaining the moments of strength and challenge that brought them to their roles. The session continued with other team- and community-building exercises to help the cohort feel more comfortable around each other. 

The remaining sessions centered on networking, fundraising, board development, staff- and team-building, development, individual and organizational priorities, and time- and self-management. Each session began by setting intentions and going over some wins from between the meetings. We brought in guest speakers—other EDs and leaders who had pertinent experience—to share their stories and help the cohort members understand the approaches and perspectives of longer-tenured EDs.  

We asked Abdi Ali, the Executive Director of WriteBoston, a 2006 Alumni of SIF’s Social Innovator Accelerator, a bit about his experience participating in the ElevatED Cohort:

Zane Diamond: What was your experience starting as WriteBoston’s ED like?

Abdi Ali: I felt really supported and welcomed by both the staff and the Board in April 2023. There were lots of opportunities to learn and ask questions through a very clear, supportive onboarding process and tools (which I have shared with others). There were also expectations to get our org moving in the same direction in a compelling way and implement agreements - and I intentionally chose to build on what the staff and Board had set up for me. It was a beautiful, multidimensional stage and I did not want to introduce anything new except to go deeper, build repertoires for our values, enact our norms, and embody our mission.

ZD: What drew you to the ElevatED Cohort? 

AA: I had sourced a number of professional development [opportunities]—I had set an individual goal to understand my leadership identity—that first prompt about leadership journeys confirmed for me that I was in the right PD. I wanted to make time to pause and be pushed to think of questions and not just my to-do list

ZD: What do you feel was the most valuable part of the cohort?

AA: For me, the pre-work and the rotating panel of EDs were the most valuable parts; I had to think about my questions and reflect and write questions that pushed me out of the day-to-day run of things. The panelists shared wisdom, and approaches to address contingent issues—I listened to how they were responding to these issues, building buy-in and credibility.

ZD: Is there anything you learned during the cohort that has changed the way you look at your role? 

AA: The most significant was I began to think deeply about achieving operational clarity and pausing on the inertia for strategic planning to assess if we have the right people in the right positions to better position us for strategic planning.

ZD: We heard feedback from many of the participants that connecting with other EDs was a highlight of the experience. What did you take away from those connections? 

AA: Affirmation of purpose, diversity of leadership sensibilities and styles—and that I am the right fit for [WriteBoston].

Although the cohort formally ended, the members continue to meet every few months to foster community and shared learning. By the end of the program, all cohort members reported having access to a more extensive network of fellow nonprofit leaders, including the guest speakers, all of whom asked to share their contact information with the cohort. The opportunity to come together, share openly, and learn from each other and other executive directors has enhanced their confidence in their roles and has built a robust community.

One of SIF’s Alumni & Nonprofit Network’s main goals is to create the feeling of connection and belonging Abdi experienced during the ElevatED Cohort by providing a platform for peer-to-peer support, relationships, and growth. We recognize that nonprofit professionals encounter unique challenges, and our most valuable resource is often one another. We look forward to continuing to provide a space for peer-to-peer connections and learning in upcoming cohorts, workshops, and round table conversations.  


About the Alumni & Nonprofit Network: 

After participating in the Social Innovator Accelerator, being selected as a Finalist but not an Innovator, participating in a Capacity Camp, or coworking with SIF, nonprofit organizations have the opportunity to join SIF’s Alumni & Nonprofit Network. The Alumni & Nonprofit Network supports organizations with topical workshops, cohort learning, and pro-bono services to support the next stages of their development.

About the Author:

Zane Diamond is the Program Coordinator for the Alumni & Nonprofit Network. Ze has a background in LGBTQ+, Jewish, and interfaith community organizing and loves helping members of the SIF community access capacity-building resources and the network of other nonprofit professionals SIF has built over the last 21 years.