The Career Path of a Nonprofit Leader

Through my work at Leading From Within over the years, I’ve had the good fortune to know many nonprofit leaders. They’re a special group of people that are uniquely called to make the world better than they found it. Many of them sacrifice a great deal in their commitment to help others.

Where do these people come from? How did they get where they are? Most are driven by some sense of vocation, service, and justice. But to be a successful nonprofit director, you also need many leadership and management capabilities. Until recently, there were few if any formal nonprofit management development programs or peer support networks. So many nonprofit leaders whom I’ve met are basically self-taught.

This lack of systematic investment in nonprofit leaders is counterproductive. The fact that the nonprofit sector doesn’t have more clear pathways to develop one’s leadership is one of its biggest failings. If you know a nonprofit Executive Director who seems to have it all together, they are the exception rather than the rule.

I’ve been thinking about this after reading a memoir entitled My Wild and Precious Life, written by one of our region’s most storied nonprofit leaders, Cynder Sinclair. Since arriving in Santa Barbara in the mid-‘90s, Cynder has served as E.D. of the Girl Scouts, Santa Barbara Neighborhood Clinics, and Community Action of Ventura County. She also has a Doctorate in Organizational Leadership.

But how did a young housewife and mother of five in the Central Valley become the self-assured, highly competent, super-educated organizational leader whom we know today as Cynder Sinclair? She begins her memoir by recounting the story of how she first dove deeply into community service, in the 1970s, in the agricultural town of Kingsburg near Fresno.

Responding to the Call

In her children’s classrooms, Cynder came face-to-face with children who did not have the most basic of needs such as food and clothing. Because Cynder spoke Spanish, her kids’ teachers asked her to help with the Spanish-speaking students, who were mostly the children of local farmworkers. Cynder had studied Spanish in school and had spent three months in Mexico as part of an exchange program. Her ability to communicate with these children placed her in close contact with people whose lives were very different from her own.

Cynder has a characteristic I see in many nonprofit leaders I know – an inherent drive to be of service. For many people, poverty and inequity is just the way things are. But there are some who encounter inequitable conditions and can’t help but respond to the need. As a volunteer, Cynder founded and built what became an award-winning social service effort in the Central Valley that involved a food bank, a thrift store, health care, preschool, and other elements.

Driven by this calling to serve, Cynder learned so much – about volunteer-management, real estate, warehousing and distribution, sales, public relations, cultural differences, and more. In spite of her steep learning curve, she was developing practical skills, and her confidence as a leader grew. This community effort also gave her a great amount of personal satisfaction.

Fast forward to the beginning of the ‘90s. After a divorce, Cynder needed to earn an income. Though she had never even written a resumé before, she had plenty of experience as a leader in community service work that she could market in applying for Executive Director jobs. And lo and behold!, she got herself hired as E.D. of the Child Abuse Prevention Council in Stockton. In her five years at CAPC, Cynder got exposed to more formalized approaches to management and organizational leadership skills.

Cynder moved to the Central Coast in 1995, when she was hired to run the tri-counties Girl Scouts organization. It was in the Girl Scouts organization that she began to learn about the idea of intentional leadership, and she started getting exposed to leadership thought-leaders such as Jim Collins, Stephen Covey, Frances Hesselbein, and Peter Drucker. In the Girl Scouts system, all regional CEOs were expected to actively participate in leadership development opportunities and to show the national organization that they were intentionally practicing what they learned.

One of the benefits of being a leader in a well-supported national organization – one that systemically provides professional development opportunities such as the Girl Scouts or the YMCA – is that you are invested in as a leader. Sadly, for leaders in many local, community-based nonprofits, there is often little expectation for professional development nor is there a systemic approach to investing in people.

Toward the end of Cynder’s Girl Scouts career (and during her two years at Santa Barbara Bank & Trust in the private sector), she pursued a master’s degree and then a Doctorate in Organizational Leadership. She had clearly caught the leadership bug! Cynder dug deeply into a wide range of theories on leadership, and she learned to recognize different modalities of leadership and to choose and mold her own personal approach. 

Armed with a clear understanding of leadership in general and her leadership style in particular, Cynder took on two more ED/CEO positions in our region: one at the Santa Barbara Neighborhood Clinics and another at Community Action of Ventura County. In those roles, Cynder used her understanding of leadership to mentor her staff members so they could grow and develop themselves, personally and professionally.

Not surprisingly, Cynder now serves as a nonprofit coach and consultant helping other leaders and organizations be their best selves. She ends her book with a series of ten principles she’s distilled from her powerful journey of service and self-actualization. 

I have so much respect for the committed nonprofit leaders I know such as Cynder Sinclair. Most of them have had to figure out so much on their own. I’d love to see a time when the nonprofit sector – including all funders and nonprofit board members – expect nonprofit organizations to systematically invest in all of their people. And to demonstrate this by budgeting for and funding it! That’s when we will see this sector really grow its potential to serve and lead in our communities.