Navigating the Nonprofit Leadership Journey Lessons Learned and Shared
Leadership Published Date, 2023

Navigating The Nonprofit Leadership Journey: Lessons Learned And Shared

Created By: Craig Shelley, CFRE
October 25, 2023

In the world of nonprofits, where the pursuit of a better world meets the complexities of reality, leadership emerges as the guiding star. With every step, leaders must navigate the treacherous terrain of change, inspiring transformation in the most challenging environments. As someone who has spent decades in this arena, I’ve come to realize that our journey as leaders is shaped by invaluable lessons, two of which stand out as foundational to my growth.

The nonprofit sector is a unique ecosystem, driven by a deep commitment to social causes but riddled with the thorns of financial constraints, bureaucracy, and unyielding challenges. Here, leadership isn’t just a role; it’s a responsibility that has the potential to impact the lives of countless individuals and communities. In this context, the significance of leadership lessons becomes abundantly clear.

At Orr Group we devote much of our time to leaders seeking to drive complex change in some of the most difficult environments. Recently, a friend preparing a leadership presentation for an upcoming conference prompted me to revisit the invaluable lessons that have shaped my leadership approach over nearly three decades, especially two lessons I often take for granted but owe to the leaders described below.

Leadership Lesson 1: Leaders are agents of change.

Leaders are always leading, but sometimes setting the example isn’t enough. Leaders have a responsibility to change behavior if it needs to be changed.

Throughout my formative years, I worked at a Boy Scout summer camp in Upstate New York. It was among the most defining experiences of my life, teaching me invaluable life lessons such as the power of a strong work ethic, the importance of friendship, and most notably, my first tangible understanding of leadership. While I understood that leaders set examples, there was a pivotal moment that revealed that leadership goes beyond mere demonstration. Sometimes you must make the effort to change people’s behavior.

My last summer working at camp, a group of us mid-tier managers got into a bit of mischief – the kind that wasn’t exactly criminal, but certainly, something we shouldn’t have been doing. We faced a stern reprimand, with me taking a larger share of the blame due to my perceived role as a ringleader. Annoyed but also awakened, I pledged to tread a different path.

However, when my friends returned to their old ways several nights later, I politely declined. They proceeded and, unsurprisingly, found themselves in trouble once more. I assumed I was in the clear, after all, I had behaved appropriately and set a good example. But then, the camp director summoned me to his office.

I protested, explaining that I wasn’t even there during their escapades. Yet, he looked me in the eyes and dropped a hard truth that still resonates with me to this day:

“Whether you want to own it or not, you’re a leader. People respond to you and for you. If you’d insisted they stop, if you’d insisted there was a better way to spend the evening, if you’d been a leader, none of this would have happened. You may not have been there, but this is on you. I expected you to change their behavior, not just yours. Leaders lead.”

I was shaken but also immediately knew what he meant. You don’t always volunteer to be a leader, but once you are one, you’re stuck with it, and you have a responsibility to wield that responsibility actively.

Leadership Lesson 2: Lead for the job you want.

Following my time as a camp counselor I moved indoors and through several twists of fate ended up with a full-time job at the Boy Scouts. It was here that I learned another pivotal lesson about leadership – leading for the job you want.

Initially charged with starting Cub Scout Packs in the South Bronx, I grew through several programmatic and organizing positions before venturing into fundraising. Early in that journey, my boss recognized my potential and continually entrusted me with tasks that extended far beyond my job description – an opportunity to project manage a new marketing effort, help staff a small fundraising event, and prepare for and attend a board meeting. While I always enjoyed and appreciated the tasks given to me, I also became frustrated that I was being asked to do more than my peers or more than I was being “paid” to do.

Eventually, I spoke up, arguing that these tasks weren’t in my realm of responsibility and more importantly, weren’t being reflected in my paychecks. It was at this moment that, just like my camp director, my current boss looked at me and shared a lesson that continues to resonate today:

“Lots of people can do what you can do, but not everyone understands why we do these things or has the ability to see the big picture. I’m giving you an opportunity to do more because you can handle it. If you want to wait until you officially get the job, you’re going to be waiting a long time. You have an opportunity here, and it’s up to you to seize it. If you don’t want to take it, then that is on you.”

I very much received this lesson and advice as a variation of the “dress for the job you want” maxim.  The most effective way to prove your value and readiness for greater responsibility is to do it. Understand the needs and challenges of the next level of leadership within your organization and act accordingly. Not in a sycophantic sort of way, but in a way that allows you to learn while proving you see the world and the needs of the organization like a leader.

In essence, lead for the job you want. Every level of organizational leadership is lonely in its own way.  Demonstrating that you not only understand your boss’s challenges but can also help alleviate them is the surest route to assuming greater responsibility, making a substantial impact, and receiving due recognition.

As I continue to learn from the remarkable leaders I collaborate with daily, it’s critical to acknowledge and credit the two leaders from my early career who imparted these invaluable lessons and so much more. Collectively, these experiences have molded me into the leader I am today, and the journey of evolution continues.

Great leaders are essential to every organization’s success. Orr Group can supply you with the leadership support you need to help you maintain stability and continuity. Get in touch to learn more.

Craig Shelley, CFRE is a Partner and Chief Growth Officer at Orr Group. Craig advances the missions of nonprofits by bringing a change-management and entrepreneurial approach to strategy, organizational development, fundraising, and board optimization.

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