Executive Directors: How to make the move to leading a larger organization

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This isn’t your first rodeo - you’ve worked as an executive director or a CEO of a small nonprofit and you’re thinking about making a move to a larger organization.

Perhaps you’re leaving the first organization because somehow it isn’t a fit for you, or maybe you’re looking for a new challenge.

The question is: how can you bring your experience to a larger organization and succeed?

Difference between first and subsequent roles as ED

Lianne Picot, leadership coach and past ED of multiple organizations, advises first-time EDs to “look for a small organization with a cause close to your heart.” But while Picot would argue that it’s always important to care about the cause, she adds, “Where a first-time ED doesn’t have organizational leadership experience and instead needs to rely on passion, knowledge and past experience, an experienced ED focuses more on leading the people within the organization. In actual fact, once you’ve been an ED, it is a transferrable skill and there’s a formula to the work that allows you to champion different causes.”

In his first role as an ED, Colin Tessier, now ED of Threshold Housing Society, says, “I think I was naïve and believed my passion and visionary leadership could will success. I am passionate in my current role but my eyes are open more. I’m using different tactics in a more measured way, doing things differently based on my experience.”

Daven Seebarran who is currently serving as the ED for two organizations, says, “Passion is great but it can only get you so far. An ED needs technical know-how in their work and that can be applied anywhere.” While Seebarran says that both of the organizations with which he’s working are doing great work, “What excites me is the opportunity to make substantive change through appropriate policies and program development, helping an organization move to the next step on its journey.”

Janet Lymer, now ED of the Calgary Catholic Education Foundation learned about this in her second ED role, which was serving a community of which she wasn’t a member. “I had no experience in the community other than as an ally but I had transferrable skills from a previous ED position that had taught me a lot about the entire landscape and the skills needed.”

But for some second-time EDs, a new role is an opportunity to find a better fit. CM, a nonprofit leader, says, “Since leaving my first ED role, I’ve been very intentional in choosing community- based, social service agencies whose mission is to provide settlement services for vulnerable populations and I hope, are aligned to my core principles of equity and justice for community members.”

Difference between sizes of organizations

“The size of an organization’s budget does not denote complexity,” says Tessier who has worked at both small and mid-sized nonprofits.

While many EDs of smaller organizations may be nervous about scaling up their work in moving to a larger organization, both Tessier and Seebarran reassure such people that a larger budget almost always brings with it more support infrastructure. Seebarran says, “As long as you have technical skills and solid structures and thought processes, budgets are a state of mind.”

This means that an ED who is aware of his or her own strengths and weaknesses has the opportunity to build in support. Seebarran says, “When I went to a larger organization, the only element that scared me was managing a bigger budget. I knew that nothing could ruin an ED’s career like financial mismanagement.” For Seebarran, “This fear forced me to create systems that eliminated those fears. It was easily remedied by hiring a good bookkeeper.” He adds, “Other EDs may have different strengths and areas that need support. Know yourself and think through what kind of support you need to succeed.”

Self-awareness around leadership style can also direct a second-time ED in terms of knowing what size of organization to work with. Tessier says, “If you’re the type of leader who wants to be involved in everything and have a high degree of control, a smaller organization is better for you. The same type of leader could suffocate a larger team. It doesn’t mean that there’s a better and worse style of leadership, but it’s a question of knowing yourself and finding a fit.” Tessier adds, “The larger the organization, the more an ED’s leadership happens at a macro and strategic level, while doing more through others.”

At the same time, Tessier cautions EDs that even medium-sized organizations often have volunteer boards and other similarities to smaller organizations. He also observes that many key ED tasks — such as implementing a strategic plan, reviewing an annual operational plan and developing key performance indicators — are part of the work of all executive directors regardless of the size of their organization.

Lessons learned

One of the keys to executive director success, says Seebarran, is to learn from your experience. “I believe that mistakes are an inevitable part of our work. What’s most important is the ability to constantly learn from those mistakes, as well as from our successes, and to become aware in a way that means we never repeat those mistakes again.”

For Seebarran, one key lesson has been around burnout. Taking on his first ED role in his mid-20s, Seebarran says, “I did what I thought it took to be successful as an ED. Because the role was so isolating, I felt I had to move the organization forward at any expense to myself. After 60-hour work weeks and no work-life balance, I challenged myself: why did I do that?” Now in new ED roles, Seebarran says, “I am more aware of my tendencies and have intentionally instituted practices that will divert burnout. I’m aware of signs and have implemented strategies that are helping with burnout, such as simply moving my email icon to the back page of my phone, and taking my vacation time.”

Of lessons learned from his first ED position, Tessier says, “I felt ready for an ED role, and I think I put on blinders when I took my first ED job because I wanted that so badly.” Although the work was successful and became even more so during his tenure, there was a divergence of vision and values between Tessier and the board of directors. Tessier stepped away from being an ED for a short time, serving as a director of programs for another nonprofit. By the time Tessier applied for the ED role of his current organization, he had reflected about what was most important to him in the fit with a new organization. “You can’t know all the challenges of an organization before you get in there, but my advice is to dig deep in the areas that matter most to you, and to learn from your previous experiences.”

Letting go of previous work

Whether your previous experience as ED was stellar or terrible, it’s very easy for it to be normative, the standard against which you measure your new role. To some extent this is healthy. Seebarran says, “I don’t think you let go of your previous organization because it’s likely one you’re still passionate about. The question is how you embrace the experience and incorporate that into the next step in your journey.”

Richard Kies, ED, Kinsmen Telemiracle Foundation says, “I really believe in the philosophy that you should never burn a bridge. You never know when someone might help you or vice versa.” Similarly, Seebarran says, “There are intersections everywhere within the sector and lots of points of interconnection. You often carry bits of work from one organization to the next, and often work with a similar sort of clientele. You can also turn to past experience and programs for ideas with programming in a new organization.”

Still, Picot advises EDs to find ways to process their past experiences and to leave responsibility for that organization behind. “It is the end of a relationship regardless of how it ends. Like any relationship that ends, we have to do the work of taking responsibility for things we did, and assigning some responsibility to other party, and then move into the next relationship with a clear fresh perspective and approach.”

When thinking about how to bring your experience to new organization, Seebarran encourages leaders to trust in themselves and their abilities. “The principles of being visionary and innovative, resilient and knowledgeable, moving forward in spite of barriers you might encounter – these are the same regardless of the size of organization.” He adds, “Being an executive director is a great job and we can forget how fun it can be.”

Susan Fish is a writer/editor at Storywell, a company that helps individuals and organizations tell their story well. She has written for the nonprofit sector for more than two decades and loves a good story.

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