Chaotic Leader/Follower Dynamics

Oakwood Arts Inc. is just two years old. Though its work and positive impact on the community are significant, it’s clear that its leadership structure has much room for improvement.

From my very first week in the position of Grants-Writing Intern, it was clear to me that, leadership-wise, this nonprofit was in absolute chaos. The Founder and Executive Director of Oakwood Arts, Shannon Castleman, has extremely high expectations of her team, that can border on unrealistic. Shannon doesn’t like being posed with questions that you can “google” or search the drive for answers to, which can make her seem really unapproachable to her employees when they are struggling with a project. I, myself have often been afraid to approach her before exhausting every Oakwood Arts document for a potential answer to my question. Shannon also tends to give vague instructions, expecting her team to follow her unspoken train of thought. This can become frustrating for both her and her followers when things don’t get done in a timely fashion.

Part of the problem is how leadership is framed in this office. While team roles vary from volunteers, to interns, to managers, all the way up to our Executive Director, the departments seem to work interchangeably, with the only requirement being that everything go through Shannon at the end. This can put a huge hold on most of our work, given that we can’t move forward until everything funnels through her.

In spite of this challenge to Shannon’s strength as a leader, her strategic leadership keeps the nonprofit afloat. She has developed a strong team and works to address each of their strengths and weaknesses in how she assigns work to them. In my second week in this position, Shannon pulled me aside to explain how she leads the group. She talked about how some of her team leaders were completely self-motivated, but also unwilling to ask for help, which slowed down their progress on most things. Other team members were naturally brilliant and perfectly suited for the work they were doing, but simultaneously lacked intrinsic motivation to get stuff done. Shannon aims to more clearly structure the work for those individuals so that they are meeting clear deadlines and making necessary progress. Knowing my interest in a career in non-profit and my talent for organizing people and tasks, she has also worked with me to make sure I am getting the most out of this internship while she is benefiting from my strengths in supporting the organization.

As a leader, Shannon focuses on strengths and works around the challenges of her team members. She can be direct which is often intimidating, as well as stubborn. But she is not so stubborn as to ignore good advice from her team members. Everyone in the organization has an influential voice, so long as they can persuade Shannon to agree with them.

The work environment may be chaotic because she has that kind of presence, but those bothered by the chaos left. Those of us still here are here because we believe in the organization that Shannon has created, as well as its mission, vision, and values. I have no doubt that stronger leadership will emerge with time as she finds more team members she can delegate work to, so that not every project or posting has to go through her like an organizational funnel. But that change requires her to trust her followers the same way that we trust her.

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