Facing Difficult Leadership Challenges for Executive Directors
Facing Difficult Leadership Challenges for Executive Directors
Being an executive director can be incredibly rewarding—but it can also be one of the loneliest jobs in an organization. You’re expected to have answers, make difficult decisions, navigate competing priorities, and carry the weight of the mission, often with few places to openly process the challenges that come with the role.
Join us for Facing Difficult Leadership Challenges for Executive Directors, an interactive Ask the Experts webinar created specifically for nonprofit leaders who want a safe space to ask tough questions and learn from peers who have been there. Whether you’re wrestling with board dynamics, staff challenges, burnout, organizational change, fundraising pressures, or simply the isolation that can come with leadership, this conversation is for you. Bring your questions, hear real-world perspectives from experienced nonprofit leaders, and leave with practical insights, fresh encouragement, and the reminder that you don’t have to lead alone.
VIRTUAL | June 17, 2026 | 1PM-2PM EST
Deena Englander helps growing nonprofits and businesses scale effectively by streamlining operations and automating workflows. Passionate about eliminating bottlenecks, Deena partners with organizations to simplify complex processes, enhance collaboration, and deploy scalable tech solutions.
With a background in business process optimization, she bridges the gap between strategic vision and day-to-day execution to deliver measurable efficiency gains and cost savings. Deena believes great systems are built around people, focusing on operational excellence to create environments where teams can drive sustainable growth and stay ahead of the curve.
Connect with Deena: LinkedIn | Website
Tamela Spicer is the founder and principal at The Intentional Catalyst, where she focuses on fostering transformative change rooted in equity. With over 30 years of dedicated service in the philanthropic sector, Tamela utilizes her deep expertise in change management to help organizations build cultures of belonging, justice, and community engagement.
Previously, she served as a Senior Program Manager at the Dorothy A. Johnson Center, honing her skills in strategic program development and culture change to strengthen the philanthropic sector. Her collaborative approach centers on leveraging both lived experience and professional training to inspire authentic dialogue, advance DEI principles, and drive sustainable capacity building.
Connect with Deena: LinkedIn | Website
Jim Irwin is a US Navy Veteran and multi-business owner with extensive experience in strategy and process improvement. He helps organizations across all sectors—including for-profit, non-profit, government, and faith-based—build customized operating systems using continual improvement methodologies like TQM, Lean, and Six Sigma.
Jim specializes in identifying root causes of organizational challenges, aligning leadership teams, and developing practical playbooks for consistent execution. Known for engaging in candid conversations that ignite positive change, his philosophy is simple: lead first, understand the work, map the organization to the process, and continually train and reinforce the team.