She Thought She Was Stuck Because She Was Overwhelmed
Jennifer Leone, CPA — Nonprofit Executive
Executive CoachingSUMMARY
Jennifer, a C-level nonprofit executive, came to coaching feeling stuck and weighed down by absorbing responsibilities beyond her core role. Through coaching on personal, relational, and structural levels, Jennifer learned to manage her reactivity, navigate her dynamic with a challenging CEO, and advocate for herself and additional headcount. Within months, she transitioned from avoidance to 'clarity conversations' and traded a reflexive 'yes' for 'not yet,' successfully delegating work and helping the leadership team build a more durable structure.
Jennifer, a C-level nonprofit executive, came to coaching describing something a lot of senior operating leaders describe: she felt stuck. Not in crisis, just weighed down — obligated in a way that left no room to step back, and unsure whether the spark she used to feel about her work was still there to find.
On the surface, this looked like a personal capacity issue. Underneath it was something more specific.
Jennifer’s senior operating role at a mission-driven organization had her working closely with a CEO whose moods and pressures shaped the tone of many interactions. As we worked together, two patterns became clear: her CEO was a Visionary, thinking in big-picture terms and increasingly preoccupied with legacy as their long tenure moved toward a close. Jennifer was the Architect — the person who translated the CEO’s vision into structure while taking on more and more operating responsibilities. Jennifer had quietly become the place where everyone’s anxiety landed.
The second issue was an organizational design issue: As a senior operator, she was saying yes to absorbing work that was not hers. Her responsibilities had expanded from finance to include operations and HR, As she stated, “I feel like I’m always wearing a ‘lead vest’, given the amount of responsibility she carried..
The coaching work we did involved three levels. Personally, Jennifer learned to slow her own reactivity — pausing before responding, and asking whether saying "yes" actually served her, both in the ‘now’ or later on. Relationally, naming the Visionary/Architect dynamic helped her understand the friction she felt. She began bringing real precision to their conversations: what does success actually look like, what are we measuring, what's genuinely urgent versus what only feels that way? Structurally, she began voicing the need for additional headcount and began to feel she could delegate work rather than absorb it.
Over several months, Jennifer moved from avoidance to what she came to call "clarity conversations" — direct, specific, and focused on the business outcome rather than the emotional temperature in the room. She traded a reflexive “yes” for "not yet." She got more comfortable letting a 10-out-of-10 reaction cool to a 7 before acting on it.
In my work with organizations, when one senior leader quietly absorbs an organization's unresolved anxiety, it's rarely confined to them. It's a signal about how the whole leadership team is built to handle pressure — and it tends to show up again with the next person in that seat if the underlying design never changes.
That's the real opportunity in moments like this. The coaching conversation helps the individual regain their footing. But the more durable fix is at the team and structural level: naming how your leaders are actually wired to operate, building real clarity around decision rights and escalation, and making sure no single person is serving as the organization's shock absorber by default.
The people who feel stuck aren't usually the problem. They're often the ones most attuned to a structure that needs attention.
TESTIMONIAL
“Before coaching, I felt completely stuck and weighed down by the amount of responsibility I carried, feeling as if I was always wearing a 'lead vest'. Through our work together, I learned to slow my reactivity and move from avoidance to direct, outcome-focused 'clarity conversations'. I traded a reflexive 'yes' for 'not yet,' which helped me regain my footing, begin delegating effectively, and advocate for the structural support and headcount our leadership team needed."
— Jennifer
