THE CONTEXT

H, a senior program manager, was rising through the ranks within a large team at a global health organization. As one of the youngest members of the extended leadership team—and one of very few women—she was looking for an approach to her increasing responsibilities that felt true to herself. She wanted to be more direct and confident while staying empathetic and emotionally attuned—and to avoid the potential pitfalls of stereotypical “masculine” or “feminine” leadership styles.

“I really wanted to show up with authenticity as a manager and as a leader in a way that was unique to me.”
- H, Interim Deputy Director

H was looking for an executive coach who understood the unique dynamics of her organization and could help her build clarity, confidence, and an authentic leadership style that truly reflected her strengths. And Jennifer Olsen was the perfect choice.

CLARIFYING THE VISION

Early in the engagement, Jennifer helped H clarify what success looked like—not just in terms of perception but in how she wanted to feel and operate as a leader. Together, they worked on developing a leadership approach that was both strategic and authentic, ensuring that H could grow as a leader without compromising her values.

“Jennifer really helped me distill how I wanted to grow professionally—what opportunities I wanted to take on, how I wanted to prove myself, and how I wanted to push myself to grow.”

H was soon tapped for an interim Deputy Director role in a different division, managing a new team. It was a significant leap, and the transition was both exciting and daunting. Jennifer helped her navigate the challenges of the role and find success, which led to another interim Deputy Director position soon after.

PERSONALIZING THE PATH

Jennifer tailored her coaching approach to H’s evolving needs, shifting from structured self-awareness tools and practices early on to more fluid, real-time coaching as H took on larger leadership roles. One of the most impactful tools Jennifer introduced was the Integrative Enneagram, which revealed that H wasn’t the “Competitive Achiever” she had assumed she would be—she was actually a Style 4, Intense Creative.

“The Enneagram helped me shift the lens I had on myself. I realized that I don’t think there’s just one way to solve a problem—I value flexibility in strategy.”

This self-awareness helped H embrace her natural inclination toward originality, creativity, and vision. Her atypical problem-solving approach involves brainstorming multiple ways to get things done, and valuing the journey as much as the goal. Jennifer helped her understand how to engage her team early in the process and encourage them to be active participants throughout all stages of a project, rather than simply executing tasks.

Understanding her Enneagram style also influenced how H built and strengthened relationships with her direct reports. Jennifer facilitated a joint session with a new team member, J, to help them understand how they could best leverage their individual Enneagram styles and avoid possible conflicts. As a Style 6 (Loyal Skeptic), J seeks to avoid risk by being careful and doing things a particular way, while H values creativity and exploring multiple ways to create growth and impact. The conversation helped the pair appreciate what each brings to the table and increased their excitement about working together. Jennifer’s caring facilitation helped turn blind spots into points of collaboration and supported growth, elevating an already strong relationship and helping set both H and J up for success in their roles.

“I was blown away by how honest and transparent we were able to be with each other. That was so valuable and revealing.”

CATALYZING GROWTH

H’s coaching journey has led to deep transformation—not just in how she leads, but in how she sees herself. She is more confident in difficult conversations, more strategic in career planning, and more intentional about how she shows up in leadership spaces.

Particularly in her new, more challenging interim Deputy Director role, H has learned to embrace the difficulties as opportunities for growth and learning.

“Jennifer helps me see the opportunities in any career step—even when I’m in a role that may not be the right long-term fit. She has helped me realize that recognizing when something isn’t working is not a failure; it’s actually a sign of maturity and self-knowledge.”

In one particularly tough moment in this new role, H needed to have a difficult conversation with a peer. She came into her coaching session feeling frustrated and unsure of how to approach the situation without escalating tension. Jennifer role played and coached her through a more productive way to frame the conversation, focusing on accountability and shared goals.

“Repeating back what I heard was a game changer! That conversation went so much better than I expected.”

Beyond day-to-day leadership skills, Jennifer also helps H feel confident and supported as she considers her long-term career trajectory.

“I told Jennifer, ‘I think maybe I want to be a CEO someday.’ And she didn’t even hesitate. She just said, ‘Yeah, you could do that.’ That level of belief and support was so powerful.”

Together, they have worked on a plan to help H elevate her leadership further by incorporating a Leadership Circle 360 assessment into their coaching. The assessment findings will help H understand whether her intended leadership impact matches how her team and the broader organization experience her. The findings will inform new development goals for her continued work with Jennifer.

H describes her work with Jennifer as one of the most transformative experiences of her career.

“I’ve grown more in the last two years than I ever thought possible. Jennifer made me feel like what I want for my career is possible—that I already have the skills and raw talent. I just need to refine them. That’s really profound.”