Case Study: Coaching Lora Through Career Transition
This career transition leadership coaching case explores how a CEO learns to adapt to a new organisational culture without losing her leadership identity.
Lora sat across from me, her posture composed, but her fingers tapped lightly against the side of her notebook. There was controlled tension in the way she held herself, as if she were containing something beneath the surface. As she exhaled, she admitted, “I know I should be excited about this transition, but I just feel… unanchored. I don’t fully understand how things work here, and that’s making me second-guess myself.”
She had arrived at this session carrying the weight of two professional worlds – the one she had left behind and the one she had yet to fully step into. Having spent years climbing the ranks from an entry-level position to CEO, she had built herself within a company that shaped her leadership instincts, her style of communication, and her expectations of workplace dynamics. Now, she found herself in a vastly different organization, one that functioned with a level of autonomy and fluidity that contrasted sharply with the tightly controlled, high-pressure environment she had known. Instead of feeling liberated, she felt lost.
“I call my boss just to check in, to make sure we’re on the same page,” she confessed. “But he seems confused when I do. He doesn’t need that kind of check-in. And I know that. But I still do it. Why?” Her words carried an urgency, not just in their content but in the way they were delivered, as if she were asking for permission to be reassured.
It was clear that she was reacting to the absence of micromanagement by seeking reassurance, falling back on behaviors that had once been necessary. But her struggles extended beyond communication with her boss. The dynamic with her team had also become a point of internal conflict. “I try to be softer with my team,” she said. “I tell myself, ‘Don’t be too demanding.’ But then- boom – I snap. I go straight back to being sharp, direct. And they don’t get it. They pull back, unsure of what to expect from me.”
Her voice carried a mix of frustration and self-doubt. She was oscillating between two extremes—on one hand, trying to fit into a more open, less hierarchical system, and on the other, instinctively retreating to the leadership style that had once brought her success. The inconsistency was eroding her confidence. The leader she had been no longer fit, but the leader she was becoming was undefined.
As I listened, I could hear the deeper tension underlying her words. It wasn’t just about adjusting to a new company’s way of operating; it was about identity. She had spent so many years perfecting one way of leading that the idea of adapting to something different made her question not just her methods, but herself. “I try to be what I think they want, but then I feel like I’m not being myself,” she admitted. “And then I push too hard. And then I regret it.”
Through the PRO model (Person, Role, and Organisation), we structured Lora’s key coaching goals: refining her leadership identity, adjusting communication with her boss, and embracing work-life balance in a way that aligned with her values. We explored how her personal need for control and validation was shaped by prior work experiences, how her role expectations were misaligned with the current organizational context, and how the cultural contrast between her former and current environments contributed to her anxiety. As we worked through these layers, I became aware of an unspoken dynamic forming between us.
Without realizing it, Lora was putting me in the role of her “reassuring boss.” She wanted confirmation that her instincts were valid, that she wasn’t making mistakes, that she was still an effective leader. “I just need to know I’m doing this right,” she said at one point, her voice almost searching.
The pull to provide that reassurance was strong. I could have told her that her struggles were normal, that she would find her footing in time. But I knew that would only reinforce her reliance on external validation. Instead, I asked, “What would it mean if you didn’t get that reassurance?”
She hesitated. “It would mean… I’d have to trust that I can find my own answers.”
Her words hung in the air for a moment. She had named the real challenge—not adapting to a new company, not managing communication with her boss, but learning to trust herself in an unfamiliar environment. It was a small but significant detachment from her need for external validation, and I could see the shift in her body language as she sat with that realization.
She sat back for a moment, reflecting. Then, almost as if thinking aloud, she said, “When you move to a new country, you don’t assume you already know how everything works. You observe, you test, you adapt. Maybe leadership is like that, too?”I let the metaphor settle between us. It was a shift—one that reframed her challenge in a way that resonated deeply with her own lived experience. She had spent years successfully navigating cultural transitions, stepping into the unknown with curiosity rather than fear. If she had been able to adapt before, what made this different?
Her posture softened as the realization took hold. “I’ve done that in every country I’ve lived in. I can do it here, too.”
Lora’s adaptation challenge also echoed broader themes of adjusting to different professional cultures—how leadership styles can vary not only between organizations but across industries, countries, and evolving workplace expectations.
Several key metaphors took shape throughout the session. One was the idea of “unused behavioral patterns under the carpet”—skills she had but had never needed to use were now surfacing. Another was the “gold shadow”—the mentor she idolized wasn’t just an external figure but a reflection of untapped leadership qualities within herself. But the most significant was “exploring a new country.” Leadership wasn’t about abandoning the past or forcing herself into a new mold; it was about navigating the transition with curiosity rather than fear.
By the end of the session, Lora had shifted from seeking reassurance to accepting the uncertainty of adaptation. “I don’t need a map,” she mused. “I just need a compass.” It was a breakthrough moment—she had moved from trying to replicate past success to understanding that leadership is an evolving practice.
For me as a coach, this session reinforced the importance of resisting the pull to become a source of validation. Lora had sought confirmation that she was on the right path, but by not providing it, I helped her take ownership of her leadership journey. It also reminded me to be aware of when I was being drawn into the client’s story rather than holding the space for them to find their own meaning. And it deepened my understanding of how metaphors can be powerful tools for cognitive reframing—allowing clients to see their challenges through a new lens, one that empowers rather than limits them.
Moving forward, our work would focus on testing new leadership behaviors in controlled environments, allowing Lora to experiment with her evolving style. She was stepping into an uncertain space, but now, she was doing so with a mindset of exploration rather than fear. Coaching isn’t about giving answers; it’s about helping clients learn to sit with uncertainty and trust themselves to navigate it. For Lora, that journey had just begun.
