Building Deeper Connections
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THE CONTEXT
B, an experienced CEO, had led an award-winning credit union for 16 years. Her ability to drive decisions based on numbers and analytics had made her successful in the role. But like all great leaders, she recognized there was room to grow.
B hadn’t worked with a coach before, but after hearing a fellow business leader rave about Jennifer Olsen, she was intrigued—and a new partnership was born.
“I just want to be the best CEO I can be.”- B, President & CEO
CLARIFYING THE VISION
Jennifer adapted her coaching style to B’s logical, direct approach. Their shared experience as women business leaders helped them establish trust quickly.
“Jennifer is really skilled at listening and at reading people—at understanding not just what you’re saying but what’s not being said.”
A detailed Integrative Enneagram assessment gave B valuable new insights into her core motivations, her communication style, and the strengths that had helped her succeed as a CEO. As a Style 5 (Quiet Specialist), she’s objective, highly analytical, and very comfortable with autonomy. But she can also be guarded, preferring to avoid anything to do with emotions and feelings—especially at work.
“[The Enneagram] made me realize why I’m so uncomfortable talking about feelings. I’m very logical. I just want the information, please—I don’t need all that personal connection. It all started to make sense.”
PERSONALIZING THE PATH
Jennifer helped B tune into her emotions through an exercise she initially found uncomfortable—mentally scanning her body before meetings to check in with how she was feeling.
“I was skeptical at first. But when I actually did it, I realized how much it helped. It made me more present, more at ease in meetings. It just centers you and focuses you (versus jumping from meeting to meeting without really thinking).”
They also focused on helping B cultivate self-compassion, which strengthened her ability to approach team interactions with greater empathy and compassion.
“Never in a million years would I have thought about reading a book on self-compassion. It was interesting. If I’m working on being compassionate with other people, I have to focus on being compassionate to myself as well. It sounds simple, but I hadn’t really put the two together.”
CATALYZING GROWTH
One of the biggest shifts B has experienced as a result of her work with Jennifer is embracing openness as a leader—not just in how she communicates, but in how she shows up for her team. With Jennifer’s guidance, B has become more intentional about inviting feedback, sharing her perspective, and allowing her team to see more of who she is as a person.
“Jennifer encouraged me to be less private with my team. She noticed that they were craving more from me—that I needed to show vulnerability, be less private, open up more.“
After working 1:1 with Jennifer for a time, B decided to gather her entire team for a group Enneagram workshop. All 23 employees completed their assessments in advance, and the results were illuminating. The vast majority of B’s team turned out to be Style 2s. These Considerate Helpers are people-focused, caring, warm-hearted, deeply empathetic—quite a contrast to B’s rational, objective Style 5.
“It really surprised me how similar all our employees are! Most were the same style, and I’m the complete opposite! It makes sense though–we are a credit union, which is all about people and taking care of people and helping people.”
This insight sparked powerful conversations in the room about how the team could strengthen communication and work together more effectively. Following the workshop and a post-session debrief, B engaged Jennifer to continue to support the team and extend their learning through quarterly one-hour Zoom workshops. The first two quarters will include all team members, and the second two will help managers and supervisors effectively provide feedback and direction to team members based on their Enneagram styles.