THE CONTEXT

M and N worked in their family-owned machine services business for several years before taking on the two most senior positions in the company—President and VP, Operations and Engineering. In this leadership transition, it was important to them to bring fresh energy to their respective roles while honoring the legacy their uncle had created and instilling confidence in the team for the future ahead. M and N shared a tight sibling bond and wanted to capitalize on their closeness to solve new complex challenges associated with business growth. Their HR consultant suggested they explore executive coaching with Jennifer Olsen. After learning more about Jennifer’s previous experience coaching pairs of leaders in similar roles, they decided she would be the ideal partner to help them make the new chapter in their second-generation family business successful.

“As part of our leadership transition for the company, we were really trying to be intentional about how to work together most effectively.”
- M, President

CLARIFYING THE VISION

M and N began their engagement with Jennifer with a few weeks of individual sessions with each brother to clarify their personal leadership coaching objectives, eventually transitioning to alternating individual and joint sessions to explore how to bring these coaching objectives together. M had worked with an executive coach before, but coaching was a new experience for N. He found that Jennifer’s calm, nonjudgmental style helped him adjust to his initial discomfort.

“Jennifer inspires a high level of trust. And for somebody like me that is more reserved and guarded, she made me comfortable opening up more and more as the sessions went on.”
- N, VP, Operations and Engineering

One of the first goals was to help the pair build confidence in their abilities and their ability to work well together. They wanted to treat the transition with care and do things in a way that would build long-term buy-in, alignment, and support from their team.

M and N had worked together on a business plan, and Jennifer helped them stay accountable to each other as they implemented it. They talked through how to handle changes to how the business operated, and how to communicate those changes.

Jennifer introduced M and N to useful tools they could put into practice right away, including reframing perceived problems to discover positive benefits, zooming out to consider what they wanted most out of key conversations and decisions, and taking the time to confirm what they thought they’d heard in important interactions.

"Jennifer has a way of questioning that allows YOU to see the truth more clearly. She helps you understand things that may be obvious from an outsider’s perspective, but when you are in the thick of things with your blinders on, you don’t see at all."
-N, VP, Operations and Engineering

PERSONALIZING THE PATH

Jennifer used the Integrative Enneagram assessment to help M and N understand their core motivations and explore how they interact with each other and with the world. M is a Style 7 (Enthusiastic Visionary), who tends to be future-oriented, entrepreneurial, and spontaneous, with a natural capacity for generating multiple ideas and options. N is a Style 1 (Strict Perfectionist), who focuses on organizing, structuring, and building process in order to do well the first time.

Jennifer helped M and N make the insights from the Enneagram analysis actionable with a custom one-page diagram of how the brothers’ specific styles mesh, including real examples from their work together.

“This is exactly why we did this coaching—to be able to understand how we function together as leaders, as brothers."
- M, President

She reinforced key concepts by following up after each session with relevant articles and podcasts on topics like reframing fears, communicating with openness and honesty, and building alignment around a new strategic direction.

“Jennifer is just so connected to learning. You can tell that she’s always learning herself, and it benefits her clients immensely.”
- M, President

CATALYZING GROWTH

Tuning in to their unique strengths and challenges helped M and N more fully understand their roles and make critical adjustments, including hiring a VP of Sales to take the growing number of operational and engineering tasks off N’s plate.

“The coaching helped us define how we execute work: who is better at the details, who is more the person to think about the big picture. It also helped us know what questions to ask, and how to make sure plans were feasible before moving forward.”
- N, VP, Operations and Engineering

Over time, the coaching has empowered both leaders to speak up and have tough conversations, to consider their own needs alongside those of their team, and to dig deeper to diagnose underlying issues instead of immediately making a process or technology change.

“Rather than just jumping into a solution, now I ask if this is the right solution.”
- N, VP, Operations and Engineering

Throughout the engagement, the new leaders appreciated Jennifer’s understanding of the nuances of family businesses, and her passion for helping them succeed. They found the coaching to be particularly helpful for creating a strong company culture and generating excitement about the future direction of the organization.

“Jennifer is so connected with the community—she loves companies and organizations that care about making a difference.”
-M, President