IMPORTANT ANNOUNCEMENT: OneDigital has acquired Resourceful, expanding the human resources services in the Pacific Northwest market.

Learn More

New Role, New Approach

Executive Coaching Case Study


500+ employees (Parent Company); Less than 15 employees (Startup technology acquired)


Seattle, Washington



Coaching Venue

Video Conference

Coaching Type


Coaching Goals

To cultivate new behaviors and embody the presence required to operate at the executive level of a large corporation.


J is the CTO of a recently acquired technology startup that empowers employers and employees to manage complex family leaves and policies.

The Need

As the technical co-founder, J must build a strong bridge with the new, much larger parent corporation. J directs a virtual team of developers responsible for mapping and spearheading the massive systems integration necessary for the parent company to realize the full value of its acquisition, by innovating how it services its own clients. In this new role, J is tasked with meeting ambitious corporate milestone objectives and delegating effectively to accelerate productivity. 

J’s CEO had been working with an executive coach for several months, and wanted other executive leaders to benefit from a coaching relationship. Jennifer Olsen from Resourceful was identified as an ideal fit to work with J during this critical period of growth and transition. 

Resourceful Response

Jennifer and J work together twice a month via videoconferencing. This video approach has allowed the coaching to fit seamlessly into J’s demanding schedule without any loss of face-to-face connection.

Jennifer used the Integrative Enneagram assessment during the coaching process to help J better understand his working style and communication approach. The assessment identified J as an Integrative Enneagram type 9—Adaptive Peacemaker. Agreeable, trustworthy, and easygoing, Peacemakers often put others’ goals before their own. While J built a successful technology career as a type 9 individual contributor, it was enlightening for him to consider that the personality traits that had served him so well throughout his years as a skilled developer might in fact hinder his effectiveness as a leader of people. 

“I’ve been successful because of my analytical skills; my thoroughness when coming up with a plan. But now in my CTO role, I no longer have the luxury of time to go away and thoroughly think things through.”

The coaching work has helped J reassess his patterns to gain a deep understanding of how he naturally approaches tasks and challenges (typically, a thorough deep dive). He is expanding emotional literacy by recognizing others’ personality types and inclinations, and realigning his approach for the most effective outcomes in these relationships.

Now I think: Here’s what I want to get out of this interaction. How can I be most successful in making that happen?”

Meaningful Results

The acquisition led to an increase in J’s workload and is heightening the need for him to respond strategically. The ongoing coaching supports J in delegating more effectively, pushing back when needed, and putting team and company goals up front. He is reimagining his approach to situations and learning to recognize when his default behaviors—such as building meticulous research or assuming all incoming requests are a top priority—aren’t the optimal way to move forward.

“What got me where I was won’t get me to the next level. All the traits that made me successful in the past are not going to make me successful in my new role. I need to be less worried about each individual’s feelings and think more about the team as a whole.”

J has found the “feedback loop” of working one-on-one with a coach to be extremely beneficial. The combination of outsider objectivity with the tools and knowledge to analyze specific situations and cultivate new habits continues to help J and his team thrive.


Executive Coaching can help managers develop a holistic team approach.