THE CONTEXT

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

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 she wanted other executive leaders to benefit from a coaching relationship. Together, they determined that Jennifer Olsen would be an ideal fit to work with J during this critical period of growth and transition.

“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.”
- J, CTO

CLARIFYING THE VISION

The acquisition led to an increase in J’s workload and heightened the need for him to respond strategically. J needed to delegate more effectively, push back when needed, and prioritize based on team and company goals. He needed to reimagine his approach to situations and recognize when his default behaviors—such as building meticulous research or assuming all incoming requests are a top priority—weren’t the optimal way to move forward.

“I was trying to do everything, and I was at the point of burnout. I needed to unlearn habits that don’t scale. The coaching has helped me figure out how to have a better work-life balance without taking on 50 percent more work.”

PERSONALIZING THE PATH

Jennifer used the Integrative Enneagram assessment to help J better understand his working style and communication approach. The assessment identified J as an Integrative Enneagram Style 9—Adaptive Peacemaker. Agreeable, trustworthy, and easygoing, Peacemakers often put others’ goals before their own. While J had built a successful technology career as a skilled developer leading a small team, it was enlightening for him to consider that the personality traits that had served him so well might hinder his effectiveness leading a larger team within the acquiring company.

“I’ve been successful in the past because of my analytical skills and my thoroughness. But now that I’m in more of an executive role, I no longer have the luxury of time to go away and thoroughly think things through. Jennifer helps me get out of thinking mode.”

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

“The Integrative Enneagram with Jennifer was far more comprehensive than what I had done previously. It helped me understand my default behaviors and how I attack a problem. When you’re just going about your job, you don’t necessarily see what patterns you’re exhibiting, and how those patterns are affecting your personal and professional life.”

CATALYZING GROWTH

J has found the safe space of working one-on-one with a coach to be extremely beneficial. The combination of outsider objectivity and personalized tools and resources has empowered him to analyze specific situations and cultivate new habits so he and his team can perform at their best.

“Having a feedback loop has been so helpful. Here are the things we know—how can we put a wedge in that process? How can we learn from it and practice new behaviors? Before, I was on autopilot. Now I think about what I want to get out of every interaction, email, and meeting—and how I can be most successful in making that happen.”