Executive Coaching

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The first responsibility of a leader is to define reality. The last is to say thank you. In between, the leader is a servant.

Max DePree


We are seasoned business executives, focused on the transformation of today’s leaders. In this fast-moving, demanding environment, executives have limited opportunity to devote time and energy to their own development as leaders. We at Vast Sky are artisans in developing leaders who are insightful, empathetic, fulfilled, and who are in tune with themselves and the people around them.

What We Do

Our coaching style focuses on emotional intelligence, interpersonal dynamics and intra-personal behavior change. We support individuals on a journey to self-awareness and meaningful connection that fosters greater humanity at work. Our clients are ready for change and discovery, and desire to work on a variety of developmental areas:

  • Self-aware, emotionally intelligent executives

  • Higher level engagement and productivity

  • Improved employee relationships

  • Exemplary team functioning

  • Leadership transition

  • Determination of purpose, motivation, and plan

  • Identification of emotional strengths and opportunities for improvement

  • Improved communication and leadership skills

  • Effective navigation of group dynamics and professional relationships

  • Stress management and staying calm under pressure


  • 9 month duration: approx 2, 90-minute sessions per month

  • Assessments and inventories included: Emotional Intelligence, Myers-Briggs, Survey based 360

  • Coaches with deep business experience to find the ideal executive match

  • Ongoing HR / Executive Sponsor Alignment

  • Quarterly reporting to HR

Client Feedback

“Heidi is among the most emotionally intelligent people I have ever met. An empathetic listener and inquisitive friend, she helped me develop explicit connections between my passion and my professional trajectory. Her emphasis on introspection and focused thinking enabled me to feel empowered to actively pave my career path. She has an uncanny ability to distill elusive personal aspirations into actionable, achievable plans and certainly made me feel a newfound sense of self-efficacy and confidence.
– Rachel, Strategic Consultant


“Heidi brings the perfect blend of coaching skills along with corporate experience to the table in her role as executive coach. Her empathic listening skills layered with intuitive and probing insights, tempered by her pragmatic understanding of the business environment comes together to show the way for the kind of self awareness and self learning to take you to the next level of performance. Anyone ready to advance their executive skills would be lucky to work with her.”
– Eli, CIO


“I’ve been fortunate to have Heidi’s guidance for the past few years of my career. As a high performer in every role she’s had, I highly value her insights and council. Heidi is an excellent listener and asks the right questions to help steer your conversations in the right direction and helps bring about thoughtful discussions which in turn bring results. Heidi has been a go-to for this kind of advice from peers, direct reports and everyone around her and anyone who works with her would call her a rock star. She is one of those people who always brings her A-game, is professional, polished, and knows how to help those around her and those who seek her advice.”
– Liz, Technology Executive


“I feel very fortunate to have found a coach of Chris Bolling's skill and experience during a time of professional transition. I worked with him over a period of months as I prepared for a sudden and unexpected promotion to the position of CE0 of a $250M credit union.

Chris was invaluable as I walked through the process of defining myself as a leader and considering how to approach some potentially thorny collegial relationships. With his intuition and his ability to observe and ask just the right questions, Chris was often able to lead me into an expanded way of viewing a situation or to help me develop existing insight on a particular issue. Throughout the process, he avoided directly advising or prescribing solutions, but instead encouraged me to create my own. He demonstrated significant flexibility, moving between coaching styles as the situation and subject matter demanded, but his approach was uniformly positive and affirming.”
-Rebecca, CEO


“I have had the distinct pleasure of working with Chris Bolling over the last six (6) months and expect to maintain the professional relationship into the future.  Prior to our professional engagement, Chris and I briefly worked on a small community project for a local not for profit.  That interaction was enough to reach out to him with my personal situation and ask for his professional assistance.

The time we have spent together over the last six months has challenged me to become more accountable to my own path and while I am happy with the direction I am moving, the process was not always comfortable.  

The approach Chris is taking is to push me with question after question, rarely if ever giving advice.  Rather, his thoughtful and steady guidance has allowed me to measure my steps and think through options I had never considered.”
-Dave, Vice President