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Executive coaching

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.

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.


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Leadership Development

The most effective leaders are those who know themselves the best, and who apply that introspection to their teams and to their company. Leadership Development initiatives are designed to equip the most important people in your organization with the mindset and skills needed to achieve your business objectives. Here at Vast Sky Leadership, our leadership development program is experiential and designed for personal introspection and action.


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Vast Sky Workshops 


& Facilitation

Whether as a stand alone event or as part of a larger training initiative, Vast Sky Leadership can lead your group through an interactive session to facilitate improved communication and maximize team performance.

Facilitated workshops are a powerful tool to bring your team together, enhance collaboration and bonding, and to establish the working rhythms and agreements needed to propel your team to their full potential. 


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Career reinvention 


Your Personal Vast Sky 

You’ve been working for decades, and now it’s time for something new. It’s not retirement. It’s not a promotion. It’s something different. Something - dare we say it? - purpose-driven. But you have no idea what that should be.

Your Personal Vast Sky is just that: it’s yours. And there’s an overwhelming number of options and possibilities, as well as voices in your head telling you to go with the status quo. But what if you don’t have to? What if there’s life and light in your 2.0? Let us help you explore it.






Chris Bolling

Chris is an insightful, collaborative executive coach and consultant who makes strategy happen. He brings over 20 years of business experience to help you get the most from your individual and organizational performance.

Chris has skillfully played a broad range of leadership roles including domestic and international business development, marketing, operations, sales force management, store development, as well as real estate and project management. Chris is known for his exceptional strategic planning skills, dedicated and passionate leadership style, and his ability to translate vision into well-executed strategies that produce results.

With a focus on increased self-awareness, authentic communication, and clarity of purpose, Chris knows how to transform the leadership conversation and build stronger, more capable leaders.

Certified by the Berkeley Executive Coaching Institute, nothing energizes Chris more than working in partnership toward new possibilities; challenging you to be your best.

When he’s not working with you on your journey to learn and grow, Chris is outdoors. On the water, or in the mountains, he enjoys everything that nature has to bring. He loves the challenge of a long distance outrigger race, the grind of a 3-hour mountain bike ride, or the solitude of time on the river with his fly rod. 

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Heidi Connal

Heidi Connal is a seasoned executive coach and advisor with over twenty years of experience building insightful, compassionate, and high performing individuals and teams. She works with visionary leaders who strive to achieve ongoing impact and purpose within their career and are hungry to identify new opportunities for growth, learning, and contributions with their hearts and souls. Her techniques cultivate empathy as well as self-awareness so her clients can have powerful impact and courageous contributions.

Heidi is known for her leadership and consulting expertise in large global enterprises, including Salesforce, Bank of America, American Express, the United Nations, and PriceWaterhouseCoopers. She has led global divisions in mergers and acquisitions, business development, strategic consulting, technology, and marketing, and has industry experience within financial services, higher-education, and nonprofit sectors as well as in international non-governmental organizations.

Heidi’s insatiable thirst for learning and exploration began as an U.S. Air Force child and later developed into a passion for travel and adventurous experiences. In the last fifteen years, Heidi has traveled to all seven continents and has volunteered in countries such as Ghana, Haiti, Laos, Thailand, and Cuba. She is a top fundraiser for the National Multiple Sclerosis Foundation’s annual Waves To Wine BikeMS ride and she provides pro bono hours to various nonprofits focused on building capacity and leadership. When she’s not building purpose-driven executives, she can usually be found underwater with whales and sharks or in third world villages where cell phone coverage does not extend.

Heidi holds an MBA in finance and marketing from NYU Stern School of Business and a bachelor’s degree in information systems from the University of Virginia. Heidi is a certified executive coach through the Berkeley Executive Coaching Institute. She’s also a certified PADI dive instructor.