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



Leadership Development

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Before you are a leader, success is all about growing yourself. When you become a leader, success is all about growing others.

Jack Welch

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.

what we do

Participants emerging from our Vast Sky Leadership Development Program:

  • Develop a personal leadership brand & understand personal learning styles

  • Leverage conflict by understanding self & others.

  • Manage stress, build resilience & leverage multiple life roles.

  • Apply the difference between management & leadership.

  • Lead  across organizational or geographical boundaries.

  • Solve complicated problems & take wise action in complex, rapidly changing conditions.

  • Build a  network of supportive leaders to continue development.

How We Do It

Examples of some of our Leadership Modules:

  • Personal Assessments: 360, Emotional Intelligence, 1-on-1 coaching session

  • Your Personal Brand: Deep dive into participants’ personal brand, leadership story, and set the stage for the creation of their development plan

  • Your Leadership Nature: Understand the neuroscience of human nature, how it impacts behavior during times of change, stress, and feedback.

  • Leadership Vision and Values: Develop vision and values for ourselves and our teams. Leading to those values with goal-based empathy.

  • Team Performance: Understand the dynamics of a team, how change impacts groups, and how to work across boundaries and geographies.

  • Leadership Presence: Develop in-depth leadership presence, communication skills, facilitation skills, and executive relationships.

  • Leadership in Action: Active work on goal setting, driving results, and leadership systems

  • Leading Leaders: Managing organizational complexity. Coaching versus managing. Developing other leaders.

Client Feedback

“This experience helped to generate a better understanding of the organization’s pain points and needs. On a professional development level this workshop helped to provide me with additional tools to track a measure success.”
-Steve, Technology Leader


“I've never been to one that was so focused on specific outcomes that would help me to succeed at my job. Additionally, having an outside facilitator really allowed all of us to participate, learn and grow.”
-Robert, Technology Partnerships Executive


Vast Sky Workshops & Facilitation

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Coming together is a beginning. Keeping together is progress. Working together is success.

Henry Ford


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.

What We Do

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.

Topics and the experience are customized to each unique group. Examples include:

  • Setting organizational / team vision

  • Defining team values

  • Structuring team goals and methods

    • Vision/Values/Methods/Obstacles/Metrics (V2MOM)

    • Objectives and Key Results (OKRs)

    • Key Performance Indicators (KPIs)

  • Learning about the neuroscience of leadership and teams

  • Interpret the level and impact of emotional intelligence on the group

  • Articulating cultural norms, goals, and action plans to shift

  • Exploring mindfulness and self-compassion in the workplace

  • Discussing team dynamics and change management

  • Giving and receiving feedback

  • Building team bonding and collaboration

How we do it

Our first order of business is to connect with the leader to determine the goals of the workshop itself, the definition of success, the obstacles the team is working through, and the most important areas of focus. With that in mind, we deep dive with a few people on the team to formulate a cohesive approach. The outcome is to get under the hood to see what’s working and what needs a bit of fine tuning.

The next step is the Vast Sky Magic: the customized assessment, approach, agenda, and exercises that meets the needs of your team. The outcome is an alignment on vision, strategy, and goals (“the what”) as well as team coaching on the processes, structures, and human factors that propel the team forward (“the how”).

Client Feedback

This workshop was 100% worth the time and investment. In an org that's predominately remote, it's critical to come together and share strategy. 60% of this org was onboarded within 6 months, so it's amazing for us to come together and learn each other's goals, aspirations, and job function.” 
-Lila, SVP of Technology Ecosystem


“Vast Sky did an amazing job of building a curriculum that allows us to collaborate. Holistically we identified goals and defined our organization.” 
-Megan, VP Product


“By bringing our entire team together to get to know each other better, while working as a team on our team and personal goals and metrics was extremely helpful, useful and productive. I feel more aligned, committed and motivated. Thanks for making this happen!”
-Kate, VP Marketing Executive


“I'm walking away with a clear vision of goals, what it takes to get there, and how to measure success!”
-Susan, Manager


“This allowed us to coordinate more effectively, reduce redundancy, better communicate the overall strategy internally/externally and think more critically about how each one of us can impact the greater good of the company in a positive way. Nothing replaces face time and especially uninterrupted, dedicated time to review ideas, share feedback and make joint decisions which we can all take ownership because we were a part of the process.”
-Mark, SVP Marketing


“We are a natural foods company committed to building a more efficient, highly effective management team.  We engaged Chris to lead our off-site after several failed attempts with other facilitators.  Chris’ approach of guiding the conversations and work sessions, while still allowing the flexibility for our group to work within our own personality dynamics was extremely effective.  Our entire management team has been thrilled with the results and look forward to continuing to work with Chris in the future.”
-Chief Revenue Officer


Career Reinvention - Your Personal Vast Sky

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People take different roads seeking fulfillment and happiness. Just because they’re not on your road doesn’t mean they’ve gotten lost.

Dalai Lama

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.

How We Do It

The Personal Vast Sky program is designed to help you better define and articulate what truly engages your heart and mind, and then put a plan together to lead you to make it a reality.

  • 2-3 sessions to dive: personal vision, values, story, themes, and what’s holding you back.

  • 2-3 sessions to outline “An Adventure in Options". Which ideas and dreams are worthwhile to look into, what’s realistic for your life, and how can you make that a reality?

  • The output: a milestone-driven plan for how you'll dig into those options.

  • Optional: 3 once-a month follow-ups as you execute your plan

Client Feedback

"Heidi is a most trusted listener and adviser. Her 20+ years of experience in the professional business world really set her apart, as a top executive coach. She applies her unique and practical business insights to help foster my career growth. Anyone would be lucky to have her as a coach."

"Gracious and genuine, Heidi is a trusted, empathic executive who provides guidance and sage advice. An attentive listener who asks deeper questions to provide a clearer vision of what's possible."

"Thanks to Heidi, I have gained the confidence to lean in at times when I otherwise would have been complacent.  This confidence has propelled my career forward and I could not have gotten here without Heidi continually challenging me to think differently, challenge myself, and step outside my comfort zone.  Heidi has a unique ability to strike a balance between careful listening and sharing her wealth of knowledge and experiences.  I am so fortunate to have worked with Heidi and I look forward to continuing to learn from her in the future.”
- Megan