Reboot Your Company

We often talk about the work of rebooting your leadership as “individual work that you can’t do alone.” If each member of your leadership team is pursuing the work of self-inquiry and actualization, that’s wonderful. But to create the company that you’d all like to work for, you must also create the opportunity for the collective to grow. Experiences like facilitated leadership groups, offsite retreats, organizational change explorations, and immersive leadership trainings move the organization closer to its fullest expression of the inherent values.

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WHAT KIND OF COMPANY DO YOU WANT TO WORK FOR?

Each day, whether we realize it or not, we are shaping the company we inhabit. Are we creating a place where dissent quietly dies in the shadow of conformity? Where the convenient is celebrated while the truly innovative is left unexplored? Where politeness prevails, but the conversations that matter most are forever deferred?

We often call our companies “families,” and repeat that “our people are our most valuable assets. ” These words may sound generous, even noble—but they carry quiet dangers. What does it mean to speak of people as assets? And what are we enacting, perhaps unknowingly, when we call our colleagues “family”? Might we be using the workplace to replay the unresolved stories of our own beginnings?

There are so many ways in which even the most well-intentioned companies construct dysfunctional (and, unfortunately, at times toxic) environments. For each of us, as leaders, doing our work–moving towards our own self-actualization–requires that we create the capacity within our organizations for each member to grow.

It requires us to allow our organization, the community members we call “colleagues,” to collectively actualize.

At Reboot, we often remind leaders: you are not alone. But we’d add something essential to that truth—while you’re not alone, you also can’t do this alone. Creating the kind of company you long to work for isn’t a solo endeavor. It calls for others—partners in vision, companions in courage, co-creators in the messy, beautiful work of building something that matters. Culture isnot a top-down dictate but a co-creative expression of a group of fierce, broken-open-hearted leaders.

WORKING WITH TEAMS

One of the most satisfying moments in organizational life is when team members finally get each other and the work between them becomes less of an effort. 1:1 coaching often begins with a focus on individuals and their moments of stress, their existential challenges, their formational experiences we often refer to as “crucible times.” The same is true for teams.

Sometimes this looks like navigating conflict between co-founders and helping them find their way back to the core beliefs that caused them to go into business together in the first place. Sometimes it looks like extended, consistent work with whole leadership teams, helping them co-create safe, meaningful containers for their work; helping the entire group thrive. Sometimes it looks like a mix of one on one coaching and more targeted, facilitated group experiences.

Coaching partners and teams requires an expanded set of skills. Sometimes it requires conflict resolution and mediation. Often it means helping people to relearn basic listening skills.

Reboot’s Team Experiences work is highly customized and varies depending on the team’s needs. For some clients, it means a steady one-on-one presence with key individuals at the same organization, enabling the process to benefit from the multiple perspectives that can be shared. For others, it means working with entire groups simultaneously with the coach holding the container for the work, facilitating deeper understanding and communication.

At its root, the challenge of managing teams is really a challenge of communication: we all benefit from learning to speak in a way that we can be heard and listen to so that we can understand.

We’re here to support you and your team members in bringing forth the best that you have, using everything that emerges from organizational life (both challenges and successes) as opportunities to grow.

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HOW WE WORK

We listen to you and the key stakeholders in your organization so that we can tease out the nuances of what’s needed in the design of our experiences.

One of the greatest benefits of an outside perspective—like the one Reboot offers—is its ability to surface blind spots, unlock stuck places, and reveal paths forward you might not have seen on your own. Our role isn’t to tell you what to do or how to lead your company. Instead, we’re here to help you co-create a more thoughtful, more aligned future for your organization. That often means pausing your usual mental models and making space—at least for a while—for new ways of seeing and thinking.

We will work to find the right solution that meets your needs and is cognizant of budget and time constraints.

But building collective resiliency and strong cultures is a practice that yields benefits over time–much like the cultivation of a garden. For example, most leadership team challenges can’t be untangled and addressed in a half-day workshop, and attempting to do so can often result in more frustration for the team than good. Our experience has been that, at times, clients underestimate the amount of time needed to do this work effectively.

Our approach to training is experiential and designed to bring practical skills to bear on the real-life challenges folks are facing in the organization. For companies looking to provide a longer-term learning arc for their leaders (from senior leadership to emerging leaders and high-potential individual contributors), we can help design an approach that will fit your unique needs.

All Reboot Team Experiences are custom designed to fit your organization’s unique needs. The following is a list of some ofour more typical engagement types:

Facilitated Offsite Sessions (held virtually or in-person)
Executive team mission, vision, and/or purpose development
Small team to full organization discovery of organizational values
Establishing leadership team operating agreements
Navigating organizational change/transitions
Facilitated company retreats

LEARNING & DEVELOPMENT: MANAGEMENT TRAINING FOR ALL LAYERS OF THE TEAM

Reboot’s leadership development modules offer tools, frameworks, reflection, and skills practice for managers at all levels of an organization to level up their leadership, leverage curiosity, and share a common language across the team. By weaving in radical self-inquiry to key lessons on becoming a leader, participants are able to experience and get curious about their mental models and the ways in which they make meaning.

Our learning and development modules lay the foundation for healthy team dynamics by teaching the conditions that support high-performing teams, adapting leadership styles to drive development and empower others, and adding practical tools to the leader’s toolkit.

The material is shaped to fit client needs and covers essential leadership topics, such as:

Understanding Psychological Safety
Communication Fundamentals
Listening Choices
Asking Good Questions
The Three Components of Trust
Creating Clear Expectations
Delegation
Making Commitments
Recovering from Broken Commitments

Giving & Receiving Feedback

Navigating Difficult Conversations

Retrospectives

Leading Through Transitions

1:1 Best Practices

Performance Management

Leader as Coach

Managing Up and Across

Understanding Power Dynamics

Better Tomorrow Ventures Founder Retreat

Two Reboot coaches flew out to the founders’ retreat for the Better Tomorrow Ventures portfolio companies. In two half day sessions to take the group of founders in a deep dive of processing and reflection via a series of exercises and group conversation.

“I’m filled with admiration and gratitude for you both — and I know the founders who were at Camp feel the same. You brought in a very special and memorable element to this year’s Camp. It was beautiful to witness. Thank you for making the long journey out to Camp, for extending your support to the mealtimes and 1:1 coaching slots, and for helping these founders explore deep and important areas!”

Sloane Gerritzen

Chief of Staff, Better Tomorrow Ventures

Veterans United

Veterans United engaged Reboot to support the development of heart-centered, business-minded, and conscious leaders. Over four years, Reboot delivered a range of services, including individual leadership coaching for emerging leaders, virtual leadership trainings for larger groups, and the creation of peer coaching circles. These circles, launched with an in-person event on-site and sustained through bi-monthly virtual sessions, enabled high-potential leaders to develop advanced communication and listening skills, unlocking transformative growth across the organization. The initiative was seamlessly integrated into VU’s broader leadership development strategy and has been widely embraced.

“One of the things I love most about our partnership with Reboot is how deeply Carl and Jerry have come to know our company, our leadership culture, and many of us individually. When they are on-site with us, or coaching us virtually one-on-one, they feel like part of our family—it’s a powerful experience in the moment. But even beyond those moments, the connection we’ve built inspires greater possibilities for our leaders and our organization. A great example of this is our peer coaching circles, which have continued meeting on their own for years now, showing just how fully embraced and impactful this work has been for Veterans United.”

Erik Morse

Director of People Development at Veterans United

Automattic - “Coaching as an Essential Tool.”

A large, diverse, global virtual organization (Automattic) embeds coaching into their organization. They work with Reboot regularly on leadership coaching programs and 1-1 coaching with key leaders. The multi-day management training retreats give the team a space to speak honestly and learn from other team leads across the org. They feel less alone. The impact of the coaching program has leveled up the performance of the leadership and management layers.

“Prior to Reboot …, we didn’t have that many tools for our leaders. Now, I feel like our leaders are really well supported.”

Steph Yiu

Chief Customer Officer at WordPress VIP

Brightfarms

Reboot engaged with BrightFarms at a pivotal stage in their growth to clarify and strengthen the company’s leadership philosophies. Beginning with interviews of the leadership team to surface current and anticipated challenges, followed by an offsite to uncover shared principles such as commitment, openness, results driven, and empowerment. These insights shaped the design of the BrightFarms Leadership Academy where participants experienced the core leadership frameworks required to lead effectively in their roles.
Reboot has been a key partner along the way, facilitating offsites and receiving feedback to further improve the Academy, setting the stage for continued growth of the people and BrightFarms.

“Working with Chris and Reboot has been game-changing for BrightFarms. Chris brings deep expertise in leadership and real-world application, but what truly sets him apart is his heart. He takes the time to understand our culture, our challenges, and what will actually work for us—not just a one-size-fits-all solution. With his guidance, we built the BrightFarms Leadership Academy, a leadership program that’s practical, impactful, and deeply embedded in our organization. Chris doesn’t just teach—he empowers. His approach ensures that the work is truly ours, making the impact real and lasting. If you’re looking for a partner who leads with both wisdom and genuine care, Chris and Reboot are the ones.”

Steve Platt

CEO, BrightFarms

Brooklyn Museum

“Chrystal and Ray are truly exceptional coaches. They met us at a time of massive transition, a time when we were riding wave after wave of crises. And with a new leadership team from varied backgrounds and different visions for the future, Chrystal and Ray helped us come together as colleagues and humans. They created an environment where we could talk through challenges openly, giving us the space to slow down and break things into bite-sized pieces that we could tackle. Most critically, they helped us find common ground, taking our base fears and transforming them into a north star vision for the future. Chrystal and Ray worked with our teams on an individual level as well, helping each of us explore our personal power and how we show up to the table. They guided us in putting names to individual patterns, enabling us to better understand each other. Throughout the process, they provided deep care and attentive listening, investigating comments further until we reached meaningful insights and answers. Their dual approach of supporting both team cohesion and individual growth proved invaluable. Without question, we are a stronger team and organization as a result.”

Anne Pasternak

Brooklyn Museum

SUPPORT YOUR TEAM TO DO THEIR BEST WORK

Clients report organization-wide changes such as:

A more psychologically safe workplace
Authentic leadership styles
Team Cohesion
Sustainable work practices
Meaningful work at scale
More conscious business practices
Improved organizational performance & health
Higher employee retention

Employees and Managers report changes such as:

Better decision-making
More effective execution
Reduced leader burnout
Increased job satisfaction
Better work-life integration
Improved relationship quality
Enhanced self-awareness

READY TO GO DEEPER?

Team experiences are just the beginning. If you’re sensing that your organization is ready for transformation that reaches every level—from individual leadership development to cultural evolution—explore how Reboot for Organizations can help you build the company you’ve always envisioned.

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We believe that in our work lies the possibility of the full realization of human potential.
Work doesn't have to destroy us. Work can be the way we achieve our fullest selves.