The problems that arrive at the CEO’s desk are the ones nobody else could solve. That’s the definition of the job.
What surprises most chief executives is how few of those problems are actually strategic:
“I think a great CEO coach can be awesome and not-great CEO coach can be very detrimental. Reboot is the best organization for supporting entrepreneurs in all aspects of the entrepreneurial journey.”
Brad Feld Foundry Group
The 6 Challenges of Leadership For CXOs
Also known as "The 6 Biggest Mistakes Founders Make" — though this wisdom applies to all leaders.
For the CEO: Things You Need to Think About As Your Company Scales
What we've learned from completing 360° performance reviews on leaders of companies at all stages of growth.
Board Management: Thoughts and Resources for Building, Managing, and Navigating Your Board
The board-leadership relationship doesn't have to be a challenge.
Why Being Real Matters: The Case for Authentic Leadership
Or, how to inspire your employees to walk through walls for you.
Why tracking your shadow is essential for being a leader — and a better human.
A Formula for Trust: Sincerity, Competence, and Character
Often, we think of trust in binaries: either we trust someone or we don't. However, the formula for trust is more nuanced than we might think.
Somewhere between the early days and now, the work stopped being about doing and started being about deciding. You are further from the product than you’ve ever been, closer to the consequences than anyone else, and the people who used to tell you the truth have started managing you a little. Your calendar is full of conversations where you’re the one expected to have the answer. And the room you most need — the one where you can say I don’t know out loud — doesn’t exist on your org chart.
Since 2014, Reboot Executive Coaching has served thousands of clients across the globe, including chief executives at companies from seed stage to Fortune 100. We help leaders bridge the gap between where they are and where they want to be.
Reboot’s approach was shaped by a conviction that the quality of your leadership is inseparable from the quality of your self-understanding. For a CEO, this isn’t a philosophical nicety. It’s operationally significant. You are the single largest input into your company’s culture, and the parts of yourself you haven’t examined are the parts that show up in your organization without your permission.
Being a CEO is different from doing CEO work, and that distinction is where coaching parts ways with mentoring and advising.
There is no shortage of people willing to tell you what worked for them. Some of that advice is genuinely useful. But operator advice comes packaged with the operator’s context, their company, their stage, their temperament, and the parts that don’t transfer are rarely labeled.
Reboot Leadership Coaching helps you unpack the mental models that drive your decisions, making the unconscious conscious, so you can see clearly what outcomes you want and how your current patterns are helping or hindering you. Better results with less friction; not by working harder, but by developing a clearer, more intentional version of yourself as a leader.
Leading well means holding two things at once.
There are the practical demands: building an accountable leadership team, running a board, making decisions with incomplete information, communicating a hard message without softening it into meaninglessness, knowing which numbers actually tell you how the business is doing.
And there’s the more personal work: understanding your own values, triggers, and patterns well enough to lead from them consistently, especially in the moments when the pressure is highest and your subroutines take over.
Reboot’s seasoned leadership coaches work across both dimensions. That combination is what produces leaders who can sustain their impact over years rather than quarters.
Our Formula
Practical Skills + Radical Self-Inquiry + Shared Experiences
=
Enhanced Leadership + Greater Resilience
Reboot’s coaching for executives brings a deep understanding of human behavior alongside genuine familiarity with what the chief executive role actually demands. Many have sat in the seat themselves.
We work with CEOs across a wide range of contexts:
The International Coaching Federation’s 2024 research shows that performance and sustainability aren’t in conflict:
%
increase in individual performance
%
increase in team performance
%
increase in organizational performance
Your growth as a leader starts with your growth as a human being. With over a decade of professional coaching experience, Reboot has developed its ability to help leaders bridge this crucial gap.
Beyond Traditional Business Coaching
Most CEOs come to executive coaching at an inflection point: a fundraising round, a scale-up, a leadership team that isn’t working, or a growing sense that the company is running them rather than the other way around.
Tactical advice can help you solve a problem. It rarely helps you stay grounded in who you are while you’re solving it. And it does nothing about the fact that the same problem will be back in six months wearing a different hat.
Working with a Reboot coach, you’ll develop the capacity to:
The Inner Work of Leadership
We believe that work does not have to destroy us. Even at the top of an organization, where the pressure is most concentrated, work can be the way in which we achieve our fullest selves.
A Reboot coach helps you examine the beliefs and patterns that shape how you lead, understand why certain situations keep producing the same frustrations, and develop a more intentional way of showing up, grounded in your own values rather than those borrowed from someone else.
Our 1:1 coaching contracts are month-to-month, with rates varying based on session length and frequency. A typical engagement includes two 60- or 80-minute sessions per month, with access to your coach between sessions — designed to fit into a demanding schedule.
Many CEOs pair 1:1 virtual executive coaching with a 360° Review, which surfaces what your organization sees and isn’t telling you, or with executive leadership team development.
Reboot was founded on the belief 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, and in doing so, we become more effective leaders, colleagues, and human beings.
We believe that helping clients develop managerial skills is important, but not enough to create the transformation they’re seeking. To be a leader, you must also cultivate a fearless willingness to look deeply through self-inquiry.
For more than a decade, Reboot has supported thousands of leaders from startups to Fortune 50 companies. We believe better leaders make better humans, and better humans create more humane organizations and places of systemic belonging.
Most leaders audit the business annually and never audit themselves. This three-part series walks through the questions worth sitting with once a year: how things are going with the company, how you’re holding up as a leader, and where the gaps are on your leadership team.
Part 1 — How Are Things Going?
When it comes to your team, company, or organization, how are things going?
Part 2 — How Are You Doing as a Leader?
When it comes to your leadership, how are things going? How are you doing?
Part 3 — How Is the Leadership Team Doing?
From your seat, where are the gaps in the leadership team? What might you want to see more of?
For over a decade, Reboot has guided leaders through the complex terrain of business and personal growth. These books capture the essence of our coaching methodology, helping you navigate the intersection of personal growth and professional excellence with humanity, courage, and purpose. They offer a roadmap to becoming not just a more effective leader, but a more complete human being.
Leadership Columns
Ongoing leadership wisdom from Jerry Colonna and Ali Schultz
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