Strong Back, Open Heart: 6 In-depth Courses to Reboot Your Leadership (and Life)

“Better leaders are better humans and better humans are better leaders. Leadership lessons, then, are, at their core, lessons in humanity.” – Jerry Colonna

How we work is as important as what we are doing. And, at the end of the day, we need to get things done, to execute–to work. Tending to the tensions caused by our humanity makes work happen more efficiently.

Clients come to us with a varied set of pain points such as bullying executives, misbehaving board members, knowing when to build an executive team and when to turn an existing one, delegating, trust, CEOs struggling to step away from the day-to-day as the company scales. Many of these are people issues, as much as they have practical tactical components. Many of these are part and parcel of the growing pains encountered as a company grows and the leader grows — or is forced to grow up  — into their role.

In most cases simply knowing what to do solves half the problem due to the human dynamics at play in any situation. The human factors make for a complexity that often isn’t touched by simply applying best practices, new systems, and methodologies. Each scenario is a unique edge case that requires a sensitivity to nuance because of what’s really happening at the human level.

As coaches, we know it takes practical skills (operational know-how) and radical self-inquiry to address most issues fully. When it comes to success in building/running/leading a business, you can’t have one without the other. Radical self-inquiry alone is aloof and bordering on being a philosopher on a log. Practical skills only may deny the human experience, the heart, and the humanity of what it means to lead an organization. And, if you don’t know yourself, especially as a leader, you’re a risk and a potential danger to your team and organization. 

Practical Skills + Radical Self-Inquiry: both are necessary parts of what it takes to grow, build, and sustain a great company.

Many clients come to us essentially to learn how to lead. Their often anxiety-driven belief is that leading is some mysterious art that they alone were never taught. If they could just figure out how to do the job then they’ll feel better, they think.

We believe the opposite is true. That is, if you can learn to manage your psyche, your anxieties, and the nearly constant sensation of failing, then you can be a leader. And the leader that emerges is essentially authentic and trustworthy.

This belief is at the heart of the Reboot formula:

PRACTICAL SKILLS + RADICAL SELF-INQUIRY + SHARED EXPERIENCES = GREATER RESILIENCY + ENHANCED LEADERSHIP

This process undergirds everything that we do. We believe that helping clients develop the managerial skills necessary to do the job is important but not enough to create the transformation they are seeking. To be an authentic leader, one must also cultivate a fearless willingness to look deeply through self-inquiry.

We define radical self-inquiry as the process by which self-deception becomes so skillfully and compassionately exposed that there’s no mask that can hide us anymore. This path of radical self-inquiry also leads us to discover what we most want in our lives, our authentic purpose, that which is in line with our most deeply held values. Along the way, we begin to see new choices emerging, and opportunities to reframe, refine, and revise our mental models that lead to new behavioral options. 

As Jerry writes in his book, Reboot: Leadership and the Art of Growing Up

“The most challenging piece of the formula—indeed, the most important—is this notion of radically inquiring within. I define it as the process by which self-deception becomes so skillfully and compassionately exposed that there’s no mask that can hide us anymore. The notion is to recognize that, if things are not okay, if you’re struggling, you stop pretending and allow yourself to get help. Even more, it’s the process by which you work hard to know yourself—your strengths, your struggles, your true intentions, your true motivations, the characteristics of the character known as “you.” The you behind the masks, the stories, the protective but no longer useful belief systems that have been presented for so long as the “you” you’d like everyone to see.”

Being part of an organization implies that “You cannot do it alone.” And, for an organization to fully self-actualize, it requires that everyone in the organization self-actualize. You can’t have one without the other. Which means you have to communicate in order to coordinate action. All communication comes from a deep set of beliefs and values and if you are unaware of what those are and are not living from them (as well as respecting others’ beliefs and values) you cannot create a non-violent or humane workplace.

Startups (and even non-startup-y organizations) can be turbulent places, but they don’t have to be. The promise is that startups are better than the corporate or cubicled alternative, but much happens when you’re scaling fast at the organizational level. It pays to be conscious about what we’re doing and how we’re doing it. On the path to doing something really amazing, an early reflex is to define ourselves by what we’re not going to be. But we have to be mindful of what we are creating and set out intentions for what’s possible.

At Reboot, we know that Better Humans Make Better Leaders and Better Leaders Make more Humane Workplaces. We believe that work can be the way we achieve our fullest selves.

We’ve amassed such a collection of resources since we began in 2014 that we wanted to bring them all together in an arc of inquiry touching on each of the aspects of our formula, echoing the work we do with clients. 

We created six zero-cost, in-depth courses that come to you in a series of daily emails as reflections on becoming better humans and what makes good leadership:

• Being Human Together: Being Relational vs. Being Transactional Over the course of 14 days, we will lay a foundation for building trust: inside of ourselves, with each other, and in our places of work. By integrating radical honesty into the fabric of our organizational cultures, we can begin to work in a new way. We need tools and skills to accomplish this work.
• Communication 101: Create Safety, Build Trust, Stay Relational–the Work of Non-Violent Workplaces
  In this 65-day course, we’ll look at empathy, listening, the art of checking in and the importance of asking good questions. We’ll share advice for navigating conflict, the relationship between power and safety, and — finally — how we can work better together. We hope to share with you tools for learning to speak in a way that you can be heard and learning to listen so that you can understand. 
• Radical Self Inquiry 101: Who Are You? What Shaped You? What Drives You? Over 52 days, we’ll take a look at our relationship to work, imposter syndrome, what it means to be on a journey of transformation, how the past and our shadow come to play in the present, and the beauty of becoming who we are. Along the way we’ll ask ourselves some hard questions like Who am I? Why do I do what I do? What does it mean to honor who I am and my gifts? At the end of this course, we hope you’ll have a better understanding of your work in the world and the guts it takes to become who you really are.
• Practical Skills 101: Putting Non-Violent Leadership Into PracticeIn life and in leadership, there are practical-tactical challenges that come from growth: both in scaling an organization and growing in your leadership. In this 58-day self-guided practical skills course, we will take a look at common challenges and how we can grow with them and, more importantly, through them. We’ll look deeply at: leading and scaling, company values, co-founder issues, cultures of inclusivity, vision and planning, and meeting and execution. Along the way, we’ll ask ourselves important questions like: what kind of company do you want to work for?
• Managing Your Psychology 101: Resilience in the Rollercoaster of Life, Work, & EntrepreneurshipThe way we manage our psychology (or don’t) shows up in our organizations. This ripples throughout organizations in positive, multiplying ways. We created this 73-day course to help you own your mental resilience on the rollercoaster of life, work and entrepreneurship. In this course we’ll look at mental health, burnout, anxiety and depression, self care and mindfulness. We’ll give you tools so you can begin to unpack yourself: your emotional competence, body wisdom, and untapped joy.
• Finding Ground, Managing FearIn this 33-day course, we will explore what it means to find your ground and manage fears when faced with struggles or feeling overwhelmed. Times of uncertainty are difficult and they can help us step more fully into the leaders we long to be. Also included is a week of guided journaling to help you unpack, reflect on, and integrate what you learn.

These are zero-cost resources for you and anyone you think might benefit. There are many ways to work through these, whether individually with your journal or collectively with a friend or colleague, or a group of like-minded folks ready to welcome self-reflection into their own leadership practice. If you did each course in succession, you’d be spending about a year with Team Reboot! You may be a different person a year from now, and it will be interesting to note what’s changed for the better. 

However and wherever you choose to dive into these courses, may your commitment to your own growth reap positive shifts prompt by prompt, day by day. We hope you walk away knowing yourself a little better and are more clear about what you need to grow into the leader you want to become.