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Executive Coaching Isn’t Just For Executives (or Coaches) Anymore
Why you should invest in group coaching
Modern executive coaching isn’t your old boss’s executive coaching. A Six Sigma Black Belt doesn’t parachute in and teach you how to manage a process or make better decisions. Rather than fix your problems, coaches today help you figure out how to fix your problems yourself. They are listeners. They are observers. And they can crack you open with a well-timed question.
Some coaches refer to themselves as mirrors, helping their clients see themselves in new ways. Others position their work as an almost spiritual practice, helping you “scale without losing your soul.” Jerry Colonna’s team at Reboot “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.”
No wonder business coaching is cheekily referred to as business therapy.
Coaching helps people excel in their jobs, improve their relationships, and realize their personal and professional goals. But the work goes deeper. In my ten-plus years of coaching, I’ve found that the best coaching relationships help people answer fundamental questions about their work and lives while connecting to their highest purpose.
“There are these two young fish swimming along and they happen to meet an older fish swimming the other way, who nods at them and says ‘Morning, boys. How’s the water?’ And the two young fish swim on for a bit, and then eventually one of them looks over at the other and goes ‘What the hell is water?’”
— David Foster Wallace, 2005
David Foster Wallace opened his famous 2005 commencement speech This is Water by reminding us that sometimes, “the most obvious, important realities are often the ones that are hardest to see and talk about.” Like the two young fish, we need outside perspective to help us see what’s most obvious. Executive coaching helps us see and talk about our important realities, especially when it’s done in groups.
What is group coaching?
Group coaching circles are often made up of 6-8 peers who gather for intentional conversation about their own personal and professional development. Groups are composed using various dimensions like shared roles, shared industries, shared life stages, or something else.
Meeting cadences and locations also vary. I’ve personally been in groups that met bi-weekly and monthly. One of my groups convened over dinner, and another was exclusively on Zoom. In all cases, what made the groups special was the shared intention to attend every session and be present for each other.
Like one-on-one coaching, groups can hire executive coaches who listen, observe, and ask timely questions to create a space for deep introspection and learning. This is where the similarities end and the magic of group coaching begins.
As my friend Rei Wang, co-founder of group coaching company The Grand, likes to say, “group coaching is showing not telling.” It’s one thing to hear from a coach that many founders have Imposter’s Syndrome. When a fellow founder in your coaching group says, “I have Imposter’s Syndrome,” it lands. You instantly connect and feel less alone when you hear it directly from someone like you.
A group coaching circle is like a personal laboratory for performing research on yourself. You are the scientist, subject, and observer in this lab all at once.
The Group Coaching Lab
How do you make people feel when you sell? How does your communication style support or undermine your desires? What limiting beliefs hold you back? As scientists in a group coaching lab, we can ask these questions and more, and design experiments to help ourselves answer them.
As the subjects in the lab, we can try things and learn by doing. For example, I’ve always admired people who set the tone of an experience by centering the room's attention. Think about a yoga teacher who opens class with a few deep breaths or an emcee who repeats, “I can’t hear you! Are you having fun tonight?!” Mimicking them feels cheesy to me, but I know it works. A group coaching circle is perfect for practicing and getting comfortable doing it myself.
This brings us to another one of Rei’s insights. One thing her members value most about group coaching is that they “get to coach and be coached.” Group participants can practice their coaching skills—like running through a difficult conversation—in a safe space before delivering the real thing to their team.
After being a scientist asking questions and a subject who practices in the lab, the third role members play is the observer. For participants it is the most overlooked and surprising value of group coaching, but it is obvious to trained psychologists. Esther Perel teaches us that, “When we listen deeply to other people we reach into their humanity. We also get to see ourselves.”
Group coaching is designed to help you listen intentionally to other people, often in moments of crippling insecurity or powerful strength. In doing so, we develop self-awareness and connection to ourselves, even when we’re not directly participating in the conversation.
In one-on-one coaching, you learn from one bi-directional relationship between you and your coach. In group coaching, a network of connections provides information all at once. In the example above, you observe how you relate to seven people and how they relate to you. Importantly, you also witness how everyone relates to each other, and the experiences become reference points for your self-awareness. Add a trained facilitator who asks expansive questions and a group coaching circle turns into a wealth of data for building your intuition.
I’ve been hosting group coaching circles since 2012, and the relationships I’ve built through this work have become some of the most cherished in my life. The people I started a group coaching circle with ten years ago are close friends who have traveled together, built businesses together, and invested in each other. We’ve supported each other through career transitions, breakups, and company failures. In helping me see and talk about my important realities, they have become part of my reality.
Opportunities for Organizations
Companies should tap into this dynamic and provide opportunities for leaders to grow. With some intentionality about group formation, participants can meet peers who help each other level up and see themselves more clearly. There are companies that make this simple for employers.
My friend Rei’s company The Grand creates peer groups for mid-level to senior managers. She and her co-founder Anita Hossain have built programs to explore leadership styles, limiting beliefs, and other management challenges. Leaders from Google, Bain & Company, LinkedIn, Stripe, Slack, and Figma have grown through their group coaching circles. The Grand believes so much in the transformative impact of peer coaching that their entire focus is on curation and facilitator training. A celebrity coach can make all the difference one-on-one, but for groups, the magic is in formation and facilitation.
Chief is built in a similar vision. In their model, women at VP-level or higher form peer groups to learn and grow with each other. Recurring sessions are facilitated by professional coaches, but like The Grand, the real alchemy is in the relationships built between members. Chief was founded in 2019 and the community has grown to over 15,000 members. At an annual cost of $5,000 - $8,000 a year for memberships, most of which are paid by employers, it’s clear companies are willing to invest in this kind of personal growth for their high achievers. Chief’s last financing round valued the business at $1.1 billion.
YPO requires you to be the top leader of your organization (President, CEO, Chairperson of the Board, Managing Director, Managing Partner, or Equivalent title) and your company has to have at least 50 employees or $2M in annual compensation.
Chief on the other hand is open to a far larger slice of leaders. To join, women must be C-level executives, accomplished VPs, or in equivalent executive leadership roles. Chief plans to expand to directors too. While The Grand is selective about who can join their highly curated groups, there are no explicit seniority requirements.
This trend is good for both employers and employees. Companies will be better off giving their most valued leaders additional tools to achieve their highest potential. Retention and output will increase. Employees who develop a stronger sense of purpose, connection, and community are happier and more productive. Of course, deep introspection will cause some people to realize they want a new job, but in the long run, that is good for their employers too.
How often are you in an intentional, present conversation with seven of your peers talking about your own personal and professional development? How often can you witness two aspirational leaders make breakthroughs together through an intimate conversation about their professional lives? If your answer is, “not enough,” go find a peer group. Your best coaches are in there.
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