One of our team members recently shared a memory of a seasoned nonprofit CEO telling them, “I didn’t realize how lonely leadership could be until I sat in this chair.”
We’ve been there. After leading small teams, large organizations, and everything in between for a number of years, we know how isolating leadership can feel. Maybe you feel it, too.
Leadership carries a unique weight—balancing vision with daily operations, making high-stakes decisions, and guiding teams through uncertainty. It’s easy to feel like you’re alone as you carry these burdens. But the truth is, you’re not alone. The challenges you face are not uncommon, and the wisdom to address them is often best found not in isolation, but in community.
Small groups of leaders create a dynamic space where experiences are shared, perspectives are broadened, and solutions are forged together. They cultivate the kind of growth that transforms not only leaders but the teams and organizations they serve.
In our world, we call these Leadership Core Groups. We put 6-8 leaders in similar industries together for a season so they can learn together and help each other grow. Part mastermind, part personal development, we believe these groups are one of the best ways we can help more leaders have more great days.
If you’ve never been a part of a small group of leaders outside of your own organization, maybe you’ve asked yourself, why should I commit to a small group?
Leadership is often framed as an individual pursuit, but the best leaders know the value of collaboration. Small groups harness the collective wisdom of diverse experiences, creating a space for innovative solutions and enhanced decision-making.
These groups become incubators for strategic insights as leaders share best practices, test ideas, and refine approaches based on real-world experiences. Additionally, having completely objective voices around you opens you up to learning in a new way.
When surrounded by other high-caliber leaders, your thinking sharpens, your problem-solving deepens, and your capacity for creative leadership expands.
Every leader faces moments of stagnation—whether it’s a strategic dilemma, a personnel issue, or an external challenge that seems insurmountable. Most leaders think they need more time to reflect alone in order to solve these problems, and there’s a lot of value in that. But what if the best insights come not in solitude, but in a room full of trusted peers? In isolation, these roadblocks can feel overwhelming, but in a small group, they become more manageable.
Small groups can serve as think tanks where leaders can bring real challenges to the table and benefit from the perspectives of others who have faced similar situations. This collaborative problem-solving accelerates progress, uncovers new possibilities, and strengthens resilience.
When you regularly engage with a group of trusted peers, challenges become stepping stones and opportunities rather than roadblocks.
Great leadership isn’t just about mastering strategy, financials, or operations—it’s about people. Your team is the engine of your organization, and the way you engage with them determines how effectively that engine runs.
Emotional intelligence—the ability to understand, navigate, and influence emotions—sets apart the most effective leaders. Small groups cultivate this skill by requiring active listening, honest reflection, and vulnerability. When you engage deeply with peers, you develop a sharper sensitivity to what motivates people, what concerns them, and what inspires their best work.
Leaders who invest in emotional intelligence don’t just manage their teams; they inspire them.
Few things are as discouraging as the thought: “Am I the only one who is:”
facing staff shortages?
navigating financial pressures?
trying to maintain a vision amidst constant challenges?
Isolation is a leadership killer, and it’s well documented. A study published in Harvard Business Review by leadership expert Dr. Thomas Saporito found that over 70% of CEOs experience feelings of loneliness, with many noting that it negatively impacts their performance. But this challenge isn’t exclusive to top executives; anyone in a position of influence can struggle with the weight of leadership, facing decisions and pressures that feel isolating and inescapable.
One of the most profound benefits of small groups is the realization that you are not alone. Time and again, we’ve seen leaders experience the power of “me too.” The moment when someone else shares a similar struggle, a parallel concern, or a shared frustration… and suddenly, leadership doesn’t feel so lonely.
This sense of camaraderie is invaluable. Even as we lead different organizations, we are bound by a common purpose: to lead well, together. And in that shared commitment, we find encouragement, strength, and the courage to lead boldly.
It’s easy to forgo investing in yourself in order to prioritize other efforts or opportunities. Leadership is a consuming endeavor, and there’s always something competing for our attention.
Lead Every Day co-founder and leadership expert Mark Miller teaches that “No organization can outgrow its leadership.” When leaders grow, their organizations grow. Often the best investment you can make in your organization is an investment in yourself. Small groups promise some of the highest return on invested time and resources because they accelerate personal and professional development by facilitating direct feedback, refining decision-making skills, and expanding leadership capacities. As you improve, so does your team.
A more self-aware, strategic, and relationally attuned leader creates a healthier, higher-performing organization.
We believe small groups are one of the most effective ways to develop leaders, because leadership is not meant to be a solitary journey. Growth happens in community. Wisdom is sharpened in dialogue. Strength is forged in shared experience.
If you’re ready to experience the power of a leadership small group, one built on trust, expertise, and a shared commitment to leading with excellence, let’s start a conversation.
Contact us today to learn more about enrolling in one of our Leadership Core Groups.
Together, we lead better.
Do I feel like I have to make difficult decisions alone, without trusted peers to process with? Am I hesitant to share my biggest leadership struggles because I don’t know who would truly understand? Do I sometimes feel like no one else faces the same challenges I do?
Have I been encountering the same leadership challenges repeatedly without clear solutions? Am I struggling to find fresh perspectives or innovative ideas for the challenges my organization faces? Do I feel stuck in my leadership development or sense that my growth has plateaued?
Am I fully aware of how my emotions and communication style influence those around me? Could I benefit from honest, constructive feedback from leaders who understand my world?
1Patrick Lencioni (The Advantage; Five Dysfunctions of a Team), Brené Brown (Dare to Lead), and Simon Sinek (Leaders Eat Last) are a couple of our favorite authors on the subjects of empathy and vulnerability in leadership.
2See Dana Maor et al., The Journey of Leadership: How CEOS Learn to Lead from the Inside Out (New York, NY: Portfolio/Penguin, 2024). See also Reichard and Johnson, “Leader Self-Development as Organizational Strategy,” The Leadership Quarterly, Volume 22, Issue 1, 2011, and Lacerenza, et al., “Leadership Training Design, Delivery, and Implementation: A Meta-Analysis,” Journal of Applied Psychology, Vol. 102, No. 12, 2017.
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