In my last post, we explored the shift from fault-finding to lifting people up. Today, I invite you to consider a deeper transformation: embracing “both/and” thinking in a world too often stuck in “either/or.”
Franciscan contemplative Richard Rohr describes contemplation as “taking a long, loving look at what is real.” It’s not just about collecting data—it’s about seeing with a spacious, open heart. For leaders, this contemplative gaze is essential.
Many organizations operate with an “either/or” mindset. While useful early on, this simplistic thinking becomes limiting as individuals and collectives mature. It thrives on simplification and clear-cut answers, often manifesting as:
- Siloed Thinking: “My department’s success or yours.”
- Blame and Scapegoating: “It’s either their fault or ours.”
- Rigid Hierarchies: “You’re either in charge or you’re not.”
- Resistance to Change: “It’s either the old way or the new way.”
But mature individuals begin to see nuance and interconnectedness. Their perspective deepens toward “both/and” thinking: collaboration over competition, shared leadership over control, and innovation through tension rather than avoidance.
When organizations fail to evolve alongside their people, they risk losing them. I recently spoke with a gifted leader in her mid-fifties who left a multi-billion-dollar company. Why? Because she’d outgrown its rigid structures. She longed for an environment that could hold complexity, foster dialogue, and embrace paradox. She’s now considering nonprofit work—not for the pay, but for the maturity.
Think about Nelson Mandela. After years in solitary confinement, he said he “came out mature.” That contemplative maturity equipped him to end apartheid—not by taking sides, but by transforming the system. Leaders like Mandela don’t just solve problems—they hold tension, embrace complexity, and make space for deeper change. Sometimes they even lead movements.
Why Organizational Maturity Matters
Embracing “both/and” isn’t just aspirational—it’s essential. Here are four advantages the contemplative leader and organization have.
- Innovation & Adaptability: Google’s Project Aristotle found that psychological safety was the top factor in team effectiveness. Innovation thrives when people can offer candid feedback and feel respected—when feedback and safety exist together.
- Employee Engagement & Retention: A 2022 Gallup report shows that highly engaged teams outperform others in profitability, productivity, and retention. Engagement rises when people are valued beyond narrow roles, and when organizations embrace less rigid structures.
- Better Decision-Making: McKinsey research on organizational health reveals that mature, communicative companies perform better financially. They understand problems aren’t linear—and that sustainable solutions require systemic, “both/and” thinking.
- Resilience in Change: A Deloitte report on the future of organizations highlights the need for adaptability, resilience, and humanity to keep the best people—all hallmarks of maturity. Immature organizations react with blame and rigidity. Mature ones stay grounded in ambiguity and paradox.
Cultivating the Contemplative Leader
So how do we lead with this contemplative maturity?
Start by challenging your own “either/or” instincts. Embrace paradox. Can we be both profitable and purpose-driven? Can we lead strongly and empower others? Yes—and more often than not, that’s the only way forward.
Practice deep listening—not just hearing, but seeking to understand perspectives that challenge you. This takes humility and openness.
Regularly question assumptions. Many “either/or” patterns are deeply ingrained. Ask: “Why?” and “What if?” more often. It’s hard at first. But slowing the conversation down for just two minutes can make a big difference.
Encourage dialogue over debate. Move from adversarial exchanges to shared inquiry. Don’t just aim to be understood—seek to understand. Turn up your ears and slow down your mouth. This is hard too. But when you’ve done this, others will be more willing to do it for you. Sometimes you’ll have to push to be heard, and that’s okay too.
And finally, cultivate self-awareness. Notice your own tendencies toward control, certainty, or division. Growth begins with noticing. It took Moses 40 years in the wilderness to become the kind of person who would notice a burning bush, turn aside, and pay attention.
Moving beyond “either/or” thinking is a lifelong practice. It calls for courage, curiosity, and compassion. But for leaders serious about building thriving, mature organizations, it’s not optional.
Contemplative leadership—taking that long, loving look at what’s true—is how we move from just eliminating blame to cultivating spaces where people and systems can grow in wisdom, wholeness, and shared purpose.