Mystery, Meaning & Multiplicity: Unlearning Old Frameworks and Leading with Questions

“It is not the answer that enlightens, but the question.” — Eugène Ionesco

In a world that rewards clarity, speed, and decisiveness, leadership has come to mean having the right answers at the right time. We celebrate the quick fix, the five-point framework, the “playbook for success.” But leadership in complex times asks something deeper of us. It asks us to unlearn the illusion of certainty and to cultivate a relationship with mystery, meaning, and multiplicity — the invisible forces that shape how we lead, connect, and create.

Algorithms tell us what to buy, whom to trust, and even what to believe. But as knowledge becomes more accessible, wisdom — the ability to navigate ambiguity with grace — becomes rarer. This is the paradox of modern leadership: the more we know, the less comfortable we become with not knowing.

The Role of Mystery

Mystery is not the absence of knowledge; it’s the presence of possibility. It’s the space where creativity, intuition, and transformation take root. Yet most of us are taught to minimize mystery; to resolve uncertainty as quickly as possible.

But what if the unknown isn’t a problem to solve, but a partner to dance with?

When I worked with a product design executive navigating a recent failure, her first instinct was to “fix the problem” by demanding more data. Instead, I invited her to pause; to live with the not knowing. What might this setback be trying to reveal? What assumptions were hiding beneath the surface? That pause allowed her to see the deeper issue: not a technical flaw, but a cultural one. The team was afraid to share bad news until it was too late. The breakthrough came not from having more information but from embracing uncertainty long enough for truth to emerge.

The best leaders I know are detectives of the unseen. They trust that the mystery itself contains signals — patterns waiting to be discovered, connections that only appear when we stop insisting on immediate clarity. As philosopher Richard Rohr wrote, “Mystery isn’t something you can’t understand; it’s something you can endlessly understand.” The courage to stay with the question — to lead within the unknown — creates space for genuine insight.

Rediscovering Meaning

Somewhere between quarterly targets and endless Zoom calls, many leaders lose touch with why they started leading in the first place. Purpose becomes a slide deck instead of a living question. Meaning, however, isn’t something you state; it’s something you continually shape. It grows through reflection and renewal. Viktor Frankl, in Man’s Search for Meaning, reminded us that meaning arises from our response to difficulty, not from a place of comfort. Leaders who hold space for reflection, inviting their teams to connect daily work to a deeper narrative, reignite intrinsic motivation.

A simple but powerful practice I have seen is to begin every team meeting with a “moment of meaning,” inviting someone on the team to share why their work matters to them, to customers, to the world. The ritual lasts three minutes, but it reframes the entire conversation. It rehumanizes the workplace.

Our job is not to manufacture motivation, but to tend to meaning; to notice when it’s fading and rekindle it through story, curiosity, and genuine connection.

Embracing Multiplicity

In an age of specialization, we’re taught to simplify. We want linear strategies, clean categories, and one-dimensional answers. But reality resists reduction. The world is not binary; it is a beautiful both/and playground if you are willing to see it that way. And as I have seen, the most effective leaders can hold the both/and paradox skillfully. They balance confidence and humility, stability and change, and logic and intuition to create a place where multiplicity is celebrated. They recognize that progress doesn’t come from eliminating tension but from expanding our capacity to hold it.

Consider Satya Nadella’s transformation of Microsoft. Rather than choosing between technical excellence and human empathy, he embraced both. He reframed Microsoft’s mission from “a computer on every desk” to “empowering every person and organization on the planet to achieve more.” That subtle shift from product to purpose, from dominance to empowerment, turned a stagnant giant into an innovation powerhouse.

Multiplicity also invites us to see ourselves as multidimensional beings. Too often, leaders fragment their identities into the professional, private, and creative selves. Yet integration — bringing all of who we are into how we lead — creates resonance and gives others permission to do the same. When we honor multiplicity, we create cultures where diverse voices, perspectives, and contradictions coexist not as noise but as harmony.

The Art of Unlearning

To lead with mystery, meaning, and multiplicity requires a radical skill: unlearning. We must let go of frameworks that promise certainty and reclaim the art of inquiry.

Unlearning is not about erasing knowledge; it’s about loosening its grip. It’s recognizing that what worked before may no longer serve what’s emerging now. This is especially true in leadership development, where outdated models of control and hierarchy still dominate. The new frontier of leadership is not mastery; it’s meta-mastery: the ability to learn, unlearn, and relearn in rhythm with change.

A leader I recently coached shared how he transformed his strategy approach. Instead of drafting a fixed plan, he designed a “living strategy room,” where his team updates assumptions monthly. Every change is treated not as a failure but as a learning opportunity. “We stopped pretending to be right,” he said. “Now we’re just trying to stay alive to what’s actually true.” That’s what unlearning looks like in practice — not passivity, but presence.

Leading with Questions

Ultimately, leading with questions is not a sign of weakness; it’s the highest form of wisdom. The poet Rainer Maria Rilke urged us to “live the questions now.” Albert Einstein said he had no special talent except for “passionate curiosity.” Great leaders are those who know which questions to ask and have the patience to let the answers unfold in their own time. So, what are the questions you’re living right now? What don’t you know, and are you willing to admit it? And what conversations are waiting to be had because someone is brave enough to ask?

When leaders model inquiry over certainty, they shift the culture from defensiveness to discovery. Teams stop hiding ignorance and start exploring together. The result is not chaos but coherence, the kind that grows when people feel safe to be both confident and curious. In times of rapid change, it’s tempting to retreat to what feels solid: data, dashboards, and definitive answers. But the future belongs to those who can dwell gracefully in the in-between — to those who treat mystery as a teacher, meaning as a compass, and multiplicity as strength. Perhaps the next era of leadership won’t be defined by who has the clearest vision, but by who has the deepest questions and the courage to live them.