Humble Inquiry Beyond Active Listening

Operationalising Humility: Bridging the Gap between Advocacy and True Innovation

Samuel Lam, Managing Partner, Third Opinion Partners & Chong Sook Leng, Partner & Senior Consultant, Third Opinion Partners

Many leaders consider themselves effective listeners. They pose questions in meetings, invite input from colleagues, and encourage their teams to contribute. Yet despite these well-intentioned efforts, conversations often follow a familiar pattern: the leader speaks last, decisions align with the leader’s perspective, and critical insights remain unvoiced. The challenge is not a lack of listening, but rather the underlying intent leaders bring into conversations – often entering with a mindset to decide, rather than to genuinely understand.

At the heart of effective dialogue is not simple the ability to ask better question, but the discipline to examine the intention behind them. Questions can serve many purposes: they can test assumptions, evaluate ideas, guide direction, or subtly persuade. Equally, they can be used to explore possibilities, surface diverse perspectives and deepen collective understanding. The difference lies not in how the question is phrased, but the intent that shapes it.

This distinction is increasingly critical in a context of growing complexity, where no single leader, regardless of experience can fully comprehend the challenges facing an organization. Conversations must therefore evolve beyond mechanisms for decision-making into spaces that enable shared thinking and collective insight to emerge.

To operate at this level of dialogue, leaders must move beyond the mechanics of active listening toward what Edgar H. Schein described as humble inquiry, a relational posture grounded in curiosity, humility, and the willingness to be influenced by others.

The Limits of Active Listening

Active listening has long been recognized as a core leadership capability. It requires leaders to remain present, attend to both verbal and emotional cues, reflect understanding, and respond with empathy and respect.

At its best, active listening signals that the speaker matters. It fosters a sense of acknowledgment and creates conditions where individuals feel heard, respected and valued. However, active listening on its own is often insufficient for the level of dialogue leadership now demands.

Many leaders believe they are listening effectively, when in practice their attention is only partially engaged. Externally, they demonstrate attentiveness by maintaining eye contact, nodding, and allowing others to complete their thoughts. Internally, however, they may already filtering input through existing assumptions, forming responses, evaluating the speaker’s logic, or seeking the fastest route to resolution.

This creates what can be described as the illusion of listening. While the conversation appears collaborative, it has already been framed in the leader’s mind as a problem to solve or a decision to make.

Such habits are understandable. As Dan Ciampa, a leadership expert, highlights in his book ‘Taking Advice’, experienced leaders are often rewarded for speed, decisiveness, and sound judgment. These capabilities are critical in many contexts, but they can become limiting when conversations call for exploration rather than immediate resolution.

When leaders approach conversations primarily as decision-making forums, questions shift in function. Instead of inviting thinking, they are used – often unconsciously – to test ideas or steer others toward a predetermined conclusion. Over time, this shapes behaviour: individuals learn that agreement is safer than challenge. The consequence is significant. Insights that question assumptions, surface emerging risks, or introduce alternative perspectives are less likely to be voiced. What is lost is not participation, but the depth and diversity of thinking required for effective leadership in complex environments.

The Difference between Asking and Inquiring

In ‘Humble Inquiry: The Gentle Art of Asking Instead of Telling’, Edgar H. Schein defines humble inquiry as the practice of asking questions to which the leader does not already know the answer, driven by a genuine intent to learn from others.

This definition highlights a subtle but profound distinction. Many leaders equate asking questions with being open-minded. However, inquiries can just as easily reinforce traditional authority as they can elicit critical insight.

Before posing a question, leaders should pause for a brief diagnostic: “Am I entering this conversation to decide, or to understand?”. When the objective is to decide, questions often function as instruments of evaluation or persuasion. Conversely, when the objective is to understand, questions serve as invitations to explore.

Humble inquiry requires leaders to remain comfortable navigating dialogue without a predetermined outcome. Many leaders find this ambiguity challenging. A willingness to wander the unknown temporarily inverts the standard hierarchy of knowledge and authority. Rather than defaulting to personal expertise, the leader acknowledges dependence on others for insight and perspective. Such moments signal something powerful to those in the room: “I do not have all the answers. Your perspective matters here.”

When leaders adopt this stance of curiosity and transparency, the interpersonal dynamics of conversation shift. Participants become more willing to share observations, voice concerns, and contribute ideas that might otherwise remain unexpressed. The difference lies not in the phrasing of the question but in the underlying intention.

Humility in Conversations

Edgar H. Schein identifies three forms of humility that govern how leaders engage in conversations: status humility, achievement humility, and dependency humility.

• Status humility acknowledges the influence of hierarchy. Leaders often underestimate the degree to which their positional authority condition dialogue. Even before an inquiry is made, contributors may already be cautious regarding what they will disclose.

• Achievement humility reflects the recognition that others may possess experiences or insights that surpass our own. Leaders who adopt this mindset create the necessary space for expertise to surface from unconventional or unexpected sources.

• Dependency humility is the most transformative. It recognizes that leaders must rely on others to perceive aspects of reality that remain outside their own field of vision. This requires tempering a sense of self-sufficiency and acknowledging that one’s internal perspective is inherently incomplete. Far from a weakness, this represents a strategic orientation toward learning. When leaders operationalize dependency humility, psychological safety increases - teams become less guarded and more willing to share authentic observations, even those that challenge prevailing assumptions.

Under these conditions, dialogue becomes a process of collective sense-making rather than individual evaluation. By removing the fear of judgment, leaders unlock the full intellectual capital of their teams, fostering a culture where the best ideas - not the highest titles - drive the path forward.

Conversations as Thinking Spaces

At the core of humble inquiry lies a fundamental shift in how leaders approach conversations. Too often, leaders treat conversations primarily as decision spaces where options are assessed, arguments are weighed, and a conclusion must be reached. While these spaces are essential for organizational function, moving into a ‘decision orientation’ too prematurely has a subtle, restrictive effect. Participants begin to defend established positions rather than explore emerging possibilities. And ideas become polished arguments rather than tentative, yet valuable, insights. In these moments, the conversation shifts from collaborative thinking to advocacy of viewpoints.

By contrast, when leaders treat conversations as thinking spaces, the objective is not immediate resolution but expanded understanding. Thinking spaces allow participants to articulate incomplete ideas, surface emerging concerns, and connect observations that might otherwise remain fragmented. These environments deliberately accommodate ambiguity and reflection. Within this framework, questions function as catalysts for exploration rather than instruments of judgment. They are not designed to test consensus, but to help the group gain clarity.

A leader might facilitate by asking:

• “What are we observing here that we don’t fully understand yet?”

• “What perspectives or data points might we be overlooking?”

Such inquiries intentionally calibrate the pace of conversation, allow deeper insight and strategic alignment to emerge before a final decision is made.

Slowing down to Think better

Cultivating thinking spaces requires leaders to intentionally moderate their internal conversational pace. In a corporate landscape that prioritizes speed, meetings often move rapidly from data updates to decisive actions, as leaders feel an inherent pressure to demonstrate immediate clarity and direction. However, complex organizational challenges rarely yield their most critical insights under high-speed conditions.

Inquiry introduces a deliberate pause in the conversation rhythm. This interval allows participants to reflect before responding and to consider perspectives that may initially seem counterintuitive or uncomfortable. Far from being an indicator of inefficiency, this deceleration represents a strategic investment in the depth of thought required for superior decision making.

In many organizations, the long-term costs of premature decisions made before underlying assumptions are rigorously explored, far outweigh the cost of an extended dialogue. Humble inquiry, therefore, serves as a vital mechanism for enhancing the quality of collective judgment.

From Conversations to Co-creation

When humility, inquiry, and active listening converge, the character of a conversation shifts fundamentally. Contributors feel sufficiently secure to speak with candor and emboldened to share their authentic observations.

These conversations enable co-creation. Rather than ideas flowing from a singular source of authority, insights emerge through dynamic interaction. Perspectives are synthesized, assumptions are challenged, and innovative possibilities materialize.

While organizations often strive to mandate outcomes like psychological safety, collaboration, and innovation through formal structures, these qualities are actually generated through the calibre of daily interactions through conversations. When leaders adopt a stance of humble inquiry, they signal that insight is decentralized and that learning is a shared endeavour.

This unlocks collective intelligence: the integrated capacity of a diverse group to observe, interpret, and respond effectively to complex environmental challenges.

Leadership Maturity in an Uncertain World

In a global landscape defined by volatility, rapid disruption, and escalating complexity, leaders can no longer rely exclusively on their own expertise. No single individual, regardless of experience or acumen, can fully synthesize the multi-faceted dynamics currently shaping modern organizations.

Humble inquiry acknowledges this reality. By critically examining the intention behind their questions and treating conversations as thinking spaces rather than decision spaces, leaders establish the requisite conditions for deep organizational understanding to emerge. These leaders do not abdicate decisiveness; rather, they enhance it by ensuring that every decision is grounded in a richer, more comprehensive pool of insight.

Furthermore, this practice fosters personal leadership maturity. The discipline of inquiring with radical openness and receiving input with humility expands a leader’s worldview, moderates the ego, and strengthens the cognitive capacity to navigate complexity with wisdom.

Ultimately, humble inquiry is not merely a communication technique. It is a foundational leadership posture that transforms daily conversations into engines of organizational learning, trust, and innovation.

In environments that prioritise speed and certainty, this discipline may appear counterintuitive. Yet, it is precisely this deliberate curiosity that enables organizations and leaders to remain resilient and flourish. The most impactful and meaningful conversations are not defined by the eloquence of the leader’s speech, but by their ability to awaken the collective intelligence around them and their willingness to be influenced by it.

Bibliography and Recommended Readings:

1. Ciampa, D. (2012). Taking Advice: How Leaders Get Good Counsel and Use It Wisely. Harvard Business Review Press.

2. 'Schein, E. H. (2013). Humble Inquiry: The Gentle Art of Asking Instead of Telling. Berrett-Koehler Publishers.

3. ‘Schein, E. H. (2015). Humble Inquiry: The gentle art of asking instead of telling. STS Roundtable.

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About Authors

Samuel Lam

Samuel Lam is Managing Partner of Third Opinion Partners, a global leadership development and organisational development consulting firm. One of the leading practitioners in the field of leadership development in Asia, Sam has created some of the most highly regarded leadership development programs for both Singapore and global clients. He serves as executive coach and adviser to a number of notable CEOs, boards, and senior government officials in Singapore, Europe, and Asia. His major clients included GlaxoSmithKline, Unilever, Prudential, AIA, Lenovo, Hasbro, Philips, Disney, CIMB Bank, and various branches of the Singapore Government. Sam’s expertise spans several areas of leadership development: executive coaching, executive selection, performance improvement of top teams, development of talent pipelines, and assessment of top talent. He co-authored Linkage Inc.’s Best Practices in Leadership Development Handbook (Second Edition, 2009) with Marshall Goldsmith and David Giber.

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Chong Sook Leng

Chong Sook Leng is a Partner and Senior Consultant with Third Opinion Partners. Sook Leng has more than two decades of senior leadership experience with MNC, family owned, public listed, and non-profits. She has successfully led and managed many change initiatives throughout her career. Prior to her appointment at Third Opinion Partners, Sook Leng started her career as an Accountant and pivoted to lead Change and HR functions. She has held multiple C-suite roles in various organizations such as CFO in HSBC Data Processing, MAS Catering, Group HR Director in Paramount Corporation, Change Management in Tokio Marine Insurance and Director Corporate Services in the Iclif Leadership and Governance Centre. Sook Leng is a certified ICF credentialed coach. She works with C-suite executives and senior professionals in the areas of career transitions, leadership effectiveness, and well-being.