Fostering a Culture of Deep Inquiry and Listening

Most, if not all, of the issues and challenges facing leaders and organizations point to the need for a culture of integrity, leadership, adaptability, creativity, engagement, respect, and camaraderie. Each of these, in turn, relies upon a foundation of skillful communication.

For many executives, issues such as building a culture of ethics, social responsibility, and sustainability are paramount, along with traditional priorities of financial health, quality, productivity, and furthering of the company’s vision and values. The realization of any and all of these issues relies upon a different level of attention to deliberate, strategic, and skillful communication.

The degree to which leaders and transformation-agents embody, communicate, foster, and require such skillfulness will define the degree of success the organization will have in meeting their greatest challenges, and aligning action with the vision and values of the organization. By leading into a culture of deep inquiry and skillful listening, leaders can strengthen the foundation from which all else stems.

To do so requires shifting the culture, which, as most of us know, is much easier said than done. The entrenched culture is strong and stubborn, and — as if a form of Artificial Intelligence (AI) made up of pre-existing systems, structures, beliefs, expectations, and old stories (history) — seems to fight back against attempts to change it, and more often than not, stifles or prevents attempts at change.

Conscious transformation to a culture of deep inquiry and listening requires us to step outside of our assumptions and dearly held processes of change, which can become yet one more agent or symptom of dysfunction. As Albert Einstein said, we can’t resolve our problems by using the same ways of thinking and acting that got us where we are.

How do we begin, then? By taking an honest and penetrating look at how dysfunction shows up within us, our group, and our organizational culture; and then seeking nontraditional sources of insight about system evolution.

Evidence of dysfunction that needs to be transformed

Evidence of dysfunction in need of conscious transformation can be found in organizations large and small, for-profit and nonprofit. In order to envision and consciously move towards the ideal, we must first have a clear idea of how dysfunction manifests in and affects the organization. Common scenarios of dysfunction include:

  • Two departments compete instead of collaborate, resulting in millions of dollars in losses due to inefficiency, redundancy, mistakes, and missed deadlines.
  • A communication and HR/OD department leader knows that communication and culture are vital to the organization’s success, because lapses have caused the company millions. Yet he feels excluded from the leadership table and reduced to technician rather than strategic advisor status.
  • Project team members rush from one meeting to the next, feeling perpetually disorganized and late, and routinely find themselves bogged down in miscommunication and mistakes that stem from being too distracted or too entrenched in routine to listen.
  • A project management group is always at the center of controversy due to missed deadlines, blown budgets, errors, and a poor reputation with client-departments, yet feels powerless to shift it because of an adherence to a particularly faulty project management process favored by an executive.
  • A company emphasizes its “customer care” and “world-class service,” yet customer satisfaction rates are low, and complaints and defection rates are high.
  • A culture of fear and cut-throat competitiveness foster major ethical violations, resulting in substantial financial losses, law suits, and damaged reputation.
  • In a culture of disempowerment, leaders and managers hoard information, resulting in low morale, high turnover, sluggish momentum, and no creativity.
  • A large-scale corporate initiative spins out of control because employees don’t feel free to question leaders, and thus don’t raise issues crucial to the initiative’s success.

These are just a few scenarios that are common in many organizations; indeed, these are real-world examples. At the center of all of these issues is dysfunction in the organizational culture; at the root of the dysfunction is habitual and systemic dysfunctional communication.

Returning to the fundamentals

Healthy companies and robust, positive transformation don’t stem from clever project charters, attractive values statements gracing the company lobby, or the number of days spent in meetings and retreats. They start from within the organization’s leaders and influencers, is catalyzed in each employee, and radiates outward to influence how individuals, groups, and the company as a whole operate and interact.

By revisiting five fundamentals, an organization can consciously reorient and create the culture of deep inquiry and listening that will allow alignment between the values of integrity (ethics), creativity, respect, effectiveness, and efficiency. The five foundation stones of a culture of deep inquiry and listening are:


Any conscious transformation starts with a clear, shared vision, and intention to refine mastery and take steps towards true excellence and alignment with espoused organizational values. While it’s optimal if the leadership team intends and embodies the change to a culture of deep inquiry and listening, it can also be adopted and modeled by any individual, small group or department. In fact, individuals and small groups are more able to adopt such initiatives than trying to make it a top-down, organization-wide initiative. Thus, working in micro-scale “pods of mastery” that can in turn affect a critical mass is optimal.


Once the individual or group has intended to move towards greater facility for a culture of deep inquiry and listening, they need to explore — inquire into — what needs to shift in individual or group habits (particularly unskillful habits) to allow the cultivation of more skillful inquiry and listening. This may include small-group, experiential training, refreshers, open space (reflection, meditation, etc.) that creates the calm mind necessary for deeper communication skillfulness.


Engaging in a deeper level of inquiry can seem daunting in an organizational culture-default of non-inquiry and frenzied activity. Champions of the culture of deep inquiry and listening must have both the courage of their convictions and the confidence to integrate deeper inquiry into the daily activities of the organization. Courage, confidence, and stamina are founded upon the shared intention, supporting practices, and ideally by the absolute commitment of the organization’s leaders. But most of all, to follow through on deep inquiry and listening requires clarity about the individual’s vision of why and how greater skillfulness and mastery matter to him, the group, the organization, and those affected by it.

Deep inquiry

Deep inquiry isn’t just about asking questions; it’s about asking the right questions, at the right time, in a skillful manner, until one has the complete picture and understanding needed to take the right next step, which leads to more optimal outcomes. Deep inquiry goes well beyond the basic “nodding, and parroting back” technique in Listening 101 classes, because it bridges a higher concept (vision, values, goal) and right action or result. It leaves “what’s known” or “how it’s always been done,” and opens up an exploration into best possibilities and potentials. Deep inquiry can also uncover the secrets and “sacred cows” that lurk in the shadows, which can be threatening at first. As such, the practice requires presence, attention, and patience, rather than being frenzied, preoccupied, and attached to pre-existing answers.

Deep listening

Just as deep inquiry goes beyond the superficial and habitual, deep listening is both receptive to what is truly being said, as well as what’s not being expressed and what needs to be shared or understood. Deep listening requires a calm, receptive state of mind, rather than a frantic, hurried, preoccupied one. From the former, clarity and precise understanding are possible; from the latter, habitual routine, assumptions, and miscommunications often result. Deep listening mastery may require not just a greater skillfulness of the techniques, but also supportive practices to help cultivate receptivity and intuition.

How might these five fundamentals “show up” within the everyday life of the organization, fostering a higher level of effectiveness and values-action alignment? A facility for skillful inquiry and listening can be useful for more deeply exploring both high-level and action-oriented meanings for values, ethics, creativity, excellence, and collaboration. Such exploration unpacks unaligned assumptions about what such themes mean, and consciously defines and connects jargon to meaningful action.

Living into new culture

There is much talk of ‘social capital,’ ‘cultural capital’, ‘viral marketing’, and other such trendy buzz-phrases, and it’s easy for these to become yet another initiative whose primary points and intentions get overpowered by the pre-existing system and culture — the way things have been done.

So while the temptation is to make this yet another corporate initiative, and kick the existing machinery and process into gear to “charter, launch and execute” it, contemporary leaders would do well to learn from several unorthodox (non-corporate) examples of how more organic, dynamic, evolutionary, and “under the radar” movements have ultimately shifted large, entrenched and intractable systems — “The Power of the Powerless,” an essay by Vaclav Havel on the “under the radar” efforts that resulted in the fall of communism); A.T. Ariyaratne’s Sarvodaya movement; nontraditional but powerful concepts of change found in indigenous and mystical thought; and some of the accounts shared by Malcolm Gladwell in The Tipping Point: How Little Things Can Make a Big Difference.

Ultimately, this sort of qualitative transformation, or evolution, begins within a small group of strongly committed individuals — both independently and in “pods of mastery” — and ripples out organically, strongly intended but loosely managed, influencing subtle shifts that create a powerful wave.

This article was originally featured at Ivy Sea Online and is reprinted with permission.