As 2025 begins, I watch the winter light stretch incrementally longer. From my new home in a new state, these early January moments invite both reflection and possibility. While many focus on personal health resolutions, I find myself considering a different kind of wellbeing: the health of our organizations.

In the world of non-profit arts, our stance is often solely reactive. Cards are dealt and we “make it work.” We are good at making it work. We pride ourselves on it. We have learned to write strategic plans for 3, 5, 10, even 15+ years in order to satisfy a number of well-meaning stakeholders. In recent years, we have learned to pivot–away from these well-laid plans and even back again. We are passionate, we are resilient, we are crafty, and much more. But are we healthy? And by that, I mean, are our organizations healthy? How do we know? What are the markers?

If we are our own primary care givers, how are we assessing our organizational health?

Defining Organizational Health
What is a healthy organization? It’s a question many leaders wrestle with, especially in the arts sector, where resources are often stretched, and the demands on teams are high. In the work we do at Tom O’Connor Consulting Group (TOCG), we’ve come to understand that healthy organizations are not born but built and rebuilt through intentional reflection, collaborative visioning, and bold decision-making. Central to this process is embracing and exploring "next practices"—innovative approaches that move beyond best practices to address emerging challenges and opportunities in a rapidly changing world.

One essential tool in developing these next practices is inquiry-based practice. Developed as an educational approach that emphasizes active, student-centered learning through investigation and questioning, inquiry-based practice in organizations is a systematic approach to strategy and problem-solving where teams actively investigate challenges through questioning, evidence gathering, and collaborative experimentation, rather than relying on top-down directives. Leaders facilitate this work by creating environments that encourage exploration and learning, leading to strategies and solutions grounded in real organizational and market insights.

In turn, this approach helps organizations critically examine their assumptions and chart new paths forward. At its core, inquiry-based practice is about asking the right questions. It’s a deliberate process that challenges the status quo, explores possibilities, and uncovers the hidden tensions that often shape organizational culture, strategy, and structure. By embedding inquiry into daily practices, organizations can foster resilience, innovation, and sustainability—qualities essential for long-term success.

The Power of Questions
One of the most transformative questions we pose is: If you had all the money you needed, how else would you measure organizational health? This shifts focus from financial metrics to impact-driven metrics, and challenges leaders to envision true thriving. Organizations can build strength through three key pillars: People, Strategy, and Structure. Each is strengthened through inquiry-based approaches that keep missions dynamic and responsive. Inquiry-based practice can be woven throughout an organization's natural rhythms and planning cycles. Some examples to consider:

Annual board retreats exploring core mission questions
Quarterly leadership meetings examining strategic assumptions
Monthly team gatherings sharing learning across departments
Weekly one-on-ones that probe individual growth and challenges

Leaders might ask: What unexpected successes did we have this quarter and why? How do our current structures enable or inhibit innovation? What voices are we not hearing? These regular touchpoints transform inquiry from an occasional exercise into an organizational muscle that strengthens resilience and adaptability.

To embed this practice deeply, we recommend an annual question-setting process where leadership teams identify 3-4 core questions that will guide exploration throughout the year. These questions cascade through every level: shaping board meeting agendas, focusing leadership team discussions, informing departmental planning, and enriching individual development conversations. For example, a core question like How might we better serve our community's evolving needs? could manifest as strategic planning discussions at the board level, program innovation workshops with leadership, cross-departmental community listening sessions, and individual goal-setting around community engagement. This intentional alignment ensures that inquiry becomes a shared practice rather than an isolated exercise.

People: The Heartbeat of Every Organization
In most nonprofits, the largest budget line is dedicated to people—both their intellectual capacity and their passionate drive. Yet, how often do organizations take a step back to truly value and nurture both? While not every choice can or should be made by committee, leaders must thoughtfully determine where collective intelligence and emotional investment intersect. Suggested questions include:

Are our staff members engaged both intellectually and emotionally in their work?
How do we honor both technical/analytical skills and heartfelt commitment? Where do we create space for both problem-solving and connection?

By fostering a culture that values both sharp thinking and deep caring organizations can create environments where both minds and hearts thrive. This means establishing protocols that respect both analytical processes (strategic planning, program evaluation) and emotional intelligence (community building, mission alignment). Regular inquiry surfaces both cognitive blind spots and emotional undercurrents, building a workplace culture focused on shared purpose.

Strategies: Intentional Choices for Impact

"If you have more than three priorities, you have no priorities."

-Brené Brown

Healthy organizations embrace this wisdom by crafting clear, intentional strategies that reflect their values and goals. The challenge lies not just in setting priorities, but in maintaining the discipline to honor them. Key questions we encourage leaders to ask include:

Have we defined what we will do—and more crucially, what we won't do?
Are our programs designed to meet the needs of our communities?
How do we measure true impact beyond basic activity metrics?

The most effective strategies create both focus and freedom—focus through clear priorities, and freedom through explicit permission to say no to distractions. When paired with inquiry-based practice, impact metrics become dynamic tools for learning rather than static measures of success. These explorations also help organizations move beyond the comforting illusions of busy-ness and urgency to the challenging reality of meaningful change and authentic impact.

Structures: Clarity and Flexibility
Frederic Laloux, in Reinventing Organizations, describes how healthy organizations move away from rigid hierarchies toward fluid systems of distributed authority and collective intelligence. However, flexibility without clarity creates chaos. The key is designing structures that provide both stability and adaptability. Core questions for structural assessment:

Does our organizational chart reflect how we actually work?
Does our budget truly reflect our priorities?
How might our structure better serve our mission?
What would it look like if our structure fully supported our strategy?

These questions help transform structures from rigid frameworks into dynamic tools that evolve with organizational needs. The most successful structures balance standardization with flexibility, creating enough consistency for efficiency while maintaining space for innovation and adaptation. They become invisible enablers of impact rather than visible barriers to progress.

The Role of Vulnerability in Inquiry-Based Practice
Vulnerability stands at the heart of truly inquiry-based organizational practice, yet it remains one of the most challenging capacities for leaders and teams to embody. Asking these questions requires vulnerability. It means admitting that we don't have all the answers and being open to feedback, critique, and change. Creating a courageous space for these conversations is critical, which is why TOCG emphasizes agreements like, No one person in the room is a single point of truth. At its core, the willingness to ask deep questions emerges from the fundamental acknowledgment of multiple perspectives. This recognition opens the door to a more nuanced and collective approach to organizational health.

The journey toward vulnerability-based leadership demands both steadfast commitment and practical wisdom. Leaders open new possibilities for transformation by bringing their full humanity to the work—sharing not only their established wisdom and expertise, but also their active wrestling with uncertainty and emerging understanding. This openness creates a powerful resonance throughout the organization, especially when paired with intentionally designed spaces for collective reflection where missteps become fertile ground for exploration. Critical to this journey is the thoughtful acknowledgment of inherent power dynamics—not to eliminate them entirely, but to consciously minimize their limiting effects on authentic dialogue and exploration.

Moving from aspiration to action requires concrete practices that make vulnerability accessible and actionable. Organizations might establish regular learning forums where teams gather not to showcase successes but to mine the rich territory of challenges and unexpected discoveries. Decision post-mortems become opportunities for collective sense-making rather than exercises in accountability, examining both triumphs and setbacks with equal curiosity. Perhaps most importantly, clear protocols for raising concerns and navigating conflicts transform vulnerability from an individual risk into a shared workplace culture and organizational capacity.

What happens when an organization fully embraces vulnerability? The emergence of a different kind of organizational health—one where questions flow as naturally as answers, where uncertainty becomes a gateway to innovation rather than a source of anxiety. In this environment, the courage to be imperfect doesn't just drive improvement; it fundamentally reshapes how teams relate, learn, and evolve together. This dynamic mirrors the very essence of artistic practice itself—where makers step daily into the unknown, embracing uncertainty as the wellspring of innovation. Just as artists must expose their unfinished works, raw ideas, and emerging visions to the scrutiny of peers and audiences, so too must arts leaders create spaces where organizational vulnerability can flourish.

The result is a living system where vulnerability transcends its status as a leadership buzzword to become the central to organizational practice, echoing the creative risk that defines great art-making. When leadership practice aligns with artistic practice in this way, organizations foster a deeper resilience—one that grows from the shared understanding that both artistic practice and organizational culture demand we stand bravely in our not-knowing, trusting in the generative power of open-hearted inquiry and collective exploration.

Next Steps for Leaders
For leaders looking to integrate inquiry-based practice into their organizations, we recommend starting with these three reflection points:

People: What steps can we take to demonstrate our commitment to community care within our staff?
Strategies: How do we ensure our decisions are intentional and transparent to our stakeholders?
Structures: Are our systems supporting our mission, or are they holding us back?

Rather than letting these questions remain theoretical, here are some suggestions for activating them as core to your organization's cycles.

Possible Cycles for Inquiry

Monthly Practice
- Dedicate focused time in leadership meetings for structured questioning
- Rotate responsibility for crafting core inquiries
- Document insights for quarterly synthesis
Quarterly Deep Dives
- Convene cross-functional teams to examine one pillar (People/Strategy/Structure)
- Create action plans with clear ownership and accountability
- Build feedback loops that inform next quarter's exploration
Annual Integration
- Synthesize the year's inquiry insights to inform strategic planning
- Identify patterns and persistent challenges
- Design specific touchpoints for the coming year's learning journey

Close each cycle with three essential questions: What have we learned, what will we change, and how will we hold ourselves accountable? This transforms inquiry from an abstract exercise into an engine for organizational growth.

Edie Demas, VP of Organizational Strategy, at the LA Balloon Museum

A Healthier Future
Healthy organizations don't happen by accident. They emerge from the deliberate intersection of rigorous inquiry, sustained commitment, and the courage to imagine beyond inherited constraints. By embracing inquiry-based practice as foundational, leaders can unlock their organization's potential, nurturing not just a culture of belonging but an ecosystem where innovation and care flow naturally from shared purpose.

In the nonprofit arts world, we've long mastered the art of adaptation—pivoting, reacting, and finding creative solutions in the face of uncertainty. Yet true organizational health demands more than this hard-won resilience; it calls for a fundamental shift from reactive survival to proactive flourishing. What if we approached organizational well-being with the same nuanced attention we bring to creative practice? What if we examined our structures, strategies, and culture with the same depth we bring to artistic inquiry? Most crucially, what if we committed to discovering next practices that could carry us beyond the comfortable territory of "making it work" into the fertile ground of what's freshly possible?

At TOCG, we believe that inquiry transcends its role as a mere tool to become a transformative mindset—one that empowers arts organizations to not just navigate but actively shape an ever-changing world. As we step into this pivotal moment, the opportunity before us extends beyond mere organizational sustainability. By embracing inquiry-based practice and nurturing the conditions for collective imagination, we can cultivate arts organizations that don't just endure but genuinely thrive—organizations ready to meet tomorrow's challenges with creativity, wisdom, and renewed purpose.

Edie Demas is the Vice President, Organizational Strategy of Tom O’Connor Consulting Group. TOCG is a NYC-based consultancy for arts and cultural institutions and leaders, offering two complementary services: organizational strategy and executive search. Edie has led organizational strategy and change projects for a range of artistic genres and settings, including producing, presenting, and academic institutions; she has also led Executive and Senior leadership searches for a range of organizations and has spent 20+ year in arts leadership across a variety of art forms and settings, ranging from performing arts venues to festivals to community and academic/school environments. She served most recently as Executive Director of the Jacob Burns Film Center in New York. Edie resides in the DC metro area and maintains strong ties to NYC’s robust network of arts leaders. In 2019, she was recognized as a Leading Woman in Business by 914INC and in 2018, she received a Responsible 100 Award from City and State Media, honoring New York's most outstanding and socially responsible thought leaders and visionaries making transformative change. She holds an MA and PhD from NYU’s Program in Educational Theatre.