Question-Based Supervision: Moving from Telling to Asking
I met with a nonprofit client seeking shared resources to help a team of managers from diverse job backgrounds come together, feel good about their roles, and receive professional development related to supervision. Most managers aren’t in their roles because they trained as supervisors; they're there because they were really good at their jobs and moved into management without much leadership development in that area. Relatable?
That conversation led to this resource, designed to help supervisors support staff autonomy through inquiry-based approaches. If you’re a nonprofit leader supporting supervisors or fellow leaders, this resource may be useful to you.
The Challenge: From Directing to Developing
When we are short on time and patience, we often want to get things done the way we would do them, and we direct our staff accordingly. We may have seen this modeled by other supervisors. We may also work in organizations where directive supervision is the default.
And if we’re looking to develop our team and strengthen our supervision skills, there is often more power in asking the right questions than in providing direct answers.
Two Supervision Frameworks
One non-profit I worked with is education-focused and has therapists on staff, so the employees' backgrounds are either educational or therapeutic.
Below are a few defining characteristics of each supervision style.
Therapy-Informed Supervision
Emphasizes parallel process - supervising others the way you'd want to be supervised
Uses reflective questioning techniques
Focuses on building capacity through guided discovery
Education-Informed Supervision
"See one, do one, teach one" modelObserving peer practice → reflection → opportunities for independent practice
Learning through doing, with scaffolded support
Direct instruction when needed, followed by practice and feedback
Both therapy-informed and education-informed supervision offer valuable tools for developing people. What this team needed was a shared way to integrate these approaches in practice. They needed a way to use questions not as a passive alternative to leadership, but as an active strategy for building their staff's skills, confidence, and autonomy.
This integration began by clarifying a small set of principles for question-based supervision.
Helping this team create some key principles for question-based supervision
When I worked with this team, the goal wasn’t to replace expertise or eliminate direct instruction altogether. It was to help them build a shared supervision language that could hold both clarity and curiosity, especially across different professional backgrounds.
Because this group included leaders trained in both educational and therapeutic models, we focused on creating a set of simple, repeatable principles that could support inquiry-based supervision without feeling abstract or overly theoretical. These principles were designed to help supervisors slow down just enough to shift from solving problems for staff to developing capacity alongside them.
Before introducing specific questions, we spent time establishing a shared understanding of what question-based supervision requires in practice.
Setting the Frame
Establish observation and reflection as core practices
Create opportunities for skills practice in low-stakes environments
Build "muscle memory" through repeated practice
Role-play challenging scenarios
Effective Questioning Strategies
Structure: Questions that start with “what” or “how,” remain open-ended, and typically contain fewer than seven words (Love letter to the movement, Using a coaching approach to healing, justice and liberation. Sarah Jawaid and Damon Azali Rojas)
Examples include:
"What do you notice here?"
"How might you approach this?"
"What questions would you ask?"
"How does this connect to our goals?"
Together, these principles created a foundation for asking better questions. I encouraged them to see these as habits to practice, rather than techniques to deploy. Once the frame was set, we turned to the kinds of questions that help supervisors reflect, prioritize, and stay aligned with both people and purpose.
Essential Reflection Questions for Supervision
Inquiry-based supervision works best when questions are doing real work: clarifying purpose, surfacing assumptions, and guiding thoughtful action. The reflection questions below are designed to support supervisors in stepping back from urgency and into intention, without losing momentum.
Rather than serving as a checklist to move through in every conversation, these questions can be used flexibly: in one-on-one supervision, team meetings, planning sessions, or moments of tension. They help supervisors examine not just what needs to be done, but why, how, and with whom.
Organized by focus area, these questions support both accountability and care. These two elements are often treated as opposites, but are deeply connected in effective supervision.
Each set of questions below supports a different aspect of supervision, from clarifying purpose to strengthening accountability and planning next steps.
Process Questions
Why this? (Why are we focusing on this issue/skill?)
Why now? (What makes this timely?)
Why us? (What's our role in this?)
Why does it matter? (What's the impact?)
People and Accountability
Who are we accountable to?
Who has the skills we need?
Who is actually ready to do this work?
Who supports our growth?
Methods and Impact
How will we approach this process?
How can we embody our values?
How will this create meaningful change?
Practical Planning
When do we need this completed?
What can we accomplish together?
What energizes and motivates us?
What serves our people best?
Used consistently and in the appropriate scenarios, these questions can help shift supervision from reactive problem-solving toward shared sense-making. They can also create space for supervisors to notice their own default habits, which brings us to an important self-reflection many leaders find helpful when adopting a question-based approach.
Management Style Reflection: Directive or Collaborative
Many supervisors move fluidly between directive and collaborative approaches, often without naming when or why. This reflection invites you to pause and examine the patterns shaping your supervision style, especially under pressure.
Directive approaches tend to surface when time is tight, stakes feel high, or clarity feels urgent. Collaborative approaches, by contrast, emphasize shared understanding, collective problem-solving, and trust-building over time. Neither approach is inherently “right” or “wrong”; the work lies in becoming more intentional about which mode you’re operating in and when.
The questions below are meant to support that awareness and help you identify small, concrete shifts toward more collaborative inquiry where it makes sense.
Consider the questions below as prompts for your own supervision practice:
What parts of your supervision style feel more directive?
What concrete steps could bring more collaborative inquiry to your supervision?
What barriers prevent you from implementing this approach? (organizational culture, time constraints, safety concerns, etc.)
Reflecting on your supervision style can surface both possibilities and constraints. If you’re looking to deepen this work or explore additional tools and frameworks that support inquiry-based leadership, the resources below offer practical guidance across management, education, and systems-oriented approaches.
Recommended Resources
Shifting supervision practices rarely happens in isolation. The following resources offer complementary frameworks, tools, and reflections that support leaders in moving from directive management toward more relational, inquiry-driven approaches.
Some focus on day-to-day management skills, others on educational questioning strategies or systems-level change. Together, they provide multiple entry points, whether you are supporting new managers, refining your own leadership practice, or navigating complex organizational contexts.
Management and Leadership
The Management Center
"Important Things for New Managers to Know"
"Managing Managers Toolkit"
"Conspire and Align" framework with reflection questions
Educational Approaches
"Asking Effective Questions" - Chicago Center for Teaching and Learning
Note: Originally designed for higher education but adaptable to workplace supervision
Social Justice and Systems Approaches
Love Letter to the Movement: Using a Coach Approach for Healing Justice and Liberation by Sarah Jawaid and Damon Azali-Rojas
Holding Change: The Way of Emergent Strategy Facilitation and Mediation by adrienne maree brown
Excellent question frameworks (page 33)
Comprehensive approach to collaborative leadership
Emergent Strategy by adrienne maree brown
"Intentional Adaptation" chapter
Self-assessment tools for building more fluid, caring approaches to supervision and leadership
This resource was created to support supervisors in shifting from directive to developmental approaches, particularly in environments where both autonomy and safety are priorities.
