I've tested 1.000+ Questions in real companies. These 5 actually work.

Have you ever worked in an organization where the same issues kept surfacing quarter after quarter? Everyone was frustrated, but no one could pinpoint why. Every "solution" just created new versions of the same problem.

I have. For years, I watched smart leaders implement strategic initiatives, process improvements, and cultural programs, only to see the same patterns emerge in new forms. It was like playing organizational whack-a-mole.

That's when I started asking a radical question: What if these persistent problems aren't actually problems to be solved? What if they're the organization trying to tell us something important?

This question launched me into a decade-long experiment. I began testing different types of questions—what I now call "moving questions"—in real organizations facing real challenges. Not theoretical frameworks or workshop exercises, but actual companies with actual stuck patterns.

I tested over 1.000 questions in various industries, including tech startups, healthcare systems, and manufacturing plants. Most didn't work. They either generated surface-level insights or sent teams down analytical rabbit holes that led nowhere.

But five questions consistently produced breakthroughs. Not gradual improvement, but actual transformation. The kind where persistent problems suddenly resolve themselves, and people ask, "Why didn't we see this before?"

Here's what I discovered: Organizations that create breakthroughs aren't the ones with better processes. They're the ones where someone asks a different type of question—one that helps the organization reveal what it's really trying to say.

Here are the five phenomenological Moving Questions that can transform how you work with persistent organizational challenges:

1. "What is actually happening right now?"

This seemingly simple question invites pure phenomenological observation. Instead of analyzing or interpreting, simply observe:

• Where is energy flowing or blocked?

• Who seems connected or disconnected?

• What physical responses are present, such as tension, excitement, or heaviness?

• What patterns are repeating?

The power of this question lies in how it shifts our focus from thinking about the system to directly perceiving it.

2. "What might be a perfect solution for this problem?"

This question fundamentally changes how we view challenges. Rather than viewing problems as failures to be fixed, it recognizes them as creative adaptations that serve a purpose within the larger system.

I worked with an organization that had a persistent pattern of launching initiatives that would gain momentum and then mysteriously stall. When we explored the purpose of this pattern, we discovered an unconscious loyalty to the founding team. Several of these founders had left feeling that their contributions weren't valued. The pattern of stalling initiatives unconsciously honored these excluded founders by ensuring that nothing would succeed without them.

Recognizing this loyalty created space to properly acknowledge the founders' contributions, which naturally resolved the pattern.

3. "Who or what has been excluded and belongs?"

Systems often become stuck when important elements have been excluded or forgotten. These might be:

• People who left under difficult circumstances

• Perspectives that conflict with the dominant narrative

• Historical events that were never properly acknowledged

• Values from the organization's founding that have been lost

• Failed projects or initiatives that weren't honored

A manufacturing company struggled with unusually high turnover in one department. When we explored what might have been excluded, we discovered that the department was formed after a significant layoff several years earlier. The layoff had never been properly acknowledged, creating a pattern in which new employees unconsciously maintained loyalty to their laid-off predecessors by leaving as well.

4. "If this system could speak, what might it be trying to tell us?"

This question encourages us to view the system as a whole instead of focusing on specific elements or issues. It acknowledges that persistent patterns often convey important information about the system's needs.

A healthcare organization was experiencing ongoing conflict between administrative staff and clinicians. When we explored the message of this conflict, we discovered that it highlighted a fundamental tension in their mission that had never been explicitly addressed: the balance between financial sustainability and patient care. The conflict itself wasn't the problem; rather, it made visible an essential tension that needed conscious attention.

5. "What becomes possible if we simply acknowledge what is?"

Perhaps the most powerful moving question is recognizing that the path to resolution often begins not with new actions, but with deeply acknowledging what already is.

• Many organizational challenges persist precisely because difficult truths remain unspoken.

• The impact of past decisions.

• Power dynamics that aren't acknowledged.

• Losses that haven't been mourned.

• Truths about market realities.

• Limitations in resources or capabilities.

I worked with a nonprofit experiencing cycles of burnout and conflict. Once they acknowledged that their mission had expanded beyond their capacity—something that everyone knew but no one had voiced—they naturally moved toward right-sizing their commitments.

Practicing phenomenology and moving questions

How can you bring these approaches into your organization? Here are some practical starting points:

1. Create space for perception

Before rushing to solve problems, deliberately create space to simply perceive what is happening.

• Take time during meetings to observe interaction patterns.

• Pay attention to physical responses and energy shifts.

• Observe where people naturally position themselves in relation to others.

• Notice which topics create resonance or tension.

2. Slow down the analysis

Our analytical minds typically jump in immediately with explanations and solutions. Practice:

• Temporarily suspend your need to understand "why."

• Stay with observation for longer than you feel comfortable.

• Notice when you're interpreting rather than perceiving.

• Be curious about patterns without trying to change them immediately.

3. Experiment with moving questions

When facing persistent challenges, try asking:

• What might this pattern be serving?

• Who or what might be missing or excluded?

• What might this situation be trying to show us?

• What becomes possible if we simply acknowledge what is?

4. Honor What Is

• Before attempting to create change, deeply acknowledge what is already present.

• Recognize the history that has shaped current patterns.

• Honor the positive intent behind seemingly problematic behaviors.

• Acknowledge difficult realities that have been avoided.

• See and respect the existing order of things before trying to change it.

5. Look for natural movement

• Rather than forcing change through willpower or authority, learn to recognize and support the natural movement that emerges when systems are properly understood.

• What natural next steps become clear after proper perception?

• Where does energy naturally want to flow when obstacles are removed?

• What happens when excluded elements are properly included?

• How does the system reorganize itself when the full reality is acknowledged?

The Transformative Potential of Phenomenological Seeing

After years of working phenomenologically with organizations, I'm still amazed by how often transformation happens naturally once systems are properly seen. Many persistent challenges don't require complex interventions; they require a different way of seeing and the right questions to create space for the system's own intelligence to emerge.

By developing our capacity for phenomenological perception and learning to ask moving questions rather than just analytical ones, we access dimensions of organizational life that conventional approaches miss entirely. We see invisible patterns and connections that drive persistent challenges and create conditions where natural movement becomes possible.

In a world of increasing complexity and interconnection, these capacities aren't just helpful—they're essential for navigating the challenges our organizations face with wisdom and grace.

What patterns in your organization might benefit from phenomenological perception? What might become possible if you approached persistent challenges with moving questions rather than analytical ones?