The Art of Inquiry: Transforming Cities Through Powerful Questions

If leadership had a secret weapon, it would be the question. Not just any questions, but the right questions, asked at the right time, in the right way. For city managers, mastering the art of inquiry isn’t just about gathering information – it’s about unlocking innovation, building consensus, and transforming how your municipality approaches challenges.

The Question Crisis in Municipal Leadership

Most city managers are drowning in questions:

• Elected officials demanding answers
• Citizens seeking explanations
• Staff looking for direction
• Media requiring statements
• Stakeholders wanting updates

In this pressure cooker environment, we often fall into the trap of rushing to answers. But as Markova and McArthur reveal in “Collaborative Intelligence,” this rush to resolution might be our biggest mistake. The most effective leaders aren’t the ones with all the answers – they’re the ones who know how to ask the questions that unleash their team’s collective wisdom.

The Four Questions That Transform Cities

1. Illuminating Questions

Purpose: Reveal hidden assumptions and uncover root causes

Example Scenarios:

• When a project is stuck: “What assumptions are we making about this challenge that we haven’t examined?”
• During budget discussions: “If resources weren’t a constraint, what would be the ideal solution?”
• In team conflicts: “What does success look like from each perspective?”

Real-World Application: Imagine your downtown revitalization project is meeting resistance. Instead of asking “Why are people opposing this?” try:

• “What does a thriving downtown mean to different stakeholders?”
• “How might this change affect different community members?”
• “What concerns haven’t we heard yet?”

2. Alignment Questions

Purpose: Build consensus and create shared understanding

Example Scenarios:

• In strategic planning: “What would make this a win for everyone involved?”
• During policy development: “How does this align with our core values?”
• In cross-departmental projects: “What does each department need to succeed?”

Real-World Application: When departments are siloed, transform the conversation:

• “How might this initiative help each department achieve its goals?”
• “What would make collaboration worth the extra effort?”
• “What shared success could we create together?”

3. Action Questions

Purpose: Move from discussion to implementation

Example Scenarios:

• After brainstorming: “What small step could we take tomorrow?”
• In project planning: “Who needs to be involved to make this work?”
• During change initiatives: “What support do you need to make this happen?”

Real-World Application: When implementing a new technology system:

• “What’s the smallest version we could test first?”
• “Who are our early adopters, and how can they help?”
• “What quick wins would build momentum?”

4. Learning Questions

Purpose: Extract insights and build institutional knowledge

Example Scenarios:

• After project completion: “What surprised us about this process?”
• During evaluations: “What made the difference between success and failure?”
• In innovation efforts: “What can other departments learn from this?”

Real-World Application: After a successful community engagement initiative:

• “What elements could we replicate in other projects?”
• “What assumptions did we challenge?”
• “How did our approach evolve as we learned?”

The Question Framework for Municipal Leaders

Before Critical Conversations

1. Prepare Your Questions:
   • What do you need to learn?
   • What assumptions need testing?
   • What possibilities need exploring?
2. Structure Your Approach:
   • Open with broad, perspective-gathering questions
   • Move to specific, detail-oriented questions
   • Close with action-oriented questions
3. Create Safety for Honest Answers:
   • Acknowledge the complexity
   • Welcome different perspectives
   • Show genuine curiosity

During Key Moments

In Council Meetings

Instead of: “Does anyone have concerns?” Try:

• “What aspects of this proposal need more exploration?”
• “How might this impact different parts of our community?”
• “What would make this proposal stronger?”

In Staff Meetings

Instead of: “Any questions?” Try:

• “What’s unclear about our direction?”
• “What obstacles do you anticipate?”
• “What resources would help you succeed?”

In Community Engagement

Instead of: “What do you think?” Try:

• “How would this change affect your daily life?”
• “What opportunities do you see that we might have missed?”
• “What would make this work better for your neighborhood?”

Moving from Questions to Impact

The art of inquiry isn’t just about asking better questions – it’s about transforming how your municipality thinks, works, and innovates. As you develop your questioning skills, you’ll notice:

• Meetings become more productive as different perspectives emerge naturally
• Solutions become more innovative as assumptions get challenged constructively
• Teams become more engaged as they feel genuinely heard and valued
• Projects move faster as real obstacles get identified and addressed early
• Relationships strengthen as understanding deepens across departments

Remember, every significant municipal breakthrough begins with a question. The challenge isn’t finding the right answers – it’s learning to ask the questions that unlock your team’s collective wisdom and move your city forward.

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Transform Your Municipal Culture in 2025

Understanding the power of questions is just the beginning. The Municipal Leadership Development Circle (MLDC), launching January 2025, provides a comprehensive environment where you’ll master the art of inquiry alongside other municipal leaders who are committed to transformation.

Through daily content, experiential learning, and peer collaboration, you’ll develop the confidence and competence to ask the questions that unlock your team’s potential and drive your city forward. Join a community of leaders who are learning to harness the power of inquiry to build more innovative, collaborative, and effective municipalities.

Discover How the MLDC Can Transform Your Leadership

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Seth Winterhalter is President of HaltingWinter Municipal Solutions, dedicated to making stronger cities through stronger leaders. Through executive coaching, consulting, and the Municipal Leadership Development Circle (MLDC), HaltingWinter helps city managers and municipal leaders transform their leadership impact and their organizational culture.