Chapter 2: Problem-Solving Questions

“The formulation of a problem is often more essential than its solution.” — Albert Einstein

When faced with a challenge—whether it’s a technical obstacle, an organizational issue, or a personal dilemma—the questions you ask shape the solutions you discover. Most people rush to solve problems before properly defining them, resulting in treating symptoms rather than addressing root causes. This chapter explores how to use questions to accurately diagnose problems and generate effective solutions.

Questions to Define the Problem Correctly

Before attempting to solve any problem, you must first ensure you’re solving the right problem. These questions help clarify the true nature of the challenge you face.

Essential Questions:

1. “What problem are we actually trying to solve?”
2. “How would different stakeholders describe this problem?”
3. “What would success look like? How would we know the problem is solved?”
4. “Is this a symptom of a deeper issue?”
5. “What’s the cost of not solving this problem?”

Example in Practice:

A software company was struggling with high customer churn. Initial discussions focused on how to improve the product’s features to retain customers. However, when the team asked, “What problem are we actually trying to solve?” and investigated further, they discovered the real issue wasn’t product functionality but poor onboarding. New customers weren’t able to quickly realize value from the software. By redefining the problem, they created a targeted onboarding program that reduced churn by 40%.

Application Exercise: Write your problem statement, then ask three different people to describe what they think the real problem is. Note the differences in perspective and use these insights to refine your problem definition.

Questions that Reveal Root Causes

Many problem-solving efforts fail because they address symptoms rather than underlying causes. These questions help penetrate to the heart of the issue.

Essential Questions:

1. “Why is this happening? And why is that happening?” (Repeat five times)
2. “What conditions allow this problem to exist?”
3. “When did we first notice this problem, and what changed around that time?”
4. “What systems or processes contribute to this situation?”
5. “If this problem could talk, what would it be trying to tell us?”

Example in Practice:

A manufacturing company was experiencing quality issues with a particular product line. Rather than simply instituting more rigorous quality checks (addressing the symptom), the operations manager used the “Five Whys” technique:

• Why are we seeing defects? Because assemblies aren’t meeting specifications.
• Why aren’t they meeting specifications? Because components are inconsistent.
• Why are components inconsistent? Because supplier quality varies.
• Why does supplier quality vary? Because our purchasing policies prioritize cost over consistency.
• Why do our policies prioritize cost over consistency? Because our metrics reward short-term savings over long-term quality.

This root cause analysis led to a fundamental change in procurement policies and metrics that solved the quality issues permanently.

Application Exercise: Select a recurring problem in your work or life. Apply the “Five Whys” technique by repeatedly asking why the situation exists, with each answer forming the basis for the next question.

Questions for Generating Creative Solutions

Once a problem is properly defined, these questions help generate innovative solutions that might otherwise be overlooked.

Essential Questions:

1. “How might we…?” (Framing the challenge as an opportunity)
2. “What would an approach from a completely different industry look like?”
3. “What if we had unlimited resources? What if we had almost no resources?”
4. “What would [specific person or organization known for innovation] do in this situation?”
5. “How have others solved similar problems in completely different contexts?”

Example in Practice:

A city government was struggling with traffic congestion. Instead of defaulting to the usual solution of building more roads, they asked, “How might we reduce the need for people to travel at the same times?” This reframing led to innovative approaches including staggered work hours for city employees, incentives for remote work, and partnerships with major employers to coordinate shift schedules—all significantly less expensive and more effective than road expansion.

Application Exercise: Generate at least 20 possible solutions to your problem using the “How might we…?” framework. Don’t evaluate any ideas until you’ve reached at least 20, no matter how impractical some might seem.

Questions to Test Potential Solutions

Before implementing a solution, these questions help evaluate its likely effectiveness and identify potential pitfalls.

Essential Questions:

1. “What could go wrong with this approach?”
2. “How would we test this solution on a small scale first?”
3. “What would need to be true for this solution to succeed?”
4. “How might this solution create new problems?”
5. “Who might resist this solution, and why?”

Example in Practice:

An educational nonprofit developed a new teaching methodology they believed would dramatically improve student outcomes. Before full implementation, they asked, “How would we test this solution on a small scale first?” They designed a pilot program in five schools with clear success metrics and comparison groups. The pilot revealed that the methodology was highly effective for certain types of learners but created challenges for others. This insight allowed them to refine their approach before the full rollout, ultimately creating a more effective and adaptable program.

Application Exercise: For your leading solution to a current problem, identify at least three assumptions it makes. For each assumption, design a small experiment that could test whether the assumption is valid.

Questions for Implementation Planning

Even the best solution will fail without proper implementation. These questions help ensure successful execution.

Essential Questions:

1. “What’s the smallest first step we could take immediately?”
2. “Who needs to be involved for this to succeed?”
3. “What resources and support will be required?”
4. “What obstacles should we anticipate, and how will we address them?”
5. “How will we measure progress and know if we’re succeeding?”

Example in Practice:

A healthcare system was implementing a new electronic medical records system. Many similar implementations had failed at other institutions due to resistance from medical staff. The implementation team asked, “Who needs to be involved for this to succeed?” They identified influential physicians and nurses from each department and created a clinical advisory group that co-designed the implementation approach. This involvement created ownership among the staff most affected by the change, leading to one of the smoothest EMR transitions in the industry.

Application Exercise: Create an implementation one-pager for your solution that answers all five questions above. Share it with stakeholders to gather input before proceeding.

Case Study: Solving “Impossible” Problems Through Questions

The IDEO Shopping Cart Redesign

In the late 1990s, the design firm IDEO was featured on ABC’s Nightline as they tackled a seemingly mundane challenge: redesigning the shopping cart, which had remained essentially unchanged for decades.

Rather than immediately sketching new cart designs, the IDEO team began with questions that reframed the entire problem:

“Who are all the different users of shopping carts?” This led them to observe not just shoppers but also store employees, maintenance crews, and even children who rode in the carts.

“What are the unmet needs in the current shopping experience?” They watched real shoppers struggle with carts, interviewed store managers about theft and damage issues, and identified numerous pain points in the current design.

“What if the cart wasn’t a cart at all?” This question liberated them from the constraints of traditional thinking about what a shopping cart should look like.

The process continued with questions focused on solution generation:

“What if we separated the basket from the wheels?” “How might we make the cart modular?” “What if the cart could nest differently for storage?”

Their questioning approach led to a revolutionary design featuring a modular basket system, scannable items, removable child seats, and easier maneuverability—all addressing needs that traditional cart manufacturers had never considered because they hadn’t asked the right questions.

The Lesson:

By using questions to reframe the problem and explore it from multiple perspectives, IDEO was able to see possibilities invisible to others who had accepted the standard definition of what a shopping cart is and should be. Their approach demonstrates how questions that challenge assumptions can lead to breakthrough solutions, even for seemingly intractable problems.

Chapter Summary: Problem-Solving Question Framework

Effective problem-solving follows this questioning sequence:

1. Definition Questions: Ensure you’re solving the right problem
2. Root Cause Questions: Identify the underlying issues, not just symptoms
3. Ideation Questions: Generate creative potential solutions
4. Evaluation Questions: Test the viability of proposed solutions
5. Implementation Questions: Plan for successful execution

This framework ensures that you don’t waste resources solving the wrong problem or implementing ineffective solutions. By disciplining yourself to move through these questions in sequence, you’ll develop more robust solutions to even the most challenging problems.

Five Questions to Transform Your Problem-Solving:

1. “What problem are we actually trying to solve?”
2. “What’s the underlying cause of this situation?”
3. “How might we approach this differently?”
4. “What would need to be true for this solution to work?”
5. “What’s the smallest first step we could take to move forward?”

In the next chapter, we’ll explore how questions can transform leadership, allowing you to inspire others, build trust, and develop your team’s capabilities through the art of asking rather than telling.

Next Page: Chapter 3: Leadership Questions