Asking the Right Questions - A Guide to Getting Better Results

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Chapter 5: Identifying Assumptions

“The questions we ask are often based on assumptions we don’t even know we’re making.” — Peter Block

Every question contains assumptions. Some are obvious, some are hidden, and some are so deeply embedded in our thinking that we don’t even recognize them as assumptions. Before you can ask truly powerful questions, you must first become skilled at identifying and examining the assumptions that shape your thinking.

The Layers of Assumptions

Assumptions exist in layers, from the most obvious to the most deeply hidden:

Layer 1: Explicit Assumptions
These appear directly in the wording of a question.

Layer 2: Contextual Assumptions
These relate to the circumstances in which the question is asked.

Layer 3: Structural Assumptions
These relate to how systems, organizations, or relationships are understood to work.

Layer 4: Paradigmatic Assumptions
These are the deepest assumptions, related to worldviews and fundamental beliefs about reality.

Questions to Uncover Your Own Assumptions

The first step in mastering powerful questions is learning to identify the assumptions in your own thinking.

Essential Questions for Self-Examination:

  1. “What must be true for my question to make sense?”
  2. “What alternatives am I not considering because of how I’ve framed this issue?”
  3. “What would someone from a completely different background or field ask about this situation?”
  4. “What words in my question contain implicit value judgments?”
  5. “If I reversed my main assumption, what new questions would emerge?”

Example in Practice:

A product manager was struggling with the question, “How can we get users to spend more time on our app?” When she asked herself, “What must be true for this question to make sense?” she realized she was assuming that more time spent in the app equaled greater user value. By challenging this assumption, she reframed her question to “How can we create more value for users in less time?” This led to a completely different product strategy focused on efficiency rather than engagement.

Application Exercise: Take a question you’re currently wrestling with and list at least five assumptions embedded in it. For each assumption, ask: “Is this necessarily true? What if the opposite were true?”

Questions to Surface Others’ Assumptions

When working with others, identifying their unspoken assumptions can be transformative for communication and problem-solving.

Essential Questions to Surface Others’ Assumptions:

  1. “What would have to be true for your suggestion to be the best approach?”
  2. “Can you help me understand what led you to that question?”
  3. “If we knew for certain that [assumption] wasn’t true, how would that change our approach?”
  4. “What experiences have shaped your thinking on this issue?”
  5. “If we were to approach this from a completely different perspective, what might we consider?”

Example in Practice:

During a strategic planning session, a team was deadlocked on whether to pursue a new market opportunity. The facilitator asked, “What would have to be true for this market entry to be successful?” This question helped the team articulate their different assumptions about customer needs, competitive response, and internal capabilities. Once these assumptions were explicit, the team could test them rather than argue based on unstated beliefs.

Application Exercise: In your next team discussion about an important issue, when you notice disagreement, ask: “What assumptions might each of us be making that are leading to different conclusions?”

Reframing Assumptions into Questions

Once assumptions are identified, they can be transformed into powerful questions that open new possibilities.

The Reframing Process:

  1. Identify the assumption
  2. Consider its opposite or alternatives
  3. Form questions that explore these alternatives
  4. Use these questions to expand thinking

Example Reframings:

Original Assumption Reframed as Questions
“We need to grow faster” “What would ‘right-sized’ growth look like for us?” “What if slower, more sustainable growth created more value?”
“Our competitors are threats” “How might we collaborate with competitors in ways that benefit both parties?” “What could we learn from our competitors?”
“Customer complaints indicate failure” “How might customer complaints be our most valuable source of innovation?” “What patterns in complaints point to unmet needs?”

Example in Practice:

A healthcare administrator was focused on the question, “How can we reduce patient complaints?” This question assumed complaints were negative. When reframed to “What are patient complaints trying to teach us about our care delivery?” the organization discovered insights that led to service innovations and process improvements that patients genuinely valued.

Application Exercise: Identify three assumptions in your current project or challenge. For each one, write down its opposite, then generate two questions that explore this alternative perspective.

Practice Exercises: Assumption Hunting

Exercise 1: The Five Whys of Assumptions

  1. State your initial question
  2. Ask: “Why am I asking this question?” (Write your answer)
  3. Ask: “Why is that important?” (About your previous answer)
  4. Repeat “Why is that important?” three more times
  5. Examine what this reveals about your deeper assumptions

Exercise 2: Assumption Reversal

  1. Write down a key question you’re wrestling with
  2. List all assumptions you can identify in this question
  3. For each assumption, write its opposite
  4. Create new questions based on these reversed assumptions
  5. Explore which new questions generate valuable insights

Exercise 3: Cross-Discipline Assumption Challenge

  1. Select a challenge you’re facing
  2. Imagine how professionals from different fields would approach it:
    • How would an artist frame this?
    • How would an engineer see it?
    • What would a psychologist ask?
    • How would a child view it?
  3. Note the different assumptions each perspective reveals about your situation

Case Study: How Questioning Assumptions Transformed an Industry

The Airbnb Story

The hotel industry operated on a fundamental assumption: travelers need purpose-built accommodations managed by hospitality professionals. This assumption was so engrained that it wasn’t even recognized as an assumption—it was simply “how things are.”

The founders of Airbnb questioned this assumption by asking, “What if ordinary people could turn their homes into hotels?” This question challenged several deep assumptions:

By questioning these assumptions and reframing them as possibilities rather than limitations, Airbnb created an entirely new paradigm in the accommodation industry.

The questioning didn’t stop at the business model. Airbnb continued to challenge assumptions:

Each questioned assumption opened new possibilities that competitors bound by traditional industry thinking couldn’t see.

The Lesson:

The most powerful innovations often come not from answering existing questions better, but from challenging the assumptions that gave rise to those questions in the first place.

Chapter Summary: Assumption Identification Framework

Becoming skilled at identifying and questioning assumptions follows this progression:

  1. Awareness: Recognize that all questions contain assumptions
  2. Identification: Develop the habit of spotting assumptions at all four layers
  3. Examination: Test whether assumptions are valid, necessary, or limiting
  4. Reframing: Transform limiting assumptions into expansive questions
  5. Application: Use assumption-aware questions to generate new possibilities

Remember that the goal isn’t to eliminate all assumptions—that’s impossible. Rather, the aim is to become conscious of the assumptions that are shaping your questions so you can choose whether to accept them, modify them, or discard them entirely.

Five Questions to Transform Your Assumptions:

  1. “What am I taking for granted that might not be true?”
  2. “How would I approach this if I held the opposite assumption?”
  3. “What assumptions would someone from a completely different culture make about this situation?”
  4. “What beliefs about how the world works are embedded in my thinking?”
  5. “What if everything I ‘know’ about this situation is wrong?”

In the next chapter, we’ll explore how to use questions to diagnose root causes, moving beyond surface symptoms to address the deeper sources of problems and opportunities.

Next Page: Chapter 6: Diagnosing Root Causes