Chapter 1: Decision-Making Questions

“The best questions are the ones that cause people to think in a new way.” — Clayton Christensen

When faced with a decision—whether it’s choosing a career path, making a business investment, or determining the direction of your team—the quality of that decision hinges on the quality of the questions you ask beforehand. In this chapter, we explore the essential questions that lead to superior decision-making.

Questions for Clarifying Options

Before evaluating options, you must first clearly define what those options are. Many poor decisions result from failing to consider the full range of possibilities.

Essential Questions:

1. “What options am I not seeing right now?”
2. “If the obvious solutions weren’t available, what would I do?”
3. “Who else has faced this decision, and what options did they consider?”
4. “What would happen if I did nothing or delayed this decision?”
5. “Are there hybrid options that combine elements of different alternatives?”

Example in Practice:

When Sarah, a marketing executive, was deciding on a new campaign strategy, her team initially presented just two options: a digital-first approach or a traditional media approach. By asking, “What options are we not seeing?” the team expanded their thinking to include a community-based guerrilla marketing approach that ultimately proved more effective and less expensive than either original option.

Application Exercise: For your current decision, list all obvious options, then force yourself to generate at least three more unconventional alternatives. Ask trusted advisors what options they see that you might be missing.

Questions to Identify Hidden Assumptions

Our decisions are often undermined by unexamined assumptions. Questioning these assumptions can reveal new possibilities or prevent costly errors.

Essential Questions:

1. “What am I assuming must be true for this option to succeed?”
2. “What would cause this decision to fail?”
3. “What expertise or information am I missing?”
4. “Am I solving the right problem?”
5. “What biases might be influencing my thinking?”

Example in Practice:

A technology company was ready to launch a new product based on the assumption that speed was the primary factor customers cared about. By asking, “What are we assuming about customer preferences?” they discovered through research that reliability was actually valued more highly than speed. This insight fundamentally changed their product development and marketing strategy.

Application Exercise: List five key assumptions underlying your current decision. For each one, ask: “How do I know this is true?” and “What evidence might challenge this assumption?”

Questions for Weighing Pros and Cons

Going beyond simple pro/con lists, these questions help you evaluate options with greater nuance and depth.

Essential Questions:

1. “How will each option affect different stakeholders?”
2. “What are the second and third-order consequences of each option?”
3. “What are the short-term versus long-term implications?”
4. “Which option aligns best with my/our core values and priorities?”
5. “What is the opportunity cost of each option?”

Example in Practice:

When considering whether to promote internally or hire externally for a leadership position, a CEO asked, “What are the second-order consequences of each option?” This question revealed that while external hiring might bring fresh expertise, it could damage morale and institutional knowledge throughout the organization—a consequence that wasn’t initially considered.

Application Exercise: For your top two decision options, identify at least three second-order consequences (effects of the effects) that might not be immediately obvious.

Questions to Surface Risks and Blind Spots

Even the best-analyzed decisions can fail due to unforeseen risks. These questions help illuminate blind spots before they become problems.

Essential Questions:

1. “What’s the worst-case scenario, and could I live with it?”
2. “Who would disagree with this decision and why?”
3. “How might this decision look in hindsight if it fails?”
4. “What information would make me change my mind?”
5. “What am I not considering that an outsider would immediately see?”

Example in Practice:

Before making a major investment in expanding to a new market, an executive team asked, “Who would strongly disagree with this decision?” They then intentionally sought out industry experts who were skeptical about the move. This process revealed regulatory complications they hadn’t considered, allowing them to address these issues before proceeding.

Application Exercise: Find someone who thinks differently from you and ask them what risks or issues they see in your preferred option that you might be missing.

Questions for Team Decision-Making

Collective decisions bring additional complexity but also the potential for greater wisdom. These questions help navigate team dynamics in decision-making.

Essential Questions:

1. “How do we ensure all voices are heard?”
2. “What does consensus really mean for this particular decision?”
3. “Who has decision rights, and who has input rights?”
4. “How will we evaluate this decision after the fact?”
5. “What information do we need to share more broadly before deciding?”

Example in Practice:

A nonprofit board was divided over a strategic direction. By explicitly asking, “Who has decision rights versus input rights on this matter?” they clarified that while the entire board should provide input, the executive committee was responsible for the final decision according to their bylaws. This clarity prevented a prolonged stalemate.

Application Exercise: Before your next team decision, explicitly define the decision-making process: Who will provide input? Who will make the final call? How will you handle disagreement?

Case Study: How Great Decisions Begin with Great Questions

The Netflix DVD-to-Streaming Pivot

In 2007, Netflix faced a critical decision about its future. With DVD-by-mail as its core business, the company needed to decide how to respond to emerging streaming technology. Instead of asking, “How can we protect our DVD business?” CEO Reed Hastings asked a fundamentally different question: “What business will our customers want us to be in five years from now?”

This question reframed the decision entirely. Rather than seeing streaming as a threat to their existing business, they saw it as the inevitable future. This led to a series of bold decisions to cannibalize their own successful DVD business and invest heavily in streaming content and technology.

The questioning didn’t stop there. Netflix leadership continued asking:

• “What if we produced our own original content?”
• “How might we use data to better understand viewing preferences?”
• “What international markets represent our best opportunities?”

Each question led to crucial strategic decisions that transformed Netflix from a $2 billion DVD rental company to a $150+ billion global entertainment powerhouse.

The Lesson:

The initial question you ask essentially determines the range of possible answers. Had Netflix asked, “How do we optimize our DVD business?” or “How do we compete with Blockbuster?” they might have missed the streaming opportunity entirely. By asking broader, more forward-looking questions, they opened themselves to transformative possibilities.

Chapter Summary: Decision-Making Question Framework

Effective decision-making follows a question sequence:

1. Option Expansion Questions: Widen the range of possibilities
2. Assumption Testing Questions: Challenge underlying beliefs
3. Evaluation Questions: Assess implications and alignment
4. Risk Assessment Questions: Identify potential pitfalls
5. Implementation Questions: Clarify execution and accountability

Remember that the initial question you ask frames everything that follows. Before rushing to answer, ensure you’re asking the most powerful question possible.

Five Questions to Transform Your Next Important Decision:

1. “What problem am I really trying to solve?”
2. “What would I advise someone else to do in this situation?”
3. “How might this decision look one year, five years, and ten years from now?”
4. “What information would make this decision obvious?”
5. “What would success look like, and how would we measure it?”

In the next chapter, we’ll explore how questions can transform your approach to problem-solving, allowing you to address challenges at their root rather than merely treating symptoms.

Next Page: Chapter 2: Problem-Solving Questions