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Aspirations and Mission: Once you’ve established motivation and purpose, you can ask what your friend wants to do or change. What difference does she want to make? Where has she directed her efforts and to what result? Does she know what you are doing and how it aligns with her interests? These questions help you find the pieces you share and the places you complement each other.

Join Forces: How can you work together to advance the cause? How would your common goals be advanced if you joined forces? Look ahead and ask what you can accomplish together. What roles will you play? What’s needed most? What will you have to show for your efforts? What difference will it make? Whether in philanthropy or in a mission-driven workplace, these are the questions that flesh out shared purpose and establish aspirations and goals.

Listen: Carefully listen for expressions of interest in a cause, a problem or a mission-driven job. Take special note of personal anecdotes or stories that bring the mission to life or examples of past activities that could indicate areas for collaboration. Pick up on comments that suggest your interests overlap and your goals are similar.

Try: A brain sharpener. Sit with a friend for half an hour and ask about his or her volunteer work or philanthropy. Don’t take notes, but find five related convictions or activities that you share. Now ask a series of questions about each. This exercise will force you to ask targeted questions and listen intently. It’s also a memory test. Be genuinely interested in the other person. Again, try to have this conversation without using the words “I” or “me.”

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SCIENTIFIC QUESTIONS

Asking through a science lens starts with a question, which becomes a hypothesis you can test. This involves observation, experimentation, and measurement—and trying to prove your hypothesis wrong. Answers to these questions are building blocks, which often raise more questions along the way, allowing you to explore the unknown. This process brings data and discipline to your discovery.

Observation: What do you see? What do you know? What are you trying to explain? Observe and define the problem you want to solve. Look around. Wonder aloud. Then craft the question.

Hypothesis: You know that more widgets sell in the afternoon, but why? Your hypothesis: More widgets sell in the afternoon because people get paid in the morning. Keep your hypothesis crisp and logical. Write it down. Come back to it. It forms the basis of what you are trying to prove or disprove.

The Data: How much, how fast, how big, how far? Ask what you need to measure and how you can do it over time. Try it. Do an experiment. Collect numbers—the data. Ask if you can replicate the data. Then do it again to see if your findings hold up. Are they supporting or contradicting your hypothesis?

The Contrarian: What disproves or contradicts your hypothesis? What evidence argues against it? Why? You went into this exercise knowing that the only way your hypothesis holds up is if you cannot prove it wrong. So ask the toughest questions. Question the data. Where did it come from? What’s weak, what’s inconsistent, what doesn’t hold up? If you can’t disprove your hypothesis, you might actually be onto something.

Conclusion: What does the data prove? How does it answer the question you started with? What’s next? Review your question, your hypothesis, your evidence, and your areas of uncertainty, and then you can draw a conclusion. Share it with other smart people and ask them what they think. Where do they see problems? What have you missed? Does your conclusion hold up?

Onward: Now what? What’s the next thing I want to figure out? Like all good science, one piece of knowledge builds on another and invites the next. Having answered the question you started with, what is the next question to ask?

Listen: Pay attention to the data. Listen to what is real and can be measured, seen, heard, felt. Listen for hints that your hypothesis is off target, misguided, or flat-out wrong. If it is, start again.

Try: Ask a what’s-going-on-here question and then come up with a hypothesis about what causes or complicates the situation. Now figure out how to test your hypothesis over a finite period of time. Think of three ways you will try to prove yourself wrong. Write those reasons down and put them someplace you’ll see them every day.

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INTERVIEW QUESTIONS

Interview questions look into the future. They try to predict whether skills and personalities will be a fit. They examine past performance as an indicator of future results. Interview questions are compatibility questions. People who are good at asking them make better interviewers and applicants alike.

Calling Card: What do you like about what you do? This is an open-ended question that may sound like small talk but illuminates big pieces of someone’s interests and personality. “Tell me about yourself” can prompt answers about how someone thinks and how she expresses herself.

The Accomplishment: What are you proudest of? What’s the wildest idea you have turned into reality? Asking about achievement should elicit discussion about examples and details, interests and capabilities. These questions don’t invite bragging; they offer an opportunity to talk about accomplishment and follow-through.

The Challenge: What’s the biggest setback you’ve had and what did you do about it?

Ask about setbacks, shortcomings, failure, and lessons learned. These questions reality-check for humility. They ask about someone’s willingness to take risks. They can prompt instructive stories about adversity and resilience.

Goals: What motivates you? What are you trying to achieve? If you could fix one thing in the world, what would it be? Explore the big picture. Is someone looking for a safe harbor or embarking on an adventure? What role does mission play? How important are values—and do they align with what you’re trying to do?

The Curvebalclass="underline" What American city would you give to New Zealand and why? Curveball questions often come sailing in out of the blue. They can be fun or a little weird. Their purpose is to prompt answers that provide a glimpse of spontaneity, creativity, humor, and the ability to deal with the unexpected.

Tough Choices: You have to cut 15 percent of your budget. What do you do? Where do you start? Questions that present a hypothetical situation allow you to see how someone works through a difficult decision or approaches and solves a problem. You’ll see if you approve or have a suddenly uneasy feeling.

The Dilemma: You’re on deadline but think you may not have enough time to finish the project the way you’d like. How do you proceed? These questions probe the thought process behind difficult decision-making.

Your Turn: What do you consider the biggest threat and the biggest opportunity? What are you trying to achieve? How creative can I be? Job candidates should do their homework and take great questions into their interview. Be specific. Ask about the organization, its strengths and its challenges; about the culture, metrics and what motivates the enterprise. Ask what is valued and what is needed. These questions allow the candidate to show interest and demonstrate both knowledge and curiosity.

Listen: Listen to see if the person comes across as direct or disjointed, uncertain or confident. When you ask about common goals and shared values is the answer comfortable and convincing? Listen for stories, examples, reflections, and lessons learned. Listen for expectations because if they don’t align, you have a problem.