Questions to Ask About Goals
Thoughtful questions that help you understand someone's aspirations, motivations, and vision for their future while building deeper connections.
1What's something you've always wanted to accomplish but haven't had the chance to pursue yet?
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What's something you've always wanted to accomplish but haven't had the chance to pursue yet?
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Why this works
Reveals hidden aspirations and priorities while showing what they value most in life.
2If you could wake up tomorrow with one new skill or ability, what would it be and why?
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If you could wake up tomorrow with one new skill or ability, what would it be and why?
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Why this works
Uncovers current limitations they're aware of and what they see as most valuable for their growth.
3What does success look like to you in five years, and how would you know you've achieved it?
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What does success look like to you in five years, and how would you know you've achieved it?
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Why this works
Reveals their definition of success and provides concrete markers for measuring progress.
4What's a goal you've achieved that you're most proud of, and what made it meaningful?
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What's a goal you've achieved that you're most proud of, and what made it meaningful?
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Why this works
Shows their values and what they consider worth celebrating, plus their motivation patterns.
5If you had unlimited resources and time, what would you want to create or build?
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If you had unlimited resources and time, what would you want to create or build?
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Why this works
Reveals their deepest passions and creative vision without practical constraints limiting their imagination.
6What's something you've been putting off that you know would make a positive difference in your life?
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What's something you've been putting off that you know would make a positive difference in your life?
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Why this works
Identifies self-awareness about procrastination and reveals what they consider important but challenging.
7What legacy do you hope to leave behind, and how do you want to be remembered?
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What legacy do you hope to leave behind, and how do you want to be remembered?
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Why this works
Reveals their values and long-term perspective on their impact and contribution to others.
8What's a goal that scares you but also excites you when you think about it?
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What's a goal that scares you but also excites you when you think about it?
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Why this works
Identifies their growth edge and shows what they consider worth the risk and effort.
9If you could change one thing about the world, what would it be and why?
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If you could change one thing about the world, what would it be and why?
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Why this works
Reveals their values, concerns, and vision for making a broader impact beyond personal goals.
10What's something you want to learn or experience that would completely change your perspective?
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What's something you want to learn or experience that would completely change your perspective?
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Why this works
Shows openness to growth and reveals what they think would be transformative for them.
11What goal have you set for yourself that others might not understand, and why is it important to you?
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What goal have you set for yourself that others might not understand, and why is it important to you?
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Why this works
Reveals personal values and motivations that may not align with others' expectations or conventional wisdom.
12If you could go back and give your younger self one piece of advice about pursuing goals, what would it be?
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If you could go back and give your younger self one piece of advice about pursuing goals, what would it be?
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Why this works
Shows self-reflection and reveals lessons learned about goal-setting and achievement.
13What's a goal you've had to let go of, and how did you decide it was time to move on?
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What's a goal you've had to let go of, and how did you decide it was time to move on?
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Why this works
Reveals their decision-making process and shows how they handle disappointment and change.
14What would you want to accomplish if you knew you couldn't fail?
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What would you want to accomplish if you knew you couldn't fail?
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Why this works
Removes fear as a barrier and reveals their true aspirations without self-imposed limitations.
15What goal are you working toward right now that you're most excited about?
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What goal are you working toward right now that you're most excited about?
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Why this works
Shows current motivation and energy, plus what they're actively investing their time and effort in.
16If you could help someone else achieve their biggest goal, what would you want to help them with?
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If you could help someone else achieve their biggest goal, what would you want to help them with?
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Why this works
Reveals their values around service and what they consider most important to help others achieve.
17What's a goal that would require you to step completely outside your comfort zone?
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What's a goal that would require you to step completely outside your comfort zone?
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Why this works
Identifies their growth challenges and shows what they consider worth the discomfort and risk.
18What do you hope to have accomplished by the end of this year that would make you feel proud?
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What do you hope to have accomplished by the end of this year that would make you feel proud?
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Why this works
Reveals short-term priorities and what they consider achievable and meaningful in the near future.
19What's a goal you've achieved that required the most persistence, and what kept you going?
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What's a goal you've achieved that required the most persistence, and what kept you going?
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Why this works
Shows their resilience patterns and reveals what motivates them to persist through challenges.
20If you could design your ideal life, what would a typical day look like and what goals would you be pursuing?
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If you could design your ideal life, what would a typical day look like and what goals would you be pursuing?
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Why this works
Reveals their vision for work-life balance and what they consider ideal in terms of daily fulfillment and purpose.
Mastering Goal-Focused Conversations
Expert tips and techniques for getting the most out of these questions.
Best Practices
Listen for Values, Not Just Goals
Pay attention to what their goals reveal about their values, priorities, and what they consider meaningful.
Ask Follow-Up Questions
When someone shares a goal, ask why it matters to them, what it would mean to achieve it, or what's holding them back.
Share Your Own Goals
Reciprocate by sharing your own aspirations to create mutual vulnerability and deeper connection.
Question Sequences
The Aspiration Explorer
The Legacy Builder
Common Pitfalls
Don't Judge Their Goals
Avoid expressing skepticism or judgment about their aspirations, even if they seem unrealistic to you.
Don't Make It About You
Focus on understanding their goals rather than immediately relating everything back to your own experiences.
Don't Push for Specifics
Some people are still figuring out their goals - don't pressure them to have everything mapped out.