Questions to Ask Your Leaders
Build stronger relationships with your leaders and advance your career with these strategic questions that demonstrate your value, gather insights, and show your commitment to organizational success.
1What's the most important thing I can do to help the team succeed?
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What's the most important thing I can do to help the team succeed?
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Why this works
Shows your commitment to team success while helping you understand how to add the most value and make the biggest impact.
2How can I better support your goals and priorities?
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How can I better support your goals and priorities?
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Why this works
Demonstrates your alignment with their objectives while helping you understand how to be a more effective team member.
3What skills should I develop to advance in my role?
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What skills should I develop to advance in my role?
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Why this works
Shows your commitment to growth while helping you understand what capabilities are most valued and how to progress in your career.
4What's the biggest challenge you're facing right now?
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What's the biggest challenge you're facing right now?
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Why this works
Reveals their current priorities and challenges while showing your interest in understanding their perspective and supporting their success.
5How can I improve my performance and contribution?
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How can I improve my performance and contribution?
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Why this works
Shows your commitment to excellence while helping you understand what you can do to be more effective and valuable to the team.
6What opportunities do you see for me to take on more responsibility?
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What opportunities do you see for me to take on more responsibility?
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Why this works
Demonstrates your ambition while helping you understand potential growth opportunities and how to position yourself for advancement.
7What's your vision for the team's future?
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What's your vision for the team's future?
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Why this works
Shows your interest in the bigger picture while helping you understand where the team is heading and how you can contribute to that vision.
8How can I better communicate with you and the team?
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How can I better communicate with you and the team?
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Why this works
Shows your commitment to effective communication while helping you understand their preferences and how to work more effectively together.
9What feedback do you have for me on my recent work?
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What feedback do you have for me on my recent work?
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Why this works
Demonstrates your openness to feedback while helping you understand what you're doing well and what you can improve.
10What's the most important lesson you've learned as a leader?
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What's the most important lesson you've learned as a leader?
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Why this works
Shows respect for their experience while providing valuable leadership wisdom that can help you grow and develop.
11How can I help reduce your workload or stress?
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How can I help reduce your workload or stress?
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Why this works
Shows your care for their wellbeing while helping you understand how to be more supportive and valuable to them.
12What's something you wish you knew earlier in your career?
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What's something you wish you knew earlier in your career?
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Why this works
Provides valuable career insights while creating a personal connection and showing respect for their journey and experience.
13How can I better align my work with the company's goals?
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How can I better align my work with the company's goals?
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Why this works
Shows your commitment to organizational success while helping you understand how to make your work more strategic and impactful.
14What's the most rewarding part of your role?
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What's the most rewarding part of your role?
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Why this works
Shows interest in their perspective while revealing what they find most fulfilling about their work and leadership.
15How can I help improve team collaboration and dynamics?
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How can I help improve team collaboration and dynamics?
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Why this works
Demonstrates your commitment to team success while helping you understand how to contribute to a positive and productive work environment.
16What's the biggest opportunity you see for the team?
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What's the biggest opportunity you see for the team?
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Why this works
Shows your strategic thinking while helping you understand potential growth areas and how you can contribute to seizing those opportunities.
17How can I better support our customers or stakeholders?
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How can I better support our customers or stakeholders?
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Why this works
Shows your customer focus while helping you understand how to be more effective in serving the people who matter most to the business.
18What's something you'd like me to take ownership of?
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What's something you'd like me to take ownership of?
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Why this works
Demonstrates your willingness to take responsibility while helping you understand areas where you can make a bigger impact and grow.
19How can I help you achieve your goals faster?
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How can I help you achieve your goals faster?
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Why this works
Shows your commitment to their success while helping you understand how to be more efficient and effective in supporting their objectives.
20What's the best way for me to stay updated on important developments?
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What's the best way for me to stay updated on important developments?
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Why this works
Shows your commitment to staying informed while helping you understand how to be more aware of changes and opportunities that affect your work.
Best Practices for Leader Conversations
Expert tips and techniques for getting the most out of these questions.
Best Practices
Show Genuine Interest in Their Success
Approach the conversation with authentic interest in helping them achieve their goals. This demonstrates your commitment to the team and organization.
Be Specific and Actionable
Ask questions that lead to specific, actionable insights rather than vague generalities. This shows you're serious about improvement and growth.
Follow Up on Their Guidance
When they provide advice or feedback, follow through on it and show them the results. This demonstrates your commitment to growth and improvement.
Question Sequences
The Performance and Growth Sequence
The Support and Alignment Sequence
Common Pitfalls
Don't Make It All About You
Balance questions about your development with questions about how you can help them and the team succeed. Show you're committed to mutual success.
Don't Ask Questions You Can Answer Yourself
Avoid questions about basic job responsibilities or obvious information. Focus on insights that only they can provide.
Don't Ignore Their Feedback
When they provide guidance or feedback, take it seriously and follow through. Ignoring their input can damage the relationship and your credibility.