Questions to Ask New Leadership
Strategic questions to understand new leadership's vision, priorities, and approach while building rapport and demonstrating your value.
1What's your vision for the team and organization?
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What's your vision for the team and organization?
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Why this works
Reveals their strategic direction and helps you understand how to align your work with their goals and priorities.
2What are your top priorities for the first 90 days?
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What are your top priorities for the first 90 days?
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Why this works
Shows their immediate focus areas and helps you understand what they value most in the short term.
3How do you like to communicate and receive updates?
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How do you like to communicate and receive updates?
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Why this works
Establishes communication preferences and ensures you can effectively share information and stay connected.
4What's your approach to decision-making and problem-solving?
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What's your approach to decision-making and problem-solving?
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Why this works
Reveals their leadership style and helps you understand how to present ideas and get decisions made.
5What are your expectations for team performance and collaboration?
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What are your expectations for team performance and collaboration?
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Why this works
Clarifies performance standards and helps you understand how to contribute effectively to team success.
6How do you handle feedback and performance discussions?
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How do you handle feedback and performance discussions?
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Why this works
Shows their approach to development and helps you understand how to receive and give feedback effectively.
7What are your thoughts on the current challenges facing our team?
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What are your thoughts on the current challenges facing our team?
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Why this works
Reveals their understanding of team dynamics and helps you understand their perspective on existing issues.
8How do you like to recognize and reward good work?
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How do you like to recognize and reward good work?
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Why this works
Shows their approach to motivation and helps you understand how to get recognition for your contributions.
9What are your expectations for professional development and growth?
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What are your expectations for professional development and growth?
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Why this works
Clarifies their approach to career development and helps you understand opportunities for advancement.
10How do you handle conflicts and difficult situations?
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How do you handle conflicts and difficult situations?
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Why this works
Reveals their conflict resolution style and helps you understand how to navigate challenging situations.
11What are your thoughts on work-life balance and flexibility?
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What are your thoughts on work-life balance and flexibility?
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Why this works
Shows their approach to employee well-being and helps you understand their policies on work arrangements.
12How do you like to approach change and innovation?
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How do you like to approach change and innovation?
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Why this works
Reveals their attitude toward change and helps you understand how to present new ideas and improvements.
13What are your expectations for meeting participation and preparation?
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What are your expectations for meeting participation and preparation?
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Why this works
Clarifies meeting expectations and helps you understand how to contribute effectively to team discussions.
14How do you like to handle deadlines and project management?
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How do you like to handle deadlines and project management?
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Why this works
Shows their approach to project oversight and helps you understand how to manage your work effectively.
15What are your thoughts on the current team structure and roles?
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What are your thoughts on the current team structure and roles?
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Why this works
Reveals their perspective on team organization and helps you understand potential changes or improvements.
16How do you like to approach risk-taking and experimentation?
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How do you like to approach risk-taking and experimentation?
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Why this works
Shows their attitude toward innovation and helps you understand how to present new ideas and approaches.
17What are your expectations for cross-functional collaboration?
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What are your expectations for cross-functional collaboration?
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Why this works
Clarifies their approach to teamwork and helps you understand how to work effectively with other departments.
18How do you like to handle mistakes and learning opportunities?
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How do you like to handle mistakes and learning opportunities?
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Why this works
Reveals their approach to failure and helps you understand how to handle setbacks and learn from them.
19What are your thoughts on the current company culture and values?
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What are your thoughts on the current company culture and values?
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Why this works
Shows their perspective on organizational culture and helps you understand how to align with company values.
20How can I best support you and the team's success?
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How can I best support you and the team's success?
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Why this works
Demonstrates your commitment to team success and helps you understand how to contribute most effectively.
Best Practices for Engaging with New Leadership
Expert tips and techniques for getting the most out of these questions.
Best Practices
Be Proactive and Engaged
Take initiative to introduce yourself and show interest in their vision and priorities. Demonstrate your value and commitment.
Listen Actively and Take Notes
Pay attention to their responses and take notes so you can follow up on their priorities and expectations.
Show Your Value
Highlight your skills, experience, and contributions while asking questions that demonstrate your understanding of the business.
Question Sequences
The Vision and Priorities Sequence
The Working Style Sequence
Common Pitfalls
Don't Focus Only on Your Needs
Balance questions about your development with questions about how you can support the team and organization.
Avoid Negative Questions
Don't ask questions that criticize previous leadership or focus on problems. Focus on positive opportunities and growth.
Don't Overwhelm Them
Space out your questions and don't ask too many at once. Give them time to respond and show genuine interest in their answers.