Questions to Ask at Skip Level Meeting
Strategic questions for skip level meetings that help you understand organizational dynamics, career development opportunities, and organizational direction while demonstrating your strategic thinking and commitment to growth.
1What is your vision for the department and how do you see it evolving?
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What is your vision for the department and how do you see it evolving?
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Why this works
Shows strategic thinking and reveals the leader's vision, goals, and strategic approach to developing the department and team.
2What are the biggest challenges facing the department right now and how are you addressing them?
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What are the biggest challenges facing the department right now and how are you addressing them?
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Why this works
Demonstrates understanding of departmental challenges and reveals the leader's approach to problem-solving and strategic decision-making.
3How do you define success for the team and what metrics do you focus on?
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How do you define success for the team and what metrics do you focus on?
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Why this works
Shows interest in performance measurement and reveals the leader's approach to measuring success and tracking progress.
4What opportunities are there for professional development and growth within the department?
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What opportunities are there for professional development and growth within the department?
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Why this works
Demonstrates your commitment to growth and shows interest in learning opportunities and career advancement within the department.
5How do you approach team building and fostering collaboration?
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How do you approach team building and fostering collaboration?
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Why this works
Shows interest in team dynamics and reveals the leader's approach to building and maintaining effective team collaboration.
6What is your philosophy on leadership and how do you develop leaders?
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What is your philosophy on leadership and how do you develop leaders?
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Why this works
Shows interest in leadership development and reveals the leader's philosophy on leadership and how they develop leadership skills.
7How do you handle difficult decisions and what factors do you consider?
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How do you handle difficult decisions and what factors do you consider?
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Why this works
Shows interest in decision-making processes and reveals the leader's approach to complex decisions and problem-solving.
8What is your approach to innovation and staying competitive?
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What is your approach to innovation and staying competitive?
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Why this works
Demonstrates strategic thinking and reveals the leader's approach to innovation and maintaining competitive advantage.
9How do you approach change management and leading through change?
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How do you approach change management and leading through change?
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Why this works
Shows interest in change leadership and reveals the leader's approach to managing and leading through organizational change.
10What is your approach to diversity and inclusion in the department?
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What is your approach to diversity and inclusion in the department?
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Why this works
Demonstrates concern for workplace diversity and reveals the leader's approach to creating an inclusive and diverse work environment.
11How do you approach talent development and succession planning?
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How do you approach talent development and succession planning?
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Why this works
Shows interest in human capital and reveals the leader's approach to developing talent and planning for future leadership.
12What is your approach to risk management and how do you balance risk with opportunity?
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What is your approach to risk management and how do you balance risk with opportunity?
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Why this works
Demonstrates understanding of risk management and reveals the leader's approach to balancing risk and opportunity.
13How do you stay informed about industry trends and market changes?
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How do you stay informed about industry trends and market changes?
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Why this works
Shows interest in continuous learning and reveals the leader's approach to staying current with industry developments.
14What is your approach to stakeholder management and building relationships?
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What is your approach to stakeholder management and building relationships?
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Why this works
Demonstrates understanding of stakeholder relationships and reveals the leader's approach to managing key relationships.
15How do you approach performance management and feedback?
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How do you approach performance management and feedback?
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Why this works
Shows interest in performance management and reveals the leader's approach to feedback and performance evaluation.
16What is your approach to technology and digital transformation?
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What is your approach to technology and digital transformation?
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Why this works
Demonstrates understanding of technology leadership and reveals the leader's approach to technology and digital transformation.
17How do you approach sustainability and corporate social responsibility?
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How do you approach sustainability and corporate social responsibility?
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Why this works
Shows interest in responsible leadership and reveals the leader's approach to sustainability and social responsibility.
18What is your approach to global expansion and international markets?
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What is your approach to global expansion and international markets?
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Why this works
Demonstrates understanding of global business and reveals the leader's approach to international expansion and global markets.
19How do you approach talent acquisition and retention?
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How do you approach talent acquisition and retention?
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Why this works
Shows interest in human capital management and reveals the leader's approach to attracting and retaining top talent.
20What is your approach to board relations and governance?
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What is your approach to board relations and governance?
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Why this works
Demonstrates understanding of corporate governance and reveals the leader's approach to board relationships and governance.
Best Practices for Skip Level Meetings
Expert tips and techniques for getting the most out of these questions.
Best Practices
Show Strategic Thinking and Business Acumen
Demonstrate your understanding of business strategy and your ability to think strategically about the department's future and challenges.
Focus on Leadership and Organizational Development
Ask about leadership philosophy, talent development, and organizational culture. This shows you understand the importance of human capital and leadership.
Demonstrate Interest in the Department's Future
Ask about the department's vision, strategic direction, and future plans. This shows you're thinking long-term and are committed to the department's success.
Question Sequences
The Strategic Vision and Direction Sequence
The Leadership and Culture Sequence
Common Pitfalls
Don't Ask Questions That Show Lack of Preparation
Avoid questions that could be answered by basic research about the department. Show you've done your homework and ask thoughtful, informed questions.
Don't Ask Questions That Are Too Personal
Avoid questions about personal matters or private information. Focus on professional and business-related topics that are relevant to the role.
Don't Ask Questions That Are Too Narrow
Avoid questions that are too specific or narrow in scope. Ask questions that are relevant to the role and show your understanding of the business.