Skip Level Meeting Questions to Ask
Strategic questions to help you make the most of skip-level meetings, understand organizational dynamics, and build relationships with senior leadership.
1What's your vision for the organization and how do you see it evolving?
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What's your vision for the organization and how do you see it evolving?
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Why this works
Reveals leadership perspective and helps you understand the organization's direction and how your work fits into the bigger picture.
2What are the biggest challenges facing the organization right now?
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What are the biggest challenges facing the organization right now?
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Why this works
Shows organizational priorities and helps you understand what problems the organization is working to solve and how you can contribute.
3What are the key initiatives and projects you're most excited about?
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What are the key initiatives and projects you're most excited about?
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Why this works
Reveals leadership priorities and helps you understand what initiatives matter most and how you can get involved.
4What are the organization's values and how do you see them in action?
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What are the organization's values and how do you see them in action?
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Why this works
Shows organizational culture and helps you understand what values drive decision-making and how they're lived out in practice.
5What are the opportunities for growth and development in the organization?
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What are the opportunities for growth and development in the organization?
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Why this works
Reveals development opportunities and helps you understand what growth paths exist and how you can advance your career.
6What are the organization's goals for the next year and beyond?
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What are the organization's goals for the next year and beyond?
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Why this works
Shows organizational objectives and helps you understand what the organization is working toward and how you can contribute.
7What are the organization's strengths and areas for improvement?
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What are the organization's strengths and areas for improvement?
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Why this works
Reveals organizational assessment and helps you understand what the organization does well and where it's looking to improve.
8What are the organization's communication and feedback processes?
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What are the organization's communication and feedback processes?
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Why this works
Shows communication culture and helps you understand how information flows and how feedback is given and received.
9What are the organization's diversity and inclusion initiatives?
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What are the organization's diversity and inclusion initiatives?
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Why this works
Reveals commitment to diversity and helps you understand how the organization approaches diversity and inclusion.
10What are the organization's innovation and change management approaches?
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What are the organization's innovation and change management approaches?
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Why this works
Shows innovation culture and helps you understand how the organization approaches change and innovation.
11What are the organization's customer and stakeholder relationships?
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What are the organization's customer and stakeholder relationships?
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Why this works
Reveals external focus and helps you understand how the organization serves its customers and stakeholders.
12What are the organization's technology and digital transformation initiatives?
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What are the organization's technology and digital transformation initiatives?
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Why this works
Shows technology focus and helps you understand how the organization is using technology to transform and improve.
13What are the organization's sustainability and social responsibility efforts?
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What are the organization's sustainability and social responsibility efforts?
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Why this works
Reveals social impact and helps you understand how the organization approaches sustainability and social responsibility.
14What are the organization's talent and people development strategies?
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What are the organization's talent and people development strategies?
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Why this works
Shows people focus and helps you understand how the organization develops and supports its people.
15What are the organization's risk management and compliance approaches?
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What are the organization's risk management and compliance approaches?
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Why this works
Shows risk awareness and helps you understand how the organization manages risk and ensures compliance.
16What are the organization's partnerships and collaboration strategies?
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What are the organization's partnerships and collaboration strategies?
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Why this works
Shows collaboration approach and helps you understand how the organization works with partners and collaborators.
17What are the organization's performance measurement and success metrics?
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What are the organization's performance measurement and success metrics?
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Why this works
Shows success criteria and helps you understand how the organization measures success and what metrics matter most.
18What are the organization's crisis management and business continuity plans?
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What are the organization's crisis management and business continuity plans?
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Why this works
Shows preparedness and helps you understand how the organization handles crises and ensures business continuity.
19What are the organization's future plans and growth trajectory?
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What are the organization's future plans and growth trajectory?
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Why this works
Shows future direction and helps you understand where the organization is headed and what growth opportunities exist.
20What makes this organization different from competitors?
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What makes this organization different from competitors?
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Why this works
Shows competitive advantage and helps you understand what sets the organization apart and what makes it unique.
Best Practices for Skip-Level Meetings
Expert tips and techniques for getting the most out of these questions.
Best Practices
Focus on Organizational Understanding
Ask questions that help you understand the organization's direction, challenges, and opportunities to better align your work with organizational goals.
Build Relationships and Trust
Use questions to build rapport with senior leadership and demonstrate your interest in the organization's success and your role in it.
Show Strategic Thinking
Ask questions that demonstrate your understanding of the bigger picture and your ability to think strategically about organizational challenges.
Question Sequences
The Vision and Direction Sequence
The Culture and Values Sequence
Common Pitfalls
Don't Ask About Personal Issues
Focus on organizational and professional topics rather than personal matters or individual performance issues.
Don't Complain About Your Manager
Avoid questions that criticize or complain about your direct manager. Focus on positive organizational topics instead.
Don't Ask About Salary or Promotions
Skip-level meetings are for organizational understanding, not individual compensation or advancement discussions.