20 Questions

Questions to Ask in a Skip Level Meeting

Strategic questions to ask in a skip level meeting to understand company direction, provide feedback, and build relationships with senior leadership.

1

What are the company's top priorities for the next quarter, and how does our team contribute to those goals?

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Why this works

Crucial for understanding company direction and how your work aligns with broader organizational objectives.

2

What are the biggest challenges facing the company right now, and how can our team help address them?

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Why this works

Shows your interest in company success and helps you understand how to contribute to solving important problems.

3

What is your vision for the company's future, and how do you see our team evolving?

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Why this works

Important for understanding the long-term direction and how your team fits into the company's growth plans.

4

What are the most important skills and qualities you look for in employees, and how can I develop them?

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Why this works

Essential for understanding what leadership values and how to advance your career within the organization.

5

What are the biggest opportunities for growth and advancement in our department?

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Why this works

Important for understanding career development opportunities and how to position yourself for advancement.

6

How do you approach decision-making, and what factors do you consider most important?

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Why this works

Shows your interest in leadership thinking and helps you understand how decisions are made at the senior level.

7

What are the most important lessons you've learned in your career, and what advice would you give to someone in my position?

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Why this works

Provides valuable career guidance and helps you understand the leadership perspective on professional development.

8

What are the biggest changes you've seen in our industry, and how is the company adapting?

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Why this works

Important for understanding industry trends and how the company is positioning itself for the future.

9

What are the most important qualities for success in our company culture?

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Why this works

Crucial for understanding what the company values and how to succeed within the organizational culture.

10

What are the biggest opportunities for innovation and improvement in our processes?

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Why this works

Shows your interest in contributing to company success and helps you understand areas for improvement.

11

What are the most important metrics you use to measure success, and how can I help improve them?

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Why this works

Important for understanding how success is measured and how you can contribute to key performance indicators.

12

What are the biggest risks facing the company, and how are we preparing for them?

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Why this works

Shows your interest in company stability and helps you understand how to contribute to risk mitigation.

13

What are the most important relationships you maintain, and how do you approach networking?

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Why this works

Provides valuable insights into leadership networking and helps you understand how to build professional relationships.

14

What are the biggest opportunities for collaboration between departments, and how can we improve cross-functional work?

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Why this works

Shows your interest in collaboration and helps you understand how to work effectively across the organization.

15

What are the most important trends in our industry, and how is the company responding to them?

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Why this works

Important for understanding industry dynamics and how the company is adapting to market changes.

16

What are the biggest opportunities for cost savings and efficiency improvements?

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Why this works

Shows your interest in operational excellence and helps you understand how to contribute to cost optimization.

17

What are the most important customer feedback trends, and how are we addressing them?

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Why this works

Important for understanding customer needs and how the company is responding to market feedback.

18

What are the biggest opportunities for employee development and training?

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Why this works

Shows your interest in professional growth and helps you understand available development opportunities.

19

What are the most important partnerships and relationships the company maintains?

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Why this works

Important for understanding the company's strategic relationships and how they contribute to success.

20

What are the biggest opportunities for technology and digital transformation?

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Why this works

Shows your interest in innovation and helps you understand how technology is driving company growth.

Making the Most of Skip Level Meetings

Expert tips and techniques for getting the most out of these questions.

Prepare Thoughtfully

Research the Leader

Learn about the leader's background, experience, and recent achievements to ask informed questions.

Understand Company Context

Research the company's recent news, financial performance, and strategic initiatives to ask relevant questions.

Prepare Your Questions

Have a list of thoughtful questions ready, but be flexible and ask follow-up questions based on their responses.

Listen Actively

Pay Attention

Give them your full attention and show genuine interest in their responses.

Ask Follow-up Questions

Show interest by asking follow-up questions based on their responses to deepen the conversation.

Take Notes

Write down important insights and information to reference later and follow up on.

Provide Value

Share Insights

Share relevant insights or observations about your work and how it contributes to company goals.

Offer Ideas

Offer ideas for improvement or innovation that could benefit the company.

Follow Up

Send a thank you note and follow up on any commitments or next steps discussed.

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