10 Questions

Questions to Ask During a Skip Level Meeting

Strategic questions to ask during a skip level meeting to understand leadership perspectives, share feedback, and build relationships with senior management while demonstrating your engagement and growth mindset.

1

What is your vision for the team and organization, and how do you see our role in achieving it?

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Why this works

Understanding their vision helps you align your work with organizational goals and see how you contribute to success.

2

What are the biggest challenges facing our team, and how can we work together to address them?

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Why this works

Learning about challenges helps you understand current issues and how you can contribute to solutions.

3

What opportunities exist for growth and development, and how can I position myself for advancement?

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Why this works

Understanding growth opportunities helps you plan your career development and identify ways to advance.

4

How do you approach decision-making, and what role do you see team members playing in this process?

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Why this works

Learning about their decision-making approach helps you understand how to contribute to important decisions.

5

What feedback do you have about my performance, and what areas should I focus on for improvement?

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Why this works

Getting their feedback helps you understand your strengths and areas for development.

6

How do you handle team dynamics and collaboration, and what support do you provide?

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Why this works

Understanding their approach to team management helps you know what support you'll receive and how to work effectively.

7

What trends do you see in our industry, and how are we preparing for the future?

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Why this works

Learning about industry trends helps you understand the business context and how to stay current.

8

How do you balance short-term results with long-term strategic goals, and what role do we play?

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Why this works

Understanding their balance helps you align your work with both immediate and long-term priorities.

9

What advice would you give to someone in my position, and what should I focus on for success?

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Why this works

Getting their advice helps you understand what's needed for success and how to focus your efforts.

10

How can I best support you and the team, and what would be most valuable?

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Why this works

Learning about their needs helps you understand how to be most helpful and contribute to team success.

Maximizing Skip Level Meetings

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

Before the Meeting

Prepare Your Questions

Think about what you want to learn and prepare questions that will give you the most valuable insights.

Review Your Goals

Consider your career goals and how this meeting can help you achieve them.

Be Professional

Approach the meeting with professionalism and respect for their time and position.

During the Meeting

Listen actively to their responses
Ask follow-up questions
Take notes on key insights
Share your own perspectives
Be respectful of their time
Express gratitude for their time
Follow up on commitments
Build ongoing relationships

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