20 Questions

Skip Level Questions to Ask Employees

Strategic questions that help you understand employee experiences, identify organizational issues, and gather valuable insights from your team members.

1

How would you describe your current role and what you enjoy most about it?

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Why this works

Understanding their role satisfaction helps you identify what's working well and what motivates them in their work.

2

What challenges are you facing in your work, and how can I help address them?

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Why this works

Identifying challenges helps you understand obstacles to productivity and employee satisfaction, and shows you're committed to supporting them.

3

How would you describe the communication and collaboration within your team?

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Why this works

Understanding team dynamics helps you identify communication gaps, collaboration issues, and opportunities for improvement.

4

What resources or support do you need to be more effective in your role?

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Why this works

Understanding resource needs helps you identify gaps in support and opportunities to improve employee effectiveness and satisfaction.

5

How would you describe the company culture, and what aspects do you value most?

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Why this works

Understanding their perspective on culture helps you assess organizational health and identify what employees value about working here.

6

What opportunities do you see for growth and development in your current role?

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Why this works

Understanding growth opportunities helps you assess career development needs and identify ways to support employee advancement.

7

How would you describe your relationship with your direct manager?

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Why this works

Understanding manager-employee relationships helps you identify management issues and opportunities for improvement.

8

What feedback do you have about our processes, systems, or workflows?

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Why this works

Understanding process feedback helps you identify inefficiencies, bottlenecks, and opportunities for operational improvement.

9

How would you describe the level of recognition and feedback you receive?

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Why this works

Understanding recognition and feedback helps you assess employee satisfaction and identify opportunities to improve appreciation and development.

10

What suggestions do you have for improving our team or department?

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Why this works

Understanding improvement suggestions helps you identify opportunities for enhancement and shows you value employee input.

11

How would you describe the work-life balance in your current role?

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Why this works

Understanding work-life balance helps you assess employee well-being and identify opportunities to improve quality of life.

12

What aspects of your job would you like to change or improve?

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Why this works

Understanding desired changes helps you identify improvement opportunities and shows you're interested in making their work better.

13

How would you describe the level of autonomy and decision-making in your role?

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Why this works

Understanding autonomy levels helps you assess empowerment and identify opportunities to increase employee engagement and ownership.

14

What training or development opportunities would be most valuable to you?

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Why this works

Understanding development needs helps you identify learning opportunities and shows you're committed to employee growth.

15

How would you describe the level of stress and workload in your current role?

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Why this works

Understanding stress and workload helps you assess employee well-being and identify opportunities to improve work conditions.

16

What feedback do you have about our company's direction and strategy?

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Why this works

Understanding strategic feedback helps you assess alignment and identify opportunities to improve communication and engagement.

17

How would you describe the level of innovation and creativity in your work?

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Why this works

Understanding innovation opportunities helps you assess creative engagement and identify ways to increase employee satisfaction and contribution.

18

What suggestions do you have for improving our customer experience?

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Why this works

Understanding customer experience feedback helps you identify opportunities for improvement and shows you value employee insights.

19

How would you describe the level of trust and transparency in our organization?

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Why this works

Understanding trust and transparency helps you assess organizational health and identify opportunities to improve communication and culture.

20

What would make you more likely to recommend this company as a great place to work?

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Why this works

Understanding advocacy factors helps you identify what employees value most and opportunities to improve employee satisfaction and retention.

Best Practices for Skip Level Meetings

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

Best Practices

Create a Safe Environment

Make sure employees feel comfortable sharing honest feedback. Assure them that their responses are confidential and won't be held against them.

Listen Actively

Pay attention to both what they say and what they don't say. Look for patterns and themes that could indicate broader organizational issues.

Follow Up on Concerns

If they raise concerns, make sure to address them appropriately. This shows you value their feedback and are committed to improvement.

Document Insights

Keep track of common themes and feedback to identify patterns and opportunities for organizational improvement.

Question Sequences

The Experience Explorer

1
How would you describe your current role and what you enjoy most about it?
2
What challenges are you facing in your work?
3
What aspects of your job would you like to change or improve?
4
What would make you more likely to recommend this company as a great place to work?

The Support Assessor

1
What resources or support do you need to be more effective in your role?
2
What training or development opportunities would be most valuable to you?
3
How would you describe the level of recognition and feedback you receive?
4
What suggestions do you have for improving our team or department?

Common Pitfalls

Don't Make It an Interrogation

Keep the conversation casual and conversational. Don't fire off questions one after another - let the conversation flow naturally.

Avoid Defensive Responses

If they raise concerns, don't get defensive or make excuses. Listen with an open mind and focus on understanding their perspective.

Don't Ignore Feedback

If they provide feedback, make sure to act on it appropriately. Nothing kills trust faster than asking for feedback and then ignoring it.

Conversation Templates

The Supportive Leader

1
Step 1: Start with: "How would you describe your current role and what you enjoy most about it?"
2
Step 2: Follow with: "What challenges are you facing in your work?"
3
Step 3: Deepen with: "What resources or support do you need to be more effective?"
4
Step 4: Connect with: "I want to make sure you have what you need to succeed."

The Improvement Seeker

1
Step 1: Start with: "What suggestions do you have for improving our team or department?"
2
Step 2: Follow with: "What feedback do you have about our processes, systems, or workflows?"
3
Step 3: Deepen with: "What would make you more likely to recommend this company as a great place to work?"
4
Step 4: Connect with: "Your feedback is really valuable for helping us improve."

Further Reading

"The Manager's Guide to Skip Level Meetings" by Harvard Business Review
"Employee Engagement" by William Kahn
"The Manager's Guide to Employee Feedback" by Sharlyn Lauby

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