20 Questions

Questions to Ask a New Supervisor

Essential questions to ask when you have a new supervisor to establish expectations, build rapport, and ensure a successful working relationship.

1

What are your expectations for my role and performance?

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Why this works

Understanding their expectations helps you know what's required and how to succeed in your position.

2

How do you prefer to communicate and how often?

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Why this works

Learning their communication style helps you establish effective working patterns and avoid misunderstandings.

3

What is your management style and how do you like to work with your team?

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Why this works

Understanding their management approach helps you adapt your working style to be most effective with them.

4

What are your priorities and goals for our department?

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Why this works

Learning about their priorities helps you align your work with their objectives and contribute meaningfully.

5

How do you handle feedback and performance reviews?

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Why this works

Understanding their feedback approach helps you know how to receive guidance and improve your performance.

6

What are the biggest challenges facing our team right now?

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Why this works

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

7

How do you prefer to receive updates and reports?

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Why this works

Understanding their reporting preferences helps you provide information in the format and frequency they want.

8

What are your expectations for team collaboration and meetings?

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Why this works

Learning about their collaboration style helps you participate effectively in team activities and meetings.

9

How do you handle conflicts and difficult situations?

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Why this works

Understanding their conflict resolution approach helps you know how to handle problems when they arise.

10

What are your thoughts on professional development and growth?

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Why this works

Learning about their development philosophy helps you understand opportunities for growth and advancement.

11

How do you prefer to handle urgent issues and emergencies?

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Why this works

Understanding their approach to urgent matters helps you know how to escalate issues appropriately.

12

What are your expectations for work-life balance?

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Why this works

Learning about their work-life balance expectations helps you manage your time and avoid burnout.

13

How do you like to recognize and reward good performance?

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Why this works

Understanding their recognition style helps you know what to expect and how to celebrate achievements.

14

What are your expectations for decision-making and autonomy?

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Why this works

Learning about their decision-making preferences helps you know when to act independently and when to consult.

15

How do you handle changes and transitions?

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Why this works

Understanding their approach to change helps you adapt and support organizational transitions.

16

What are your expectations for innovation and new ideas?

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Why this works

Learning about their innovation approach helps you know how to contribute new ideas and improvements.

17

How do you prefer to handle mistakes and learning opportunities?

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Why this works

Understanding their approach to mistakes helps you learn from errors and grow professionally.

18

What are your expectations for customer or client relationships?

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Why this works

Learning about their client relationship expectations helps you represent the organization effectively.

19

How do you like to celebrate team successes and milestones?

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Why this works

Understanding their celebration style helps you participate in team recognition and build morale.

20

What advice do you have for someone new to this role?

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Why this works

Learning their advice helps you understand what they value and how to succeed in your position.

Best Practices for Working with a New Supervisor

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

Best Practices

Be Proactive and Engaged

Show initiative by asking thoughtful questions and demonstrating your commitment to success.

Listen and Observe

Pay attention to their communication style, preferences, and how they interact with others.

Be Open to Feedback

Welcome constructive feedback and use it to improve your performance and working relationship.

Build Trust Through Consistency

Be reliable, meet deadlines, and follow through on commitments to build trust and credibility.

Question Sequences

The Expectations Sequence

1
What are your expectations for my role and performance?
2
What are your priorities and goals for our department?
3
What are the biggest challenges facing our team right now?
4
What are your expectations for decision-making and autonomy?

The Communication Sequence

1
How do you prefer to communicate and how often?
2
How do you prefer to receive updates and reports?
3
What are your expectations for team collaboration and meetings?
4
How do you prefer to handle urgent issues and emergencies?

The Development Sequence

1
What are your thoughts on professional development and growth?
2
How do you like to recognize and reward good performance?
3
How do you prefer to handle mistakes and learning opportunities?
4
What advice do you have for someone new to this role?

Common Pitfalls

Don't Assume Their Style Matches Your Previous Supervisor

Each supervisor is different. Don't assume they'll work the same way as your previous manager.

Don't Wait for Them to Initiate Everything

Take initiative in building the relationship. Don't wait for them to reach out to you.

Don't Ignore Their Communication Preferences

Pay attention to how they communicate and adapt your style to match their preferences.

Don't Be Afraid to Ask Questions

It's better to ask questions early than to make assumptions that could lead to problems later.

Conversation Templates

The Initial Meeting Framework

1
Step 1: Start with: 'What are your expectations for my role and performance?'
2
Step 2: Follow with: 'How do you prefer to communicate and how often?'
3
Step 3: Ask: 'What are your priorities and goals for our department?'
4
Step 4: Close with: 'What advice do you have for someone new to this role?'

The Follow-up Framework

1
Step 1: Start with: 'How are things going so far? Are there any adjustments I should make?'
2
Step 2: Follow with: 'What are your thoughts on professional development and growth?'
3
Step 3: Ask: 'How do you like to recognize and reward good performance?'
4
Step 4: Close with: 'Is there anything else I should know about working with you?'

Further Reading

"The First 90 Days" by Michael Watkins
"Crucial Conversations" by Kerry Patterson
"The Manager's Path" by Camille Fournier
Harvard Business Review on managing up

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