Questions to Ask Your New Supervisor
Strategic questions to ask a new supervisor to clarify expectations, build rapport, and set yourself up for success in the reporting relationship.
1What are your expectations for communication frequency and methods?
Click to see why this works
What are your expectations for communication frequency and methods?
Click to see why this works
Why this works
Understanding preferred communication styles prevents misalignment and ensures you're connecting in ways that work best for your supervisor.
2What does success look like in this role over the next 90 days?
Click to see why this works
What does success look like in this role over the next 90 days?
Click to see why this works
Why this works
Clear short-term goals help you prioritize effectively and demonstrate quick wins that build credibility early in the relationship.
3How do you prefer to give and receive feedback?
Click to see why this works
How do you prefer to give and receive feedback?
Click to see why this works
Why this works
Feedback preferences shape how you'll grow together and ensure developmental conversations are productive rather than defensive.
4What are the biggest challenges or priorities for our team right now?
Click to see why this works
What are the biggest challenges or priorities for our team right now?
Click to see why this works
Why this works
Understanding team context helps you align your efforts with what matters most and contribute meaningfully from the start.
5How do you like to make decisions - collaboratively or independently?
Click to see why this works
How do you like to make decisions - collaboratively or independently?
Click to see why this works
Why this works
Decision-making styles affect how much autonomy you have and when you should seek input versus act independently.
6What's your management style, and how can I best work with you?
Click to see why this works
What's your management style, and how can I best work with you?
Click to see why this works
Why this works
Self-awareness about management approaches helps you adapt your working style for a more effective partnership.
7Are there any projects or tasks you'd like me to take ownership of immediately?
Click to see why this works
Are there any projects or tasks you'd like me to take ownership of immediately?
Click to see why this works
Why this works
Identifying quick priorities shows initiative and gives you concrete ways to demonstrate value early in the relationship.
8What's the best way to bring problems or concerns to your attention?
Click to see why this works
What's the best way to bring problems or concerns to your attention?
Click to see why this works
Why this works
Knowing escalation preferences ensures you raise issues appropriately without being seen as complaining or withholding information.
9How do you define work-life balance, and what are your expectations around availability?
Click to see why this works
How do you define work-life balance, and what are your expectations around availability?
Click to see why this works
Why this works
Boundary clarity prevents burnout and helps you understand unspoken expectations about responsiveness and working hours.
10What professional development opportunities do you see for me in this role?
Click to see why this works
What professional development opportunities do you see for me in this role?
Click to see why this works
Why this works
Growth conversations early signal your ambition and help you understand whether your supervisor will invest in your development.
11Who else on the team or in the organization should I build relationships with?
Click to see why this works
Who else on the team or in the organization should I build relationships with?
Click to see why this works
Why this works
Strategic networking guidance helps you quickly understand key stakeholders and build the connections you need to be effective.
12What's one thing your previous direct reports did that you really appreciated?
Click to see why this works
What's one thing your previous direct reports did that you really appreciated?
Click to see why this works
Why this works
Positive examples reveal what behaviors and approaches your supervisor values most in their team members.
13How do you prefer to handle conflicts or disagreements within the team?
Click to see why this works
How do you prefer to handle conflicts or disagreements within the team?
Click to see why this works
Why this works
Conflict resolution approaches help you navigate interpersonal challenges in ways your supervisor will support and appreciate.
14What metrics or indicators will you use to evaluate my performance?
Click to see why this works
What metrics or indicators will you use to evaluate my performance?
Click to see why this works
Why this works
Performance criteria clarity ensures you're focusing on what actually matters for evaluation rather than guessing what counts.
15Are there any projects or initiatives from the past that I should be aware of?
Click to see why this works
Are there any projects or initiatives from the past that I should be aware of?
Click to see why this works
Why this works
Historical context prevents you from repeating failed attempts and helps you understand sensitivities or lessons learned.
16What's your preferred meeting cadence for one-on-ones?
Click to see why this works
What's your preferred meeting cadence for one-on-ones?
Click to see why this works
Why this works
Regular check-in schedules establish accountability rhythms and ensure you have dedicated time to discuss progress and concerns.
17How much autonomy do you typically give team members in their work?
Click to see why this works
How much autonomy do you typically give team members in their work?
Click to see why this works
Why this works
Autonomy expectations help you understand when to check in versus when to make independent decisions and move forward.
18What aspects of the role or team are you most excited about?
Click to see why this works
What aspects of the role or team are you most excited about?
Click to see why this works
Why this works
Enthusiasm reveals what your supervisor values and where they're investing energy, helping you align with their priorities.
19Are there any unwritten rules or cultural norms on the team I should know?
Click to see why this works
Are there any unwritten rules or cultural norms on the team I should know?
Click to see why this works
Why this works
Informal expectations often matter as much as formal ones, and early awareness helps you navigate team dynamics successfully.
20What questions do you have for me about my work style or background?
Click to see why this works
What questions do you have for me about my work style or background?
Click to see why this works
Why this works
Inviting their questions demonstrates openness and helps them understand how to work effectively with you from the start.
Building a Strong Supervisor Relationship
Expert tips and techniques for getting the most out of these questions.
Best Practices
Schedule a Dedicated Meeting
Request a focused conversation in the first week to ask these questions rather than squeezing them into other meetings.
Listen More Than You Talk
Use these questions to understand your supervisor's perspective and priorities rather than pushing your own agenda immediately.
Take Notes and Follow Up
Document key points from the conversation and reference them as you work to show you're listening and aligning with expectations.
Be Genuine and Professional
Ask questions out of genuine interest in building a good relationship, not as a performative exercise to impress.
Conversation Flow
The Getting Started Sequence
The Working Relationship Builder
Common Pitfalls
Don't Ask About Promotion Too Soon
While growth questions are fine, asking about promotion paths in the first meeting can seem presumptuous before proving yourself.
Avoid Comparing to Previous Supervisor
Don't reference how your last boss did things - focus on understanding this supervisor's approach without implied comparisons.
Don't Overwhelm with Questions
Choose 5-7 most important questions for the first conversation rather than running through an interrogation checklist.