Good Questions to Ask a New Boss
Strategic questions to ask your new boss to establish rapport, understand expectations, and set yourself up for success in your new role.
1What are your top priorities for this team/department?
Click to see why this works
What are your top priorities for this team/department?
Click to see why this works
Why this works
Helps you understand the boss's focus areas and align your work with their most important goals.
2How do you prefer to communicate and receive updates?
Click to see why this works
How do you prefer to communicate and receive updates?
Click to see why this works
Why this works
Establishes effective communication patterns and ensures you're providing information in their preferred format.
3What does success look like in this role from your perspective?
Click to see why this works
What does success look like in this role from your perspective?
Click to see why this works
Why this works
Clarifies performance expectations and helps you understand how your work will be evaluated.
4What are the biggest challenges facing our team right now?
Click to see why this works
What are the biggest challenges facing our team right now?
Click to see why this works
Why this works
Reveals current pain points and opportunities where you can make an immediate impact.
5How do you like to give and receive feedback?
Click to see why this works
How do you like to give and receive feedback?
Click to see why this works
Why this works
Establishes a feedback culture and ensures you can provide and receive constructive input effectively.
6What's your management style and approach to leadership?
Click to see why this works
What's your management style and approach to leadership?
Click to see why this works
Why this works
Helps you understand how to work best with your boss and adapt to their leadership preferences.
7What are your expectations for the first 30, 60, and 90 days?
Click to see why this works
What are your expectations for the first 30, 60, and 90 days?
Click to see why this works
Why this works
Provides clear milestones and helps you prioritize your early efforts and learning goals.
8How do you handle decision-making and when should I involve you?
Click to see why this works
How do you handle decision-making and when should I involve you?
Click to see why this works
Why this works
Clarifies your decision-making authority and when to escalate issues or seek approval.
9What resources or support do you need from me?
Click to see why this works
What resources or support do you need from me?
Click to see why this works
Why this works
Shows you're thinking about how to support your boss and identifies ways you can add value.
10What's the best way to approach you with questions or concerns?
Click to see why this works
What's the best way to approach you with questions or concerns?
Click to see why this works
Why this works
Establishes open communication channels and ensures you know how to get help when needed.
11How do you prefer to handle meetings and one-on-ones?
Click to see why this works
How do you prefer to handle meetings and one-on-ones?
Click to see why this works
Why this works
Helps you prepare for and participate effectively in regular check-ins and team meetings.
12What are your pet peeves or things I should avoid?
Click to see why this works
What are your pet peeves or things I should avoid?
Click to see why this works
Why this works
Helps you avoid common mistakes and understand their preferences and boundaries.
13How do you like to recognize and celebrate team achievements?
Click to see why this works
How do you like to recognize and celebrate team achievements?
Click to see why this works
Why this works
Reveals their approach to motivation and helps you understand how to contribute to team success.
14What's your vision for where this team/department is heading?
Click to see why this works
What's your vision for where this team/department is heading?
Click to see why this works
Why this works
Provides context for your role and helps you understand the bigger picture and long-term goals.
15How do you handle conflict resolution and team dynamics?
Click to see why this works
How do you handle conflict resolution and team dynamics?
Click to see why this works
Why this works
Shows their approach to managing relationships and helps you navigate team interactions effectively.
16What professional development opportunities do you support?
Click to see why this works
What professional development opportunities do you support?
Click to see why this works
Why this works
Reveals their commitment to your growth and identifies learning opportunities they can facilitate.
17How do you balance work and life, and what are your expectations for the team?
Click to see why this works
How do you balance work and life, and what are your expectations for the team?
Click to see why this works
Why this works
Establishes work-life balance expectations and helps you understand their approach to employee well-being.
18What's the best way to build relationships with other team members?
Click to see why this works
What's the best way to build relationships with other team members?
Click to see why this works
Why this works
Helps you integrate effectively into the team and understand the team culture and dynamics.
19How do you handle mistakes and learning opportunities?
Click to see why this works
How do you handle mistakes and learning opportunities?
Click to see why this works
Why this works
Reveals their approach to failure and growth, helping you feel comfortable taking calculated risks.
20What would make you feel confident that I'm succeeding in this role?
Click to see why this works
What would make you feel confident that I'm succeeding in this role?
Click to see why this works
Why this works
Provides specific success criteria and helps you understand what behaviors and outcomes matter most.
Best Practices for New Boss Relationships
Expert tips and techniques for getting the most out of these questions.
Building the Relationship
Schedule Regular Check-Ins
Establish consistent one-on-one meetings to maintain open communication and address questions proactively.
Observe and Adapt
Pay attention to their communication style, preferences, and working patterns to build effective collaboration.
Be Proactive
Anticipate needs and provide solutions rather than just reporting problems or waiting for direction.
Effective Communication Strategies
The Weekly Check-In
Common Mistakes to Avoid
Don't Assume Their Preferences
Ask about their communication style, meeting preferences, and expectations rather than making assumptions.
Avoid Over-Communication
Respect their time and attention by being concise and focusing on the most important information.
Don't Wait for Perfect Information
Provide updates and ask questions even when you don't have complete information - it's better than silence.