20 Questions

Questions to Ask Your Manager on the First Day

Start your new job strong by asking these strategic first-day questions that help you understand expectations, build rapport with your manager, and set yourself up for success.

1

What are your top priorities for me in the first 30, 60, and 90 days?

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Why this works

Establishes clear expectations and helps you focus your efforts on what matters most to your manager.

2

How do you prefer to communicate and how often should we check in?

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Why this works

Aligns on communication style and frequency to ensure you stay connected without over or under-communicating.

3

What does success look like in this role?

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Why this works

Clarifies the metrics and outcomes your manager will use to evaluate your performance.

4

What are the biggest challenges the team is currently facing?

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Why this works

Helps you understand the context you're stepping into and where you might make the biggest impact.

5

Who are the key people I should meet and build relationships with?

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Why this works

Identifies important stakeholders and helps you prioritize relationship-building efforts.

6

What's your management style and how can I work best with you?

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Why this works

Reveals their approach to leadership and helps you adapt your working style to their preferences.

7

What are the team's current projects and where do I fit in?

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Why this works

Provides context on ongoing work and clarifies your immediate role and responsibilities.

8

What resources and tools will I need to do my job effectively?

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Why this works

Ensures you have everything you need to be productive from the start.

9

How should I prioritize if I have multiple competing deadlines?

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Why this works

Establishes decision-making guidelines for managing your workload when things get busy.

10

What's the best way for me to ask questions as I'm getting up to speed?

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Why this works

Shows you want to learn while respecting their time and preferred communication channels.

11

Are there any immediate tasks or projects you'd like me to start with?

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Why this works

Gives you clear direction on where to focus your initial efforts.

12

What's the team culture like and what should I know about how we work together?

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Why this works

Helps you understand unwritten norms and expectations about collaboration and communication.

13

What are the growth and development opportunities in this role?

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Why this works

Shows ambition while understanding the potential career path and skill-building opportunities.

14

How do you like to receive updates on my progress?

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Why this works

Ensures you're keeping your manager informed in the way they find most useful.

15

What mistakes should I avoid in my first few months?

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Why this works

Learns from past experiences and helps you navigate common pitfalls that trip up new hires.

16

What's the process for decision-making on the team?

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Why this works

Clarifies when you can act independently versus when you need approval or input.

17

How does our team's work contribute to the company's overall goals?

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Why this works

Provides big-picture context that helps you understand the impact of your work.

18

What feedback do you have for me based on the interview process?

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Why this works

Shows openness to feedback and helps you understand what they're looking for in your performance.

19

What's the best way to stay informed about company news and updates?

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Why this works

Ensures you're plugged into relevant information channels from the start.

20

Is there anything else I should know that would help me be successful here?

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Why this works

Opens the door for any additional context or advice they think is important.

Best Practices for First Day Conversations

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

Best Practices

Take Notes

Bring a notebook and write down key information. You'll be overwhelmed with new information and won't remember everything.

Show Enthusiasm and Curiosity

Your questions demonstrate your interest and engagement. Ask thoughtfully and show genuine interest in the answers.

Balance Listening and Asking

Don't rapid-fire questions. Give your manager time to share and have a natural conversation.

Question Sequences

The Expectations and Success Sequence

1
What are your top priorities for me in the first 30, 60, and 90 days?
2
What does success look like in this role?
3
What mistakes should I avoid in my first few months?

The Communication and Working Style Sequence

1
How do you prefer to communicate and how often should we check in?
2
What's your management style and how can I work best with you?
3
How do you like to receive updates on my progress?

Common Pitfalls

Don't Pretend to Know Things You Don't

It's your first day—no one expects you to know everything. Ask questions when you're unclear rather than guessing.

Don't Overwhelm Your Manager

Space out your questions throughout the day or week. You don't need to ask everything in one conversation.

Don't Skip the Relationship Building

While tasks are important, investing time in understanding your manager and building rapport is equally crucial.

Conversation Templates

The Comprehensive First Day Approach

1
Step 1: Start with: "What are your top priorities for me in the first 30, 60, and 90 days?"
2
Step 2: Clarify communication with: "How do you prefer to communicate and how often should we check in?"
3
Step 3: Understand success with: "What does success look like in this role?"
4
Step 4: Get immediate direction with: "Are there any immediate tasks or projects you'd like me to start with?"

The Context and Relationships Focus

1
Step 1: Begin with: "What are the biggest challenges the team is currently facing?"
2
Step 2: Build network with: "Who are the key people I should meet and build relationships with?"
3
Step 3: Understand dynamics with: "What's the team culture like and what should I know about how we work together?"

Further Reading

"The First 90 Days" by Michael D. Watkins
"You're In Charge—Now What?" by Thomas J. Neff and James M. Citrin
"The New Leader's 100-Day Action Plan" by George Bradt

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