20 Questions

Questions to Ask on Your First Day on the Job

Strategic questions to ask on your first day at a new job to set yourself up for success, build relationships, and clarify expectations.

1

What does success look like in this role during my first 30, 60, and 90 days?

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Why this works

Establishes clear performance milestones so you can prioritize effectively and meet expectations.

2

Who should I go to with different types of questions or issues?

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Why this works

Maps out your support network early so you know who to approach for technical, administrative, or strategic guidance.

3

What are the most important priorities I should focus on immediately?

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Why this works

Helps you distinguish urgent tasks from long-term projects and make a strong initial impact.

4

How does this team prefer to communicate—email, Slack, meetings, or something else?

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Why this works

Ensures you align with established communication norms and don't miss important updates.

5

What systems, tools, or software will I be using regularly?

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Why this works

Identifies the technology you need to learn quickly to be productive in your role.

6

Are there any unwritten rules or cultural norms I should be aware of?

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Why this works

Reveals office culture subtleties that aren't in the handbook but are important for fitting in.

7

What meetings should I attend, and which are optional?

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Why this works

Clarifies your schedule and helps you manage time without overcommitting to unnecessary meetings.

8

How are performance reviews conducted, and when is my first one?

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Why this works

Sets expectations for feedback cycles so you can prepare and track your progress accordingly.

9

Who are the key stakeholders I'll be working with regularly?

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Why this works

Helps you identify and prioritize relationship-building with the people who matter most to your success.

10

What resources are available for learning and professional development?

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Why this works

Shows initiative and helps you leverage training opportunities to accelerate your growth.

11

What's the best way to stay updated on company news and announcements?

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Why this works

Ensures you're informed about organizational changes, updates, and important information.

12

Are there any ongoing projects I should be aware of or get up to speed on?

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Why this works

Provides context for current work streams and where you might contribute immediately.

13

What are the expectations around working hours and flexibility?

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Why this works

Clarifies boundaries around start/end times, remote work, and availability expectations.

14

How does the team typically collaborate on projects?

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Why this works

Helps you understand workflows, decision-making processes, and how to contribute effectively.

15

What challenges has this role or team faced recently?

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Why this works

Gives insight into pain points you can address and demonstrates strategic thinking.

16

Are there any company events or traditions I should know about?

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Why this works

Helps you participate in cultural moments that build camaraderie and integration.

17

Who handles IT support, and what's the process for getting technical help?

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Why this works

Ensures you can resolve technical issues quickly without lengthy interruptions.

18

What's the process for requesting time off or reporting sick days?

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Why this works

Clarifies administrative procedures so you follow the right protocols from day one.

19

How can I best support you and the rest of the team?

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Why this works

Shows collaboration and willingness to contribute beyond your immediate responsibilities.

20

Is there anything I should read, review, or familiarize myself with to get up to speed?

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Why this works

Demonstrates eagerness to learn and helps you proactively close knowledge gaps.

Best Practices for Your First Day on the Job

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

Best Practices

Be Curious, Not Demanding

Frame questions with genuine interest and humility. You're learning, not interrogating.

Take Notes

Write down names, processes, and systems. It shows attentiveness and prevents asking the same question twice.

Observe Before Acting

Spend time watching how things are done before jumping in with suggestions or changes.

Express Gratitude

Thank people for their time and assistance. Building goodwill early pays dividends throughout your tenure.

Question Sequences

The Priorities Sequence

1
What are the most important priorities I should focus on immediately?
2
What does success look like in this role during my first 30, 60, and 90 days?
3
Are there any ongoing projects I should be aware of or get up to speed on?

The Integration Sequence

1
Who should I go to with different types of questions or issues?
2
Who are the key stakeholders I'll be working with regularly?
3
Are there any unwritten rules or cultural norms I should be aware of?

The Learning Sequence

1
What systems, tools, or software will I be using regularly?
2
Is there anything I should read, review, or familiarize myself with to get up to speed?
3
What resources are available for learning and professional development?

Common Pitfalls

Don't Overwhelm People with Questions

Spread your questions throughout the day and across multiple people. Nobody wants to be bombarded.

Don't Criticize or Compare

Avoid saying 'At my last company we did it this way.' Listen and learn before suggesting changes.

Don't Pretend to Know Things You Don't

It's okay to be new. Admitting you don't know something is far better than making mistakes.

Don't Skip the Small Talk

Building rapport through casual conversation is just as important as asking work-related questions.

Conversation Templates

The New Hire Check-In

1
Step 1: Start with: 'Thanks so much for taking time to help me get oriented'
2
Step 2: Follow with: 'What should I prioritize learning in my first week?'
3
Step 3: Ask: 'Who else should I connect with to get up to speed?'
4
Step 4: Close with: 'I really appreciate your guidance. Can I check back in with you if I have more questions?'

The Stakeholder Introduction

1
Step 1: Start with: 'Hi, I'm [name], I just joined as [role]. Great to meet you!'
2
Step 2: Follow with: 'I understand we'll be working together on [project/area]'
3
Step 3: Ask: 'What's the best way for us to stay in touch and collaborate?'
4
Step 4: Close with: 'Looking forward to working with you!'

Further Reading

"The First 90 Days" by Michael Watkins
"Radical Candor" by Kim Scott
"Who Moved My Cheese?" by Spencer Johnson

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