20 Questions

Questions to Ask Before Accepting a Remote Job

Essential questions to evaluate a remote job opportunity and ensure it's the right fit for your work style, career goals, and lifestyle.

1

What does the typical workday look like for this role?

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Why this works

Helps you understand the daily expectations, schedule flexibility, and whether the role matches your preferred work style and productivity patterns.

2

What tools and technology will I need to provide versus what the company provides?

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Why this works

Critical for understanding your setup costs and ensuring you have the necessary equipment to perform your job effectively.

3

How does the company handle communication and collaboration across remote teams?

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Why this works

Reveals their remote work culture and whether their communication style aligns with your preferences and working style.

4

What are the expectations for availability and response times?

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Why this works

Important for understanding work-life balance boundaries and whether the expectations are realistic for your time zone and lifestyle.

5

How often are team meetings and what's the format?

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Why this works

Helps you gauge the level of interaction and whether the meeting schedule works with your productivity and personal schedule.

6

What opportunities are there for career advancement and professional development?

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Why this works

Essential for understanding growth potential and whether remote work will limit your career progression opportunities.

7

How does the company handle performance reviews and feedback for remote employees?

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Why this works

Shows their approach to managing remote workers and ensures you'll receive proper guidance and recognition for your work.

8

What's the company's policy on remote work expenses and home office setup?

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Why this works

Important for understanding what costs you'll bear versus what the company will reimburse or provide.

9

How does the team handle onboarding and training for new remote employees?

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Why this works

Reveals their experience with remote workers and whether you'll receive adequate support during your transition into the role.

10

What are the biggest challenges of working remotely at this company?

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Why this works

Shows their honesty about remote work difficulties and helps you prepare for potential challenges you might face.

11

How does the company maintain team culture and connection in a remote environment?

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Why this works

Important for understanding whether you'll feel connected to your colleagues and the company culture despite physical distance.

12

What are the expectations for travel to the office or company events?

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Why this works

Helps you understand the level of travel required and whether it fits with your lifestyle and budget constraints.

13

How does the company handle time zone differences and scheduling conflicts?

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Why this works

Critical if you're in a different time zone, as this affects your work schedule and work-life balance.

14

What support systems are in place for remote employees' mental health and well-being?

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Why this works

Shows the company's commitment to employee wellness and whether they understand the unique challenges of remote work.

15

How does the company handle project management and task assignment for remote teams?

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Why this works

Reveals their workflow processes and whether their project management style aligns with your working preferences.

16

What are the company's policies on remote work security and data protection?

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Why this works

Important for understanding security requirements and ensuring you can meet their data protection standards from your home office.

17

How does the company handle remote employee recognition and team building?

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Why this works

Shows whether remote workers receive equal recognition and opportunities for team connection and professional relationships.

18

What happens if there are technical issues with your home internet or equipment?

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Why this works

Important for understanding backup plans and support systems when technical problems arise that could affect your work.

19

How does the company measure productivity and success for remote employees?

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Why this works

Reveals their approach to performance evaluation and whether their metrics are fair and achievable for remote work.

20

Can you connect me with other remote employees to learn about their experience?

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Why this works

Allows you to get honest feedback from current remote workers about the company culture, challenges, and overall experience.

How to Evaluate a Remote Job Opportunity

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

Best Practices

Assess Your Remote Work Readiness

Honestly evaluate your self-discipline, communication skills, and ability to work independently. Remote work requires strong time management and self-motivation.

Test the Technology

Ask to test the company's communication and collaboration tools before accepting. Ensure you're comfortable with their tech stack and that it works well with your setup.

Understand the Company Culture

Research how the company maintains culture remotely. Look for evidence of virtual team building, regular check-ins, and efforts to keep remote workers engaged.

Clarify Expectations Early

Get specific details about work hours, availability requirements, and performance metrics. Clear expectations prevent misunderstandings and stress later.

Question Sequences

The Technology and Setup Sequence

1
Start with: 'What equipment do I need to provide?'
2
Follow with: 'What software and tools will I be using?'
3
Deepen with: 'How do you handle technical support for remote employees?'

The Work-Life Balance Sequence

1
Begin with: 'What are the expected work hours?'
2
Explore with: 'How do you handle time zone differences?'
3
Clarify with: 'What's the policy on after-hours communication?'

Common Pitfalls

Don't Assume All Remote Jobs Are the Same

Remote work varies greatly between companies. Some offer flexibility while others have strict schedules and monitoring. Understand the specific expectations.

Avoid Ignoring Career Development

Remote work can limit visibility and advancement opportunities. Ensure the company has clear paths for remote employee growth and recognition.

Don't Underestimate the Isolation

Remote work can be lonely. Look for companies that actively work to maintain team connections and provide support for remote worker well-being.

Avoid Vague Communication Policies

Get specific details about communication expectations, meeting schedules, and response times. Vague policies lead to misunderstandings and stress.

Evaluation Templates

The Comprehensive Remote Work Assessment

1
Step 1: Start with role expectations and daily workflow
2
Step 2: Move to technology and equipment requirements
3
Step 3: Explore communication and collaboration processes
4
Step 4: Discuss work-life balance and boundaries
5
Step 5: End with career development and company culture

The Lifestyle Compatibility Check

1
Step 1: Assess your personal work style and preferences
2
Step 2: Evaluate the company's remote work culture
3
Step 3: Consider your home office setup and environment
4
Step 4: Think about long-term career goals and growth

Further Reading

"Remote: Office Not Required" by Jason Fried and David Heinemeier Hansson
"The Year Without Pants" by Scott Berkun
Remote Work Best Practices Guide
Digital Nomad Community Resources

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