15 min read

    How to Hire Your First Remote Worker

    A step-by-step guide to making your first remote hire successful, from job posting to onboarding.

    Is Your Company Remote-Ready?

    Before you hire, ensure you have the basics in place:

    Communication infrastructure:

    Slack, Teams, or similar for async communication. Video conferencing for meetings.

    Documentation habits:

    Remote work requires writing things down. If everything lives in hallway conversations, you'll struggle.

    Trust mindset:

    Remote work fails when managers don't trust employees to work without supervision. If you need to see butts in seats, reconsider.

    Clear expectations:

    Remote workers need clarity on goals, availability expectations, and communication norms.

    • Communication tools selected and team trained
    • Core processes documented
    • Results-based performance metrics defined
    • Time zone and availability expectations clear
    • Management team aligned on remote work approach

    Writing a Remote Job Post That Attracts Top Talent

    Remote-specific details matter. Include:

    - **Time zone requirements:** Are there core hours? How much overlap do you need? - **Equipment policy:** Do you provide equipment or a stipend? - **Communication expectations:** Sync vs. async balance - **Location restrictions:** Any countries you can't hire from? - **Travel requirements:** Any in-person gatherings?

    Be honest about challenges. "We're still figuring out remote work" is fine—the right candidates will appreciate transparency.

    Interviewing for Remote Success

    Remote work requires specific traits beyond job skills:

    Self-direction:

    "Walk me through how you structure your workday when no one's watching."

    Written communication:

    "How do you decide when to send a message vs. schedule a call?"

    Proactivity:

    "Tell me about a time you felt disconnected from your team. What did you do?"

    Time management:

    "How do you handle multiple deadlines with no one checking in?"

    Also evaluate their video presence—are they comfortable on camera? Clear audio setup? Professional background?

    Pro tip: Do at least one interview asynchronously—send questions and have them respond via video. This mimics real remote work.

    Onboarding a Remote Employee

    Remote onboarding requires more intentionality than in-office:

    Before Day 1:

    - Ship equipment with setup instructions - Send welcome package with company swag - Schedule all first-week meetings - Assign an onboarding buddy

    Week 1:

    - Daily video check-ins with manager - Virtual coffee chats with team members - Clear first-week goals and success criteria - Access to all necessary tools and documentation

    First 30 days:

    - Weekly 1:1s with manager - Introduction to cross-functional partners - First real project with clear deliverables - Feedback checkpoint at day 30