TECH-SAVVYNESS

You’ll want candidates to have:

• a great internet connection with no dropping out;
• a high-quality microphone—you can hear them well;
• good speakers—they can hear you well;
• an appropriate space for video calls; and
• facility with the equipment and protocols concerning online apps, video conferencing, and instant messaging.

EXCELLENT COMMUNICATION SKILLS

• Look for admirable responses to all application-relevant communication, both verbal (phone and video) and written (cover letter, emails, texts, IM)—as well as to any assignments, as appropriate.

GOOD WORK HABITS

You’ll want to assess their:

• ORGANIZATIONAL SKILLS—for which you could prompt: “Describe your workspace.” “How do you normally start your workday? What determines your first task or activity?”
• TASK-MANAGEMENT SKILLS—for which you could ask: “What task- or project-management tools have you used? Which do you prefer and why?”
• PRIORITIZING/TIME-MANAGEMENT STRATEGIES. For this you might present a jumbled list of daily or weekly tasks and ask in what order the candidate would tackle them and why.

PROBLEM-SOLVING/TROUBLESHOOTING SKILLS

• I personally like describing a tricky scenario and asking candidates how they’d go about solving it. Or I might assign a quandary to solve after the interview, requesting they get back to me describing their process. Similarly, the Entrepreneur on Fire podcast asks all its guests, “If you woke up tomorrow morning, and you still possessed all the experience and knowledge you currently have—but your business had completely disappeared, forcing you to start somewhere, anywhere, from scratch—what would you do?”¹ This question provides a sense of how each entrepreneur guest thinks; a comparable question targeted to your industry could produce some illuminating answers.
• Ask candidates to complete a very small project. For example, a programmer could write a short program; a marketer could create a newsletter; a virtual assistant could organize and assign tasks in a project list. How well they fare on this assignment would give you a glimpse of how well they’d fare for you across the board.

PREVIOUS EXPERIENCE WORKING REMOTELY

Some possible questions include:

• “What do you like most and least about working remotely?”
• “What do you do to address loneliness?”
• “What’s meaningful to you about working remotely?” (For some this question can flush out a situational motivation—like “spending my commute time with my family”—that would underlie a candidate’s dedication to making the position work. For others, this or a similar question could identify if the candidate has worked remotely long enough to have somewhat philosophical thoughts on the subject.)

INDEPENDENCE: PROACTIVE/SELF-MOTIVATED

Some considerations include:

• Work history: Upward movement within or across companies? Rehired by former bosses?
• Outside interests? Long-term pursuits? Personal development?
• Preferred tricks to staying motivated.
• Examples of resiliency in response to setbacks or hardship.

GOOD TEAM PLAYER/INTERPERSONAL GOOD FIT

You’ll want the candidate to:

• be pleasant to interact with;
• demonstrate a collaborative, supportive nature; and
• demonstrate productive receptivity to feedback.

Possible questions include:

• “Describe the last misunderstanding you had with a coworker and how you handled it.”
• “What do people like most about working with you? What annoys people about working with you?”

TEAM-FOCUSED WORK ETHICS

Possible questions include:

• “Are you willing to make work visible to others?” “Describe how you work out loud.” “Are you amenable to other approaches?”
• “What do you think email is best for? What other tools do you use to communicate different work-related information?”

And, finally, note if the candidate

• responds quickly in all aspects concerning the application and interview process.