Collage image of people speaking to each other through computer screens

Among the storm clouds known as COVID-19, there were few silver linings. One was that being forced to work from home all of a sudden changed our collective ideas about remote work. Though the pandemic is no longer front-page news, the dust has yet to settle on the long-term fate of remote work. Return-to-work and hybrid mandates continue to cause controversy, even as research increasingly shows that remote work makes for happier and more productive teams.

We firmly believe that remote work is the future, and those who are looking for work – and the managers hiring them – had better be ready. Employees who are particularly well-suited for remote roles tend to be intrinsically motivated and have a sense of purpose, which means they’ll meet or exceed expectations without anyone looking over their shoulder all day. They have world-class communication skills and emotional intelligence. They aren’t afraid to ask for support when they need it or take on new challenges when they’ve got bandwidth.

If you’re in a position to hire a remote candidate, here are the strategic questions to ask to ensure they have what it to rock remote.

“What’s the most ambitious project you’ve ever dreamed up and pursued?”

Speaks to: self-motivation.

Contact between managers and remote employees is unavoidably sparser than with co-located workers. You need to know they’ll keep plugging away (on the right things) without constant check-ins from you. 

People who are self-motivated will have a solid answer to this question. They love a good challenge and stay focused on it, even when they face a setback or a shiny new object enters their field of vision. 

“Tell me about a time you took a calculated risk and failed – what did you learn?”

How (and why) you should embrace a growth mindset

Speaks to: growth mindset.

Remote workers need to be flexible, persevering, and eager to experiment, and shouldn’t assume they already know the best way of doing things. And those just so happen to be the key components of a growth mindset. 

A candidate who is all about growth and continuous improvement will have at least one story in this vein. Listen carefully to how they frame the failure, though. Do they take ownership, or shift the blame elsewhere? Unless they openly accept responsibility, they probably didn’t learn anything. Owning the failure also demonstrates a desirable blend of humility, confidence, and integrity.

“If you’re hired, what’s the first thing you want to work on?”

Speaks to: amazing communication skills.

Okay, this is sort of a trick question. It’s unlikely anyone you’re interviewing would walk in with enough information to answer it authoritatively. And that’s the point. A good remote worker will ask clarifying questions right away. What are the team’s priorities right now? What projects are already in flight? What have we already tried that didn’t work?

Once they’ve got enough context to formulate an answer, look for candidates who get right to the point. A low signal-to-noise ratio is key for effective, efficient remote work. 

It’s also important that remote workers communicate effectively via multiple mediums: email, chat, talking live, slide decks, etc. Make a point to incorporate several of these into the interview processes so you get a holistic view of their communication skills and style.

“What are 3 things that struck you about… “

Speaks to: initiative. 

This question varies based on what type of role you’re interviewing for. If it’s a design or marketing role, ask what struck them about the company’s website. If it’s a finance role, ask what struck them about the numbers you released last quarter. And so on. “What struck you about our company values?” is a good all-purpose variant. 

What you’re sniffing out here is how proactive the candidate is. Did they take the initiative to research the company a bit? As a manager, you have better things to do that prod remote workers into action all the time. So make sure you won’t have to. 

“When have you had to give a colleague difficult feedback?”

Emotional intelligence is on the decline – what does it mean for the future of work?

Speaks to: emotional intelligence.

When all your interactions with colleagues are virtual – either voice, video, or text – it’s easy to miss out on social cues like body language or tone of voice. That’s why remote workers with a high level of emotional intelligence are more successful. They’re able to empathize and anticipate that person’s concerns or mood, then let that influence their communications with that person.

This question will reveal whether the candidate imagined themselves in the other person’s shoes before speaking with them, and how they took that into account. Candidates with an especially high EQ will talk about how they focused the feedback on the other person’s actions and behaviors, rather than their innate characteristics or worth. Also, take note of whether they offered to help the other person work on a solution or make changes – another sign of emotional intelligence.

“What worries you about not being part of an office community?”

Speaks to: self-awareness.

Even the most introverted remote workers need a little social nourishment. How does your candidate plan to get it? It’s less important what exactly their answer is. Really, you want to see that they’ve considered how being remote will affect them and have some idea what they’ll do to adapt. 

In an office setting, people tacitly look out for each other (“Hey, you look really tired today – everything ok?”). Remote workers, on the other hand, have to be keenly self-aware and good at self-care or they risk burning out.

“What excites you most about this role?”

Speaks to: purposefulness.

Effective remote workers are hyper-engaged in their work. They understand why it’s valuable, and that shows through. It’s hard to course-correct someone’s sense of purpose if they’re remote, so make sure your candidate nails this one.

Ideally, they’ll say that they’re passionate about the company’s mission. Or they might be excited to hone a new skill. Or work at a different type of company. However they answer, make sure their sense of purpose and yours are in alignment.

“When have you had to make a decision without all the information you needed?”

Speaks to: independent decision-making.

You’ll have an easier time managing remote team members who you can trust to make the right call on small and medium-sized decisions autonomously. The best remote workers take time to understand the bigger picture, as well as what they need to optimize for at all costs versus where they can be flexible so they can evaluate trade-offs effectively.

Hearing how they’ve handled decisions where they were flying blind to some extent gives you an especially good window into their decision-making process. It reveals what information they sought out and what information they felt they could do without. Keep an eye ear out for how they thought about their decision’s impact on customers and stakeholders – not just themselves or their immediate team.

“How would you go about getting a new project off the ground?”

Speaks to: leadership skills.

Even if the job isn’t managerial, leadership skills are still important – especially if your company is one where individual contributors frequently play the role of project lead.

Leading from afar means being extra intentional about coordinating and communicating. So listen carefully to how they’d build the business case for the project and convince the leadership team to give it the green light. Then, how would they pull a project team together? A good remote worker will instinctively think about all the different job functions or skills needed for the project and won’t hesitate to get other teams involved if need be.

Special thanks to Sarah Goff-Dupont for her contribution to this article.

9 interview questions successful remote workers will ace