I estimate that I’ve interviewed a couple hundred remote workers in the last 15 years. Some were for long, permanent jobs. Others were for one-off projects that only lasted a couple of months. Regardless of the exact situation, good questions are the centerpiece of an interview.
In this post I want to dive into some great questions that you should ask as a hiring manager, and what you should prepare for as a candidate. I recently gave a presentation about managing remote workers in an autonomous way vs an authoritarian way, and there were many questions about hiring practices and methodologies. Because of this, I’m putting together a comprehensive list of questions that hiring managers can use in their interviews. Understanding the answers to the basics surrounding education,
I’m breaking these questions into the following categories:
- Remote Work Experience
- Time Management
- Strategic Thinking
- Problem-solving and Adaptability
- Cultural Fit
- Tools and Technology
- Collaboration and Teamwork
- Self-motivation and Discipline
- Communication Skills
Questions about Remote Work Experience
Having remote work experience already is, in my opinion, a huge difference in candidate quality. At my marketing company, we’ve hired freelancers almost exclusively. This is because they typically had the remote part of their job down completely. That was huge for us/me because I wasn’t the handholding kind of manager.
Nowadays it’s just as important to understand how you work best while remote, as it is to do your actual job. They go hand in hand. About half the questions below are questions we used in our actual interviews, and they specifically aim to give us an idea of how good they are at working remotely.
- What initially attracted you to remote work?
- Describe a project you successfully completed entirely remotely.
- How do you handle feelings of isolation or disconnection in a remote setting?
- What strategies have you used to build rapport with a team you’ve never met in person?
- How do you ensure you’re aligned with your team’s goals when working remotely?
- Can you share an instance where remote work posed a significant challenge and how you addressed it?
- How do you handle distractions at home or in your remote workspace?
- What’s the biggest misconception people have about remote work, in your opinion?
- Do you have any methods that help you separate work life from personal life when working from home?
Questions about Time Management
Assuming the candidate has a good amount of experience working remotely (years), they should understand how best to manage their time. But again, asking intelligent questions on this topic is the best way to confirm this. If you’re a hiring manager reading this, I would encourage you to think about how you manage your time while working remotely. That will help you come up with additional questions that dig deeper as it relates to your company.
- How do you prioritize tasks when you’re juggling multiple projects remotely?
- Describe a time when you missed a deadline. What did you learn from it?
- How do you handle urgent requests or last-minute changes from colleagues in different time zones?
- Are there specific tools or techniques that you use to manage your time effectively when working remotely?
- How do you ensure you take regular breaks during the workday?
- Describe how you set daily and weekly goals for yourself.
- How do you handle tasks that require deep concentration in a remote setting?
- What strategies do you employ to avoid procrastination?
- How do you ensure you meet deliverables when faced with unforeseen personal distractions?
Questions about Strategic Thinking
Strategic thinking in a remote context involves a forward-looking mindset and the ability to plan with a focus on long-term success. It’s about understanding the big picture and making decisions that will benefit the team and company, even when face-to-face interactions are limited. Questions about strategic thinking probe into how candidates set goals (for themselves and team members they manage), anticipate challenges, and build/tweak processes when working remotely. They reveal how a candidate’s individual contributions align with the broader organizational objectives while still driving growth. I’m leaving these questions purposefully broad, as you may want to alter and/or create new ones that relate more heavily to your organization.
- How do you align your individual goals with the broader objectives of a remote team or organization?
- Describe a time when you proposed a long-term strategy or initiative for a remote team.
- How do you ensure that strategic decisions you make are communicated and understood by a remote team?
- How do you handle differences in strategic vision within a remote team?
- What’s a book or resource that has influenced your strategic thinking in the context of remote work?
- How do you ensure continuous learning and growth in a remote role?
Questions about Problem-solving and Adaptability
Remote work is a very dynamic environment, almost by definition. It requires a lot of flexibility and an ability to solve problems and adapt to new situations is critical when in-person troubleshooting isn’t an option. This section’s questions explore how candidates approach difficulties, whether they’re technical glitches or project roadblocks, and how they pivot in response to change (the most important IMO). A remote worker’s problem-solving and adaptability skills are key indicators of how they will perform in an environment that is constantly evolving and where they must often rely on their resourcefulness. For me personally, it’s what I look at the most when interviewing remote candidates.
- Describe a situation where you had to quickly adapt to a big change or unexpected challenge in a remote setting.
- How do you approach problems that arise due to technological issues during remote work? Feel free to use an actual example.
- Can you share an instance where you had to mediate a conflict in a virtual team setting?
- How do you ensure you have all the information needed to solve a problem when working remotely?
- Describe a time when you took a creative approach (that made you nervous) to solve a remote work-related issue.
- How do you handle feedback or criticism in a virtual environment? (this could involve them, or their direct reports)
- How do you stay adaptable to changing project requirements or team dynamics in a remote setting?
- What steps do you take to ensure you’re not stuck in a rut or routine when working remotely?
- How do you seek out diverse perspectives to aid in problem-solving in a virtual team?
- Describe a time when you had to make a decision with limited information in a remote context.
Questions about Being a Cultural Fit
Cultural fit is about more than shared values and work styles; it’s about coalescing around a shared mission and vision, especially when the team is dispersed. Assuming you’re a manager who is invested in hiring for culture, you know that having a candidate who is equally invested in finding the right company culture is very important. In fact, Glassdoor found that 77% of candidates say that they consider company culture before even applying to a new role.
In remote work, where interactions are all through screens, weaving oneself in the company culture requires extra effort and intentionality. Questions in this category assess how candidates will contribute to the company’s ethos, engage with their colleagues, and embody the company’s values in their daily work. Understanding a candidate’s alignment with the company culture is crucial for nurturing a remote workforce.
- What aspects of a company’s culture are most important to you in a remote setting?
- Describe a time when you felt out of sync with a company’s culture. How did you address it?
- How do you handle cultural or communication differences in a global remote team?
- What practices have you seen that effectively promote company culture in a remote environment?
- How do you ensure you’re not just a “face on a screen” and actively engage in company culture remotely?
- How do you handle situations where company values might conflict with the realities of remote work?
- How do you celebrate successes and milestones in a virtual team setting?
Questions about Tools and Technology
In a remote work setting, tools are the lifelines that connect individuals and teams across the digital divide. Proficiency with these tools is not just about technical know-how; it’s about leveraging technology to enhance collaboration, efficiency, and engagement. This section’s questions aim to gauge a candidate’s familiarity with the digital tools that facilitate remote work and their ability to adapt to new platforms. It’s also an opportunity to understand how candidates handle technical issues and maintain productivity amidst technological disruptions.
- What tools do you rely on most for working remotely with team members?
- How do you handle situations where a tool or platform you rely on is unavailable or malfunctioning?
- Are there any tools or technologies you believe are underutilized in remote work settings?
- How do you ensure data security and privacy when using various tools?
- Describe a time when you introduced a new tool or technology to a remote team. How did you facilitate its adoption?
- How do you handle situations where team members are using different tools or platforms for the same task?
- Describe a tool that significantly improved your productivity in a remote setting.
- When managing remote employees, do you think it’s important that everyone use the same tools to do certain tasks?
Questions about Collaboration and Teamwork
Teamwork takes on a different definition when it’s based in remote work. One of my first hires I ever made with my marketing company was someone based in the Phillipines and worked for us over 7 years. All without ever meeting. Other that long of a time period, there are plenty of challenges that are bound to come up, so how does your candidate stack up when they need to work with others, or put the team first (when that team might be halfway around the world)?
Questions in this category explore how candidates communicate, share ideas, and build relationships without the benefit of physical proximity. They reveal how a candidate contributes to team projects, navigates the complexities of virtual teamwork, and what their mutual support looks like. Effective collaboration in a remote setting is a blend of proactive communication, shared responsibility, and a commitment to moving in the same direction as everone else.
- How do you foster a sense of team unity and collaboration in a virtual environment?
- How do you handle situations where remote team members aren’t contributing equally to a project?
- What strategies do you use to ensure clear and effective collaboration across different time zones?
- How do you handle disagreements or conflicts in a virtual team setting?
- What practices or rituals have you found effective for building rapport in remote teams?
- How do you ensure that collaboration doesn’t lead to burnout or overwork in a remote setting?
- Describe a challenge you faced with a remote team and how you all worked to overcome it together.
- In a globally remote team, would you rather make a decision while the rest of the team is asleep, or would you wait for them to wake up before taking any action?
Questions about Self-motivation and Discipline
Self-motivation and discipline are the cornerstones of successful remote work. This is a big overlap as it relates to freelancers and WFH employees. They both have to have extreme discipline in the face of distrations and, well…life.
Without the structure of a physical office environment, remote workers must cultivate an inner drive and a disciplined approach to their work. In fact, a study by VoucherCloud found that the average UK office worker is only productive for 2 hours and 53 minutes out of the workday. Whoa…With a stat like that, you’ve got to be extra sure that you’re hiring someone that can get their shit done without constant oversight.
The goal of the questions in this category is to uncover how candidates motivate themselves, stay focused amidst home distractions, and maintain a consistent work ethic. It’s about discerning whether a candidate possesses the self-starting spirit and the disciplined mindset to deliver results when working independently.
- How do you set and maintain your daily routine when working remotely?
- Describe a time when you had to push through a lack of motivation. How did you overcome it?
- How do you ensure you’re consistently delivering high-quality work in a remote setting?
- How do you set boundaries between work and personal time when working remotely?
- Describe a time when you took on additional responsibilities or challenges in a remote setting. What drove you?
- How do you handle the potential feelings of isolation or loneliness that can come with remote work?
- What personal habits or rituals have you developed to ensure discipline in your remote work?
- Similarly, have you discovered that there are times of day that you are more productive than other times?
- How do you ensure you’re taking care of your mental and physical well-being while working remotely?
- How do you stay motivated when faced with repetitive or monotonous tasks in a remote setting?
Questions about Communication
I’ve saved the best for last. This is arguably the most important category of questions. Communication connects team members, conveys ideas, and resolves conflicts when you can’t simply walk over to someone’s desk. And I don’t mean just the ability to email or Slack someone, but how they communicate. Whether or not they’re skilled at that says just as much about them as a person as it does as an employee.
Questions about communication skills assess how candidates express themselves, ensure understanding, and maintain connections with colleagues and clients in a virtual setting. These questions help employers understand how candidates will contribute to a culture of open and effective communication, which is essential for the success of any remote team.
- How do you ensure clarity in your written communication with remote colleagues?
- Describe a time when you had to convey complex information to a remote team. How did you approach it?
- How do you handle situations where there’s a communication breakdown or misunderstanding in a virtual setting?
- What strategies do you use to ensure you’re actively listening during virtual meetings?
- How do you provide feedback or constructive criticism in a remote environment?
- How do you ensure you’re staying connected and available to your team when working remotely?
- Describe a time when you had to advocate for yourself or your ideas in a virtual meeting.
- How do you handle sensitive or difficult conversations in a remote setting?
- What practices do you employ to ensure regular and effective communication with remote team members in different time zones?
- How do you ensure that your non-verbal communication is effective in virtual meetings?
No matter how you cut it, in today’s hiring world, managers (and candidates!) have their work cut out for them. It’s so difficult to find truly great employees, that’s why this step is so crucial. It’s a matter of measuring twice and cutting once. Use these questions and the categories that they’re in to come up with your own great ones. Or feel free to steal as many of these as you want! Good luck!
Jared has worked remotely for 15 years in various marketing capacities, and has managed hundreds of marketing campaigns along the way. He has held freelance, agency, and in-house positions for companies large and small.