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10 Questions to Ask When Applying for a Remote Job

Hannah Oppenheimer
May 15 · 5 min read

1. Is your team (A) remote-first, (B) office-first with a large remote group, or (C) am I one of the only remote employees?

If the team is remote-first, they might have excellent remote practices, but if there’s no office to go to, extroverts might want to ask if the company reimburses for the use of co-working spaces.

If the team is office-first but some or all employees are allowed to work remotely, then you might have the benefits of both worlds — or…both worlds might be not ideal. If the folks in the office have in-person ad-hoc meetings, you might not have an excellent remote experience. If the remote workers don’t communicate as much, they might not have the camaraderie of folks in the office. Ask about how often or what percentage of folks are in the office vs. remote, and how they ensure meetings are inclusive to remote workers.

If you’re one of the first or only remote employees, find out if they’re transitioning to remote, or if this will always be a one-off option. It might be great for a short-term situation when you want to travel while working or if you have a temporarily family situation that requires work flexibility. But, due to isolation and collaboration challenges, this option may not be sustainable long-term.

2. If you have an office, what are the differences between office-goers and remote employees?

For example, is the office space strictly for a certain department (like finance or legal, for regulatory purposes), or does the company only offer remote flexibility to senior or C-level employees? Does management trust employees and their work more from one group over the other? Is one group more likely to see promotions or take the lead on projects?

3. What is your on-boarding experience for remote employees?

On-boarding for remote employees might happen virtually or in-person. It might be a 2-day group of meetings, or it might be a 3-month in-person trust building before you’re actually allowed to work remotely.

4. How often do we meet in person?

Some companies run annual in-person summits for all-staff and on a team-by-team basis. Sometimes those gatherings happen at the company’s headquarters; other times the team lead will choose a retreat location (I’ve seen everything from a ski resort to a cruise ship!).

Find out why they meet in person — what activities do they find helpful to do in person? How soon after you start will their next off-site be?

Also, ask if any of their other remote employees live near you. If you live in a big city, you’ll likely have a cohort to meet up with for coffee, happy hour, or co-working days.

5. When do you communicate via asynchronous chat vs. video call?

Most companies have a good balance of video call, email, and Slack. Ask about how they include folks in conversations that happen in private (either through direct messages or video chat).

Some remote companies — especially those with large international spread — don’t have video calls at all, communicating solely through chats like Slack. Make sure that’s what you want before committing.

While unlikely, some companies go the other extreme and lean too heavily on video call. If it seems like they check in on remote workers too much, that’s a sign that they either don’t trust their remote workers, or like countless non-remote companies, they simply don’t have a good meeting culture.

6. How do you work on highly collaborative projects together remotely?

Hopefully, they have a suite of tools and are comfortable running things like remote design sprints or remote white-boarding. If not, you might find that a lot of your brainstorming or diverging ideation stages of work will tend to be less collaborative than your previous office-based experiences.

7. How do your company values manifest themselves in your remote culture practices?

This is where I hope to hear answers about transparency and kindness.

Companies who are remote should operate on a pretty transparent level. They should prioritize public Slack channels over private direct messages, and they should lean toward over-documenting their processes to on-board new folks and avoid misunderstandings that are common without body language and constant contact. (That being said, transparency can also get overwhelming with so many unread Slack messages, so many documents to read through).

Remote companies should also be aware of the challenges of text-based communication, prioritizing kindness and thoughtfulness in their written words. Sarcasm doesn’t usually come off great in Slack. Your interview process should give at least some idea of how kind their communication style is.

8. How do your employees get to know each other on a personal level remotely?

Are there Slack channels just for special interests? Do employees have 1:1s that aren’t meetings, but just get-to-know-you times? There’s a tool called Donut, that automatically pairs you with another teammate and encourages you to schedule a video chat for fun. There’s another tool called that allows you to skip the small talk and just play games remotely with your teammates. You don’t need an office with a ping pong table to have fun!

9. What hours will I be expected to keep, given timezone differences?

You might be able to work whatever hours you choose. Or, you may have to shift your schedule slightly to maintain overlap with major regions of employees. But if you live in Berlin, and and are expected to keep entirely consistent with L.A. hours, that would probably be unrealistic for maintaining your personal and family life.

10. Do most of your chats happen in private or public Slack channels?

I referenced this above in the values section, and it’s important for non-remote companies as well, but even more-so for distributed teams. When a company has mostly private chats, they likely don’t have a transparent or inclusive culture. That being said, hopefully they take a few steps to making sure those public channels don’t become overwhelming (disable the “@ here” and “@ channel” features of Slack; make sub-channels for projects and temporary groups; encourage “offline” mode for times when you need to go heads-down without distractions).

Best of luck in your job search! If you’re still looking, HashiCorp is hiring.

HashiCorp Design

Design for Devops

Hannah Oppenheimer

Written by

Senior Product Designer at HashiCorp. Ice cream maker, outdoor woman, and aspiring multipotentialite.

HashiCorp Design

Design for Devops

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