Even though some companies say they're remote-friendly, remote-first or all-remote, they all operate differently. When applying for a job, you should be able to evaluate how much remote they really are despite what says on their fancy website.
Here are some questions you might want to ask during the recruitment process:
Where does leadership work?
If the company's executives aren't working remotely, they might not be so committed to remote work as they're saying. Also, they'll have a harder time understanding the daily issues you'll face as a remote worker.
How do employees obtain information about internal processes?
All information about the company should be available in its handbook. By asking how they obtain information, you can understand if they care about writing down their processes.
How many times did you reference your company's handbook last month and proposed changes to it?
Probably, they won't answer a precise number. However, their answer can give you a clue about how often they iterate with their internal processes and practices and how much they really use their handbook. Companies that don't care about remote work's best practices will often make verbal decisions rather than using their handbook.
How much of your communication is asynchronous?
Asynchronous communication is one of the most important things for improving remote work. If they aren't sure about how to answer this question, they're probably not doing it frequently. An efficient remote company uses asynchronous communication by default: most interactions happen asynchronously.
If you message someone, when do you expect a reply?
This question is directly related to the previous one. Managers who don't understand asynchronous communication will often expect an immediate reply to their messages.
How many meetings did you have last week?
The number of meetings a company has can tell a lot about their culture. Meetings should be a last resort. If a company had multiple meetings in the past week, that should be a huge red flag and they definitely don't encourage asynchronous communication.
What do you consider flexibility?
Many job descriptions say they offer flexibility. But different managers have different ideas of what flexibility means. Some managers think allowing you to be 15 minutes late in the morning is offering flexibility.
Make sure you ask them how much flexibility they offer regarding working hours and days. Do they have a set of working hours? Flexibility also tells a lot about how much they're willing to trust you. Flexible organizations usually look for managers of one: professionals who know what has to be done and have the freedom to do so.
How is informal communication encouraged?
Great remote companies have channels for informal communication. Ask for specific examples of how they encourage it in their organization.
How many team members were hired without an in-person meeting?
If the company is committed to remote work, they'll trust the whole recruitment process can be done remotely. Ask them if they require an in-person meeting and why. You'll learn a lot about an organization's faith in virtual conversations by asking this question.
Ask them if they're using any monitoring tools. Some companies are spying on remote employees by tracking everything they do. You can tell a lot about a company if they spy on people. They certainly don't trust their employees and it's probably not a nice place to work.