Learning more about a remote working position

I’m in the process of wrapping up a long period of working remotely at least part-time from home, beginning in 2006 when I enrolled in a PhD program and continuing through my time at the Ada Initiative and at Stripe to this year.

My take on working remotely in future is really “it depends on the details” (and likely different details for different organizations). To that end, I contributed some suggested questions you could ask to Hypothesis’s Working remotely guide, which they’ve incorporated in a slightly edited form. Here’s my original questions; I’ve also added a few more at my end after some feedback from Andrew (himself a veteran of around seven years of remote work).


Before you start working remotely at a new organization, you should explore how they structure remote working and if there are any expectations mismatches between you and the organization. A particular remote job may or may not be a match for a particular remote worker.

Important: I don’t think there is any one right answer to any of these questions. It’s a question of fit between your working style, the position itself, and the relationship of the position to the rest of the organization. But the answers are worth knowing so that you can evaluate your fit and make plans for effective remote working.

Sources of information

This entry has a lot of questions, too many for a “do you have any questions?” section of an interview. But you can use other sources of information to get most answers, especially about organization-wide questions:

  • the job description, and descriptions of similar roles
  • the organization’s website, particularly the About and Careers pages
  • the section of the employee handbook dealing with remote work
  • the LinkedIn pages or websites of your future manager and colleagues
  • longer, separate, conversations with your recruiter or hiring manager
  • your offer conversation or letter, or your contract

Some questions you also may only need to ask if you hear of concrete plans to make a change to the organization (eg, you learn that a new office is about to open near you).


How are you remote and who are you remote from? This post is using ‘remote’ to mean something like “most days, you are not in face to face contact with any colleagues.” But you should be aware of the details: will you be working without in person contact with teammates or with the wider organization almost all of the time? Do you have any colleagues in your team or your wider organization in your city or region, or who regularly visit? Will you work on any joint projects with them? Will you be able or be expected to sometimes work with them in person even if there’s not a permanent office space?

Separately, is in-person contact with vendors or customers part of the job?

Is your immediate team remote? Is your manager remote? Being a remote member of a team that is all working remotely from each other is different from a team which is mostly located in an office with each other. Likewise, being managed by someone who is in an office has some potential advantages (for example, access to information circulating through verbal grapevines, being able to access answers from colleagues for you quickly), as does being managed by someone who is themselves remote (a direct appreciation for experiences specific to remote workers, a personal interest in advocating for them).

How many remote workers are there at the rest of the organization? What percentage of teams you will work closely with are working remotely, and what percentage of employees overall are working remotely? Working as one of very few remote workers for an organization where most employees are in an office together is different from a mostly or entirely remote-working organization.

What’s the future of remote work at the organization? If the organization is mostly or entirely remote, are there any plans to change that? If the organization is mostly office-based, are there any plans to change that? If an office is likely to be founded in your city or region soon, will you be able or be expected to work from it?

You may be considering a job on the understanding that the remote work will be of very short duration (eg, an office is opening in your city in two months time). Is there any chance the time will be longer, and are you OK with that?

What is your manager’s approach to remote workers? How frequently will they speak with you and through what media? Will they expect you to travel to them? Will they sometimes travel to you? Have they managed remote workers before?

How long have there been remote workers for? Is the organization new to having remote workers or has it had remote workers for a long time and bedded down a remote working style?

What is the remote working culture like? Is most collaboration over email, text chat, phone, video conf, or some other means? Are there watercooler-equivalents like social IRC channels or video chats? How active are they? Are remote workers mainly working from home or from co-working spaces? Are there occasional team gatherings for remote workers to meet colleagues in person and are they optional or compulsory?

How flexible are the hours? Not all remote work has flexible hours; you may have mandated work hours, or core hours, or shifts, as in any other role.

Are the remote workers spread across multiple timezones? If so, are your team and closest collagues in your timezone or another one? Are you expected to adapt your working hours to overlap better with your colleagues? How are meetings and other commitments scheduled across timezones? Do they rotate through timezones or are they always held in a certain timezone? Are you ever expected to attend meetings well outside your working hours, and if so, how often is this expected and do your colleagues in other timezones face the same expectations?

What are the benefits for remote workers? Will the organization reimburse any of your remote working expenses, such as membership of a co-working space, home office furniture, or your home Internet connection costs? If you’re working in a different country from most of your colleagues, will you get equivalent benefits to your colleagues (eg, health insurance coverage)?

What are the travel expectations for remote workers? Are you expected to travel to headquarters or other offices or customers, and if so, how often and for how long? What are the travel policies and allowances for remote workers? How do these travel expectations compare to those of non-remote colleagues?

Sometimes you will be remote from an organization with an office or even headquarters in the same city as you. Will you be able or expected to visit the office? How often? Will there be resources for you (eg, hot desks, meal provisioning)?

What are the career progression possibilities for remote workers? As a remote worker in a partly non-remote organization, could you move into more senior positions over time, such as team leader, middle manager, or executive? Could you move into other teams in the organization, and if so, which ones? Are there some roles that are closed to remote workers? Match these answers to your own career goals.

What’s the training process like? Must you or can you spend a period of time in an office or visiting a colleague for training? Must you or can you do your training remotely using documentation, videos and similar? Will a trainer or colleague have some time assigned to remotely train you?

Is there support for first-time remote workers? If you haven’t worked remotely before, will the organization support you in learning how to work remotely, and if so, how?

See also

A very partial list of resources, focussing on individual remote workers and their experiences and strategies:

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Learning more about a remote working position by Mary Gardiner is licensed under a Creative Commons Attribution-ShareAlike 4.0 International License.