How To Find A Remote Job
How To Find A Remote Job
Ep #76: 5 Questions To Ask In A Remote Interview

What does a company mean when it says they’re remote-friendly or remote-first?

It’s a good idea to prepare a few questions in advance of your first interview so you can get a better understanding of what their remote culture & philosophy is like. It’s also one of the best ways to demonstrate yourself as an ideal remote worker.

Having your finger on the pulse of the most important aspects of working remotely will undoubtedly impress the hiring manager or team (especially if they know this is your first remote role!).

In this episode of Thriving Empire we talk:

  1. The 5 specific questions to ask about a company’s remote culture & philosophy
  2. The kind of answers to listen for that demonstrate a company that’s consciously cultivating a healthy, proactive & evolving remote culture
  3. How to tune in to your own needs to assess if it’s the right career and remote culture fit for you


Get the Podcast Study Pack 3 and receive a worksheet, guide or checklist workbook for every episode, so you can make your remote career & transition a reality ASAP.


Ok, so what are the questions you can ask at interview to convey yourself as an ideal remote candidate AND learn more so you can assess if you WANT to be part of this team & company?

You’ll already have a few questions lined up as a result of doing the initial research we talked about in the last episode. So now you can formulate questions about their remote culture & philosophy that really demonstrate your awareness of subtle (and sometimes not so subtle) nuances of working within a remote company. 

These questions are taken directly from John O-Duinn’s Book: “Distributed Teams: The Art and Practice of Working Together While Physically Apart” because they are perfect as they are and need no amending. I’ve added the kind of answers you might hope to receive & ref flags to listen out for.


Question #1:

“I’ve worked remotely for a few companies now. Some companies handled remote work well, and some did not. How do you make sure that remote people don’t feel like second class citizens?”

This is a great question and will reveal whether the company has considered this, yet alone put systems and initiatives in place to build a sense of equality amongst their entire team whether remote or co-located. They might touch on different areas of the business in their answer. What you’re looking for is acknowledgement of the question as a good one, confirmation that the company has put a great deal of thought into it, and have or are experimenting with various ideas, systems and initiatives to enable a sense of team amongst the team whether remote or co-located.  And of course you’re looking to decide if their answer feels good to you. 


Question #2:

“How many other people in the team are remote, and can I interview with some of them?”

This is a beautiful question because well first of all how cool would it be to chat to people about what it’s really like to work at the company, but also because it conveys that you’re really interested in knowing more about what it’s like to work there, enough to invest more time in the interview process to assess the right career and culture fit for you. If they say no, I’d say that’s a bit of a red flag, especially if the reason is because teammates ‘don’t have the time to spare”. Sweat shop or what?!


Question #3:

“How tightly knit is the team, including the remote people? How was this group cohesion created?” 

What I like to learn here are the daily, weekly, monthly and annual initiatives they have in place, and the sense that this is a constant experiment & evolution so they can keep upping their game. 

You want a sense that they are really clear on the company culture they want to create, how they think about growing their team in terms of culture-fit and culture-add, and how they think of ‘people’ (hopefully as their most important resource & asset). Daily initiatives might include water cooler chat on slack, like a themed photo of the day each teammate has to add; weekly initiatives might be a buddy call with a member of your team, or a different team; monthly initiatives might be a social video chat on Zoom where you ‘hang out with’ 10 colleagues and bring your own beverage; annual initiatives might be a company-wide in-person retreats, or smaller team function retreats like the Marketing team retreat. They can take any form, but what you’re looking for again is that a) they’ve thought about how to create group cohesion and B) they are deeply passionate about implementing & experimenting & evolving it.


Question #4:

“How do you know if a remote person is doing their job well? How does a remote person know if their manager is doing their job well?” 

I love this question because as a remote worker you can’t really see how your work ‘lands’. Expressions on people’s faces and the energy in the room mean so much and can help you interpret whether people are happy with your work. On one hand you can get used to this as a remote worker, and rely on your own barometer on a job well done to brief or whether it exceeds expectations. I like to know that deliverables & KPIs will be co-created by me and my hiring manager during my probationary period, and that I’ll be held to results or output or outcomes and NOT hours. That’s like gold dust to my ears.

On the other hand some people need to see or at least ‘feel’ how their work lands, and one person shared with me when I was doing research for this podcast. She said: 

[As a remote worker] you can feel disconnected from how well your work is being received… you almost need more validation from clients. I’m currently good at working with clients who are good at telling me they appreciate me ( one gave me scented candle as Christmas present), so I was feeling loved. They want me to do more work which is the biggest endorsement, them wanting to do more work with you, [which gives me a ] stronger element of security. [When you’re ] physically present you can tell work is landing, if you’re doing conference or video calls you don’t have that sense that ‘I’ve read the room’ where you can tell if you’ve done a good job or not.”

So that said, if this sentiment resonated with you, you’ll want to pay particular attention to how they answer the first half of this question, and ask yourself if their answer satisfy you.

As to the second half of the question — How does a remote person know if their manager is doing their job well? — this is something even co-located companies struggle with, and there’s no one right answer. You might be satisfied with knowing they have 360 reviews in place, monthly feedback sessions, open door CEO policy, or even a regular call with the CEO. If you’re like me and have had bad experiences with managers in the past, you’ll know exactly what answer you’re looking for, and likely one that demands transparency and accountability of every individual in the company.


Question #5:

“Can you give me an example of the last time a remote person was promoted, and why?”

This question is fab and again speaks to how your work ‘lands’ and if it lands well, what does your career progression within the company look like. This is particularly tricky at startups and within smaller teams where people wear multiple hats to ‘get the job done’ but I think it’s good to know upfront: what do you need to do to progress within the company, how long might that take, and what might it look like? Could you switch between disciplines, or eventually join the executive team? 

You want to hear stories of people progressing within the company so you can understand the shape of career progression within the company without asking specific questions about it too soon! They are after all hiring you to do this job right now and want to know you’re focused on that and will do it well.

So that it’s the question part of the remote questions.


A couple of other quick tips for the logistics of the interview:

  • 24 hrs before: Double check time zones so you show up to the call at the right time.
  • 30 mins before: Set yourself up, take 5 mins to centre yourself 10 mins before, and show up on the ‘line’, logged in, 5 mins early.


But above all, remember that while they’re evaluating you, you’re evaluating them, too. 

The interview itself, the interviewers and the company, and evaluating whether you want them as your future teammates. This is not a one-sided endeavor, so as in ALL worthwhile relationships: you also need to decide if this is the right fit for you, and mustn’t just wait to be chosen.I hope this helps you confidently & diligently prepare for your audio or video interview. Crack open the worksheet that you can use in the interview itself so you can take notes on their answers to these questions — called  worksheet 23 — in the podcast study pack.

If you don’t have the podcast pack yet don’t worry, head over here to get your copy there.

That’s it from me this week. See you next week on Thriving Empire Live!


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