[AMA] The Biggest Mistakes to Avoid When Applying For a Remote Job with Andrew Gobran, People Operations Generalist, Doist

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If you've been applying for a bunch of remote jobs and haven't heard back yet, now's the time to try something new! Have you been making the common mistakes tech companies find when hiring? In this AMA, Andrew provides some great pointers, gathering from his experience as People Ops Generalist at remote-first company, Doist. Here's the transcript:

Justine Shu
Welcome to today’s AMA with Andrew Gobran (People Ops Generalist at Doist): The Biggest Mistakes to Avoid When Applying For a Remote Job

If you’ve been applying for a bunch of remote jobs and haven’t heard back yet, now’s the time to try something new!

Thanks for being here, Andrew — really grateful that you’re here in our community to help provide us with some pointers.

Let’s get started 🙂

Andrew Gobran
Hi everyone! I'm very happy to be here with all of you and excited to answer your burning questions! 🙂

Question 1
How has the pandemic influenced hiring for you and the team at Doist? Has it changed your process at all?

Andrew Gobran
Great question! For those who are unfamiliar Doist is a fully remote company without a physical HQ, so in many ways we've been fortunate that the pandemic has had minimal impact on our hiring process.

Early on, as a precaution, we implemented a hiring freeze, but have since continued our typical remote hiring efforts.

Question 2
Hey Andrew! Big fan of doist and have been for a long time. Interested in how you see your teams culture during the hiring process. Is there a question you ask that's designed to draw someone out a bit and find out if they'd be a good fit for your team, culture wise?

Andrew Gobran
Thank you 🙏

Yes, our hiring process actually places a lot of weight on value-alignment (which is the core driver of our culture). We ask a lot of questions that don't have a right or wrong answer that are purely intended to give candidates an opportunity to show us how self-aware they are, how they leverage their skills, and how they manage their schedule.

Since there's a lot of independence involved in remote work, these "soft skills" carry a lot of weight in someone's ability to be successful and thrive in our culture beyond their role-related skills.

Interesting. Is managing their schedule and process there something that you instill during the onboarding, or leave up to them to set up themselves independently?

Andrew Gobran
It's a combination of both. We definitely expect that the people we're bringing on our team have strong self-management skills, but naturally there's a learning curve that we guide them through during a 3-month mentoring period when they join the team :)

Question 3
What are the biggest mistakes you see candidates make when applying for jobs at Doist?

Andrew Gobran
That's a loaded question! 😅

The biggest mistake I see candidates make is that they submit applications that are uninspired. This is either in the form of being incomplete, disorganized, or providing responses that lack any indication that they've actually taken the time to get to know Doist.

Yes, that makes sense! Can you give any examples or provide insight on what a successful application looks like?

Andrew Gobran
Yes, absolutely! For context, we read every single application we receive. It's a manual, demanding process, but that's how important value-alignment is to us, not just the right skill set.

At a high level, a complete application is a great start (I know it's crazy to hear that). More than anything else though, it's seeing that candidates have a genuine motivation and reason for wanting to join our team that reflects an alignment with our values and mission.

You can tell very easily when a candidate has taken time to get to know us beyond the job ad and taken great care to craft a thoughtful and personal application.

Question 4
How would you describe Doist’s culture in your own words? And why do you like working there?

Andrew Gobran
That's a great question. Doist's culture is quite multifaceted, but the thing that has always stood out most to me is authenticity in how we interact with one another on the team and with our users. That goes a long way and it naturally creates trust and engagement on the team.

Question 5
Hi! and thanks for doing this!! I've seen some people suggesting using templated cover letters to "beat the bots" - do you appreciate -bespoke- cover letters or do you make use of bots to weed out poorly matched candidates?

Andrew Gobran
Great question! Speaking from my experience at Doist, we manually read every application we receive so this doesn't really make much of a difference to us.

I think what's most important is the quality of the application and that it's presented in a clear way.

Templated cover letters are pretty easy to spot and always come off as being impersonal. These should definitely be personalized to the company and role.

The resume templates are okay from where I stand since the content is what matters most.

Question 6
That’s pretty amazing that you read through every application, Andrew — I’m assuming you folks get thousands for each role… could you shed some light on what the hiring process looks like at Doist?

Andrew Gobran
Yes! Maybe not thousands for each role, but we've definitely crossed the thousand mark before. In total i've probably read 30K applications in a bit over 2.5 years on the team. Yes, after a candidate submits their application here's an overview of what happens:
  1. The PeopleOps team shortlists applications that are complete, show basic role-related alignment, and value alignment (through short answer responses).
  2. The hiring committee reviews those applications to approve applications that have correct role-related experience.
  3. Candidates are invited to the process which consists of 3 interviews and a test project.

Question 7
Since Covid forced our team (we make digital product for our company: developers, designers, data scientists, product managers, etc) to work remote, we’ve noticed that our team is becoming more distant. I’ve had ideas about how to create virtual game sessions and meetups for our team - I’m curious about what has worked for your team(s)? Do you leave these events as voluntary or mandatory (because I’m sure there are some who will always abstain if given the chance)?

Andrew Gobran
Great question! This can be a really tough one especially during this time where daily life feels a bit different than usual.

The suggestions are endless, but ultimately the best thing you can do is to listen to your team and understand what they need. Sometimes work in and of itself is the escape they need to get their mind of off things happening in the world. At other times, it might be opportunities to socialize with their team members.

I would always approach these activities as voluntary because not everyone derives the same joy and satisfaction from them. However, creating a variety of opportunities that appeal to different personalities and then encouraging participation is always a great approach.

At the end of the day, engagement can't be forced so leaving things open gives people a sense of control and ensures that those who do participate really want to be there.

Question 8
Thanks for doing this, Andrew. With such a heavy remote workforce in many different countries, how do you handle compliance and ensuring you are following all local laws where your employees reside? Has that created any issues or challenges in terms of the people you hire or the places you're willing to hire remote employees?

Andrew Gobran
Most of our team members are hired as independent contractors which enables us to hire from anywhere in the world without having to get bogged down my the compliance implications that would exist if we had to register a business in each of these companies.

Thanks 🙂  Has that limited the hiring pool with the requirement to hire folks at contractors? Any stories of losing good talent because they were unwilling to work as a contractor?

Andrew Gobran
I guess I don't know what the alternative looks like since this is how we've always done things at Doist, but I can only recall a few times where someone wasn't interested in being hired as a contractor. Regardless, this is just a trade off that we make to have a truly borderless company. :)

Question 9
My job safely allowed me to work from home (I understand distinct from remote) this spring and I absolutely loved it. In order to make that jump to a remote position, is the best practice to seek out the perfect individual fit or are remote jobs flexible in responsibilities in the same way that you see "office" jobs adjust to candidates?

Andrew Gobran
Great question! Success in a remote role is ultimately an alignment of role related skills and personal skills. Any time we hire someone, there's an expectation we will need to guide and support them through that transition as they acclimate to the company and our culture, but there are some skills that we've generally seen that people need to be successful in a remote role.

Question 10
How do can you organise small social interactions in remote work while you don't want to disrupt the day of your teammate?

Andrew Gobran
Great question! At Doist we work asynchronously, so this happens pretty naturally because people can fit social interactions into their schedule based on their availability.

For example, we do monthly casual hangouts that our team can opt into. Once they are grouped with other Doisters, they get to self-organize a meeting time that works for them.

Question 11
Do you require people to have worked remotely before? Or are you mostly focused on bringing people on that have no remote experience in order to train them without biases?

Andrew Gobran
Great question! Remote work experience is helpful, but not a hard requirement. We often see candidates over-emphasize that part of their experience and forget that they'll still have a job to do if hired.

Generally speaking, we look for skills that are necessary to be successful in a remote role like strong communication (especially in writing), self-motivation, continuous learners, etc.

Question 12
What is the most frequent reason you face being constrained to refuse a candidate?

Andrew Gobran
It depends, but most often, the upfront reason is that candidate's haven't crafted a compelling application to stand out in the midst of hundreds of other candidates.

I'm sure I've rejected many excellent candidates who simply didn't think it was important to take care to provide personal responses to the short answer questions.

Justine Shu
And that’s a wrap! I’ll let Andrew finish up these last questions here — if any other questions come up, feel free to leave them here and Andrew will kindly answer them asynchronously 🙂

Thank you to everyone who participated, and thank you, Andrew for offering your time and knowledge to the WWR community. 👏

Andrew Gobran
It's been a pleasure! Thank you Justine (and the whole WWR team) for inviting me. It was awesome to spend this time with all of you.

As Justine mentioned, i'm happy to answer any additional questions you have asynchronously or in a DM :)

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