The biggest challenge with remote job interviews
4 min read

The biggest challenge with remote job interviews

Today I'm telling you about remote job interviews. I've interviewed thousands of candidates for my remote teams over the past decade, and I can tell you where most of them fail, and how the best candidates stand out.


I'm Sergio Pereira, and this is the Remote Work newsletter 👋

Last week, I told you what it takes to have a successful remote career in the time of AI, and I used some hints from the past, as technology continues to grow and take over the world.

Today I'm telling you about remote job interviews. I've interviewed thousands of candidates for my remote teams over the past decade, and I can tell you where most of them fail, and how the best candidates stand out.

This is a key part of the Remote Jobs Braintrust, my course+community for remote job seekers, and today I'm sharing the knowledge here with you.

I understand there's a lot of anxiety about remote job interviews. Getting an interview for a high paying remote jobs is increasingly competitive. So, the last thing you want is to screw up the opportunity when you have it.

The biggest challenge is the temptation to make the interview flow purely transactional:

• Interviewers are guilty for this, since they drive the interview through a bunch of "checkboxes" they need to check for each candidate.

• But most candidates don't even try to build a connection, they just go with that flow.

That's why you should understand what your interviewer's "checkboxes" are, and lead the interview with story telling. I know it doesn't come natural for technical folks like most of us, but it's easier that you might think.

There are fundamentally 3 big "checkboxes" that your interviewer is looking to find out if you check or not:

  1. Is your past experience relevant to this role?
  2. Do you fit the requirements for this job?
  3. Have you worked in a similar company before?

However, the interviewer will ask these "checkbox" questions in a lot of tangential ways. So, it's your job as the candidate to use each transactional question as an opportunity to actually show why you're a fit to the job.

Take this classic interview opening question:

• “Tell me about yourself”

Most candidates answer with some variation of "I'm Sergio, I've been a software developer for 15 years, my last job was at Company X". See, 100% transactional. Feels like the candidate is reading their Linkedin bio.

That's where your opportunity to stand out comes to you. You have an opportunity to show your interviewer why you're a great fit to the job, and give them some memorable line they can use to talk about you in the company's slack.

See this example opening reply:

"I'm Sergio, and I love to build software products that bring value to clients. I see you've just raised a funding round, so you must have an exciting roadmap ahead. I've been developing a Fintech product for the past 2 years, in a tech stack similar to yours, which are now used by thousands of users around the world. With this experience I bring you, I will add a lot of value to your team".

See, I gave the interviewer a bunch of hooks to hint for the the next interview question:

• Roadmap - I could learn more about the company and link it to my past experience.

• Funding - I can show interest about the company and learn where to steer next.

• Tech stack and industry - I can show relevancy and why I fit the requirements.

• Past product traction - I can show track record and relate past experience with this company/product.

With this, I've just steered the conversation away from transactional "Why are you interested in the job?" type of questions, and directly to the important points the interviewer actually needs to hear about.

You can apply this same reasoning to any interview question, really. Take this example from Cristian, in the Remote Jobs Braintrust:

Remote interview story telling

By joining my course+community, Cristian went from mostly failing in interviews, to having 3 offers on the table. And the key change was this exact approach to the interview questions. I wrote more about Cristian's story here.

I had a breakout session with Cristian, and he shared a specific example. The interviewer asked:

• Do you have experience with indexes in MySQL?

But Cristian figured this could be the only question about databases in the whole interview, so he explained his experience with MySQL more broadly beyond just indexes, some specific challenges he had and how he solved it. That helped him stand out as the top candidate for that specific role. The recording is available for everyone who joins the Braintrust, and I highly recommend watching.


Keep in mind that your interviewer probably has 5-10 back to back interviews the whole day. If you don't have this proactive story telling approach they won't even remember you by the end of the day. You should stand out and give them specific content they'll use to talk about you with their colleagues on Slack. That's how you get through interview rounds and land a solid offer on the table.


I'm sharing all my learnings to land interviews and get offers for remote jobs in the Remote Jobs Braintrust. We're now a 115 people strong community, which is growing every month. Such exciting times! There are still seats available to join us for cohort 5, starting in February. Join us here.

Thanks for reading this newsletter until the end. You can read all past editions here. Make sure to share it with your friends and colleagues so they can read it too.

See you next Friday,

Sergio Pereira, 
Startup CTO & Remote Work Lover

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