Questions to ask companies when you are looking for a new role

By December 22, 2015 December 30th, 2019 No Comments

Chris Leow joined ComplyAdvantage from his start-up Blast-Out. Here, he shares his insights into what to look for when you’re looking. Below are some of the questions that you might like to ask a company when you’re thinking of joining.

The Company

It might help to ask the person interviewing you why they joined the company that you are interviewing with. What process shaped their decision making process?

  • How long have you been at the company?
  • What other options did you have when you chose this company?
  • Why did you choose to join this company?

Quality of work

  • What kind of projects do you work on at the company?
  • What is the most challenging project that you’ve worked on?
  • What is something you wish were different about your job?
  • Which team are you right now? Have you moved teams?
  • When’s the last time you interacted with a founder? What was it regarding? Generally how involved are the founders in the day-to-day?


  • What does your average day look like?
  • What is your stack?
  • Why did you choose this specific stack?
  • How often do you add new tools to the mix?
  • How often do you use your own solutions versus third party applications? Why?
  • What kind of test coverage do you have?
  • Is your engineering culture as more pragmatic or more theoretical?
  • What portion of your time is spent working on new stuff rather than iterating on existing stuff?
  • How long are your release cycles?
  • What’s been the worst technical fuckup that’s happened in the recent past? How did you guys deal with it? What changes were implemented afterwards to make sure it didn’t happen again?
  • What is the most costly technical decision made early on that the company is living with now?

Impact on product

The answer to these questions can be useful for getting some idea of what the space looks like and what traction the company in question might have. Most importantly, though, it’ll give you some insight into whether the people at the company care about the product and the business side of things or not and how much they’ve thought about stuff like this.

  • What are you working on right now?
  • If you had an idea for something new to build, what would you have to do to make it happen?
  • What is some of the more meaty new stuff that got pushed in the last release? Where did the idea for that feature originate? Where do product ideas generally come from?
  • Who are the other major players in this space? What advantages do we have over them?

Avoiding potential bad companies

Nobody wants to join a bad company and be happy. As such, it pays to do your diligence on the company.

  • How often do people leave the company?
  • How long do people stay at the company?

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