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Last active June 16, 2024 20:20
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I bundled these up into groups and wrote some thoughts about why I ask them!

If these helped you, I'd love to hear about it!! I'm on twitter @vcarl_ or send me an email

Onboarding and the workplace

  • How long will it take to deploy my first change? To become productive? To understand the codebase?
  • What kind of equipment will I be provided? Will the company pay/reimburse me if I want something specific?
  • How will you know if I’m doing a good job?
  • How often do two developers work together on a single task? Three or more developers?
  • How many of the developers have been here less than 6 months?
  • How many developers have been here 2 years? 4 years?

Development and emergencies

  • How long does it take to do a complete deployment?
  • What is a big pull request, in lines of code or files affected? How long is it open?
  • How many repositories would I touch to make routine changes?
  • How often do developers have to make simultaneous changes across repositories?
  • How often do you have major outages? What constitutes a major outage for you?
  • Do you have a defined process for handling an outage?
  • Would I be expected to be on-call?
  • What does your on-call process look like?


  • About what fraction of their time are developers given (implicitly or explicitly) the freedom to explore or learn?
  • How do you define success and growth for developers?
  • How often do you do lunch and learns, or other semi-formal knowledge sharing?
  • How often would my manager have 1:1s with me?
  • What kinds of topics are usually discussed in 1:1s?
  • Do you pay for conferences?

Project management and prioritization

  • How do you balance shipping new features and maintaining the codebase?
  • What's the lifecycle of new development, from somebody's idea to deployment?
  • How do you track tasks? How are those tasks created?
  • Do you do agile/scrum?
  • How do you decide what to build?
  • Do you have "swimlanes" in your task tracking? What are they called?
  • How do you know when something is done?
  • What project management software do you use?
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What are your call schedules and at what intervals are they held?

Yeah, very relevant if the team is distributed across multiple timezones.

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Here's my smarmy list when I start getting that toxic feeling from the interviewer

  • How many people have held this position before me? Am I here for growth or attrition?
  • If I'm here because of attrition, why did my successor(s) leave? Can I get references from former employees?
  • How much did you pay my successor? I'll need to see proof before I'll consider an offer
  • How exciting are your on-call rotations?
  • Does on-call get any extra compensation for interrupting their personal lives for work?
  • What support does on-call get from other teams? Will they be there with us in the trenches or is it "Tag, you're it!" ?
  • How much time do you spend in meetings?
  • What's your vacation culture like? Do employees actually take vacations? How much do they take? Is there a mandatory minimum?
  • Have any of the managers or c-levels made it a point to call the team "a family"?

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Sharing mine as well :)


  • What is the problem you’re solving?
  • How have you come to discover this problem?
  • How are you solving the problem? How are you different from existing solutions?
  • Who is your ideal customer?
  • What are your key metrics?
  • What does success look like?
  • What are the company’s current priorities and challenges?
  • What’s your runway?


  • What values do you hold related to product building?
  • What is your product development process?
  • In your opinion, what makes a great product, great?
  • What are examples of products that inspire you and why?
  • What does quality/craftsmanship means to you?
  • How do you ensure quality within with your product?
  • When and how do you make space for polishing during product development?
  • How do engineers collaborate with designers?
  • Who is the designer I’d be working with?
  • How often does each developer commit to trunk/master/main?
  • How often do two developers work together on a single task? Three or more developers?
  • How often code is released to production?
  • Can I see an example of an issue/feature?
  • Do you do code reviews? How?


  • How is your team currently structured?
  • What is the company culture like?
  • How do you guys communicate? Where are decisions made primarily?
  • How do you decide on what to work on next?
  • How do you know when something is done?
  • How often do two developers work together on a single task? Three or more developers?
  • Who is talking to customers?
  • What is your process for setting goals?
  • What is your process for planning?
  • What rituals do you practice as a team?


  • Can you walk me through the hiring process?
  • What do you think will make for success in this role?
  • If I get hired, how will you know I’ve done a great job a year from now?


  • What would be my fully diluted percentage (or fully diluted share count)?
  • What is the strike price and the investor/preferred price?
  • Are you about to go to a new round of financing that might void the current 401A?
  • What is the company current valuation?
  • What is the FMV?
  • What is the post-termination exercise period?
  • What is the equity band for this role? Carta Total Comp or Pave
  • What is the current 409A? Are you fundraising at the moment? Can you hit the board with an electronic consent before the funding round?
  • For what level is the job offer? Senior or mid level?
  • Love to understand levels a bit more, what distinguishes a mid-level over a senior-level?
  • Can you hit the board with an electronic consent ASAP before the funding round? (Go to your lawyers to get a board consent)

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