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A list of questions to ask potential employers.

Work Style


  • Does one single person own a unit of work (task, project, product, etc)?
  • Can that single person's manager override the decisions made by that person on that unit of work?


  • How are goals communicated throughout the organization?
  • How is mentorship approached?
  • What does a week look like when the stars align and everything goes the very best it can?
  • What does a bad week for your team look like?
  • Tell me about your last vacation
    • Looking for more about how detached did they get, and did they take a vacation at all more than the details
  • How many weeks over 40-50 hours have you put in in the last year?
  • How much turnover has your team/org/company had in the last year?
  • When you think about your company, what fills you with gratitude? Optimism? Concern?
  • What do you enjoy about your job?
  • If you were to leave this company, what is the most likely cause of your departure?
  • Do you like your job? Why or why not?


  • What are your organization's values?
  • What characteristics to you look for in employees to exemplify those values?
  • Tell me about a time where values were considered as part of making a tough decision. How did values affect the outcome?

Leadership / Management

  • Do managers regularly meet 1-1 with their reports?
  • How responsive is your management to your questions and concerns?
  • What does success look like for a manager here? How about failure?
  • What sort of training do you give managers? Even if not interviewing for a manager role
  • What does organizational leadership do well?
  • How could organizational leadership improve?

Other teams

  • How does this role relate to other teams?
  • Do people regularly interact across departments?

Defining Success and Failure

  • How might this role help with the organization's challenges and opportunities?
  • Imagine it's a year from now, and you're thinking "I'm so glad we hired Your Name Here". What are the top 3 things I did that made you glad you hired me?
  • Who is currently making important contributions to your organization? What qualities do they have that are adding such value?
  • Who has gotten ahead in your org? To what do you attribute their advancement?
  • What 3 things differentiate someone who is really great in this org from someone who is merely good?
  • What does success look like in this position?
  • Imagine it's a year from now, and you're thinking to yourself "We made a poor choice in hiring for this role". What are the things the person you hired did that make you regret the hire?
  • What concerns do you have about my suitability for this role?

Employee Health and Fatigue

Work Hours

  • How many days do employees work over the standard working hours?
  • What are the standard working hours?


  • Can employees work outside of the office ("work from home")?
  • Are there any restrictions on when employees can work outside the office?
  • Do employees each have their own office?
  • Are there partitions or space between each employee's workspace?

Time Off

  • How much time off is given per employee?
  • Do different employees get a different amount of time off?
  • Is there a minimum amount of time off required/expected of each employee?
  • Is sick leave counted as time off?

Parental leave

  • Who is eligible for parental leave?
  • How much parental leave is given?
  • How much parental leave is taken?
  • How do other employees view someone who takes parental leave?

On Call

  • Are employees expected to be on call?
  • If employees are expected to be on call, is a device provided or compensated?
  • How often do on-call employees get notified?
  • What sorts of tasks does your team do to reduce the number of on-call incidents?



  • How much room for growth do you feel people here have on average?
  • How much room for growth do you individually feel you have?
  • Do you have a clear understanding of your career ladder?
  • Tell me about a new idea that someone brought to you that was a surprise, either because you hadn't thought of that solution or hadn't even considered the problem they solved.
  • What do you see as the most challenging aspects of this role?

Challenges and Opportunities

  • What are the biggest challenges facing the team/org/company?
  • Where are the biggest opportunities right now?
  • If you had a magic wand and could change anything about your org, what would you change?
    • Variant: If you had an infinite amount of money & the CTO's job, what would you do?
    • Variant: If you could improve 3 things about your org, what would you improve?
  • What challenges and opportunities will the person you hire for this role encounter in their first year?

Compensation and Benefits

How is compensation calculated?

  • Are pay bands used to determine compensation?
  • Is compensation negotiable?

How transparent is your compensation?

  • Is all employee compensation public knowledge?
  • Is all employee compensation known within the company?
  • Is employee compensation shared within the team?

What kind of meals are compensations?

  • Is breakfast provided?
  • Is lunch provided?
  • Is dinner available and provided?
  • Is there non-meal time food available?

Organizational Structure

Who do people report to?

  • Does every individual have one single manager they report to?

Distributed teams

  • How do you approach distributed teams?
  • Are managers and reports co-located?
  • Are teams co-located?
  • How are decisions handed off between time zones and locations?

Tech / Tools

How are devices supported?

  • Are personal devices allowed to connect to the company network?


How is diversity approached?

  • Composition of team you will be joining?
  • Does your company have an active diversity policy/program?
  • How do you define diversity?
  • Does this company value diversity? If so, how do employees individually and the organization broadly demonstrate this?
  • What are you doing to ensure diverse teams?
  • What resources are available to provide safe spaces for people in the organization?

"Org smells"


  • What is the customer churn and/or renewal rate?
    • Whether they know the rates is a good indicator, separate from what it is.
  • (If a startup) What is your runway? How many employees do you have?

See also


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