Questions I Ask Companies

Recruiter

Must ask:

• What are the headcount targets for this team/org in the upcoming year?
• I’m sure you’ve seen a spectrum of how different hiring managers treat their recruiting partners. Would you please give an example of an interaction that shows how the experience of working with the hiring manager of this role is different than your past experience working with other hiring managers?

Could to ask:

• How is the culture in the engineering org different from the rest of the company?

Hiring Manager

Must ask:

• What is your roadmap and what role would I personally play in that answer?

  • What is the mission + strategy/“how” of the team for next 6-18 months?

• Are there any landmines? Any difficulties you’d expect anyone taking over this team and its responsibilites would hit? How would you support someone through them?

• What risks/concerns do you have about my ability to perform into this role and, more importantly, what would your plan be to mitigate them?

• Who is on the team?

  • What made you choose to open this role up to external candidates?
  • Who would be my lieutenants?

Could ask:

• Would you please give an example of a time when you coached a senior manager.
• Who are the most important stakeholder relationships for this team and what you would hope I would preserve or change about the nature of them?
• What are your key disagreements with your stakeholders and why? How are they resolved?
• Please talk about the last time you decided to allocate headcount to one team vs another. How did you make that decision? How did you know it was the right now?
• How do you support a manager when their team is underwater?
• Would you please talk about a recent organizational change you made and how you ensured it was successful?
• Would you please talk about a time when two people on your team had a non-trivial disagreement and how that was resolved?
• Would you please talk about a time when you curated a sense of belonging amoung your “first team?”
• Would you please talk about a time when you changed the mind of a manager reporting to you?
• Would you please talk about the performance review process?

Skip Manager / Exec

Must ask:

• What is your roadmap/goals for the next 6-18 months and what role would I personally play in that answer?

  • What is the mission + strategy/“how” of the team?

• What will separate someone who is good at this job from someone who is really stellar?

• I’m trying to understand the org’s strategy. Would you please tell me about a good idea (a new feature, not tech debt), that didn’t get funded? What was it and what made the cut instead? How did that decision get made?

Like to ask:

• How is my hiring manager different than other directs of yours?
• Would you please talk about a recent organizational change you made and how you ensured it was successful?
• What are your key disagreements with your stakeholders and why? How are they resolved?
• Please talk about the last time you decided to allocate headcount to one team vs another. How did you make that decision? How did you know it was the right now?

Peer

Must ask:

• Would you please give an example of how HM has coached you in the past year?
• Would you please talk about a project that required collaboration with my team and how that went, from start to finish?
• What are the non-code parts of the most recent successful project which made it successful?
• Please talk about the last time a project was slowed down / de-prioritized to work on some technical debt?

Like to ask:

• I’m trying to understand the org’s strategy. Would you please tell me about a good idea (a new feature, not tech debt), that didn’t get funded? What was it and what made the cut instead? How did that decision get made?
• If you were me and were taking over this team, what would you focus your attention on initially?
• Would you please talk about a time the HM changed your mind?
• Would you please talk about the performance review process?
• What differentiates a good day from a bad day for you?

Crossfunctional Partner or Stakeholder

Must ask:

• Would you please talk about a project that required collaboration with my team and how that went, from start to finish?
• I’m trying to understand the org’s strategy. Would you please tell me about a good idea (a new feature, not tech debt), that didn’t get funded? What was it and what made the cut instead? How did that decision get made?
• Please talk about the last time a project was slowed down / de-prioritized to work on some technical debt?
• What are the non-code parts of the most recent successful project which made it successful?

Like to ask:

• What are you hoping I’d preserve and change the relationship between my group and yours?
• What differentiates a good day from a bad day for you?
• Should engineers talk to customers?

Direct

Must ask:

• Who is on the team?

  • Do you know why the manager opened this role to external candidates?
  • Who would be my lieutenants?

• Would you show me a non-trivial code review?

• What differentiates a good day from a bad day for you?

• What do you find interesting about your work? (No not hard, interesting).

• Would you please show me a non-trivial design document?

Like to ask:

• If you were me and were taking over this team, what would you focus your attention on initially?
• Would you please talk about a project that didn’t get funded during the most recent planning cycle? Why not? How did that process go?
• What does this team need that isn’t being done right now?
• How do you feel about deploying code on Fridays?

Misc

These are useful fall-back questions:

• What is one way you’d expect me to contribute beyond the job listing responsibilities?
• What one noticeable difference in how working at this company is different from your previous company?

Other Reading

• The 40 Best Questions to Ask in an Interview – How to Go Deeper than “What’s the Culture Like?” has some great questions
• Reverse Interviewing Your Future Manager and Team also has some good questions