Questions about the actual work
- "What does a normal week look like for whoever takes this role?"
- "What is the first thing you would want this person to take off your plate?"
- "What would make you say, six months in, that this hire went really well?"
- "What is the hardest part of this job that isn't obvious from the posting?"
The last one is the most useful question in an interview. A thoughtful answer tells you the real shape of the job; a defensive one tells you something too.
Questions about the team
- "How does the team decide what to work on?"
- "How long have most people on the team been here?"
- "What happens when something goes wrong — what did the last incident look like?"
- "Who would I work with most closely, and what do they need from this role?"
Questions worth asking the hiring manager specifically
- "What is your management style, and what do you expect from people who report to you?"
- "What is the team under the most pressure about right now?"
- "Why is this role open?" — growth, backfill, and a role someone just left are three very different situations.
What not to ask, and when
- Anything answered on the careers page — it shows you did not look.
- Salary and benefits in a first-round technical interview. Ask the recruiter; that is their job.
- "How did I do?" — it puts the interviewer in an awkward position and rarely gets a useful answer.
- A list of ten questions read from a page. Three good ones, asked in response to what they said, beats a checklist.
Listen to the answers as data
If nobody can describe what success looks like at six months, the role is not defined. If everyone on the team joined in the last eight months, ask why. If the answer to "what goes wrong" is that nothing does, you are either talking to someone new or someone managing you. You are interviewing them too, and this is the only part of the process where that is literally true.