Nine Questions I Now Ask in Interviews That I Wish I'd Asked Five Years Ago

Or: how to interview the company while they think they're interviewing you.

Photo by Daniel McCullough on Unsplash

The interview is a two-way conversation in the same way that a job offer is a negotiation: technically yes, in practice almost nobody acts like it. The candidate, particularly the candidate who needs the job or wants the job badly, treats the interview as an exam. The exam framing is the framing the company benefits from. The candidate’s job, if they have any seniority and any choice, is to refuse the framing.

I have done a lot of interviews on both sides of the table by now, and I have learned that the questions you ask at the end of the interview - the “do you have any questions for us?” portion that most candidates use to ask about the tech stack or the team’s working hours - are the single most under-priced part of the process. They are under-priced because the company has, by that point in the conversation, dropped their guard. They are answering, not assessing. Which means you can learn things about the company that you cannot learn from the careers page, the Glassdoor reviews, or the LinkedIn profiles of the people you’d be working with.

Here are nine questions that have served me well. Some of them are diagnostic. Some of them are trapdoors. All of them have, at one point or another, told me something the company did not realise they were telling me.

---

1. “Can you walk me through the last time someone in this team got promoted? What did the promotion look like, and how long had they been here?”

The answers cluster into three patterns. The good answer is specific: “Yes, [Person] was promoted from senior to staff about eight months ago, the timeline from first conversation to formal promotion was around six months, the promotion criteria they hit were X, Y, and Z.” The mediocre answer is general: “We do promote internally, we have a calibration cycle twice a year, people generally do well here.” The bad answer is some version of “well, we haven’t had one in this team recently” or “the process is being revamped.” The bad answer is a flag. It does not mean nobody gets promoted; it means promotions are not happening in a way that this person can describe specifically, which means the path is not legible, which means it depends on factors you cannot see.

2. “What’s the longest someone in this role has been at the company, and what are they doing now?”

Tenure data is more informative than people realise. A team where the longest-serving person in your role has been there fourteen months is a different team than one where the longest-serving person has been there four years. Neither is automatically bad - fast-growing companies churn - but the answer tells you something about the trajectory. Pair it with: what are they doing now? If the answer is “they moved into management” or “they’re leading [bigger thing]”, you have an internal-progression signal. If the answer is “they left” or hesitation, you have a different signal.

3. “What’s something the team is genuinely bad at?”

This question is a trap, and the trap is by design. Almost everyone has been coached to deflect weakness questions with a humblebrag: “we move so fast that documentation sometimes lags” or “we care so much about quality that we can be slow to ship.” If you get the humblebrag, you have learned that the person you are talking to is interview-trained, which is itself useful information, but you have not learned anything about the team.

If you get a real answer - “we are bad at finishing things, we start more than we ship” or “the senior engineers are spread too thin and code review is a bottleneck” - you have learned two things. You have learned what the actual weakness is, which is useful. And you have learned that the person you are talking to is willing to be honest with you about something costly, which is much more useful, because it tells you what working with them will be like.

4. “How does the team handle disagreement with a decision from leadership?”

The good answers describe a process: “we raise it in our team meeting, the manager takes it up the chain, sometimes the decision changes, sometimes it doesn’t, but we always get a reason.” The bad answers are silence, or “we trust leadership to make the right call,” or a quick pivot to how aligned the team always is. Teams that are always aligned are either lying or not thinking. Neither is what you want.

5. “What’s the headcount plan for this team over the next twelve months?”

This question is a hiring-manager question, asked of the hiring manager. The answer tells you whether you are joining a team that is growing, holding, or being quietly run down. “We’re hiring two more in the next quarter” is one thing. “We don’t have approved headcount beyond this role” is another. “I’m not sure, that’s being discussed at the leadership level” is a third, and is the one to pay attention to. Headcount uncertainty at this point in your conversation means the team’s future is being debated above the person who is hiring you, which means your role’s future is being debated above the person who is hiring you.

6. “Who would I be working with most closely, and can I speak with them as part of the process?”

This is partly about getting the meeting and partly about watching the response to the request. A confident hiring manager says yes immediately and arranges it. A less confident one says yes but takes a week to schedule, or schedules it with someone who is not who you’d actually be working with, or quietly forgets. The friction is the data. The people you would be working with should be findable, available, and willing to talk to you. If they are not, you are about to join a team that does not introduce its incoming members to its existing members until after the offer is signed, and that is a team that has, somewhere, a reason for the gating.

7. “What does success in this role look like at the six-month mark? And what does failure look like?”

The success question is normal. Most people will answer it. The failure question is the one that does the work. Most interviewers have not prepared for it, which means you are getting an unscripted answer, which means you are learning what failure mode they have actually seen before in this role. “Failure looks like someone who can’t navigate the ambiguity” tells you the role is ambiguous. “Failure looks like someone who builds in isolation and doesn’t bring people along” tells you the role is more political than technical. “Failure looks like someone who burns out” tells you what you need to know.

8. “When was the last reorg, and what triggered it?”

The frequency of reorgs is a measure of organisational instability that does not show up anywhere else. A reorg twelve months ago is normal. A reorg three months ago is recent and you should ask why. A reorg pending is information they may not volunteer but might confirm if you ask directly. The trigger is also informative: reorgs driven by strategy shifts are one thing, reorgs driven by a leadership change are another, reorgs driven by underperformance are a third. The three feel very different from the inside.

9. “Why is this role open?”

This is the simplest question and the one most candidates do not ask. The answers fall into three categories. Growth: the team is expanding, the role is new, somebody got promoted out of it. Replacement: someone left. Restructuring: the role is being reshaped or split out of a previous role. All three are normal. What you are listening for is which one applies and whether the answer is delivered cleanly or with a pause. The pause is the thing. If “why is this role open?” produces visible hesitation, there is a story underneath, and you should ask one more follow-up question. “Did the previous person move internally or leave the company?” is a fair one. The answer to that question, more often than people realise, is what tells you whether this is a role you want.

---

The thing I want to leave you with is this. The interview is set up to make you feel like the variable being assessed. You are not. You are choosing between options that are imperfect in different ways, and the questions above are how you find out which way each option is imperfect.

If a company punishes you for asking these questions - visibly bristles, gives you short answers, makes you feel like you’re being difficult - you have learned the most important thing about that company in the cheapest possible way. The company that does not want to be interviewed is the company that has not earned your interview. Let them go.