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The application process of the companies I apply to typically involve about 6 interviews, including some interviews with people not on the team I'd be working with. Each interviewer leaves some time for me to ask questions. They seem to be expecting about 2-3 questions each.

I usually find I only have a few genuine questions, especially since a lot of answers are available from people critiquing their organizations online.

What's the best way of dealing with this?

For example, should I prepare 18 unique questions? Should I explain that I've had my questions answered in previous interviews? I've done the latter a few times thinking that they would appreciate me not wasting their time, but they seemed surprised by that.

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    ask the q in a slightly different way and 6 interviews! I wouldn't go back after the 3rd interview lifes to short. – Pepone Jan 31 '15 at 23:30
  • 6 interviews can involve talking to 2 or 3 people consecutively in the same round. – Laconic Droid Feb 1 '15 at 15:41
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Take a step back for a moment. Why do you feel you need to ask questions? I appreciate that people want to be seen in the most positive light possible but if you are asking questions for the sake of asking questions, we need another approach.

The best way to handle questions in an interview is to turn the interview more into a conversation. For example, a few years back an interviewer asked me many questions about dealing with remote workers. I took the opportunity to ask about their company structure, how many remote workers they had and how they were managed (e.g. through a third party or employees, management structure, metrics). No only did this show I had some experience in the area but I was able to give them much better answers to their questions.

There are many techniques for this. For example, "Can I ask you a bit more about your situation to answer the question better?", "Let me answer that question in a moment. First, can I ask you ...?" or "Before I answer that, do you use technique X or Y because that will influence the answer?".

If you must prepare questions, you need to tailor questions to the interviewer and interview process stage. For example, questions about the salary and benefits are best left towards the end. General questions about the company should be asked early. Questions about strategy, direction and metrics are best asked to management. Questions about culture, tools and technical details are best asked to individual contributors or subordinates.

Questions you should always ask are included below. I am trying to keep these general. In some roles, the answers will be obvious or not applicable. Remember to ask peers and subordinates, too, as they will give you different perspectives to your prospective manager.

  1. Who will I be reporting to? Am I answerable to multiple people (matrix management)? If so, who are they and what do they expect/require?
  2. Who will be reporting to me? What is my approximate budget? (If you are not in a management role, ask whether you will be mentoring or assisting junior staff instead)
  3. Who will I be working with (number of people, number of different roles)? How big is my team? How experienced are the team members? Will I be working with anyone remote or in a different time zone?
  4. How is the role measured e.g. metrics? If I am successful, what will I have done? Are there any immediate problems as you see it?
  5. Is this role a new role or am I replacing someone? If I am replacing someone, why did they leave? If this is a new role, what triggered the role creation? (Best asked to your prospective manager. You could ask HR this but you will likely get a sanitized answer.)
  6. Does the role involve overtime or travel? If so, what is the expectation? (The next question is best asked to a peer) What overtime or travel have you done in the last week/month/quarter? Do people keep regular hours? Do people regularly work from home?
  7. Where is the role located? Is it just in one office or is it multiple locations? Is the company planning to move in the foreseeable future?
  8. What tools (e.g. software, programming languages) will I be using? Am I considered the expert or are others already familiar with them? Does the company have any specific policies or standards that apply to this role?
  9. What do you expect a day in this role to be like? Do you follow any standard practices or techniques (e.g. scrum, six sigma, cash versus accrual accounting)? If so, have you customized it?
  10. How do you see this role growing or changing overtime? In a year's time, how will it be different to today?

If you find all your questions are answered throughout the interview, say that. For example. "I had some questions about my goals and metrics but we already covered that earlier so I have no questions for now. However, if I have further questions can I contact you?"

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First, write notes during the interview because you may find that something they say will inspire a question or two. "How many hours did you say your typical week was?" But if inspiration fails during the interview, have a couple of non-traditional questions ready. If you're facing a business person, ask "What was your biggest technology challenge?" If you're across the table from a technologist, ask "Is it easy or challenging [for him/her] to understand the business needs that drive the firm's technology solutions?" If you're talking with a manager, ask "Recalling your least favorite manager, which qualities did that person lack?" (Be ready for follow-up to their response of "What do you mean?")

These curve-ball questions have two redeeming qualities: 1) They don't sound canned. Avoid those! 2) They force the other person to think for a moment (and avoid an equally-canned answer). These types of questions can elicit personal stories and take an otherwise stiff meeting and loosen it up a bit. Just make sure the questions are real. Snark is never appreciated by the other side of the table.

I've had interviews that resembled arguments before the Supreme Court: Six to eight employees at once with one employee asking me a question and the others listening closely, ready to pounce. The occasional curve-ball does wonders to break the ice, illicit a chuckle/personal story and reduce the overall tension of the whole affair.

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