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I previously interviewed for a position at a company through three rounds, each time meeting with the boss. They ended up not hiring anyone for the position.

A week later, the company posted a similar position in the same department - a restructured version of the job for which I had interviewed. I applied, figuring it was pretty low-stakes & that they wouldn't pick my resume again. For this job, however, I've again made it to the third round through HR (which doesn't seem to know I interviewed for the previous job), and I'm meeting with the boss again.

At this point, I'm exasperated. I've exhausted all the questions I've had, I've met with several members of the staff & visited the offices, I've researched this company, and I still really want this position. But I can't imagine she has any new questions for me that we haven't discussed the previous 4-5 hours we've met. How can I prepare this time around? What new things can I ask for an interview essentially five rounds in?

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    You sound exasperated. I would focus on being in a pleasant mood and taking all this in stride, because no matter what questions you prepare for, an interviewer will likely pick up your mood. – Chan-Ho Suh Oct 9 '18 at 3:42
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    Maybe you could ask why they restructured the job and why they decided to interview you again after not hiring you the first time. It could be an interesting story. – AffableAmbler Oct 9 '18 at 3:53
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  • You could ask how many more interviews there will be? – R-D Oct 9 '18 at 10:31
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Maybe instead of asking questions you could tell them how much you already know about the company. Show them how much you are interested in their company and the job by repeating what you've learned in the latest interviews.

Interviewer: "Do you have any questions?"
You: "Well, we covered all of the basics in a previous interview. The last time I've been here I heard that you offer (sports program / social benefit / whatever). Is that still the case?"

Or if the questions are more precise:

Interviewer: "Would you like me to show you around?"
You: "Thank you very much for the offer, but I've had the opportunity to see the offices and speak with coworkers before. I was quite impressed and would really love to work for you."

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Any futher time and energy you put into discussions with this company are a waste of your talents, skills, time and energy itself. It shows that the company does not value your earnest efforts and certainly does not value your time. They also appear to not know what exactly they want. I strongly suggest stop wasting valuable resources and move on.

No matter how much you may like, love or want to work there, be aware that you may be placing this job and the company on a pedestal. The reality may change and may be quite different, especially if it appears they are trying but may not have the right fit for you - this can cause even further issues down the line.

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    ... i'm not sure about this. showing eagerness to work somewhere is never a bad thing. OP wants something, why not go for it? – bharal Oct 9 '18 at 8:10
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    @bharal I think eagerness and so on is excellent and it's nice to see that the OP is passionate about the job. In my experience though if they don't "seal the deal" after the 3rd interview that's a huge red flag for me, whatever the reason. It just means it's best to move on at the time, and OP may be having to high expectations which can lead to significant disappointment down the line. – SaltySub2 Oct 12 '18 at 3:31
  • i'm not sure if it's a worthwhile life if you actively flee from high expectations? i suppose you can always "settle", but it seems very... well, it just seems like you settled, right? – bharal Oct 12 '18 at 12:32

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