Do you have a go-to question that you always ask when you're interviewing for a new role that you use to tell if you're going to truly get along with your new superiors?

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CIO in Government, 10,001+ employees
Yes. We ask if they have they have ever failed and if so, what did you learn?
CIO in Education, 1,001 - 5,000 employees
I always ask about the criteria for success. That usually gives some light to how folks manage, how you're measured, and a peek into the culture.
Chief Information Technology Officer in IT Services, 201 - 500 employees
What is your management style and what are your challenges? Lastly, how do you prefer to communicate and stay updated on our interactions? The response to this question will help me evaluate a method of control for my future superior.
Information Security Director in Media, 10,001+ employees
Yes, It is what is your management style?  As I look for it to inform me (with follow-up questions) if they micro manage, create autonomy and/or have a team collaborative approach
Director, Experience Design in Education, 1,001 - 5,000 employees
I flip the behavioural descriptive questions back to them:

Can you please tell me about a time that someone failed/caused a roadblock/etc. How did you handle it and what was the outcome?

Another one:

What is your leadership philosophy?

I really am interviewing them as much as they are interviewing me...  :)
Director of IT in Software, 201 - 500 employees
What is the biggest mistake you've made, and what did you learn from it? 
CEO in Healthcare and Biotech, 11 - 50 employees
Yes, "how would you deal with your senior manager asking you to initiate a program that you know in your experience won't work?"
Director of IT in Healthcare and Biotech, 10,001+ employees
To what extent does the role and I work I do help the company achieve it's goals? By asking this, I can better grasp the company's long-term goals, my place within them, and whether or not our respective priorities are aligned.
Chief Information Officer in IT Services, Self-employed
applicants tend to know the usual questions - biggest fail - etc. so I tend not to go there much but if i do it looks like this 'Walk me through a project that did not work out as planned and tell me your part and the lessons you learned.'   Some other questions - what do you believe is the culture of this company and how will you enhance it? How would your friends describe you?    What research did you complete to prepare for today?
CIO Strategic Advisor in Services (non-Government), 2 - 10 employees
I'm always interested in an individual's motivations and what they are curious about. Curiosity is a core trait that I'm always looking for. It can highlight how someone thinks, what motivates them and where their interests lie. It also highlights the potential for someone to learn new things.

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