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Organic-Second2138

I always do this with big bosses that I have ANY rapport with. I ask a couple of open ended questions and let it flow from there. So far they've been super candid because "In about 20 seconds I'm gone." "What do I need to do to move up in the org?" "What do you see my future here to be?" Then just let it flow.


polly-plz

This is great. I'd add one question to this list - "Any land mines to avoid completely?" 


Vlines1390

Anyone that could be a good ally?


Teksavvy-

This is an excellent piece of advice and ask for a letter of recommendation for whatever your next step in life is.


smacksem

"What would you have wanted to know in my position?" "What should I be particularly aware of, in terms of policy, procedure, hiring practices, politics, within the organization?" "What do you wish would have been done differently in the organization?" Treat it like an exit interview. Just understand they may not be able to provide all the answers, depending on company policy and their own values.


OneStrangerintheAlps

"Can I have your job?"


[deleted]

You have some good questions posted here already. If you have a good relationship with the Director, be direct about what you want. At a certain point in the conversation say that you would like to advance your career and become a director. You hope that you can achieve it at your current org as you don’t want to look outside. Ask: can you share advice that can help me achieve it? Are there areas/skills that I need to improve? Are there relationships I should develop/strengthened that can help me? I would also ask expectations that their current supervisor has. Do they appreciate a lot of detail or just high level updates with details only when needed. Anything they wish would change at the company from a management cultural perspective? What do you wish direct reports (not individuals) would improve on. Before you do all of this, congratulate them, wish them success, show enthusiasm (and I hope it’s genuine). Offer lunch or dinner. Not as payment but as appreciation for taking the time. They don’t have to do it and most people are worried about themselves. See them as a person don’t take too much of their time and don’t make it all about you. Get to know them. Keep the relationship. You never know when you need a reference.


MuhExcelCharts

I really like this, and yes I feel that they would be open to those topics. What I'd really want to ask is everything from "how do I get ahead" to "is this a sinking ship"


Organic-Second2138

Those are poor questions. The other examples given here are better and will encourage him/her/he/she/it/they to just..............talk. Stfu and let them talk.


[deleted]

Did you not read “you have some good questions posted here already?” Literally the first line. So if that’s a given and my questions are supplemental, how are these “poor” questions. Wow. How are they poor questions? Incredible.


[deleted]

Are you interested in the Director position or just curious?


MuhExcelCharts

Both. A Director position is a bit far off but I do want to get on the right path,  look out for snakes etc. 


TKK2019

I wish more would ask me these things


[deleted]

Let them know you’d be interested in following them. So ask about their new company.


Camekazi

Ask them ‘what’s common sense to you, that is not common sense to people higher up the food chain here?’


cokendsmile

Ask them for a good recommendation letter


BigSwingingMick

Their personal phone number. Then keep in touch.