Which question from the following you are asking your boss on a regular basis?

"The good relationship between a manager and his/her employees  allows for transparency on both ends''. So don't be hesitate to ask your boss the following questions:

1. How Are You Doing Today?

Yes, I  already might ask this one. This concept used earlier in my career. I just assumed that because my manager was my manager, things were pretty good for him. so that was a start.

And I mean, he was a boss, right? Things couldn’t be so bad then!

But when I started asking him how he was doing and made it clear I was really asking, I realized that as much as I valued the times when he checked in on my overall state of mind, it was something he appreciated even more when I responded.

So don’t be shy about checking in on your boss’ well-being.

Maybe he’ll say “fine,” or maybe he’ll tell he’s really stressed about an upcoming deadline …etc. Either way, there’s no downside to asking….just go ahead…

2. Am I Doing a Good Job?

There are few feelings worse than the uncertainty of how well or not you’re doing at your job, so if you’re ever in doubt, don’t be afraid to ask your boss for him thoughts.

Some companies are better than others about providing constant feedback, even beyond yearly review periods.

In Pfizer Pharma I was fortunate to work under someone who will tell me when I’m doing a particularly good job or if something needs to improve.

But if that’s not the case for you, there’s no harm in asking for feedback about your overall performance to find the area of improve.

3. What Do You Prefer When it Comes to Communication?

My work became easy to access on my phone, the world changed!  “I can work all the time now,” I thought, “I never have to wonder if I’ve left anything undone!

Turns out that wasn’t the case at all and that he didn’t expect or want!  to receive my completed assignment and non-urgent questions on a Saturday morning .

From his response, I simultaneously learned how my work habits could affect people in a negative way, as well as how to communicate better with my manager.

Along those same lines, posing this question’s also a good way to find out if your supervisor even expects you to check in after hours.  The responses will only improve your relationship.

4. How Did You Get to Where You Are Today?

OK!  so this might be the type of question you asked when you were interviewing for your current job. If so, that’s great.

But even if you’ve scratched the surface, there’s a lot you can learn from your boss’ career story, especially if you’d like to be in a similar position down the road.

And what you’ll learn will probably surprise you. I used to think that anyone who managed people got that status because they never made a career mistake, ever!

But the more I’ve asked people about their paths, the more I’ve realized that all of them overcame a number of obstacles before landing in their current role.

All the above questions are good & helpful in one way or the other but what ultimately matters, is your boss' attitude & behavior. Some bosses can be fine & cool when you ask them such questions, they might not answer all of them but still remaim fine & cool with you. On the hand, some bosses can be very irritating & hard on you for "disturbing their peace" in that case. So therefore, before you think about asking & which questions to ask, first study your boss carefully & understand their likes & dislikes, their attitudes & moods. From here, you can then decide on what do or what to say & how or when to say it

1. How are you doing today?

Above-mentioned is the question which I frequesntly ask my boss on a regular basis.

Well i simply shake hands and greet him, he asks about my progress. I give him my input but yes when i am having some problems i directly not ask him but inquire my lead engineer first.

Basm allah alrahman alrahim

not just one question , million questions (if he is a good boss) like :

How did you start your carrier (companies you work for) , what is you best books , how do you troublshoot any problems , what are your plans for company future ..etc

I agree with Mr Mohmmed Bin Salmah and Mr Sameer

It would be question number one..........

The questions we intend to ask our bosses are purely depend upon the intimacy / wave-length both have towards each other. I could able to ask all these with my ex-German boss - CPT within a week of his joining that I couldn't with the bosses of my own nationalities.  

Thanks for your invitation, My option is No. 1.

Thank you for the kind invitation answer No. 1 How are you today?

I agree with M's Ghada answers, .thanks for the invitation. .