Q:

How to navigate asking for structure when director asks for a gentler touch

I'm a designer who works with many clients a day. Often everything is a rush and it's often left to the designers on my team to translate quick decisions into designs. 
To alleviate this, I've tried to apply a more structured approach. As my co-workers and I have found, clients poorly structure tickets and requests all the time. Often leaving details and assets completely missing, leaving typos and speaking informally with vague jargon. Thus, I've made it a habit to always request for the missing blanks, as anybody would. I don't think I'm being condescending with my language, correct me if it sounds that way but my usual schpeel is "Can you help me clarify X, I'm failing to understand the request. What asset are you referring to? Please share in this ticket." Etc.. 
Does this sound condescending and should I work on being more kind in my tone? I'm trying to be frank and to the point and my director constantly fights with me on this because I feel giving too much leeway and allowing clients and managers to be vague makes it harder for me to do the work. Has anybody else struggled with management or their superiors (directors) not implementing structure? 

A:

In my experience, there are three general reasons people leave a textbox blank when entering a ticket.

They don't know what the question is asking for.
They think they've already given sufficient information with other entries
They don't consider it their responsibility, and are putting the onus on you

In your example, you ask "What asset are you referring to?"
I have known a lot of end users who would have no idea what you're looking for if you asked for an "asset".  It might be clear for the users who repeatedly use your ticket system, but for the ones who use it infrequently, they would probably rather leave it blank than put in the wrong answer and feel embarrassed.
I try to combine reason 1 with reason 2, to make sure my end-user doesn't think I'm assuming they're stupid.  So in my email, I try to ask for clarification while providing examples.  

"I'm trying to find [Generic Request Name], and I'm unsure whether
  you're referring to one of the Web Site Tools available [here], one of
  the reports available [here], or one of the SQL Data Tables available
  [here].  Could you please provide me with the exact name of the tool
  you would like me to address, as well as a screenshot, so I can find
  it more easily?"

Note that this is generic enough that it can be copy-pasted and used for pretty much every time you have to ask the end-user for clarification, which saves you time -- but at the same time, it doesn't sound blunt.  If you have some idea what they're looking for,  you can tailor it accordingly -- this is a pro, because it may cause the users to believe that you're paying attention to them and doing your best to help.
As for people who are number 3 -- well, the ball's back in their court, and they will now be forced to acknowledge that they have to enter an answer if they want the ticket to keep moving.

