Which specific questions do you ask your sales reps when they request content?

For me, I generally start with questions to determine if new content is actually needed (versus piling on to an already long list of requests).

In addition, to your examples above...

Evaluating If Content Is Needed

• What is the asset that you're requesting? 
  • Ask yourself: Does it exist already? =D 
• What is the goal of the new asset? 
  • Ask yourself: Does it exist already? =D 
• What part of the sales stage do you think it would benefit? / When would this be used? 
• What is the main message that you had in mind? 

Once you get the baseline information, you can then determine if this will fit in with your GTM plan. If it does, you can go further with the goal of developing that new asset.

I like to ask:

• Who is this for
• Who else would use this
• What are you trying to achieve with this
• Why now
  
  In some cases a sales rep may come asking for a very specific piece of content they think can help in a sales situation. Going through the questions above helps me understand what exactly they need it for and why. Some times they have the right intention but the wrong delivery… in the end is all about understanding the ‘ask’ before you spend too much time working on it.

It's really mainly two primary questions for reps when it comes to content requests: 

-What problem are they trying to solve? 

-Who is the audience? 

-What is the distribution and adoption plan? 

...maybe a 4th, depending on the answers to the above, is if there are examples they can point you to. It helps with any miscommunication or misaligned expectations. 

All three questions above will help you prioritize how this request fits with your overall priorities and whether it merits being added to the list or not. 

in addition to the above, having alignment ahead of time across Product marketing and sales leadership - about customer segments,personas, sales conversation roadmap/challenger framework, appropriate content (standardized, articulated well), all help to ensure sales always has all the content they need. I would also consider "educating" on the core pieces of collateral that will be always available. The one thing we learnt to do really well at cisco for example was At-A-glance -- it was so standardized and very multipurpose built - events, leave behind etc. That along with TDM and BDM deck. Worked like a charm. :-)

"What part of no don't you understand?"

That's the question I usually end up asking. =D

Sarcasm aside, at least 95% of the requests I get don't need new content, either because an appropriate option exists or the rep's request is for a one-off piece that isn't necessary. Other than that I will ask who it's for and when they need it, and other questions specific to our sales process and products.

I find that reps typically underestimate the time needed to generate content by a factor of about 5. So if they need it in a day, I probably would have needed a week to do it given other commitments!

1. What step in the buyer's journey on you on?

2. What buyer persona are you dealing with?

3. What problem/objection are you encountering?

4. What have you tried?

Sales reps ask for content they *think* will help them close a single deal. They have little regard for content that is effective across a market segment of buyers.