If you are on Jira server, you can implement this using the behaviour plugin that is bundled with Scriptrunner.
There may be other possible alternatives but unfortunately, I am unaware of any that isn’t a bit of a hack such as directing users to add comments via a transition which has a field pre-populated with your questions .
You can also check the marketplace to see if any addons provide such a functionality.
Connect with like-minded Atlassian users at free events near you!Find an event
Connect with like-minded Atlassian users at free events near you!
Unfortunately there are no Community Events near you at the moment.Host an event
You're one step closer to meeting fellow Atlassian users at your local event. Learn more about Community Events