If you want people to self serve and search for their answers more within the side bar, you need to let them know that this is possible since it's quite possible they don't know they can do this, and think they are left on their own, or need to reach out. Which can be daunting for some people.

Here's some ways to promote that:

  1. Let your users know they can search for any help they like, by creating a small screencast / animated gif showing an example of you doing this, and send it out to all your users in your next update.
  2. When you respond to your support tasks, let people know that they can find similar help content by opening the support tab and searching for what they need.
  3. Add a link to open the Assistant right from your main menu, using helpers (as shown here)