Yes you can! To do so, navigate to your Account Settings and and scroll to the Automatic Sharing section. From there, you can choose to turn Automatic Sharing on for Observations and Self Assessments.
Once you select 'On,' click the pencil icon and select the users or groups with whom you'd like to automatically share your Observations and/or Self Assessments. Click the blue checkmark when you're done!
Now you're all set to automatically share your Observations and Self Assessments!