Hi Alison,
Apologies for the delayed response. I missed the notification indicating you had replied.
Unfortunately with so few steps in the workflow and the loop back to Launch Arcmap which needs to be manual it is difficult to meet the Automatic Execution's needs appropriately. Here are a couple of workarounds for you.
The easiest way would be to add a dummy procedural step between Launch Arcmap and the Question step, that is set with Automatic execution, can't be skipped and proceed to next. The user responsible for step 2 would then just need to execute the step to preserve your workflow logic.
Another alternative would be to remove auto-execute when the job is created. Then you could check Automatic Execution on the Launch ArcMap step. To fix the loop you would need to insert a dummy step in the loop so that Launch Arcmap doesn't execute automatically. It doesn't need a special configuration it just cannot have Automatic execution checked.
Cheers,
Michael