Observation Checklist Not Appearing

​@dmontrey Without looking at your specific set-up I can give you some general steps to check, some are basic, but want to just confirm them.

1. Is the manager really the employee's Direct Manager?

Open the employee's user record and confirm the Direct Manager field names the manager you expect. My team only lists checklists for people in the manager's team hierarchy. Managers see their own team and the teams of managers beneath them, when the relationships use the same manager type, such as Direct Manager → Direct Manager 
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Check that the manager is active, not deleted or deactivated 
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If the manager changed after the checklist was scheduled, the approver is set from the Direct Manager at that time. It doesn't update retroactively 
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2. Does the schedule target the employee?

If you picked the employee through a group or branch, the selection only covers people who were members when you scheduled it. People added later are not included automatically. You have to assign them individually 
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Selecting a branch doesn't select its sub-branches. You have to add those manually 
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If you assigned the employee as an individual user, the limit is 10 users 
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3. Is the observer set as a manager type?

In Step 2, choose Other observers > Managers and select the manager type, for example Direct Manager. If you chose Self observer or a custom user list, the checklist won't route to the manager 
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The My team Checklists tab lists manager observations of team members and the manager's own self-observations 
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Other observers appear there too. Managers can see in-progress checklists for their reports even when someone else is the observer, as long as those reports sit in their hierarchy 
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4. Has the trigger fired and the schedule populated?

If the checklist is set to become available on course completion, it won't show until the employee completes the course you named as the trigger 
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Check the Observation checklists dashboard, in the Reports area. The Assigned checklists table shows the observer, the user to check, and the status for each row 
. If no row exists for the employee and manager, the checklist was never assigned. In that case, look at the trigger and the targeting.

5. Does the checklist have items?

A checklist that was created and scheduled without any items won't be assigned or sent. Support has seen this happen with a Direct Manager checklist whose Items tab was empty