You will need a scripted post-function to do that. My issue here is how do you determine the assignee's manager? If that won't be a problem, try different scripted post-functions for automatically setting Watchers based on a condition. There's a lot of them in the marketplace (Try the JIRA ScriptRunner).
To determine the manager of a user, we normally recommend the following strategy:
Obviously a custom add-on is always a solution. This would include a manager admin UI and a post-function to add manager as watcher.
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