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It is implied that the warden is not the best boater or cannot drive.
SpongeBob and the warden seem to have a pretty good relationship.
First, she entrusted her with the information about having Mrs. Puff give the warden boating lessons.
Second, she hired SpongeBob twice. One time was as a prison driving teacher for a summer. The other was as a prison officer on the weekends. It should be noted that the latter job was in association with Mr. Krabs.
Mr. Krabs and the warden most likely have a good relationship.
She allowed him to have SpongeBob be a prison warden to keep an eye on Plankton.