The county may slap Assistant Utilities Director Jesse Goodwin with a verbal warning for comments made to a female employee under his supervision five years ago.
Another department supervisor is also facing the possibility of a warning for her failure to report the incident.
The punishments, if any, will be formally decided after the holidays, when county officials return from vacation.
Goodwin's conduct was "unbecoming of a supervisor" and violated the county's anti-harassment policy, according to an investigation report issued last week by Director of Administrative Services Cheryl Marsden.
Goodwin said in the report that he tends to have a friendly attitude to female subordinates which they could perceive to be "flirtatious."
This latest incident coincides with a county report issued last week that found no substantial evidence that Goodwin harassed another employee, Chris Soto, a utilities department inspector.
Soto said Goodwin created a hostile work environment and subjected him to harassment because he was a union steward.
It was during the course of that investigation that the five-year-old sexual harassment complaint came to light.
There are two separate accounts of the incident, which occurred in October 2007.
According to the employee, Bobbie Hamilton, just prior to her transfer to the utilities administration office, Goodwin conducted an exit interview with her. At the end of the interview, Hamilton said Goodwin asked her to "lift her shirt."
She didn't do so, even after Goodwin repeated his request, she said.
Hamilton didn't report the incident to her then-superior or to the county human resources department. Asked why, she said she had previously served in the U.S. Navy and was accustomed to men saying inappropriate things to her.
However, Hamilton said she did mention the incident to several co-workers at the utilities administration and her new supervisor, Grace Sheppard.
Hamilton said Goodwin subsequently made an inappropriate, but not sexual, remark to her during a phone conversation and later apologized.
Goodwin did not deny the alleged incident occurred but remembered it differently.
He told an investigator that Hamilton came to his office, not for an exit interview, but to say goodbye before transferring to a new position.
Goodwin said he had been experimenting with his new cell phone when Hamilton asked what he was doing. He explained he was learning to use it and to take pictures.
Hamilton then jokingly said she would "flash" him for a photograph. Goodwin reportedly said, "Yeah, go ahead," the investigative report said.
Hamilton said she was just kidding and left the office. Goodwin said he realized his comment was in poor taste and apologized the next day.
He did not deny making an inappropriate, but not sexual, comment to her during a subsequent phone conversation and again apologized.
"Whether Mr. Goodwin made the comment unprompted or in the context of joking with the employee is irrelevant," Marsden wrote in the report.
"Supervisors simply cannot make sexually suggestive comments to subordinates."
The alleged incident occurred five years ago and before Hernando County began providing anti-harassment training to supervisors, Marsden noted in her report.
"That fact mitigates, but dos not excuse, Mr. Goodwin's behavior," she wrote.
It was also recommended Sheppard receive a verbal warning for not immediately informing human resources about Hamilton's allegation.