Help I Sexted My Boss is a comedic podcast in which two friends offer advice for modern humanity. Jordan North is a British DJ and TV host well-versed in pop culture. William Hanson has been an etiquette expert since he was 16 years old. Despite their differences, the hosts have an entertaining rapport. This is a popular podcast with a large and avid fanbase.

The title of the podcast refers to the kinds of issues listeners seek advice about. Much of the show's content comes from its audience. For example, one listener has a question about how to respond to her neighbors. She found some dog poop on her doorstep that she knew her dog didn't leave there. The hosts don't judge their listeners for their questions. They treat all queries with equal concern, even when unsavory.

Discussions on the podcast feel lighthearted in general. Half an episode may share opinions on great train snacks. In another section, the hosts may chat about the antics they got up to over a weekend. Talking about their own lives as well as their listeners ensures the hosts connect with their audience.

Sometimes, the hosts toast their listeners at the start of the show. One episode begins with William and Jordan toasting Julie and Alejandro. William reads a letter Julie sent to them. Julie is a recent widow and expresses gratitude to Help I Sexted My Boss. She explains that the podcast brings her joy and comfort during a hard period in her life.

Listeners also appreciate the educational aspect of the podcast. William has an "Etiquette Explained" segment. He uses this opportunity to explain his popular social etiquette tips. For example, folks may want to know when and why to take the straw out of an iced coffee. Jordan quips that sometimes, he thinks William makes these rules up as he goes along. There's also “William's Wacky Etymology of the Week.” This might appeal to listeners curious about where certain words come from.

New episodes of Help I Sexted My Boss debut on Mondays and Thursdays each week.