Most of the sketches included in Season 1 were previously rejected skits from Tim Robinson's time as a writer/cast member on Saturday Night Live.
Tim Robinson looked to cast non-comedic actors for most of the roles on the sketches in order for the performances to be more grounded and make the characters seem more like genuine people.
Unlike many comedy shows, I Think You Should Leave did not feature a writer's room in Season one. All sketches were written by Tim Robinson and co-creator Zach Kanin. John Solomon came in later in the writing process, to help when Robinson said his brain was "getting fried trying to put these things together".
Originally, each episode was going to be around 22 minutes long, but during the editing process Robinson said he felt that the episodes were "easier to take in" when the they were shorter.
The color palette of the transitions was created based on how Tim Robinson dresses in real life.