WARNING: The following contains spoilers for Pokémon Twilight Wings episodes 4 and 5 available to watch in English from The Official Pokémon Channel on YouTube now.
Pokémon: Twilight Wings' main storyline follows John, an ill boy who wishes to one day watch his favorite Champion Leon battle at the Pokémon Stadium. As the series progresses it presents numerous supporting characters and their journeys as well, specifically highlighting the strengths and weaknesses of the Galar region's female characters.
Pokémon: Twilight Wings isn't the first Pokémon original net animation (ONA). Pokémon Origins and Pokémon Generations also follow stories involving the videogame's characters outside of the adventures of Ash Ketchum. The backstories of many Pokémon Sword & Shield characters are contained in short segments of the videogame, with a lot of their story only being conveyed through tales written on League cards. Thus, despite Twilight Wings episodes running for only about six minutes, they are able to describe characters such as Nessa, Oleana, Bea, and even Sonia in ways the videogame series fails at.
Pokémon: Twilight Wings Episode 4, "Early-Evening Waves"
Nessa is struggling with losing her Pokémon matches. After yet another loss, Chairman Rose confronts Nessa, waving around Nessa's modeling work in magazines. With an image of Champion Leon on-screen, Rose remarks to Nessa to consider what her goals are and just how far she wants to go.
Annoyed and stressed by the Chairman's remarks, Nessa confides in Sonia at a café over what she should do. Nessa found the remarks of the Chairman to be disparaging, and imply she should give up her modeling work if she wants to become a better trainer. However, Sonia tells Nessa rather than over-reading what the Chairman said, she should consider what she wants to do moving forward.
Later, while at a photoshoot, Nessa realizes she was at this location long ago. As a child, she had interacted with the cutest bullied Feebas in existence. Feebas is typically a rather ugly fish Pokémon, and is most similar to Magikarp in terms of fighting capabilities. Feebas faces an ugly duckling scenario though, as when it evolves it becomes the beautiful and strong Pokémon Milotic. When Nessa talked with Feebas as a child, she encouraged the Pokémon and asked if one day it would let her ride it when it grows up.
The Feebas remembered her request many years later, and as a Milotic, gave Nessa the ride of her life. After viewing Nessa's commercial, Sonia remarks on the phone to Nessa that she should try to be like Milotic, beautiful and strong, she doesn't have to choose just one. Moved by these words, Nessa model walks to the Chairman's office where she informs Oleana she'll reach the top, both as a gym leader and as a model - and that she'll win the next match too. Nessa embodies strength in both beauty and physicality, like Bea, she learns to confide her problems with others and learn from Pokémon what she should strive to be like.
Pokémon: Twilight Wings Episode 5, "Assistant"
Throughout Pokemon, both in the video games and Twilight Wings, Oleana is a constant presence around Chairman Rose. She makes sure he is on schedule, whether they are meeting with kids at a hospital or providing advice to the Galar region's gym leaders. Episode 5 provides some backstory to Oleana and her personality.
Oleana was always a workaholic, even before working with Chairman Rose. Her tendencies to overwork drove her assistants away from her, as they became exhausted with the hopelessness of researching Dynamax and Gigantamax. One night, Chairman Rose walked into Oleana working alone in her lab, recognizing her efforts as special and bringing her onto his team.
Cut to the present, a day where Rose is unavailable and Oleana has to take on the role of leader. In a montage sequence, the episode showcases how flawlessly Oleana can accomplish any job, whether it be overseeing construction, giving presentations in meetings, or even cracking the code for a Rotom virus in computers. As opposed to in her laboratory, everyone relies on Oleana for everything and looks up to her as a star.
Oleana loves to work, and also loves that Chairman Rose gave her the opportunity to showcase her talent in a setting that would rightfully appreciate her. While in a Flying Taxi with Chairman Rose she berates the taxi driver for not knowing the difference between Dynamax and Gigantamax, but this is just further proof of how much she loves her job, her research, and Pokémon.