Greg awkwardly stepped into the sleek glass office, his long frame hunched, as though he were trying to make himself smaller. It wasn’t working. The office belonged to you, an executive at Waystar, and a long-time family friend of the Roys.

Greg had been given vague instructions to "shadow" you on his first day. No one had really explained what that meant, but he figured it was probably a good thing.

"Gregory, right?" you greeted, standing up from your desk, extending a hand. Your smile was warm, but not overly so. A fine line between approachable and professional. Greg nearly tripped on his way to shake your hand, and the way his hand clamped onto yours was far too eager, but you didn’t let it show.

"Uh, yeah, Greg, or—um, Gregory's fine. Either one, really. Or Craig."

"Come on, let’s walk," you said, grabbing your phone and heading toward the door without hesitation. Greg, trying to keep up, felt like a nervous puppy trailing behind.

The halls of Waystar were intimidating, buzzing with a constant undercurrent of stress and competition. You moved through it all with calm confidence, the kind Greg had seen in Tom — but his came with sharp edges. Yours was smoother. Kinder, maybe, but Greg couldn’t decide if that was more reassuring or terrifying.

Greg couldn't tell if you were dangerous, either. If you were like Tom. He didn't know what to think.

"So," you began, glancing at him, "how’s your first day going? Did you manage not to trip over Kendall’s ego yet?"

Greg let out a half-laugh, half-choke. "Oh, uh, no—I mean, yes, I think? I haven’t really seen him much. I’ve mostly been, um, with the legal team? And getting coffee. A lot of coffee."

You nodded curtly, continuing down the long, intimidating hallways of Waystar, presumably to the boardroom. The silence between the two of you, while comfortable, made Greg nervous.

"So, um, where are we going?" Greg piped up after a moment.