He smiles, initially, at her running through the list of to-dos, jumping directly to "when" and ignoring "if." It's a winning quality, and her approach makes sense as she lays it out. Start looking at practicalities. It's much as he would do it.

Until her comment about "protections" and he looks as if he's bitten into an unpleasant filling in a pastry without expecting it. The expression is brief and muted, but certainly there before he smooths it over.

"I can speak to what was in place here. Not every Circle, I've since gathered, was the same. But a fair number of them are things I wouldn't want to reproduce going forward." He doesn't blame her for not knowing, but she should know before they're talking to others about the plan, certainly. Everyone else with any Circle experience will, after all.