Mr. Saddler always wanted to be a cop as a kid, but decided to try security first. Among security gigs, he added, working at Times Square is considered a prized assignment: You have to earn it. Mr. Saddler’s time came several winters ago, as a public safety officer in Bryant Park. He landed an interview after jumping in to help a man — now his Times Square boss — who broke his wrist at Bryant Park’s ice rink.

For Mr. Saddler and his colleagues, the ambassador training was minimal. Some preparation centered on the artist and how the statue was created, but a lot focused on anticipating what questions visitors would ask.

Sometimes, visitors will spot them and head over with questions. More often, the ambassadors see someone stop to look up or read the display, and that’s their chance to move in and start a discussion. They not only provide the basic details, but also try to engage people with questions: How would you describe what this work means to you in one word? If you were to build a monument, to whom or for what would it be?

Conversations can go long, with families turning their questions away from the statue and toward the ambassadors themselves — how did they get here, and how do they know so much about the statue?

Other encounters are brief. On Wednesday, Mr. Saddler approached three 60-ish men who were hovering near the text display that describes the monument. He asked if they were familiar with Mr. Wiley’s work. One was a fan, but it was his first time seeing the statue.