“Have you ever had to let anyone go?”
Your friend is the owner of a small company. She's telling you about all the difficulties of running her own company. You wonder whether she's fired any employees.
Have you ever had to let anyone go?
"Have you...?" is a way to ask about things that a person has experienced in the past. Here's an example:
A: Have you been to Singapore?
B: No, I haven't.
It's also very common to ask "Have you ever...?" like this:
A: Have you ever taken a yoga class?
B: Yeah, a few times.
We use the word "anyone" in negative sentences and questions:
I don't know anyone who works on old Volkswagens.
Do you know anyone who works on old Volkswagens?
In positive sentences, use "someone":
Yeah, I know someone who works on Volkswagens over in New Jersey.
"Letting someone go" is a way to talk about firing someone or laying them off.
Drew, I'm sorry to say this, but we're letting you go.
Rumor is, they're going to let their entire engineering staff go.
"Let ___ go" sounds a little softer than "fire ___".