I have to admit, I don't like "No problem." Or even worse, "No problemo." as if that were legitimate Spanish. Instead of a gracious "you're welcome," or "my pleasure," "no problem" just sounds like a brush off. So "no problem" doesn't work for me.
But I digress.
The reason I like "So, how's that working for you?" is that it makes me laugh. I once had a box of books that I was giving away. A friend selected several to add to her bookshelf and lighten mine. In the box was a book about an apple cider vinegar diet. She held it up and asked, "Does this work?"
I pointedly looked down at my very round self and said, "no."
As flawed human beings, we have a tendency to persist when the evidence before our eyes should deter us. A young man has trouble attracting the attention of a certain young lady. He talks louder, laughs louder, makes inappropriate noises, and wonders why she's always looking the other way. Someone needs to say, "How's that working for you?"
A teen wants independence so she sneaks out, prevaricates over where she has been, and lifts a couple of dollars from her mother's purse on a regular basis. Her parents tighten the reins and keep a very close eye on her. "Hmm? How's that working for you, young lady?"
It's not as difficult to change behavior if we look at the truth. When I run head on into the same frustrating situation over and over again, I ask myself what brings me to this point.
It's still funny, and not nearly as humiliating, if I ask myself "So, how's that working for you?"
God has a way of helping us when we are honest with ourselves.