Disclaimer: I have no idea if the translation is correct.
If it is correct, then "You go on ahead, I'll catch you up" is used for a short delay. For a longer delay, you could use "You go on, I'll catch you up later" or "You go on, I'll come along when I'm ready".
It's a polite negative question form of [saki ni itte] (go earlier, go ahead). If you translate it literally, it's something like, "Why don't you go first?" or "Why don't you go earlier?" In English, just as in Japanese, the "I will catch up with you later" is not stated, but implied.
"You go (on) ahead" implies "And I'll catch up later" in English, too. "Why don't you go (on) ahead?" would be more polite and in the same question form.
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If it is correct, then "You go on ahead, I'll catch you up" is used for a short delay. For a longer delay, you could use "You go on, I'll catch you up later" or "You go on, I'll come along when I'm ready".
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