Hollis keeps it under wraps, for the most part. He realizes that he works with the top people in their field and it would be impossible to hide everything, he just does damage control and manipulates details. He abhors people in his personal life. He probably enjoys sharing jokes with Cassidy as an aside to the actual conversations going on around them. With Lucas, he probably just watches him with that same deadpan expression regardless of whether the man's overtures to Juno bug or amuse him. Lucas is not Hol's charge and he probably just studies him like a scientific specimen.
Levi, poor poor Levi. He probably would have no idea what to do with the advice given to him by Lucas or how to properly utilize a wingman. He would most likely either use the advice completely wrong or rephrase it in a way that is cringe-inducing. Cassidy, well she could be his handler. There will be days when she hates him and days where he's ideal. Because he's all for helping people--he just wants to do good--but it probably will meet a great deal of resistance if it interrupts his binge watching of Three's Company in it's entirety.