say a connection oriented full-duplex communication can work better than a connectionless one-way comunication

it’s a way to pass the problem to Tom, showing him you are available to discuss it and in the meantime passing him some hints that could avoid him to loose time.

Of course it will depend on how Tom is and whic is the exact purpose.

The risk in giving the hints is that Boss could already put Tom in a specific way and if Tom is not one of those people who keep the hints but still think with their mind, Boss will get the result he wants, but he cannot be sure if there is another way to solve the problem.

so here is a possible other way:
Boss3: Tom, have a look at the problem, try to find what you think is the best solution, then come to me and we will check it together and with some ideas I could have. Of course if you have questions, feel free to come to me to discuss it.

or

Boss1 “Tom, have a look at the problem and let me know if you are in troubles”
Me “I don’t know very well this problem, can you suggest me something ? “

or

Boss1 <>
Me <>

And yes, I’m talking from the technical side of the fence. i just spent the whole day dealing with the logistics and the paperwork of a long-distance travel, and this was an healthy reminder that non-technical jobs have their own share of difficult and stressful challenges. I’m guilty of forgetting that myself all too often.