"I'll be in town after visiting a customer on Friday, can we get together?" is much more likely to have a positive response than "should I fly out to meet with you on Friday?". If the meeting is very important to you (high EV, even if maybe low odds?), it's sometimes worth not making it clear how important.
In other cases, being willing to make what seem like big sacrifices (getting a plane the next hour, changing your flight plans, driving cross-country, etc.) will help your case, if known.
"I'll be in town after visiting a customer on Friday, can we get together?" is much more likely to have a positive response than "should I fly out to meet with you on Friday?". If the meeting is very important to you (high EV, even if maybe low odds?), it's sometimes worth not making it clear how important.
In other cases, being willing to make what seem like big sacrifices (getting a plane the next hour, changing your flight plans, driving cross-country, etc.) will help your case, if known.
The parallels with dating are very apparent.