Back to aviation …
Yes, we listen to everything everybody says and try to build a mental picture of who is where doing what. And we compare what we’re asked to do with what makes sense for our own state & goals, but also for compatibility with the larger context of everybody and everything else. That’s what we call “situational awareness”. You must know your own state, but it’s far better to know, at least approximately, everyone’s state. It’s more or less the aerial equivalent of defensive driving. Be mentally modeling the other drivers’ thought processes and inputs, not just your own.
If we do hear something that doesn’t make sense either there’s a mistake in the instructions themselves, or in our understanding of them, or in who they’ve been given to, or in who thinks the instructions were given to them.
Every pro pilot and every controller has made all of those errors. And heard others make them countless times. And it’s never 100% true that everyone is aggressively monitoring everyone else’s state. Sometimes attention to that level of abstraction doesn’t happen.
As to this specific incident in the OP.
It’s not at all uncommon at airliner airports to fly light aircraft over the middle of the airport on a track more or less 90 degrees to the runways in use. Directly over a runway, the airliners are either on the ground or close to it. Usually.
The runways at Orlando are very long. The 757 is a very high-performance airliner. If they were only going a short distance, e.g. to Atlanta, they’d have very little fuel onboard and even with a full load of people would climb much more steeply than, say, a 777 going to Europe.
If the Cessna’s track was a little farther towards the far end of the runways / airport than the controller quite realized AND the 757 climbed more steeply than the controller quite expected, it’s entirely possible the 757 would be up near the Cessna’s altitude before they crossed paths, rather than well afterwards. Oops.
Or perhaps the controller had expected the Cessna to progress eastward more quickly than he did due to unexpectedly high winds even at that fairly low altitude. So the controller’s mental pacing of how far past the runways the Cessna would be by the time the 757 got there was too optimistic. Oops again.
Ideally the controller should have mentioned the Cessna to the 757 as part of the takeoff clearance. Which would have clued the 757 pilots to look for the Cessna on the TCAS and out the window and perhaps detect the impending conflict before they even started the takeoff.
One of the challenges with building that situational awareness in general is that when you first join a new frequency you have zero information about any of the players other than yourself. Only over time does more and more puzzle pieces fall into place as you hear people talking on the radio. Then just about the time you’ve got it mostly sussed out, it’s time to move on to the next freq & start over.
Applied specifically to takeoffs, at airline airports it’s pretty common to only switch from the taxi controller to the runway controller very close to the end of the runway, when you’re just about ready to go. So you may only be able to listen to the global state of play for 20 seconds before it’s your turn to go. During which time nothing may be said to anyone about anything and you’re still totally in the dark.
During this specific incident, the Cessna may well have been set on his course by the tower controller then handed off to the radar controller before the 757 was even able to monitor any of that. They were cleared for takeoff into a silent sky that should have also been an empty sky but wasn’t. Oops.
I hate it when that happens.