Poe’s entire character is a rebuttal of Han Solo. He’s a masculine, cocky expert pilot who likes to buck the system and do things his own way. The Very Special Lesson he learns is that sometimes you need to listen to authority figures and follow orders and trust the system. You can’t always do things your own way even if it would be cool. In-universe this could have some logic to it because the rebellion is supposed to be a military organization with a chain of command, and in the original trilogy, it was. Hypothetically it would look a lot like the episodes of Star Trek TNG with Admiral Jellico, a by-the-book rules stickler coming into contact with our heroes who tend to play everything fast and loose, and after some conflict they both come away with more respect for each other.
The Admiral Jellico comparison is interesting. Star Trek is full of these “no-nonsense” by the book authority figures who meet our awesome, more laid-back crew, so that personality-conflict antics ensue. Although sometimes it happens in reverse, where the TNG crew (usually Riker) is the by-the-book stickler, as in the case with Ensign Ro or Command Shelby. Generally, neither side is proven 100% “correct”, and they both learn from each other in some way.
With Admiral Holdo, the script vindicates her actions through circumstance… I guess. Although, her plan barely makes sense, as it involved escaping to a random nearby planet which presumably would be easily detectable by the First Order. Holdo’s plan doesn’t actually work, because the First Order finds them anyway. But the script vindicates Holdo regardless, at least within the scope of her conflict with Poe, suggesting it wasn’t her fault that the First Order managed to follow the (obvious) escape pods to the surface. (Vader’s crew in A New Hope had no trouble detecting that one escape pod had landed on the surface of Tatooine.)