My take on this is that I believe Ainge is a short-timer. He stepped out to "retire" at the last place and even though they're doing good now, it seemed to have some drama with his exit. He comes here and gets to do the half-time thing. He thought he was coming in getting a top 3 seed that just needed a little help to go over the top. It was short-to-mid-term goals that would allow him to pick up some low-hanging fruit to add another feather in his cap and jewel to his legacy. Then we nose dived, ended up 5th, got bounced quickly, and have a lot of drama. I don't think he has any incentive for a long game because he isn't going to be here that long, and he wants the credit of doing something now and not waiting until later when so many other hands are on deck that nobody is focusing on "wow, Danny really did a good job here!" I believe his timeline favors wanting to compete now. The only problem is if he really believes that he's going to win in the short term by going deep into appeasing Donovan. Like trading Rudy and keeping DM and Quin. If he really has gotten in this season and thinks that's a viable solution for winning, then we're screwed.
Ainge has short-term goals.
Wade is a part owner and can jump ship much easier. He doesn't have to stress as much about long-term issues.
Ryan should be taking a perspective that doesn't totally burn the franchise down in the long-run. But his two closest guys have been in the league at all levels, they have much different goals, and they're not going to be pointing out "hey, you should really look at what this means for you individually numerous years down the road," so he's riding with the short-term perspective.
This isn't too much different than lockout seasons. It's always amazing to me that the NBA and the NBAPA end up squabbling about a small amount of money difference, the type of money differences that are entirely negated many times fold if any of these players actually miss a season or portion of it, but it really benefits those with long-term skin in the game (agents, etc.) who have enough time to be able to recoup. So what are the agents advising the players? This is just like that except inverting who is advising whom and what their timeline is on their goals.