"You listen to what he says, and he knows it," Bosh said. "I remember he was talking to me as we were having a meeting and I wanted to start the season that minute. He just has that 'been there, seen it all and this is what you have to do [element]' about him. He comes around you, and you stand up straight."
And it's usually then when Riley executes his go-to move.
He pulls out one of the nine championship rings he has won as a player, executive, head coach and assistant coach.
And he proposes.
Riley dropped a bag full of title rings on LeBron's table in Cleveland during their 2010 meeting. He has flashed at least one of them to a few other free-agent targets over the years.
Bosh took matters a step further.
"He gave me one of his championship rings from 2006, and was like, 'You give me that back when you come here and win yours.'" Bosh said. "So I took it. I was like, 'Oh, man!' Don't tell me to take something if you don't want me to take it. I've still got it, too. But I told him I'd give it back after this year."
But Riley admits he's had to adapt in some other ways to better relate to modern NBA culture. In the past few seasons, he has opened a Twitter account, relented on his stance against players wearing headbands and has allowed James' manager and the personal trainers for James and Wade greater access.
But mostly, Riley steps back and allows coach Erik Spoelstra to legislate the team culture.
"LeBron, being who he is in this world, in this game, has a very heavy load," Riley said. "There's a heavy load off the court and on the court. It's a lot different than what it used to be. He manages everything he has to manage that maybe Magic Johnson didn't have to manage back in the 1980s. I've adapted to that."
The evolution hasn't been easy but it has become necessary.
"It doesn't mean that it's so rigid that it can't change somewhat," Riley continued. "And there's a plan. I think we take great pride as an organization in how we do things. Even though some things are blurted out on Twitter or Instagram that sometimes I cringe at. But hey, it's their life. As long as it's not detrimental to us and what we're trying to do, then that's the nature of the life we're living today."
In the past four years, James has grown into a two-time champion who also added a total of four regular-season and Finals MVP trophies to his collection in Miami. Arison, Riley and Spoelstra will certainly have to retool the roster again this offseason -- one way or another -- to convince James, 29, he can compete for championships long term with the Heat.
But James remains confident in Riley's track record. James also acknowledged the challenges a harsher luxury tax in the CBA represents, "the business side that hurts relationships," but that his "connection with Riles" is always something he can fall back on regardless of looming decisions.
"He doesn't have to prove anything to anyone. Not me, not Dwyane, not Chris. No one," James said. "His résumé speaks for itself. His stature speaks for itself. So we'll see what happens."
Riley didn't build his reputation as one of the NBA's must successful team architects on losses.
Not in games, nor in personnel matters.