Dolson is in a tough spot.
Everything I think he needs to be doing, right now, should involve discussions with the President and the BOT. Buckner's presence on the BOT potentially throws a huge wrench in that.
What's needed is for Dolson to call a meeting with the President, Buckner, and himself. And I lay out a vision for what IU basketball can, and should be. And assuming its already talked with Woody about all this, multiple times...something needs laid out, bullet point by bullet point, how Woody aligns with the vision for the program. And assuming that for most of the bullet points he doesn't fit, it should conclude with the formal request to fire him at seasons end.
Practically, he has to get Buckner on board with this. And the risk to Dolson is that if Buckner isn't on board with this, and he makes a move like this, it could end up costing Dolson his own job. But if Dolson believes its the right thing to do, then he has to have the fortitude to do it now.
The Buckner dynamic, and him being done next year, leads me to believe Dolson will kick the can down the road another year. Its what most AD's in his position would do. And I'm not naïve enough to say I wouldn't do the same thing, for personal job preservation.
Dolson has shown the willingness to move on coaches before contracts are up. He's shown the chops to get the required funding to get that done. Dolson made the move on Archie, with going hard after Stevens as one of his first moves. Woody wasn't his top choice, evidently...so I doubt Dolson himself views him all that favorably at this point...obviously could be wrong on that, its just a guess. But an educated one, I think, with how the hire went, and then how the Matta/Fife experiment went... Woody's buyout isn't a problem, in the big scheme of things. But his relationship with Buckner is a problem...if Buckner still believes in him and wants him to remain the coach.
So if I'm Dolson, and I'm being honest and realistic, I spend the next 4-5 months actively pushing Woody to change his program, change his staff, etc... With hopes that he will, and that it translates to a better season next year. We don't need to win a national title any time soon, we just need to start playing good basketball again.
If I'm my best version of Dolson, the one with huge balls and tons of fortitude...I have the meetings right now with Buckner and the President, and I push hard to make a coaching change after this season.