For me there isn't any one thing or thing(s) that have to happen to continue the Richard Pitino experience its much more of a big picture "where is the program headed?"
Two different seasons:
Season A: Gophers have a season much like 2018 lead by an All B1G Amir Coffey and an improving Daniel Oturu. The team finished somewhere between 9-11 and 11-9 with some frustrating losses but manages to advance to the round of 32 for the second straight year. Pitino misses out on Suggs and loses Garcia and Danja to non Blue Bloods and has a class of kids committed that's currently 10th or worse in the conference.
Season B: Gophers finish around 8-12/7-13 in conference and were never in the big dance mix, but finish the season strong (somewhere in the Illinois to Penn State range this year) on the heels of strong play from Daniel, Gabe, and at least one or two more players with eligibility remaining for 2020. In this scenario Coffey is either not on the roster, simply doesn't have a huge Senior season, etc. Pitino has landed some combination of Suggs/Garcia/Danja/out of state kids that results in a top 5 class in the conference.
I'd be much more inclined to stick with Pitino after season B than season A. With season B, you can point to the future and see the real possibility of upward movement behind the young players and a renewed confidence in Pitino's ability to recruit. With season A, yes you made the tournament but where are you going in 2020? Where are your players coming from? What is the plan moving forward? It would be two bad recruiting years in a row and now there's no Amir Coffey to (hypothetically) carry you.
We're in bad situation right now in that Pitino did well enough on the court to keep his job this year (though the overall 6 years...), but not well enough to get himself off the hot seat and as long as he's on the hot seat, recruiting will be more of a challenge. I personally hope he knocks it out of the park on the recruiting trail first in the next month or so (impact guys for 2019) and continuing until November (some key 2020 commits between this Summer and signing day). If that happens, we will be making a dent in that 30 games under .500 conference record and a real extension and some security can be expected by this time next year.