Given the frequency with which his players are selected in the NBA Draft, the meetings are a source of intrigue. That was particularly true this year with so many players facing difficult decisions about whether to stay or leave.
But anyone who wanted to be a fly on the wall when Willie Cauley-Stein stepped into Calipari's office would have been disappointed. The meeting was short and the message simple.
"I could leave this year, go late first round or come back next year and have an opportunity to go really early," Cauley-Stein said.
Then again, that's probably exactly what any UK fan would have wanted to hear: The skilled 7-footer would be returning for his sophomore season. Cauley-Stein had seen where he was projected in the draft and he decided he could do better.
"I heard a wide variety of things, which kind of that's what set me off," Cauley-Stein said. "I heard anywhere from eight to 10, 15 to 20, 22 to 25. That's the whole dang scale. That's everywhere. I didn't feel real comfortable taking a chance on it and landing somewhere that I'm not going to be good at or ending up hurting myself and coming back and helping."
Just like his meeting with Calipari, Cauley-Stein's decision was an easy one and a quick one. For Alex Poythress, it was a bit of a different story. Poythress talked at length about what to do with his family and UK's assistant coaches, in addition to Coach Cal.
"It was a long process," Poythress said. "You just want to make sure your heart is all in it, make sure you made the right decision, and I feel like I did."
The decision he settled on ended up being the same. Cauley-Stein and Poythress believed they could improve their draft stock with another season, but reducing the choice to that one factor is a vast oversimplification.
At the top of that list of reasons is a little unfinished business.
"You don't want next year to end like this year," Poythress said. "It shouldn't happen with the guys coming and the people returning. We're going to have that much of a fire burning in our belly."
Though it's been more than a month, neither Poythress nor Cauley-Stein need any reminding of the way UK's season ended with back-to-back losses to Vanderbilt and Robert Morris in the Southeastern Conference Tournament and NIT, respectively.
"It just left a bad taste in your mouth," Cauley-Stein said. "I feel like something's empty and I want to fill it. Next year, we're going to have a great opportunity to do that."
Cauley-Stein's optimism, of course, is based in large part on the unprecedented volume and quantity of talent coming to Lexington next season. In terms of recruiting rankings, Calipari has signed his most highly regarded class to date, an eight-member group that features six five-star prospects and the top point guard, shooting guard and power forward in the class according to Rivals.
"It's going to be a nice roster," Poythress said. "The competition at practice is going to be very good. You're going to have to go hard every day."
Cauley-Stein arrived at UK an unheralded prospect - at least relative to the standards of the Calipari era at Kentucky - but contributed immediately and even dominated at times as the year wore on. Intense matchups with a potential No. 1 overall pick in practice for the first three-and-a-half months should not be overlooked as a reason for that.
"I think honestly for me that's going to be the best thing to come out of next year is you're going against pros every day," Cauley-Stein said. "This year it was like that until Nerlens (Noel) got hurt, and then we were going against Brian Long. ... You're not getting better. You're going to dominate practice and get into a game and struggle. Next year, it's going to be a lot different."
Though practices will undoubtedly be different, Cauley-Stein is quick to caution that it's in the Cats' hands whether things change in games.
This time a year ago, Cauley-Stein and Poythress were members of a recruiting class generating more than its fair share of championship talk. UK entered last season ranked No. 3 and is likely to be ranked in the same range in 2013-14. Having gone through what he just did, Cauley-Stein knows how insignificant hype can be.
"The potential is exactly that," Cauley-Stein said. "We had the potential this year and didn't capitalize on it. We could easily be, you know, we had the best recruiting class coming in and not do anything with it. It's that simple. If you don't come together and do things right, then you're just a bunch of talented kids that didn't get anything accomplished."
Cauley-Stein also realizes it's up to him and his teammates to write the script for next year.
"It's different if you make it different," Cauley-Stein said. "It could easily be the same where you come in here and you don't work as hard. But the thing is I don't think Cal's going to let that happen and us guys coming back's not going to let that happen just because how we finished, you can't leave off there."
After that ignominious end, Cauley-Stein has already noticed in himself reason to believe things will be different.
"Once the season ended it was kind of like my whole mentality changed instantly - which I wish it would have changed before the tournament happened," Cauley-Stein said. "I kind of got like a dominating mindset going into this next year. I want to be the best in everything I do. ... This time I want come in here and do it. I don't want to try to do it."
That mentality sounds a lot like that of a leader, and it's no coincidence. Other than the concise advice he gave to Cauley-Stein about coming back, Calipari told his big man he needed to step up in the leadership department. Heeding that advice, Cauley-Stein wants to do what Terrence Jones and Doron Lamb did for Anthony Davis and Michael Kidd-Gilchrist for the likes of Julius Randle and Andrew Harrison.
"I think that's exactly what we missed this year is a guy that played a lot minutes as a freshman (and) decided to come back and take on the role of a leader," Cauley-Stein said. "We didn't have that this year. Kyle was that kind of guy, but he still didn't play big minutes his freshman year. This year, we've got three guys (Cauley-Stein, Poythress and Kyle Wiltjer) - including (Jarrod Polson) - that were playing almost thirty minutes a game. That coming back is going to help tremendously."