The number eight has been in outstanding form since returning from injury, earning a nomination for the 2025/26 Investec Player of the Year award after starring in Glasgow's perfect Champions Cup pool campaign, where he leads the competition for carries.
With his contract expiring at the end of the season and interest building from England and France, Carolan is hopeful that Dempsey can be convinced to extend his stay.
Asked if he hopes the back-row forward will commit his future to Glasgow, Carolan told Scotland Rugby News: "Definitely. He's a big game player. It's not that he's not good when you play the other teams at the other end of the table.
"But in those big games, the international games, that's Jack's arena. He's a big game player. He knows which buttons to press emotionally and physically.
"He's a beast with the ball in hand and he knows how to go forward like no other. Thankfully, it's been recognised with the Champions Cup player of the first few rounds. I think he's huge to the club but again, he's going to attract interest from elsewhere as well.
"I hope that between Glasgow Warriors and the SRU, they'll see the merits in trying to keep him here and continue his rugby here for the next few years."
Carolan also reflected on the challenges of squad turnover, with Adam Hastings and Huw Jones set to depart in the summer.
"It's not easy but it's also the way of life, isn't it?" he added. "You're not going to be able to hang on to 20-odd international players, their stock continues to rise. Especially when you're winning, everyone's stock is going to go up and it's the nature of the game that some players are going to attract interest elsewhere.
"That's why these windows are so important. The opportunity to bring the next crop of talented players through is so important. Even if Adam goes or Shugsy goes, there are guys like Kerr Yule. Let's see what he's like over this period.
"If Matty Urwin gets an opportunity over the next couple of games, let's see what he's like in the side and how he drives the team around. I think it's interesting times ahead."
Preparations for Friday night's clash with Munster continue amid uncertainty over player availability due to Six Nations commitments.
"Yeah, good question. One we don't have the answer to as yet. We're prepping with the players that we have and I think anyone that we get back is a bonus.
"No one has fully agreed, they're still training so they've got another training session tomorrow. But we're working together and there's a hope that there might be one or two. But we've prepared a team to play based on if we get nobody back. If we get one or two back we'll try and drop them in on Thursday if that's the case."