Cherington said principal owner John Henry is expected to be a part of the Milwaukee envoy, although he was not certain. The GM meetings run from Monday through Tuesday, with the owners' meetings set for Tuesday through Wednesday.
Boston's decision may need to be reactionary, if not hasty. The Cubs' final candidates include three of the Red Sox's options: Pete Mackanin, Dale Sveum and Sandy Alomar Jr. Mike Maddux, who declined to interview in Boston, is Chicago's fourth.
"We keep abreast of who they're bringing in for interviews," Cherington said. "Obviously, the Cubs' list is a lot like ours, so they're looking at a lot of the same candidates. I'm not sure what their time frame is for making a decision. The reality is it's possible that we could be looking at some of the same finalists. That's something that we'll have to work through."
The candidates the Sox interviewed on Friday and Saturday -- Torey Lovullo and Lamont -- are not on the Cubs' list.
Lamont, who turns 65 in December, has been the Tigers' third-base coach under manager Jim Leyland since 2006, going to the World Series that year and the American League Championship Series this past season.
Lamont is the oldest candidate of the five the Red Sox interviewed -- Mackanin is 60, Sveum turns 48 this month, Alomar Jr. is 45 and Lovullo is 46 -- but he's also the only candidate who's previously been a full-time manager in the Majors. He went a combined 553-562 in eight seasons with the White Sox (1992-95) and Pirates (1997-2000).
Like Sveum and Lovullo, Lamont has also coached in the Red Sox organization before, serving as the third-base coach in Boston under Jimy Williams in a disappointing 2001 season. Before Saturday, though, Lamont and Cherington had rarely crossed paths.
"Some of the candidates, I've had more of a pre-existing relationship with," Cherington said. "I didn't with Gene, even despite the year he was here. I was in a different part of the organization, so I didn't get a chance to know him well. When we were looking for an experienced candidate to include in the process, we did a lot of work on a number of people and just kept getting good stuff back on Gene as a baseball guy, as a person. His experience in Chicago and Pittsburgh, if you kind of dig deeper into it, I feel he did a very good job."
Lamont made clear that despite his close relationship with Leyland, he would not be a Leyland clone. Though Lamont hasn't managed in over a decade, he said the desire has always been there.
The Boston experience and the Chicago experience are positives on Lamont's resume, giving him a big-market familiarity, but Lamont acknowledged that times have changed.
"Being here for a year, it wasn't quite then like it is now," Lamont said. "It was getting there, but this is the thing to do now, the thing to do is say, 'Hey, I went to the Red Sox game last night.' That's when you really have something for me as a franchise. That wasn't quite there yet. We're trying to get that in Detroit. But the players I handled in Chicago, be it Carlton Fisk, Frank Thomas, Jack McDowell, Robin Ventura, Ozzie Guillen -- heck, some are even managers -- I'm sure it helps.
"People talk about personalities, I think you're managing more egos. That's what you have to handle more, are the guys' egos more than, say, their personalities."
The first round of meetings now all-but-certainly concluded, Cherington said there were no major surprises in the process.
Once a skipper is in place, Cherington said a coaching staff could come together "fairly quickly." The team has some names in mind already, but a manager must feel comfortable with his right-hand men.
"I think each candidate has fairly specific ideas on what they'd do," Cherington said Friday. "Some of those positions we'd defer mostly to the manager, and others would be more collaborative. We've got a list of names that would be attached to each candidate, and again, we hope that some of our current staff is here and expect some of our current staff to be here. So, I would think it would unfold pretty quickly."
Some members of last year's coaching staff have already been let go, but for those whose future is still open-ended -- like bench coach DeMarlo Hale -- Cherington is still in communication.
"I've tried to keep in touch with them every three to four days, so I think they have an idea of what's going on," Cherington said. "And again, they know we've got to get this decision made and there's going to be an opportunity to talk more about their position on the staff and making sure there's a good fit; not just for us, but for them, too. They've got to know who they're working for. So, we'll deal with each guy on a case-by-case [basis]."