Ross made a point to sit down with every Cubs department head who was available at the Winter Meetings, with his goal being to learn about the essence of their jobs and goals and how that affects his team. Ross needed to take the time to listen because he enters his new job with no managerial experience and without a full understandings of everything that will await him.
As an example, Ross spent an entire 12-hour workday with the Cubs' pro scouts, learning exactly what they're looking for and who in their perspective could fit with the Cubs in 2020 and beyond. On another day, he picked the brains of new director of hitting Justin stone and director of pitching Craig Breslow.
"Since taking the job, I have been really busy creating my staff," Ross said last week. "I have been diving in with the front office and R&D (research and development). I have gotten involved in the business side and the Ricketts family. There have been a lot more sides of the organization I have gotten to touch than I first thought -- things like the hitting plan to how the minor league system will work. I have been with the player development people."
Ross does have the benefit of being a 15-year MLB veteran and working as a special assistant in the Cubs front office from 2017-'19.
"Being data-driven is a part of baseball everywhere now," Ross said. "We just are making sure with stay current with the times. You will see a good mix from us using analytics and just going out and competing. That will be just playing good old-school baseball as well. The important thing about putting my staff together was finding good energy people, hard workers. Delegating will be an important part of what I do, because I will need a lot of help in different areas."
The Cubs added former Padres manager Andy Green as Ross' bench coach and right-hand man. They also made external hires in adding in Craig Driver as the first base/catching coach, Chris Young as bullpen coach and Mike Napoli as quality assurance coach.
Ross is still getting to know a lot of his coaches, though he was teammates with Napoli on the 2013 Red Sox team that won the World Series.
"I have been drawn to people with a catching background," Ross said of Napoli and Driver. "Napoli was such a big hire for me. He checks a lot of the boxes. He was a catcher. He converted into a first baseman. He was a terrific base-runner. He will do a lot for our group and touch a lot of areas."
Still on Ross' to-do list is having more extensive conversations with the players on the Cubs' roster. He's close with a handful of them as he was a part of the Cubs' championship team in 2016. Ross knows those relationships will change somewhat as he's now the boss, while he wants to forge new relationships with the players whom he doesn't know.
"I have kept up with the guys I already know," Ross said. "I have waited to reach out to the entire group until the new year. I want to let these guys enjoy their offseason. Also, I want to have a plan in place to present to them. I did not want to call them and small talk them. I want to give them some information and get a little feedback from them as well. The guys I know have asked stuff, like what is the dress code going to be and things like that. We haven't got to that yet.
"Until spring training, I want to keep it pretty casual with the guys until they hear my true voice and speak real truths to the guys I know and respect. There will be some change in the relationships and some boundaries in line, but I do not want to change as a person. Remember that is why I got this job, that is why the guys respected me a the time. There will be a true balance on all of that and that will come from me"
Ross indicated he'll run a different operation than former manager Joe Maddon did in spring training. Maddon was known -- and praised for -- his laid-back style.
"I hope there will be a little bit of shock for the players," Ross said. "I want to be different. As much as Joe brought to the table and all that the has done, I will keep some of the music on. I like the vibe he created. I will mix up some new things early on. There will be a little bit more structure. I want guys working together rather than guys on their own plans. I want to have them do some things to recreate that bond. We have a good group of guys who know a whole lot about winning. I want them to impact the whole organization. Joe changed the whole culture and created a lot of great things I want to keep that around here."
The Cubs let Maddon go after a disappointing 84-78 season. It marked the first time since 2014 that they had missed the playoffs.
Ross was asked if expectations are lower in 2020 given the struggles of 2019.
"My goal is to win," Ross said. "As the roster stands right now, this is a group that is expected to win. We have a chance to win the division and the World Series. There is a lot of talent in this group, and my expectations will never falter from that goal. I would never not expect to win the World Series, that is for sure."